Prefer an available OAuth flow instead of hard-coding device code

e2e/harness documents itself as feature-agnostic, but three details
assumed the caller lives in this repo, so the terraform provider's
acceptance suite would otherwise carry a second harness for the same
product.

repoRoot took the first module root above the working directory as the
Docker build context, which from another module is the caller's own
root, with no combined/Dockerfile.multistage in it. It now requires that
ancestor to be this module, and otherwise asks the go tool for the
source: for a dependent, the extracted directory of the version it pins,
so the server matches the client library it was compiled against. That
lookup uses -mod=readonly, since automatic vendor mode otherwise reports
an empty Dir.

Geolocation was disabled unconditionally. Agent-network ingest does not
use it, but location-based posture checks need the database, and a rule
management cannot evaluate fails rather than passing.
StartClient pinned one network alias and set no hostname, so a second
agent could not start and a peer's name was arbitrary. Management
records that hostname, making it the peer's name in the API.
The client entrypoint is copied with an explicit mode: git tracks it
100755, but the module cache extracts 0444, so a dependent's build
produced a container exiting with "permission denied".

Adds CombinedOption, WithGeolocation, WithServerEnv, ClientOption and
WithClientName.

.goreleaser_ui.yaml

@@ -96,6 +96,7 @@ nfpms:
       - netbird (>= 0.75.0)
       - libgtk-4-1 (>= 4.14)
       - libwebkitgtk-6.0-4
+      - xdg-utils
 
   - maintainer: Netbird <dev@netbird.io>
     description: Netbird client UI.
@@ -119,6 +120,7 @@ nfpms:
       - netbird >= 0.75.0
       - (gtk4 >= 4.14 or libgtk-4-1 >= 4.14)
       - (webkitgtk6.0 or libwebkitgtk-6_0-4)
+      - xdg-utils
 
     rpm:
       signature:

.goreleaser_ui_gtk3.yaml

@@ -43,19 +43,17 @@ archives:
       - netbird-ui-gtk3
 
 nfpms:
-  # Same package_name as the GTK4 packages -- the two are mutually-exclusive
-  # alternatives served from separate repo paths (see uploads below); a given
-  # distro points at exactly one of them. The file names must still differ:
-  # the Debian pool is shared storage keyed by file name, so a default-named
-  # gtk3 .deb would overwrite the stable one.
+  # Mutually-exclusive alternative to the GTK4 netbird-ui package -- both
+  # ship the same /usr/bin/netbird-ui from the shared stable/yum repos, so
+  # this one carries its own name and conflicts with the GTK4 package.
   - maintainer: Netbird <dev@netbird.io>
     description: Netbird client UI.
     homepage: https://netbird.io/
     license: BSD-3-Clause
     vendor: NetBird
     id: netbird_ui_deb_gtk3
-    package_name: netbird-ui
-    file_name_template: "{{ .PackageName }}-gtk3_{{ .Version }}_{{ .Os }}_{{ .Arch }}"
+    package_name: netbird-ui-gtk3
+    file_name_template: "{{ .PackageName }}_{{ .Version }}_{{ .Os }}_{{ .Arch }}"
     builds:
       - netbird-ui-gtk3
     formats:
@@ -67,10 +65,15 @@ nfpms:
         dst: /usr/share/applications/org.wails.netbird.desktop
       - src: client/ui/build/appicon.png
         dst: /usr/share/pixmaps/netbird.png
+    conflicts:
+      - netbird-ui
+    replaces:
+      - netbird-ui
     dependencies:
       - netbird (>= 0.75.0)
       - libgtk-3-0
       - libwebkit2gtk-4.1-0
+      - xdg-utils
 
   - maintainer: Netbird <dev@netbird.io>
     description: Netbird client UI.
@@ -78,8 +81,8 @@ nfpms:
     license: BSD-3-Clause
     vendor: NetBird
     id: netbird_ui_rpm_gtk3
-    package_name: netbird-ui
-    file_name_template: "{{ .PackageName }}-gtk3_{{ .Version }}_{{ .Os }}_{{ .Arch }}"
+    package_name: netbird-ui-gtk3
+    file_name_template: "{{ .PackageName }}_{{ .Version }}_{{ .Os }}_{{ .Arch }}"
     builds:
       - netbird-ui-gtk3
     formats:
@@ -91,10 +94,15 @@ nfpms:
         dst: /usr/share/applications/org.wails.netbird.desktop
       - src: client/ui/build/appicon.png
         dst: /usr/share/pixmaps/netbird.png
+    # No `replaces` here: nfpm maps it to rpm Obsoletes, which would make
+    # dnf swap installed GTK4 netbird-ui packages for this one on upgrade.
+    conflicts:
+      - netbird-ui
     dependencies:
       - netbird >= 0.75.0
       - (gtk3 or libgtk-3-0)
       - (webkit2gtk4.1 or libwebkit2gtk-4_1-0)
+      - xdg-utils
 
     rpm:
       signature:
@@ -109,23 +117,20 @@ changelog:
   disable: true
 
 uploads:
-  # The gtk3 packages reuse the netbird-ui package name, so they live in
-  # dedicated repo paths (deb distribution `gtk3`, yum path `yum-gtk3`) that
-  # legacy distros point their repo config at.
-  - name: debian-gtk3
+  - name: debian
     skip: "{{ .Env.SKIP_PUBLISH }}"
     ids:
       - netbird_ui_deb_gtk3
     mode: archive
-    target: https://pkgs.wiretrustee.com/debian/pool/{{ .ArtifactName }};deb.distribution=gtk3;deb.component=main;deb.architecture={{ if .Arm }}armhf{{ else }}{{ .Arch }}{{ end }};deb.package=
+    target: https://pkgs.wiretrustee.com/debian/pool/{{ .ArtifactName }};deb.distribution=stable;deb.component=main;deb.architecture={{ if .Arm }}armhf{{ else }}{{ .Arch }}{{ end }};deb.package=
     username: dev@wiretrustee.com
     method: PUT
 
-  - name: yum-gtk3
+  - name: yum
     skip: "{{ .Env.SKIP_PUBLISH }}"
     ids:
       - netbird_ui_rpm_gtk3
     mode: archive
-    target: https://pkgs.wiretrustee.com/yum-gtk3/{{ .Arch }}{{ if .Arm }}{{ .Arm }}{{ end }}
+    target: https://pkgs.wiretrustee.com/yum/{{ .Arch }}{{ if .Arm }}{{ .Arm }}{{ end }}
     username: dev@wiretrustee.com
     method: PUT

CONTRIBUTING.md

@@ -112,6 +112,7 @@ aligns with our security standards and design expectations.
         - [Test suite](#test-suite)
     - [Checklist before submitting a PR](#checklist-before-submitting-a-pr)
     - [When we close a PR](#when-we-close-a-pr)
+    - [Translations](#translations)
     - [Other project repositories](#other-project-repositories)
     - [Contributor License Agreement](#contributor-license-agreement)
 
@@ -612,6 +613,17 @@ A closed PR is not a rejected idea. Take it back to the
 [discussion](https://github.com/netbirdio/netbird/discussions), settle the
 approach, and reopen the work from there.
 
+## Translations
+
+Desktop UI translations are not contributed through pull requests. Translate on
+[Crowdin](https://crowdin.com/project/netbird) instead: no ticket needed, just
+join the project and pick your language. Crowdin syncs with this repository and
+opens the service PRs itself, so hand-edited locale files would conflict with
+the next sync. Style, terminology, and review guidance live in
+[client/ui/i18n/TRANSLATING.md](client/ui/i18n/TRANSLATING.md). To request a
+language the project does not offer yet, ask on the Crowdin project page or in
+a [discussion](https://github.com/netbirdio/netbird/discussions).
+
 ## Other project repositories
 
 NetBird project is composed of 3 main repositories:

client/android/client.go

@@ -15,6 +15,7 @@ import (
 
 	log "github.com/sirupsen/logrus"
 
+	nbAnonymize "github.com/netbirdio/netbird/client/anonymize"
 	"github.com/netbirdio/netbird/client/iface/device"
 	"github.com/netbirdio/netbird/client/internal"
 	"github.com/netbirdio/netbird/client/internal/debug"
@@ -32,6 +33,13 @@ import (
 	types "github.com/netbirdio/netbird/upload-server/types"
 )
 
+// AnonymizeLevelDefault and AnonymizeLevelStrict are the accepted
+// anonymizeLevel values for DebugBundle.
+const (
+	AnonymizeLevelDefault = nbAnonymize.LevelDefaultString
+	AnonymizeLevelStrict  = nbAnonymize.LevelStrictString
+)
+
 // ConnectionListener export internal Listener for mobile
 type ConnectionListener interface {
 	peer.Listener
@@ -278,8 +286,10 @@ func (c *Client) GetTunSettings() (*TunSettings, error) {
 }
 
 // DebugBundle generates a debug bundle, uploads it, and returns the upload key.
-// It works both with and without a running engine.
-func (c *Client) DebugBundle(platformFiles PlatformFiles, anonymize bool) (string, error) {
+// It works both with and without a running engine. anonymizeLevel is "default"
+// or "strict"; strict also anonymizes internal IP ranges, peer names, and
+// WireGuard public keys, and implies anonymize.
+func (c *Client) DebugBundle(platformFiles PlatformFiles, anonymize bool, anonymizeLevel string) (string, error) {
 	cfg, cacheDir, cc := c.stateSnapshot()
 
 	// If the engine hasn't been started, load config from disk
@@ -298,6 +308,7 @@ func (c *Client) DebugBundle(platformFiles PlatformFiles, anonymize bool) (strin
 		InternalConfig: cfg,
 		StatusRecorder: c.recorder,
 		TempDir:        cacheDir,
+		StatePath:      platformFiles.StateFilePath(),
 	}
 
 	if cc != nil {
@@ -321,6 +332,7 @@ func (c *Client) DebugBundle(platformFiles PlatformFiles, anonymize bool) (strin
 		deps,
 		debug.BundleConfig{
 			Anonymize:         anonymize,
+			AnonymizeLevel:    nbAnonymize.ParseLevel(anonymizeLevel),
 			IncludeSystemInfo: true,
 		},
 	)

client/anonymize/anonymize.go

@@ -2,6 +2,7 @@ package anonymize
 
 import (
 	"crypto/rand"
+	"encoding/base64"
 	"fmt"
 	"math/big"
 	"net"
@@ -15,13 +16,88 @@ import (
 
 const anonTLD = ".domain"
 
+// Level selects how much the anonymizer redacts. Levels are ordered: a higher
+// level redacts strictly more. On the wire (protos, flags) levels travel as
+// their string form.
+type Level int
+
+const (
+	// LevelDefault anonymizes public IP addresses, IPv6 ULA, domains, and MAC
+	// addresses. Internal IPv4 ranges (RFC 1918, CGNAT, link-local) are
+	// preserved so support can reason about the real topology.
+	LevelDefault Level = iota
+	// LevelStrict additionally anonymizes internal IP ranges, peer names, and
+	// WireGuard public keys.
+	LevelStrict
+)
+
+// LevelDefaultString and LevelStrictString are the wire forms of the levels,
+// for boundaries that pass levels as strings (flags, protos, mobile bindings).
+const (
+	LevelDefaultString = "default"
+	LevelStrictString  = "strict"
+)
+
+// ParseLevel maps s to a Level. Empty means LevelDefault; anything
+// unrecognized maps to LevelStrict so an unknown request never yields less
+// anonymization than intended.
+func ParseLevel(s string) Level {
+	switch strings.ToLower(s) {
+	case "", LevelDefaultString:
+		return LevelDefault
+	default:
+		return LevelStrict
+	}
+}
+
+// String returns the wire form of the level: "default" or "strict".
+func (l Level) String() string {
+	if l >= LevelStrict {
+		return LevelStrictString
+	}
+	return LevelDefaultString
+}
+
+// protectedDomains are NetBird-operated suffixes that stay recognizable in an
+// anonymized bundle. At LevelStrict the labels in front of them (the peer
+// name) are still replaced, except under netbird.io, which only hosts
+// NetBird infrastructure (api, signal, flow), never peer names.
+var protectedDomains = []string{"netbird.io", "netbird.selfhosted", "netbird.cloud", "netbird.stage"}
+
+const infraDomain = "netbird.io"
+
+var (
+	macColonRegex = regexp.MustCompile(`\b[0-9a-fA-F]{2}(?::[0-9a-fA-F]{2}){5}\b`)
+	macDashRegex  = regexp.MustCompile(`\b[0-9a-fA-F]{2}(?:-[0-9a-fA-F]{2}){5}\b`)
+	wgKeyRegex    = regexp.MustCompile(`\b[A-Za-z0-9+/]{43}=`)
+)
+
 type Anonymizer struct {
 	ipAnonymizer     map[netip.Addr]netip.Addr
 	domainAnonymizer map[string]string
-	currentAnonIPv4  netip.Addr
-	currentAnonIPv6  netip.Addr
-	startAnonIPv4    netip.Addr
-	startAnonIPv6    netip.Addr
+	// domainOrder caches the keys of domainAnonymizer sorted longest-first
+	// for AnonymizeString; it is rebuilt when the map gains entries.
+	domainOrder     []string
+	labelAnonymizer map[string]string
+	labelAnonymized map[string]struct{}
+	labelCounter    uint32
+	macAnonymizer   map[string]string
+	macCounter      uint32
+	wgKeyAnonymizer map[string]string
+	wgKeyAnonymized map[string]struct{}
+	currentAnonIPv4 netip.Addr
+	currentAnonIPv6 netip.Addr
+	startAnonIPv4   netip.Addr
+	startAnonIPv6   netip.Addr
+
+	// LevelStrict also anonymizes internal ranges (RFC 1918, CGNAT,
+	// link-local), replacing them from the dedicated internal pools below so
+	// a reader can still tell an internal address from a public one.
+	level                   Level
+	currentAnonInternalIPv4 netip.Addr
+	currentAnonInternalIPv6 netip.Addr
+	startAnonInternalIPv4   netip.Addr
+	startAnonInternalIPv6   netip.Addr
 
 	domainKeyRegex *regexp.Regexp
 }
@@ -32,25 +108,50 @@ func DefaultAddresses() (netip.Addr, netip.Addr) {
 	return netip.AddrFrom4([4]byte{198, 51, 100, 0}), netip.MustParseAddr("2001:db8:ffff::")
 }
 
+// InternalAddresses returns the pool starts used in strict mode for internal
+// ranges. Both are reserved ranges that cannot collide with real addressing:
+// 198.18.0.0 (RFC 2544 benchmarking), 2001:db8:1:: (RFC 3849 documentation).
+func InternalAddresses() (netip.Addr, netip.Addr) {
+	return netip.AddrFrom4([4]byte{198, 18, 0, 0}), netip.MustParseAddr("2001:db8:1::")
+}
+
 func NewAnonymizer(startIPv4, startIPv6 netip.Addr) *Anonymizer {
+	internalIPv4, internalIPv6 := InternalAddresses()
 	return &Anonymizer{
 		ipAnonymizer:     map[netip.Addr]netip.Addr{},
 		domainAnonymizer: map[string]string{},
+		labelAnonymizer:  map[string]string{},
+		labelAnonymized:  map[string]struct{}{},
+		macAnonymizer:    map[string]string{},
+		wgKeyAnonymizer:  map[string]string{},
+		wgKeyAnonymized:  map[string]struct{}{},
 		currentAnonIPv4:  startIPv4,
 		currentAnonIPv6:  startIPv6,
 		startAnonIPv4:    startIPv4,
 		startAnonIPv6:    startIPv6,
 
+		level:                   LevelDefault,
+		currentAnonInternalIPv4: internalIPv4,
+		currentAnonInternalIPv6: internalIPv6,
+		startAnonInternalIPv4:   internalIPv4,
+		startAnonInternalIPv6:   internalIPv6,
+
 		domainKeyRegex: regexp.MustCompile(`\bdomain=([^\s,:"]+)`),
 	}
 }
 
+// SetLevel selects the anonymization level. The zero value of a new
+// Anonymizer is LevelDefault.
+func (a *Anonymizer) SetLevel(level Level) {
+	a.level = level
+}
+
 func (a *Anonymizer) AnonymizeIP(ip netip.Addr) netip.Addr {
+	// Normalize 4-in-6 addresses so ::ffff:192.168.1.1 classifies and maps
+	// like 192.168.1.1.
+	ip = ip.Unmap()
+
 	if ip.IsLoopback() ||
-		ip.IsLinkLocalUnicast() ||
-		ip.IsLinkLocalMulticast() ||
-		ip.IsInterfaceLocalMulticast() ||
-		(ip.Is4() && ip.IsPrivate()) ||
 		ip.IsUnspecified() ||
 		ip.IsMulticast() ||
 		isWellKnown(ip) ||
@@ -59,18 +160,100 @@ func (a *Anonymizer) AnonymizeIP(ip netip.Addr) netip.Addr {
 		return ip
 	}
 
+	if isInternal(ip) && a.level < LevelStrict {
+		return ip
+	}
+
 	if _, ok := a.ipAnonymizer[ip]; !ok {
-		if ip.Is4() {
-			a.ipAnonymizer[ip] = a.currentAnonIPv4
-			a.currentAnonIPv4 = a.currentAnonIPv4.Next()
-		} else {
-			a.ipAnonymizer[ip] = a.currentAnonIPv6
-			a.currentAnonIPv6 = a.currentAnonIPv6.Next()
-		}
+		a.ipAnonymizer[ip] = a.nextAnonIP(ip)
 	}
 	return a.ipAnonymizer[ip]
 }
 
+func (a *Anonymizer) nextAnonIP(ip netip.Addr) netip.Addr {
+	// At the strict level, internal addresses (including IPv6 ULA, matched
+	// by IsPrivate) come from the internal pools so they remain recognizable
+	// as internal without disclosing the real values.
+	if a.level >= LevelStrict && (isInternal(ip) || ip.IsPrivate()) {
+		if ip.Is4() {
+			anon := a.currentAnonInternalIPv4
+			a.currentAnonInternalIPv4 = a.currentAnonInternalIPv4.Next()
+			return anon
+		}
+		anon := a.currentAnonInternalIPv6
+		a.currentAnonInternalIPv6 = a.currentAnonInternalIPv6.Next()
+		return anon
+	}
+
+	if ip.Is4() {
+		anon := a.currentAnonIPv4
+		a.currentAnonIPv4 = a.currentAnonIPv4.Next()
+		return anon
+	}
+	anon := a.currentAnonIPv6
+	a.currentAnonIPv6 = a.currentAnonIPv6.Next()
+	return anon
+}
+
+// AnonymizeMAC replaces a MAC address with a consistent placeholder from the
+// locally administered range starting at 02:00:00:00:00:01, at every
+// anonymization level. Broadcast, multicast, all-zero, and already assigned
+// placeholder addresses are preserved. The colon and dash spellings of the
+// same address share one placeholder; the output keeps the input's separator.
+func (a *Anonymizer) AnonymizeMAC(mac string) string {
+	hw, err := net.ParseMAC(mac)
+	if err != nil || len(hw) != 6 {
+		return mac
+	}
+
+	if isWellKnownMAC(hw) || a.isAnonymizedMAC(hw) {
+		return mac
+	}
+
+	key := hw.String()
+	anon, ok := a.macAnonymizer[key]
+	if !ok {
+		a.macCounter++
+		anon = fmt.Sprintf("02:00:00:%02x:%02x:%02x", byte(a.macCounter>>16), byte(a.macCounter>>8), byte(a.macCounter))
+		a.macAnonymizer[key] = anon
+	}
+
+	if strings.Contains(mac, "-") {
+		anon = strings.ReplaceAll(anon, ":", "-")
+	}
+	return anon
+}
+
+// isAnonymizedMAC reports whether hw is a placeholder this anonymizer already
+// handed out, so a second pass over anonymized output leaves it unchanged.
+func (a *Anonymizer) isAnonymizedMAC(hw net.HardwareAddr) bool {
+	if hw[0] != 0x02 || hw[1] != 0 || hw[2] != 0 {
+		return false
+	}
+	value := uint32(hw[3])<<16 | uint32(hw[4])<<8 | uint32(hw[5])
+	return value <= a.macCounter
+}
+
+// AnonymizeWGKey replaces a WireGuard public key with a consistent random
+// placeholder of the same shape. Keys are only anonymized at LevelStrict;
+// placeholders already handed out pass through unchanged.
+func (a *Anonymizer) AnonymizeWGKey(key string) string {
+	if a.level < LevelStrict || !looksLikeWGKey(key) {
+		return key
+	}
+	if _, ok := a.wgKeyAnonymized[key]; ok {
+		return key
+	}
+
+	anon, ok := a.wgKeyAnonymizer[key]
+	if !ok {
+		anon = generateAnonymousKey()
+		a.wgKeyAnonymizer[key] = anon
+		a.wgKeyAnonymized[anon] = struct{}{}
+	}
+	return anon
+}
+
 func (a *Anonymizer) AnonymizeUDPAddr(addr net.UDPAddr) net.UDPAddr {
 	// Convert IP to netip.Addr
 	ip, ok := netip.AddrFromSlice(addr.IP)
@@ -89,12 +272,12 @@ func (a *Anonymizer) AnonymizeUDPAddr(addr net.UDPAddr) net.UDPAddr {
 
 // isInAnonymizedRange checks if an IP is within the range of already assigned anonymized IPs
 func (a *Anonymizer) isInAnonymizedRange(ip netip.Addr) bool {
-	if ip.Is4() && ip.Compare(a.startAnonIPv4) >= 0 && ip.Compare(a.currentAnonIPv4) <= 0 {
-		return true
-	} else if !ip.Is4() && ip.Compare(a.startAnonIPv6) >= 0 && ip.Compare(a.currentAnonIPv6) <= 0 {
-		return true
+	if ip.Is4() {
+		return inPoolRange(ip, a.startAnonIPv4, a.currentAnonIPv4) ||
+			inPoolRange(ip, a.startAnonInternalIPv4, a.currentAnonInternalIPv4)
 	}
-	return false
+	return inPoolRange(ip, a.startAnonIPv6, a.currentAnonIPv6) ||
+		inPoolRange(ip, a.startAnonInternalIPv6, a.currentAnonInternalIPv6)
 }
 
 func (a *Anonymizer) AnonymizeIPString(ip string) string {
@@ -118,14 +301,17 @@ func (a *Anonymizer) AnonymizeDomain(domain string) string {
 		baseDomain = domain[:len(domain)-1]
 	}
 
-	if strings.HasSuffix(baseDomain, "netbird.io") ||
-		strings.HasSuffix(baseDomain, "netbird.selfhosted") ||
-		strings.HasSuffix(baseDomain, "netbird.cloud") ||
-		strings.HasSuffix(baseDomain, "netbird.stage") ||
-		strings.HasSuffix(baseDomain, anonTLD) {
+	if strings.HasSuffix(baseDomain, anonTLD) {
 		return domain
 	}
 
+	if suffix := protectedSuffix(baseDomain); suffix != "" {
+		if a.level < LevelStrict || baseDomain == suffix || suffix == infraDomain {
+			return domain
+		}
+		return withTrailingDot(a.anonymizePeerName(baseDomain, suffix), hasDot)
+	}
+
 	parts := strings.Split(baseDomain, ".")
 	if len(parts) < 2 {
 		return domain
@@ -141,12 +327,53 @@ func (a *Anonymizer) AnonymizeDomain(domain string) string {
 	}
 
 	result := strings.Replace(baseDomain, baseForLookup, anonymized, 1)
-	if hasDot {
-		result += "."
+	if a.level >= LevelStrict && len(parts) > 2 {
+		prefix := strings.TrimSuffix(baseDomain, "."+baseForLookup)
+		result = a.anonymizeLabels(prefix, "host") + "." + anonymized
+		// The full mapping feeds AnonymizeString so seeded FQDNs are caught
+		// in log lines as a whole, labels included.
+		a.domainAnonymizer[baseDomain] = result
+	}
+	return withTrailingDot(result, hasDot)
+}
+
+// anonymizePeerName replaces the labels in front of a protected suffix with
+// numbered peer placeholders, keeping the suffix, and records the full
+// mapping for string replacement in logs. The numbering keeps a peer
+// recognizable across the whole bundle without disclosing its name.
+func (a *Anonymizer) anonymizePeerName(baseDomain, suffix string) string {
+	prefix := strings.TrimSuffix(baseDomain, "."+suffix)
+	result := a.anonymizeLabels(prefix, "peer") + "." + suffix
+	if result != baseDomain {
+		a.domainAnonymizer[baseDomain] = result
 	}
 	return result
 }
 
+// anonymizeLabels replaces each dot-separated label with a consistent
+// numbered placeholder ("<placeholder>-<n>"). Wildcard labels and
+// placeholders already handed out pass through unchanged.
+func (a *Anonymizer) anonymizeLabels(prefix, placeholder string) string {
+	labels := strings.Split(prefix, ".")
+	for i, label := range labels {
+		if label == "*" {
+			continue
+		}
+		if _, ok := a.labelAnonymized[label]; ok {
+			continue
+		}
+		anon, ok := a.labelAnonymizer[label]
+		if !ok {
+			a.labelCounter++
+			anon = fmt.Sprintf("%s-%d", placeholder, a.labelCounter)
+			a.labelAnonymizer[label] = anon
+			a.labelAnonymized[anon] = struct{}{}
+		}
+		labels[i] = anon
+	}
+	return strings.Join(labels, ".")
+}
+
 func (a *Anonymizer) AnonymizeURI(uri string) string {
 	u, err := url.Parse(uri)
 	if err != nil {
@@ -181,16 +408,70 @@ func (a *Anonymizer) AnonymizeString(str string) string {
 	str = ipv4Regex.ReplaceAllStringFunc(str, a.AnonymizeIPString)
 	str = ipv6Regex.ReplaceAllStringFunc(str, a.AnonymizeIPString)
 
-	for domain, anonDomain := range a.domainAnonymizer {
-		str = strings.ReplaceAll(str, domain, anonDomain)
+	for _, domain := range a.sortedDomains() {
+		str = strings.ReplaceAll(str, domain, a.domainAnonymizer[domain])
 	}
 
 	str = a.AnonymizeSchemeURI(str)
 	str = a.AnonymizeDNSLogLine(str)
 
+	// MAC handling runs after the IP passes so preserved IPv6 addresses are
+	// already out of the way; the separator guard skips matches embedded in a
+	// longer colon- or dash-separated sequence (such as an IPv6 tail).
+	str = a.anonymizeMACsInString(str, macColonRegex, ':')
+	str = a.anonymizeMACsInString(str, macDashRegex, '-')
+
+	if a.level >= LevelStrict {
+		str = wgKeyRegex.ReplaceAllStringFunc(str, a.AnonymizeWGKey)
+	}
+
 	return str
 }
 
+// sortedDomains returns the domain mappings longest-first, so a full-FQDN
+// mapping (strict level) is applied before the base-domain mapping it
+// contains. The order is rebuilt only when domainAnonymizer has grown.
+func (a *Anonymizer) sortedDomains() []string {
+	if len(a.domainOrder) == len(a.domainAnonymizer) {
+		return a.domainOrder
+	}
+
+	a.domainOrder = a.domainOrder[:0]
+	for domain := range a.domainAnonymizer {
+		a.domainOrder = append(a.domainOrder, domain)
+	}
+	slices.SortFunc(a.domainOrder, func(x, y string) int {
+		if d := len(y) - len(x); d != 0 {
+			return d
+		}
+		return strings.Compare(x, y)
+	})
+	return a.domainOrder
+}
+
+// anonymizeMACsInString replaces MAC addresses matched by re, skipping
+// matches that directly adjoin another sep so a six-group run inside a longer
+// separated sequence is left alone.
+func (a *Anonymizer) anonymizeMACsInString(str string, re *regexp.Regexp, sep byte) string {
+	matches := re.FindAllStringIndex(str, -1)
+	if len(matches) == 0 {
+		return str
+	}
+
+	var b strings.Builder
+	last := 0
+	for _, m := range matches {
+		if (m[0] > 0 && str[m[0]-1] == sep) || (m[1] < len(str) && str[m[1]] == sep) {
+			continue
+		}
+		b.WriteString(str[last:m[0]])
+		b.WriteString(a.AnonymizeMAC(str[m[0]:m[1]]))
+		last = m[1]
+	}
+	b.WriteString(str[last:])
+	return b.String()
+}
+
 // AnonymizeSchemeURI finds and anonymizes URIs with ws, wss, rel, rels, stun, stuns, turn, and turns schemes.
 func (a *Anonymizer) AnonymizeSchemeURI(text string) string {
 	re := regexp.MustCompile(`(?i)\b(wss?://|rels?://|stuns?:|turns?:|https?://)\S+\b`)
@@ -239,10 +520,79 @@ func isWellKnown(addr netip.Addr) bool {
 		"128.0.0.0", "8000::", // 2nd split subnet for default routes
 	}
 
-	if slices.Contains(wellKnown, addr.String()) {
+	return slices.Contains(wellKnown, addr.String())
+}
+
+// isInternal reports whether ip identifies a host only within the local
+// network: IPv4 private (RFC 1918), CGNAT (RFC 6598), and link-local (v4 and
+// v6). These are preserved at the default level so support can reason about
+// the real topology, and replaced from the internal pools at the strict
+// level. IPv6 ULA is deliberately not internal: its random global ID uniquely
+// fingerprints the network, so it is anonymized at every level.
+func isInternal(ip netip.Addr) bool {
+	return (ip.Is4() && ip.IsPrivate()) ||
+		ip.IsLinkLocalUnicast() ||
+		isCGNAT(ip)
+}
+
+func inPoolRange(ip, start, current netip.Addr) bool {
+	return ip.Compare(start) >= 0 && ip.Compare(current) <= 0
+}
+
+// isWellKnownMAC reports whether hw carries no stable host identity: all-zero
+// or a group address (broadcast and multicast).
+func isWellKnownMAC(hw net.HardwareAddr) bool {
+	if hw[0]&1 == 1 {
 		return true
 	}
+	for _, b := range hw {
+		if b != 0 {
+			return false
+		}
+	}
+	return true
+}
 
+// looksLikeWGKey reports whether s has the shape of a WireGuard key:
+// 44 base64 characters decoding to 32 bytes.
+func looksLikeWGKey(s string) bool {
+	if len(s) != 44 || s[43] != '=' {
+		return false
+	}
+	decoded, err := base64.StdEncoding.DecodeString(s)
+	return err == nil && len(decoded) == 32
+}
+
+func generateAnonymousKey() string {
+	buf := make([]byte, 32)
+	if _, err := rand.Read(buf); err != nil {
+		return strings.Repeat("A", 43) + "="
+	}
+	return base64.StdEncoding.EncodeToString(buf)
+}
+
+// protectedSuffix returns the protected NetBird suffix baseDomain ends with,
+// or empty. The match is label-anchored so an unrelated domain that merely
+// ends in the same characters is not preserved.
+func protectedSuffix(baseDomain string) string {
+	for _, d := range protectedDomains {
+		if baseDomain == d || strings.HasSuffix(baseDomain, "."+d) {
+			return d
+		}
+	}
+	return ""
+}
+
+func withTrailingDot(domain string, hasDot bool) string {
+	if hasDot {
+		return domain + "."
+	}
+	return domain
+}
+
+// isCGNAT reports whether addr is in 100.64.0.0/10 (RFC 6598), the range
+// NetBird assigns overlay peer addresses from.
+func isCGNAT(addr netip.Addr) bool {
 	cgnatRangeStart := netip.AddrFrom4([4]byte{100, 64, 0, 0})
 	cgnatRange := netip.PrefixFrom(cgnatRangeStart, 10)
 

client/anonymize/anonymize_test.go

@@ -1,8 +1,11 @@
 package anonymize_test
 
 import (
+	"bytes"
+	"encoding/base64"
 	"net/netip"
 	"regexp"
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -44,6 +47,301 @@ func TestAnonymizeIP(t *testing.T) {
 	}
 }
 
+func TestParseLevel(t *testing.T) {
+	tests := []struct {
+		input  string
+		expect anonymize.Level
+	}{
+		{"", anonymize.LevelDefault},
+		{"default", anonymize.LevelDefault},
+		{"DEFAULT", anonymize.LevelDefault},
+		{"strict", anonymize.LevelStrict},
+		{"STRICT", anonymize.LevelStrict},
+		// Unknown values must never yield less anonymization than requested.
+		{"garbage", anonymize.LevelStrict},
+	}
+
+	for _, tc := range tests {
+		t.Run("input="+tc.input, func(t *testing.T) {
+			assert.Equal(t, tc.expect, anonymize.ParseLevel(tc.input), "parsed level should match")
+		})
+	}
+}
+
+func TestAnonymizeIP_DefaultLevelInternalRanges(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+
+	tests := []struct {
+		name   string
+		ip     string
+		expect string
+	}{
+		{"RFC1918 10/8", "10.1.2.3", "10.1.2.3"},
+		{"RFC1918 172.16/12", "172.16.5.5", "172.16.5.5"},
+		{"RFC1918 192.168/16", "192.168.1.1", "192.168.1.1"},
+		{"CGNAT", "100.64.0.5", "100.64.0.5"},
+		{"IPv4 link-local", "169.254.1.1", "169.254.1.1"},
+		{"IPv6 link-local", "fe80::1", "fe80::1"},
+		// ULA is anonymized even at the default level: its random global ID
+		// uniquely fingerprints the network, unlike shared RFC 1918 space.
+		{"IPv6 ULA", "fd12:3456:789a::1", "2001:db8:ffff::"},
+		// 4-in-6 addresses classify like their unmapped IPv4 form.
+		{"4-in-6 RFC1918", "::ffff:192.168.1.1", "192.168.1.1"},
+		{"4-in-6 CGNAT", "::ffff:100.64.0.5", "100.64.0.5"},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			result := anonymizer.AnonymizeIP(netip.MustParseAddr(tc.ip))
+			assert.Equal(t, tc.expect, result.String(), "default level should preserve internal ranges except ULA")
+		})
+	}
+}
+
+func TestAnonymizeIP_StrictLevel(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+	anonymizer.SetLevel(anonymize.LevelStrict)
+
+	// Order matters: internal pool addresses are assigned sequentially.
+	tests := []struct {
+		name   string
+		ip     string
+		expect string
+	}{
+		{"RFC1918 192.168/16", "192.168.1.1", "198.18.0.0"},
+		{"Second RFC1918", "192.168.1.2", "198.18.0.1"},
+		{"Repeated RFC1918", "192.168.1.1", "198.18.0.0"},
+		{"RFC1918 10/8", "10.1.2.3", "198.18.0.2"},
+		{"RFC1918 172.16/12", "172.16.5.5", "198.18.0.3"},
+		{"CGNAT", "100.64.0.5", "198.18.0.4"},
+		{"IPv4 link-local", "169.254.1.1", "198.18.0.5"},
+		{"Public IPv4 uses public pool", "1.2.3.4", "198.51.100.0"},
+		{"IPv6 link-local", "fe80::1", "2001:db8:1::"},
+		{"IPv6 ULA", "fd12:3456:789a::1", "2001:db8:1::1"},
+		{"Public IPv6 uses public pool", "2607:f8b0:4005:805::200e", "2001:db8:ffff::"},
+		{"Loopback IPv4", "127.0.0.1", "127.0.0.1"},
+		{"Loopback IPv6", "::1", "::1"},
+		{"Unspecified", "0.0.0.0", "0.0.0.0"},
+		{"Multicast", "224.0.0.251", "224.0.0.251"},
+		{"Well known resolver", "8.8.8.8", "8.8.8.8"},
+		{"Well known split marker", "128.0.0.0", "128.0.0.0"},
+		{"In internal pool range", "198.18.0.3", "198.18.0.3"},
+		{"In public pool range", "198.51.100.0", "198.51.100.0"},
+		{"4-in-6 repeated RFC1918", "::ffff:192.168.1.1", "198.18.0.0"},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			result := anonymizer.AnonymizeIP(netip.MustParseAddr(tc.ip))
+			assert.Equal(t, tc.expect, result.String(), "strict level should replace internal ranges from the internal pools")
+		})
+	}
+}
+
+func TestAnonymizeString_StrictInternalIPs(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+	anonymizer.SetLevel(anonymize.LevelStrict)
+
+	input := "route 10.20.30.0/24 via 192.168.1.1 dev eth0 src 100.64.0.7"
+	firstPass := anonymizer.AnonymizeString(input)
+	secondPass := anonymizer.AnonymizeString(firstPass)
+
+	assert.NotContains(t, firstPass, "10.20.30.0", "private network address should be anonymized")
+	assert.NotContains(t, firstPass, "192.168.1.1", "private gateway should be anonymized")
+	assert.NotContains(t, firstPass, "100.64.0.7", "CGNAT address should be anonymized")
+	assert.Contains(t, firstPass, "/24", "prefix length should be preserved")
+	assert.Equal(t, firstPass, secondPass, "second pass should not further anonymize the string")
+}
+
+func TestAnonymizeMAC(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+
+	first := anonymizer.AnonymizeMAC("aa:bb:cc:dd:ee:0f")
+	assert.Equal(t, "02:00:00:00:00:01", first, "first MAC should get the first placeholder")
+	assert.Equal(t, first, anonymizer.AnonymizeMAC("aa:bb:cc:dd:ee:0f"), "repeated MAC should map to the same placeholder")
+	assert.Equal(t, first, anonymizer.AnonymizeMAC("AA:BB:CC:DD:EE:0F"), "case should not affect the mapping")
+	assert.Equal(t, "02-00-00-00-00-01", anonymizer.AnonymizeMAC("AA-BB-CC-DD-EE-0F"), "dash form should keep its separator but share the mapping")
+
+	second := anonymizer.AnonymizeMAC("10:22:33:44:55:66")
+	assert.Equal(t, "02:00:00:00:00:02", second, "second distinct MAC should get the next placeholder")
+
+	tests := []struct {
+		name string
+		mac  string
+	}{
+		{"Broadcast", "ff:ff:ff:ff:ff:ff"},
+		{"IPv4 multicast", "01:00:5e:00:00:fb"},
+		{"IPv6 multicast", "33:33:00:00:00:01"},
+		{"All zero", "00:00:00:00:00:00"},
+		{"Assigned placeholder", "02:00:00:00:00:01"},
+		{"Invalid", "not-a-mac"},
+	}
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			assert.Equal(t, tc.mac, anonymizer.AnonymizeMAC(tc.mac), "should be preserved")
+		})
+	}
+}
+
+func TestAnonymizeString_MACAddresses(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+
+	tests := []struct {
+		name   string
+		input  string
+		expect string
+	}{
+		{
+			name:   "nftables ether rule",
+			input:  "ether saddr aa:bb:cc:dd:ee:ff drop",
+			expect: "ether saddr 02:00:00:00:00:01 drop",
+		},
+		{
+			name:   "Windows dash form",
+			input:  "Physical Address : AA-BB-CC-DD-EE-FF",
+			expect: "Physical Address : 02-00-00-00-00-01",
+		},
+		{
+			name:   "IPv6 address tail is not treated as MAC",
+			input:  "addr fe80:0:11:22:33:44:55:66 scope link",
+			expect: "addr fe80:0:11:22:33:44:55:66 scope link",
+		},
+		{
+			name:   "broadcast MAC preserved",
+			input:  "dst ff:ff:ff:ff:ff:ff type ARP",
+			expect: "dst ff:ff:ff:ff:ff:ff type ARP",
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			result := anonymizer.AnonymizeString(tc.input)
+			assert.Equal(t, tc.expect, result, "MAC addresses should be anonymized at every level")
+			assert.Equal(t, result, anonymizer.AnonymizeString(result), "second pass should not change the result")
+		})
+	}
+}
+
+func TestAnonymizeWGKey(t *testing.T) {
+	key := base64.StdEncoding.EncodeToString(bytes.Repeat([]byte{0x42}, 32))
+
+	t.Run("default level preserves keys", func(t *testing.T) {
+		anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+		assert.Equal(t, key, anonymizer.AnonymizeWGKey(key), "default level should not touch WireGuard keys")
+	})
+
+	t.Run("strict level replaces keys", func(t *testing.T) {
+		anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+		anonymizer.SetLevel(anonymize.LevelStrict)
+
+		anon := anonymizer.AnonymizeWGKey(key)
+		assert.NotEqual(t, key, anon, "strict level should replace the key")
+		assert.Regexp(t, `^[A-Za-z0-9+/]{43}=$`, anon, "placeholder should keep the WireGuard key shape")
+		assert.Equal(t, anon, anonymizer.AnonymizeWGKey(key), "repeated key should map to the same placeholder")
+		assert.Equal(t, anon, anonymizer.AnonymizeWGKey(anon), "an assigned placeholder should pass through unchanged")
+
+		assert.Equal(t, "not-a-key", anonymizer.AnonymizeWGKey("not-a-key"), "non-key values should be preserved")
+	})
+}
+
+func TestAnonymizeString_WGKeys(t *testing.T) {
+	key := base64.StdEncoding.EncodeToString(bytes.Repeat([]byte{0x42}, 32))
+	input := "peer " + key + " handshake completed"
+
+	t.Run("default level preserves keys", func(t *testing.T) {
+		anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+		assert.Equal(t, input, anonymizer.AnonymizeString(input), "default level should not touch WireGuard keys in strings")
+	})
+
+	t.Run("strict level replaces keys", func(t *testing.T) {
+		anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+		anonymizer.SetLevel(anonymize.LevelStrict)
+
+		firstPass := anonymizer.AnonymizeString(input)
+		assert.NotContains(t, firstPass, key, "the key should not survive strict anonymization")
+		assert.Equal(t, anonymizer.AnonymizeWGKey(key), extractKey(t, firstPass), "string replacement should be consistent with AnonymizeWGKey")
+		assert.Equal(t, firstPass, anonymizer.AnonymizeString(firstPass), "second pass should not change the result")
+	})
+}
+
+func extractKey(t *testing.T, logLine string) string {
+	t.Helper()
+	fields := strings.Fields(logLine)
+	require.Len(t, fields, 4, "log line should keep its structure")
+	return fields[1]
+}
+
+func TestAnonymizeDomain_StrictLevel(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+	anonymizer.SetLevel(anonymize.LevelStrict)
+
+	t.Run("netbird peer name", func(t *testing.T) {
+		result := anonymizer.AnonymizeDomain("my-laptop.netbird.cloud")
+		assert.Regexp(t, `^peer-\d+\.netbird\.cloud$`, result, "peer name should be anonymized, suffix kept")
+		assert.NotContains(t, result, "my-laptop", "the peer name should not survive")
+		assert.Equal(t, result, anonymizer.AnonymizeDomain("my-laptop.netbird.cloud"), "repeated domain should map consistently")
+		assert.Equal(t, result, anonymizer.AnonymizeDomain(result), "an anonymized domain should pass through unchanged")
+	})
+
+	t.Run("bare netbird domain", func(t *testing.T) {
+		assert.Equal(t, "netbird.cloud", anonymizer.AnonymizeDomain("netbird.cloud"), "the bare protected suffix should be preserved")
+	})
+
+	t.Run("netbird infrastructure preserved", func(t *testing.T) {
+		assert.Equal(t, "api.netbird.io", anonymizer.AnonymizeDomain("api.netbird.io"),
+			"netbird.io hosts infrastructure, not peer names, and should stay readable")
+	})
+
+	t.Run("leading labels of other domains", func(t *testing.T) {
+		result := anonymizer.AnonymizeDomain("host1.corp.example.com")
+		assert.Regexp(t, `^host-\d+\.host-\d+\.anon-[a-zA-Z0-9]+\.domain$`, result, "every label should be anonymized")
+		for _, label := range []string{"host1", "corp", "example"} {
+			assert.NotContains(t, result, label, "no original label should survive")
+		}
+		assert.Equal(t, result, anonymizer.AnonymizeDomain("host1.corp.example.com"), "repeated domain should map consistently")
+	})
+
+	t.Run("same label maps consistently across domains", func(t *testing.T) {
+		first := anonymizer.AnonymizeDomain("shared.one.com")
+		second := anonymizer.AnonymizeDomain("shared.two.com")
+		assert.Equal(t, strings.Split(first, ".")[0], strings.Split(second, ".")[0], "the shared host label should get one placeholder")
+	})
+
+	t.Run("wildcard label preserved", func(t *testing.T) {
+		result := anonymizer.AnonymizeDomain("*.example.com")
+		assert.Regexp(t, `^\*\.anon-[a-zA-Z0-9]+\.domain$`, result, "the wildcard label should stay a wildcard")
+	})
+}
+
+func TestAnonymizeDomain_DefaultLevelKeepsPeerNames(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+
+	assert.Equal(t, "my-laptop.netbird.cloud", anonymizer.AnonymizeDomain("my-laptop.netbird.cloud"),
+		"default level should preserve netbird FQDNs including the peer name")
+	assert.Regexp(t, `^sub\.anon-[a-zA-Z0-9]+\.domain$`, anonymizer.AnonymizeDomain("sub.example.com"),
+		"default level should keep subdomain labels")
+}
+
+func TestAnonymizeString_StrictPeerNames(t *testing.T) {
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+	anonymizer.SetLevel(anonymize.LevelStrict)
+
+	// Seed like the bundle generator does from the status: base first, then
+	// the full FQDN, so replacement must prefer the longer mapping.
+	anonBase := anonymizer.AnonymizeDomain("example.com")
+	anonPeer := anonymizer.AnonymizeDomain("peer1.netbird.cloud")
+	anonHost := anonymizer.AnonymizeDomain("host1.example.com")
+
+	logLine := "connected to peer1.netbird.cloud via host1.example.com endpoint"
+	firstPass := anonymizer.AnonymizeString(logLine)
+	assert.NotContains(t, firstPass, "peer1", "the peer name should not survive in logs")
+	assert.NotContains(t, firstPass, "host1", "the host label should not survive in logs")
+	assert.Contains(t, firstPass, anonPeer, "the seeded peer mapping should be applied")
+	assert.Contains(t, firstPass, anonHost, "the seeded host mapping should be applied, not just the base mapping")
+	assert.NotContains(t, firstPass, "host1."+anonBase, "the base mapping must not preempt the longer FQDN mapping")
+	assert.Equal(t, firstPass, anonymizer.AnonymizeString(firstPass), "second pass should not change the result")
+}
+
 func TestAnonymizeDNSLogLine(t *testing.T) {
 	anonymizer := anonymize.NewAnonymizer(netip.Addr{}, netip.Addr{})
 	tests := []struct {

client/cmd/debug.go

@@ -27,8 +27,8 @@ import (
 const errCloseConnection = "Failed to close connection: %v"
 
 var (
-	logFileCount        uint32
-	systemInfoFlag      bool
+	logFileCount             uint32
+	systemInfoFlag           bool
 	uploadBundleFlag         bool
 	uploadBundleURLFlag      string
 	uploadBundleInsecureFlag bool
@@ -156,6 +156,11 @@ func debugConfigDump(cmd *cobra.Command, _ []string) error {
 // request. Returns an error if the RPC fails or if the daemon reports
 // an upload failure reason.
 func debugBundle(cmd *cobra.Command, _ []string) error {
+	anonymizeEnabled, anonymizeLevel, err := effectiveAnonymize()
+	if err != nil {
+		return err
+	}
+
 	conn, err := getClient(cmd)
 	if err != nil {
 		return err
@@ -168,10 +173,11 @@ func debugBundle(cmd *cobra.Command, _ []string) error {
 
 	client := proto.NewDaemonServiceClient(conn)
 	request := &proto.DebugBundleRequest{
-		Anonymize:    anonymizeFlag,
-		SystemInfo:   systemInfoFlag,
-		LogFileCount: logFileCount,
-		CliVersion:   version.NetbirdVersion(),
+		Anonymize:      anonymizeEnabled,
+		AnonymizeLevel: anonymizeLevel.String(),
+		SystemInfo:     systemInfoFlag,
+		LogFileCount:   logFileCount,
+		CliVersion:     version.NetbirdVersion(),
 	}
 	if uploadBundleFlag {
 		request.UploadURL = uploadBundleURLFlag
@@ -229,6 +235,11 @@ func runForDuration(cmd *cobra.Command, args []string) error {
 		return fmt.Errorf("invalid duration format: %v", err)
 	}
 
+	anonymizeEnabled, anonymizeLevel, err := effectiveAnonymize()
+	if err != nil {
+		return err
+	}
+
 	conn, err := getClient(cmd)
 	if err != nil {
 		return err
@@ -368,10 +379,11 @@ func runForDuration(cmd *cobra.Command, args []string) error {
 	cmd.Println("Creating debug bundle...")
 
 	request := &proto.DebugBundleRequest{
-		Anonymize:    anonymizeFlag,
-		SystemInfo:   systemInfoFlag,
-		LogFileCount: logFileCount,
-		CliVersion:   version.NetbirdVersion(),
+		Anonymize:      anonymizeEnabled,
+		AnonymizeLevel: anonymizeLevel.String(),
+		SystemInfo:     systemInfoFlag,
+		LogFileCount:   logFileCount,
+		CliVersion:     version.NetbirdVersion(),
 	}
 	if uploadBundleFlag {
 		request.UploadURL = uploadBundleURLFlag

client/cmd/login.go

@@ -5,7 +5,6 @@ import (
 	"fmt"
 	"os"
 	"os/user"
-	"runtime"
 	"strings"
 
 	log "github.com/sirupsen/logrus"
@@ -121,7 +120,7 @@ func doDaemonLogin(ctx context.Context, cmd *cobra.Command, providedSetupKey str
 	loginRequest := proto.LoginRequest{
 		SetupKey:            providedSetupKey,
 		ManagementUrl:       managementURL,
-		IsUnixDesktopClient: isUnixRunningDesktop(),
+		IsUnixDesktopClient: util.HasGraphicalSession(),
 		Hostname:            hostName,
 		DnsLabels:           dnsLabelsReq,
 		ProfileName:         &handle,
@@ -189,7 +188,8 @@ func doExtendSession(ctx context.Context, cmd *cobra.Command) error {
 
 	client := proto.NewDaemonServiceClient(conn)
 
-	req := &proto.RequestExtendAuthSessionRequest{}
+	// the CLI runs in the user's session, the daemon does not: tell it what we can see
+	req := &proto.RequestExtendAuthSessionRequest{HasGraphicalSession: util.HasGraphicalSession()}
 	// Pre-fill the IdP login hint from the active profile so the user
 	// doesn't have to retype their email. Best-effort: we still proceed
 	// without a hint if the lookup fails.
@@ -408,8 +408,13 @@ func foregroundGetTokenInfo(ctx context.Context, cmd *cobra.Command, config *pro
 		hint = profileState.Email
 	}
 
-	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, isUnixRunningDesktop(), false, hint)
+	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, util.HasGraphicalSession(), false, hint)
 	if err != nil {
+		// enrolling a device is the one flow a setup key can replace
+		if auth.IsSSOUnavailable(err) {
+			return nil, fmt.Errorf("%w. Set this device up with a setup key instead: "+
+				"https://docs.netbird.io/how-to/register-machines-using-setup-keys", err)
+		}
 		return nil, err
 	}
 
@@ -458,14 +463,6 @@ func openURL(cmd *cobra.Command, verificationURIComplete, userCode string, noBro
 	}
 }
 
-// isUnixRunningDesktop checks if a Linux OS is running desktop environment
-func isUnixRunningDesktop() bool {
-	if runtime.GOOS != "linux" && runtime.GOOS != "freebsd" {
-		return false
-	}
-	return os.Getenv("DESKTOP_SESSION") != "" || os.Getenv("XDG_CURRENT_DESKTOP") != ""
-}
-
 func setEnvAndFlags(cmd *cobra.Command) error {
 	SetFlagsFromEnvVars(rootCmd)
 

client/cmd/root.go

@@ -21,6 +21,7 @@ import (
 	"github.com/spf13/pflag"
 	"google.golang.org/grpc"
 
+	"github.com/netbirdio/netbird/client/anonymize"
 	daddr "github.com/netbirdio/netbird/client/internal/daemonaddr"
 	"github.com/netbirdio/netbird/client/internal/profilemanager"
 )
@@ -69,6 +70,7 @@ var (
 	autoConnectDisabled     bool
 	extraIFaceBlackList     []string
 	anonymizeFlag           bool
+	anonymizeLevelFlag      string
 	dnsRouteInterval        time.Duration
 	// lazyConnEnabled is the parse target for the deprecated --enable-lazy-connection
 	// flag. The flag is inert; the value is no longer read (use NB_LAZY_CONN instead).
@@ -156,7 +158,8 @@ func init() {
 	rootCmd.MarkFlagsMutuallyExclusive("setup-key", "setup-key-file")
 	rootCmd.PersistentFlags().StringVar(&preSharedKey, preSharedKeyFlag, "", "Sets WireGuard PreSharedKey property. If set, then only peers that have the same key can communicate.")
 	rootCmd.PersistentFlags().StringVarP(&hostName, "hostname", "n", "", "Sets a custom hostname for the device")
-	rootCmd.PersistentFlags().BoolVarP(&anonymizeFlag, "anonymize", "A", false, "anonymize IP addresses and non-netbird.io domains in logs and status output")
+	rootCmd.PersistentFlags().BoolVarP(&anonymizeFlag, "anonymize", "A", false, "anonymize public IP addresses, MAC addresses, and non-netbird.io domains in logs and status output; private, CGNAT, and link-local IP ranges are kept (see --anonymize-level strict)")
+	rootCmd.PersistentFlags().StringVar(&anonymizeLevelFlag, "anonymize-level", "", "anonymization level: \"default\" or \"strict\"; strict also anonymizes private, CGNAT, and link-local IP ranges, peer names, and WireGuard public keys. Setting this flag implies --anonymize")
 	rootCmd.PersistentFlags().StringVarP(&configPath, "config", "c", profilemanager.DefaultConfigPath, "Overrides the default profile file location")
 
 	rootCmd.AddCommand(upCmd)
@@ -293,6 +296,19 @@ var CLIBackOffSettings = &backoff.ExponentialBackOff{
 	Clock:               backoff.SystemClock,
 }
 
+// effectiveAnonymize resolves the --anonymize and --anonymize-level flags:
+// setting a level implies anonymization, and an invalid level is rejected.
+func effectiveAnonymize() (bool, anonymize.Level, error) {
+	if anonymizeLevelFlag == "" {
+		return anonymizeFlag, anonymize.LevelDefault, nil
+	}
+	level := anonymize.ParseLevel(anonymizeLevelFlag)
+	if !strings.EqualFold(anonymizeLevelFlag, level.String()) {
+		return false, anonymize.LevelDefault, fmt.Errorf("invalid anonymize level %q: use %q or %q", anonymizeLevelFlag, anonymize.LevelDefault.String(), anonymize.LevelStrict.String())
+	}
+	return true, level, nil
+}
+
 func getSetupKey() (string, error) {
 	if setupKeyPath != "" && setupKey == "" {
 		return getSetupKeyFromFile(setupKeyPath)

client/cmd/status.go

@@ -121,8 +121,14 @@ func statusFunc(cmd *cobra.Command, args []string) error {
 		sessionExpiresAt = ts.AsTime().UTC()
 	}
 
+	anonymizeEnabled, anonymizeLevel, err := effectiveAnonymize()
+	if err != nil {
+		return err
+	}
+
 	var outputInformationHolder = nbstatus.ConvertToStatusOutputOverview(resp.GetFullStatus(), nbstatus.ConvertOptions{
-		Anonymize:            anonymizeFlag,
+		Anonymize:            anonymizeEnabled,
+		AnonymizeLevel:       anonymizeLevel,
 		DaemonVersion:        resp.GetDaemonVersion(),
 		DaemonStatus:         nbstatus.ParseDaemonStatus(status),
 		StatusFilter:         statusFilter,

client/cmd/up.go

@@ -21,8 +21,8 @@ import (
 	"github.com/netbirdio/netbird/client/internal"
 	"github.com/netbirdio/netbird/client/internal/peer"
 	"github.com/netbirdio/netbird/client/internal/profilemanager"
-	"github.com/netbirdio/netbird/client/proto"
 	nbnet "github.com/netbirdio/netbird/client/net"
+	"github.com/netbirdio/netbird/client/proto"
 	"github.com/netbirdio/netbird/client/server"
 	"github.com/netbirdio/netbird/client/system"
 	"github.com/netbirdio/netbird/shared/management/domain"
@@ -626,7 +626,7 @@ func setupLoginRequest(providedSetupKey string, customDNSAddressConverted []byte
 		NatExternalIPs:      natExternalIPs,
 		CleanNATExternalIPs: natExternalIPs != nil && len(natExternalIPs) == 0,
 		CustomDNSAddress:    customDNSAddressConverted,
-		IsUnixDesktopClient: isUnixRunningDesktop(),
+		IsUnixDesktopClient: util.HasGraphicalSession(),
 		Hostname:            hostName,
 		ExtraIFaceBlacklist: extraIFaceBlackList,
 		DnsLabels:           dnsLabels,

client/firewall/firewalld/firewalld.go

@@ -2,8 +2,8 @@
 // its wg interface into firewalld's "trusted" zone. This is required because
 // firewalld's nftables chains are created with NFT_CHAIN_OWNER on recent
 // versions, which returns EPERM to any other process that tries to insert
-// rules into them. The workaround mirrors what Tailscale does: let firewalld
-// itself add the accept rules to its own chains by trusting the interface.
+// rules into them. Trusting the interface makes firewalld itself add the
+// accept rules to its own chains instead.
 package firewalld
 
 // TrustedZone is the firewalld zone name used for interfaces whose traffic

client/firewall/iptables/acl_linux.go

@@ -42,6 +42,7 @@ type aclManager struct {
 	optionalEntries map[string][]entry
 	ipsetStore      *ipsetStore
 	v6              bool
+	ipsetSupported  bool
 
 	stateManager *statemanager.Manager
 }
@@ -60,6 +61,8 @@ func newAclManager(iptablesClient *iptables.IPTables, wgIface iFaceMapper) (*acl
 func (m *aclManager) init(stateManager *statemanager.Manager) error {
 	m.stateManager = stateManager
 
+	m.ipsetSupported = m.probeIPSetSupport()
+
 	m.seedInitialEntries()
 	m.seedInitialOptionalEntries()
 
@@ -91,6 +94,12 @@ func (m *aclManager) AddPeerFiltering(
 	if m.v6 && ipsetName != "" {
 		ipsetName += "-v6"
 	}
+	// When the kernel lacks the required ipset hash module, fall back to
+	// per-IP iptables rules (pre-0.68 behavior) so ACLs keep working instead
+	// of silently leaving the chain empty.
+	if ipsetName != "" && !m.ipsetSupported {
+		ipsetName = ""
+	}
 	proto := protoForFamily(protocol, m.v6)
 	specs := filterRuleSpecs(ip, proto, sPort, dPort, action, ipsetName)
 
@@ -498,6 +507,40 @@ func transformIPsetName(ipsetName string, sPort, dPort *firewall.Port, action fi
 	}
 }
 
+// probeIPSetSupport checks whether the kernel can create the ipset type used for
+// ACL rules. On kernels lacking the required ipset hash module, ipset creation
+// fails (e.g. "invalid argument"), which would otherwise leave the ACL chain
+// empty and silently drop all policy-permitted inbound traffic. When unsupported,
+// the manager falls back to per-IP iptables rules.
+func (m *aclManager) probeIPSetSupport() bool {
+	// Use a unique name so concurrent processes don't collide and we only ever
+	// destroy the set we created ourselves. ipset names are limited to 31 chars,
+	// so use a short random suffix.
+	probeName := "nb-probe-" + uuid.New().String()[:8]
+
+	opts := ipset.CreateOptions{
+		Replace: true,
+	}
+	if m.v6 {
+		opts.Family = ipset.FamilyIPV6
+	}
+
+	if err := ipset.Create(probeName, ipset.TypeHashNet, opts); err != nil {
+		log.Warnf("ipset is not available (failed to create probe set: %v); "+
+			"falling back to per-IP iptables ACL rules. Ensure the kernel provides "+
+			"the ipset hash:net module (ip_set_hash_net) for better performance with large rule sets", err)
+		return false
+	}
+
+	defer func() {
+		if err := ipset.Destroy(probeName); err != nil {
+			log.Debugf("destroy ipset probe set %q: %v", probeName, err)
+		}
+	}()
+
+	return true
+}
+
 func (m *aclManager) createIPSet(name string) error {
 	opts := ipset.CreateOptions{
 		Replace: true,

client/firewall/iptables/dnat_refcount_linux_test.go

@@ -0,0 +1,240 @@
+//go:build privileged
+
+package iptables
+
+import (
+	"net/netip"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	fw "github.com/netbirdio/netbird/client/firewall/manager"
+	"github.com/netbirdio/netbird/client/iface"
+	"github.com/netbirdio/netbird/client/iface/wgaddr"
+)
+
+func iptRefcountIfaceV4() *iFaceMock {
+	return &iFaceMock{
+		NameFunc: func() string { return "wt-refcount" },
+		AddressFunc: func() wgaddr.Address {
+			return wgaddr.Address{
+				IP:      netip.MustParseAddr("10.20.0.1"),
+				Network: netip.MustParsePrefix("10.20.0.0/24"),
+			}
+		},
+	}
+}
+
+func iptRefcountIfaceDual() *iFaceMock {
+	return &iFaceMock{
+		NameFunc: func() string { return "wt-refcount" },
+		AddressFunc: func() wgaddr.Address {
+			return wgaddr.Address{
+				IP:      netip.MustParseAddr("10.20.0.1"),
+				Network: netip.MustParsePrefix("10.20.0.0/24"),
+				IPv6:    netip.MustParseAddr("fd00::1"),
+				IPv6Net: netip.MustParsePrefix("fd00::/64"),
+			}
+		},
+	}
+}
+
+func newIptRefcountManager(t *testing.T, dual bool) *Manager {
+	t.Helper()
+	var ifMock *iFaceMock
+	if dual {
+		ifMock = iptRefcountIfaceDual()
+	} else {
+		ifMock = iptRefcountIfaceV4()
+	}
+	m, err := Create(ifMock, iface.DefaultMTU)
+	require.NoError(t, err, "create manager")
+	require.NoError(t, m.Init(nil), "init manager")
+	t.Cleanup(func() {
+		require.NoError(t, m.Close(nil), "close manager")
+	})
+	return m
+}
+
+func iptDnatV4(port uint16) fw.ForwardRule {
+	return fw.ForwardRule{
+		Protocol:          fw.ProtocolTCP,
+		DestinationPort:   fw.Port{Values: []uint16{port}},
+		TranslatedAddress: netip.MustParseAddr("10.20.0.2"),
+		TranslatedPort:    fw.Port{Values: []uint16{80}},
+	}
+}
+
+func iptDnatV6(port uint16) fw.ForwardRule {
+	return fw.ForwardRule{
+		Protocol:          fw.ProtocolTCP,
+		DestinationPort:   fw.Port{Values: []uint16{port}},
+		TranslatedAddress: netip.MustParseAddr("fd00::2"),
+		TranslatedPort:    fw.Port{Values: []uint16{80}},
+	}
+}
+
+// TestIptablesRouting_RepeatedEnableSingleReference verifies that EnableRouting
+// (called on every network-map update) holds at most one reference per family
+// and a single DisableRouting drops both back to zero.
+func TestIptablesRouting_RepeatedEnableSingleReference(t *testing.T) {
+	m := newIptRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	require.NoError(t, m.EnableRouting(), "first enable")
+	require.NoError(t, m.EnableRouting(), "second enable")
+	require.NoError(t, m.EnableRouting(), "third enable")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 1, v4, "repeated enable holds a single v4 reference")
+	assert.Equal(t, 1, v6, "repeated enable holds a single v6 reference")
+
+	require.NoError(t, m.DisableRouting(), "disable")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "single disable releases the v4 reference")
+	assert.Equal(t, 0, v6, "single disable releases the v6 reference")
+}
+
+// TestIptablesRouting_DisableKeepsDNATReference verifies that an unpaired
+// DisableRouting does not release references held by active DNAT rules.
+func TestIptablesRouting_DisableKeepsDNATReference(t *testing.T) {
+	m := newIptRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(iptDnatV6(9095))
+	require.NoError(t, err, "add v6 dnat")
+
+	require.NoError(t, m.DisableRouting(), "unpaired disable")
+	_, v6 := state.Counts()
+	assert.Equal(t, 1, v6, "DNAT-held reference survives unpaired DisableRouting")
+
+	require.NoError(t, m.DeleteDNATRule(r1), "delete v6 dnat")
+	_, v6 = state.Counts()
+	assert.Equal(t, 0, v6, "delete releases the DNAT reference")
+}
+
+// TestIptablesDNAT_RefcountBalancedV4 covers a Balanced Add/Delete pair on v4.
+func TestIptablesDNAT_RefcountBalancedV4(t *testing.T) {
+	m := newIptRefcountManager(t, false)
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(iptDnatV4(7081))
+	require.NoError(t, err, "add v4 dnat 1")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 1, v4, "v4 refcount after first add")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+
+	r2, err := m.AddDNATRule(iptDnatV4(7082))
+	require.NoError(t, err, "add v4 dnat 2")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 2, v4, "v4 refcount after second add")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+
+	require.NoError(t, m.DeleteDNATRule(r1))
+	v4, v6 = state.Counts()
+	assert.Equal(t, 1, v4, "v4 refcount after first delete")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+
+	require.NoError(t, m.DeleteDNATRule(r2))
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount after second delete")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+}
+
+// TestIptablesDNAT_RefcountBalancedV6 checks the v6 path increments v6 only and
+// decrements back to zero.
+func TestIptablesDNAT_RefcountBalancedV6(t *testing.T) {
+	m := newIptRefcountManager(t, true)
+	require.NotNil(t, m.router6, "v6 router")
+	require.Same(t, m.router.ipFwdState, m.router6.ipFwdState, "shared state")
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(iptDnatV6(9081))
+	require.NoError(t, err, "add v6 dnat 1")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 1, v6, "v6 refcount after first add")
+
+	r2, err := m.AddDNATRule(iptDnatV6(9082))
+	require.NoError(t, err, "add v6 dnat 2")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount unchanged")
+	assert.Equal(t, 2, v6, "v6 refcount after second add")
+
+	require.NoError(t, m.DeleteDNATRule(r1))
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount unchanged")
+	assert.Equal(t, 1, v6, "v6 refcount after first delete")
+
+	require.NoError(t, m.DeleteDNATRule(r2))
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 0, v6, "v6 refcount after second delete")
+}
+
+// TestIptablesDNAT_DuplicateAddNoLeak verifies the duplicate-rule path returns
+// without bumping the refcount.
+func TestIptablesDNAT_DuplicateAddNoLeak(t *testing.T) {
+	m := newIptRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	rule := iptDnatV4(7083)
+	r1, err := m.AddDNATRule(rule)
+	require.NoError(t, err)
+	v4, _ := state.Counts()
+	assert.Equal(t, 1, v4)
+
+	_, err = m.AddDNATRule(rule)
+	require.NoError(t, err, "duplicate add")
+	v4, _ = state.Counts()
+	assert.Equal(t, 1, v4, "duplicate add must not increment")
+
+	require.NoError(t, m.DeleteDNATRule(r1))
+	v4, _ = state.Counts()
+	assert.Equal(t, 0, v4, "single delete must drop to zero")
+}
+
+// TestIptablesDNAT_DeleteMissingNoUnderflow verifies Delete on an unknown rule
+// neither errors nor releases the refcount.
+func TestIptablesDNAT_DeleteMissingNoUnderflow(t *testing.T) {
+	m := newIptRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	phantom := iptDnatV4(7099)
+	require.NoError(t, m.DeleteDNATRule(&phantom), "delete missing v4")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 0, v6)
+
+	phantom6 := iptDnatV6(9099)
+	require.NoError(t, m.DeleteDNATRule(&phantom6), "delete missing v6")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 0, v6)
+
+	r1, err := m.AddDNATRule(iptDnatV4(7100))
+	require.NoError(t, err)
+	v4, _ = state.Counts()
+	assert.Equal(t, 1, v4, "real add still increments after phantom delete")
+	require.NoError(t, m.DeleteDNATRule(r1))
+}
+
+// TestIptablesDNAT_DoubleDeleteNoUnderflow verifies a second Delete on the same
+// rule is a no-op.
+func TestIptablesDNAT_DoubleDeleteNoUnderflow(t *testing.T) {
+	m := newIptRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(iptDnatV6(9083))
+	require.NoError(t, err)
+	_, v6 := state.Counts()
+	assert.Equal(t, 1, v6)
+
+	require.NoError(t, m.DeleteDNATRule(r1), "first delete")
+	_, v6 = state.Counts()
+	assert.Equal(t, 0, v6)
+
+	require.NoError(t, m.DeleteDNATRule(r1), "second delete must be no-op")
+	_, v6 = state.Counts()
+	assert.Equal(t, 0, v6, "double delete must not underflow")
+}

client/firewall/iptables/manager_linux.go

@@ -89,7 +89,7 @@ func (m *Manager) createIPv6Components(wgIface iFaceMapper, mtu uint16) error {
 	}
 
 	// Share the same IP forwarding state with the v4 router, since
-	// EnableIPForwarding controls both v4 and v6 sysctls.
+	// Forwarding refcounter is per-family but shared between v4 and v6 routers.
 	m.router6.ipFwdState = m.router.ipFwdState
 
 	m.aclMgr6, err = newAclManager(ip6Client, wgIface)
@@ -402,17 +402,12 @@ func (m *Manager) SetLogLevel(log.Level) {
 }
 
 func (m *Manager) EnableRouting() error {
-	if err := m.router.ipFwdState.RequestForwarding(); err != nil {
-		return fmt.Errorf("enable IP forwarding: %w", err)
-	}
-	return nil
+	// v6 only when the overlay actually has v6.
+	return m.router.ipFwdState.RequestRouting(m.router6 != nil)
 }
 
 func (m *Manager) DisableRouting() error {
-	if err := m.router.ipFwdState.ReleaseForwarding(); err != nil {
-		return fmt.Errorf("disable IP forwarding: %w", err)
-	}
-	return nil
+	return m.router.ipFwdState.ReleaseRouting()
 }
 
 // AddDNATRule adds a DNAT rule

client/firewall/iptables/manager_linux_test.go

@@ -291,3 +291,40 @@ func TestIptablesCreatePerformance(t *testing.T) {
 		})
 	}
 }
+
+// TestIptablesACLIPSetFallback verifies that when the kernel lacks ipset support,
+// the ACL manager falls back to per-IP iptables rules (-s <ip>) instead of
+// silently leaving the chain empty. See discussion #6125.
+func TestIptablesACLIPSetFallback(t *testing.T) {
+	ipv4Client, err := iptables.NewWithProtocol(iptables.ProtocolIPv4)
+	require.NoError(t, err)
+
+	// Use Create()/Init() so the router-owned chains (chainRTFWDIN/OUT) are
+	// created before the ACL manager's createDefaultChains() references them.
+	manager, err := Create(ifaceMock, iface.DefaultMTU)
+	require.NoError(t, err)
+	require.NoError(t, manager.Init(nil))
+
+	aclMgr := manager.aclMgr
+	// Simulate a kernel without the ipset hash module.
+	aclMgr.ipsetSupported = false
+
+	defer func() {
+		require.NoError(t, manager.Close(nil))
+	}()
+
+	ip := netip.MustParseAddr("10.20.0.42")
+	port := &fw.Port{Values: []uint16{22}}
+
+	rules, err := aclMgr.AddPeerFiltering(nil, ip.AsSlice(), "tcp", nil, port, fw.ActionAccept, "nb0000001")
+	require.NoError(t, err, "AddPeerFiltering should succeed via fallback")
+	require.NotEmpty(t, rules)
+
+	rule := rules[0].(*Rule)
+	require.Empty(t, rule.ipsetName, "fallback rule must not reference an ipset")
+	require.Contains(t, strings.Join(rule.specs, " "), "-s 10.20.0.42", "fallback rule must match by source IP")
+	require.NotContains(t, strings.Join(rule.specs, " "), "--match-set", "fallback rule must not use ipset matching")
+
+	// The rule must actually be present in the ACL chain (not silently dropped).
+	checkRuleSpecs(t, ipv4Client, rule.chain, true, rule.specs...)
+}

client/firewall/iptables/router_linux.go

@@ -102,7 +102,7 @@ func newRouter(iptablesClient *iptables.IPTables, wgIface iFaceMapper, mtu uint1
 		wgIface:        wgIface,
 		mtu:            mtu,
 		v6:             iptablesClient.Proto() == iptables.ProtocolIPv6,
-		ipFwdState:     ipfwdstate.NewIPForwardingState(),
+		ipFwdState:     ipfwdstate.NewIPForwardingState(wgIface.Name()),
 	}
 
 	r.ipsetCounter = refcounter.New(
@@ -770,10 +770,6 @@ func (r *router) updateState() {
 }
 
 func (r *router) AddDNATRule(rule firewall.ForwardRule) (firewall.Rule, error) {
-	if err := r.ipFwdState.RequestForwarding(); err != nil {
-		return nil, err
-	}
-
 	ruleKey := rule.ID()
 	if _, exists := r.rules[ruleKey+dnatSuffix]; exists {
 		return rule, nil
@@ -840,18 +836,34 @@ func (r *router) AddDNATRule(rule firewall.ForwardRule) (firewall.Rule, error) {
 
 	for key, ruleInfo := range rules {
 		if err := r.iptablesClient.Append(ruleInfo.table, ruleInfo.chain, ruleInfo.rule...); err != nil {
-			if rollbackErr := r.rollbackRules(rules); rollbackErr != nil {
-				log.Errorf("rollback failed: %v", rollbackErr)
-			}
+			r.cleanupFailedDNATAdd(rules)
 			return nil, fmt.Errorf("add rule %s: %w", key, err)
 		}
 		r.rules[key] = ruleInfo.rule
 	}
 
+	if err := r.ipFwdState.RequestForwarding(r.v6); err != nil {
+		r.cleanupFailedDNATAdd(rules)
+		return nil, fmt.Errorf("enable forwarding: %w", err)
+	}
+
 	r.updateState()
 	return rule, nil
 }
 
+// cleanupFailedDNATAdd removes the bookkeeping written by a partially applied
+// AddDNATRule before rolling back the kernel rules, so no entries remain that
+// never got a forwarding refcount. rollbackRules re-adds entries it failed to
+// remove from the kernel.
+func (r *router) cleanupFailedDNATAdd(rules map[string]ruleInfo) {
+	for key := range rules {
+		delete(r.rules, key)
+	}
+	if err := r.rollbackRules(rules); err != nil {
+		log.Errorf("rollback failed: %v", err)
+	}
+}
+
 func (r *router) rollbackRules(rules map[string]ruleInfo) error {
 	var merr *multierror.Error
 	for key, ruleInfo := range rules {
@@ -868,32 +880,47 @@ func (r *router) rollbackRules(rules map[string]ruleInfo) error {
 }
 
 func (r *router) DeleteDNATRule(rule firewall.Rule) error {
-	if err := r.ipFwdState.ReleaseForwarding(); err != nil {
-		log.Errorf("%v", err)
-	}
-
 	ruleKey := rule.ID()
 
+	_, hadDNAT := r.rules[ruleKey+dnatSuffix]
+	_, hadSNAT := r.rules[ruleKey+snatSuffix]
+	_, hadFWD := r.rules[ruleKey+fwdSuffix]
+	if !hadDNAT && !hadSNAT && !hadFWD {
+		return nil
+	}
+
 	var merr *multierror.Error
 	if dnatRule, exists := r.rules[ruleKey+dnatSuffix]; exists {
 		if err := r.iptablesClient.Delete(tableNat, chainRTRDR, dnatRule...); err != nil {
 			merr = multierror.Append(merr, fmt.Errorf("delete DNAT rule: %w", err))
+		} else {
+			delete(r.rules, ruleKey+dnatSuffix)
 		}
-		delete(r.rules, ruleKey+dnatSuffix)
 	}
 
 	if snatRule, exists := r.rules[ruleKey+snatSuffix]; exists {
 		if err := r.iptablesClient.Delete(tableNat, chainRTNAT, snatRule...); err != nil {
 			merr = multierror.Append(merr, fmt.Errorf("delete SNAT rule: %w", err))
+		} else {
+			delete(r.rules, ruleKey+snatSuffix)
 		}
-		delete(r.rules, ruleKey+snatSuffix)
 	}
 
 	if fwdRule, exists := r.rules[ruleKey+fwdSuffix]; exists {
 		if err := r.iptablesClient.Delete(tableFilter, chainRTFWDOUT, fwdRule...); err != nil {
 			merr = multierror.Append(merr, fmt.Errorf("delete forward rule: %w", err))
+		} else {
+			delete(r.rules, ruleKey+fwdSuffix)
+		}
+	}
+
+	// Release the refcount only once all rules are gone from the kernel. On
+	// partial failure the failed entries stay in r.rules so a retry can remove
+	// them and release then.
+	if merr == nil {
+		if err := r.ipFwdState.ReleaseForwarding(r.v6); err != nil {
+			log.Errorf("%v", err)
 		}
-		delete(r.rules, ruleKey+fwdSuffix)
 	}
 
 	r.updateState()

client/firewall/nftables/dnat_refcount_linux_test.go

@@ -0,0 +1,249 @@
+//go:build privileged
+
+package nftables
+
+import (
+	"net/netip"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	fw "github.com/netbirdio/netbird/client/firewall/manager"
+	"github.com/netbirdio/netbird/client/iface"
+	"github.com/netbirdio/netbird/client/iface/wgaddr"
+)
+
+func nftRefcountIfaceV4() *iFaceMock {
+	return &iFaceMock{
+		NameFunc: func() string { return "wt-refcount" },
+		AddressFunc: func() wgaddr.Address {
+			return wgaddr.Address{
+				IP:      netip.MustParseAddr("100.96.0.1"),
+				Network: netip.MustParsePrefix("100.96.0.0/16"),
+			}
+		},
+	}
+}
+
+func nftRefcountIfaceDual() *iFaceMock {
+	return &iFaceMock{
+		NameFunc: func() string { return "wt-refcount" },
+		AddressFunc: func() wgaddr.Address {
+			return wgaddr.Address{
+				IP:      netip.MustParseAddr("100.96.0.1"),
+				Network: netip.MustParsePrefix("100.96.0.0/16"),
+				IPv6:    netip.MustParseAddr("fd00::1"),
+				IPv6Net: netip.MustParsePrefix("fd00::/64"),
+			}
+		},
+	}
+}
+
+func newNftRefcountManager(t *testing.T, dual bool) *Manager {
+	t.Helper()
+	if check() != NFTABLES {
+		t.Skip("nftables not supported on this system")
+	}
+	var ifMock *iFaceMock
+	if dual {
+		ifMock = nftRefcountIfaceDual()
+	} else {
+		ifMock = nftRefcountIfaceV4()
+	}
+	m, err := Create(ifMock, iface.DefaultMTU)
+	require.NoError(t, err, "create manager")
+	require.NoError(t, m.Init(nil), "init manager")
+	t.Cleanup(func() {
+		require.NoError(t, m.Close(nil), "close manager")
+	})
+	return m
+}
+
+func dnatV4(port uint16) fw.ForwardRule {
+	return fw.ForwardRule{
+		Protocol:          fw.ProtocolTCP,
+		DestinationPort:   fw.Port{Values: []uint16{port}},
+		TranslatedAddress: netip.MustParseAddr("100.96.0.2"),
+		TranslatedPort:    fw.Port{Values: []uint16{80}},
+	}
+}
+
+func dnatV6(port uint16) fw.ForwardRule {
+	return fw.ForwardRule{
+		Protocol:          fw.ProtocolTCP,
+		DestinationPort:   fw.Port{Values: []uint16{port}},
+		TranslatedAddress: netip.MustParseAddr("fd00::2"),
+		TranslatedPort:    fw.Port{Values: []uint16{80}},
+	}
+}
+
+// TestNftablesDNAT_RefcountBalancedV4 verifies that Add/Delete pairs leave the
+// v4 refcount at zero.
+func TestNftablesDNAT_RefcountBalancedV4(t *testing.T) {
+	m := newNftRefcountManager(t, false)
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(dnatV4(8081))
+	require.NoError(t, err, "add v4 dnat 1")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 1, v4, "v4 refcount after first add")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+
+	r2, err := m.AddDNATRule(dnatV4(8082))
+	require.NoError(t, err, "add v4 dnat 2")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 2, v4, "v4 refcount after second add")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+
+	require.NoError(t, m.DeleteDNATRule(r1), "delete v4 dnat 1")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 1, v4, "v4 refcount after first delete")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+
+	require.NoError(t, m.DeleteDNATRule(r2), "delete v4 dnat 2")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount after second delete")
+	assert.Equal(t, 0, v6, "v6 refcount unchanged")
+}
+
+// TestNftablesDNAT_RefcountBalancedV6 verifies the v6 path increments v6 only
+// and decrements back to zero on Delete.
+func TestNftablesDNAT_RefcountBalancedV6(t *testing.T) {
+	m := newNftRefcountManager(t, true)
+	require.NotNil(t, m.router6, "v6 router")
+	require.Same(t, m.router.ipFwdState, m.router6.ipFwdState, "shared state")
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(dnatV6(9091))
+	require.NoError(t, err, "add v6 dnat 1")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount unchanged")
+	assert.Equal(t, 1, v6, "v6 refcount after first add")
+
+	r2, err := m.AddDNATRule(dnatV6(9092))
+	require.NoError(t, err, "add v6 dnat 2")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 2, v6, "v6 refcount after second add")
+
+	require.NoError(t, m.DeleteDNATRule(r1), "delete v6 dnat 1")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount unchanged")
+	assert.Equal(t, 1, v6, "v6 refcount after first delete")
+
+	require.NoError(t, m.DeleteDNATRule(r2), "delete v6 dnat 2")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 0, v6, "v6 refcount after second delete")
+}
+
+// TestNftablesDNAT_DuplicateAddNoLeak verifies that a duplicate Add (same
+// ForwardRule) does not double-increment the refcount.
+func TestNftablesDNAT_DuplicateAddNoLeak(t *testing.T) {
+	m := newNftRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	rule := dnatV4(8083)
+	r1, err := m.AddDNATRule(rule)
+	require.NoError(t, err, "add v4 dnat")
+	v4, _ := state.Counts()
+	assert.Equal(t, 1, v4)
+
+	// duplicate add: same rule ID, must be a no-op for the refcount.
+	_, err = m.AddDNATRule(rule)
+	require.NoError(t, err, "duplicate add")
+	v4, _ = state.Counts()
+	assert.Equal(t, 1, v4, "duplicate add must not increment")
+
+	require.NoError(t, m.DeleteDNATRule(r1), "delete v4 dnat")
+	v4, _ = state.Counts()
+	assert.Equal(t, 0, v4, "single delete must drop to zero")
+}
+
+// TestNftablesDNAT_DeleteMissingNoUnderflow verifies deleting a rule that was
+// never added does not underflow the refcount.
+func TestNftablesDNAT_DeleteMissingNoUnderflow(t *testing.T) {
+	m := newNftRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	// Construct a Rule reference for something never added. The router stores
+	// rules by ID(), and DeleteDNATRule looks them up in r.rules; a missing
+	// entry must be a no-op rather than calling Release.
+	phantom := dnatV4(8099)
+	require.NoError(t, m.DeleteDNATRule(&phantom), "delete missing v4 dnat")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 0, v4, "v4 refcount unaffected by missing delete")
+	assert.Equal(t, 0, v6, "v6 refcount unaffected")
+
+	phantom6 := dnatV6(9099)
+	require.NoError(t, m.DeleteDNATRule(&phantom6), "delete missing v6 dnat")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4)
+	assert.Equal(t, 0, v6, "v6 refcount unaffected by missing delete")
+
+	// And after a phantom delete, a real add still results in count=1.
+	r1, err := m.AddDNATRule(dnatV4(8100))
+	require.NoError(t, err, "add v4 dnat after phantom delete")
+	v4, _ = state.Counts()
+	assert.Equal(t, 1, v4, "real add still increments after phantom delete")
+	require.NoError(t, m.DeleteDNATRule(r1))
+}
+
+// TestNftablesRouting_RepeatedEnableSingleReference verifies that EnableRouting
+// (called on every network-map update) holds at most one reference per family
+// and a single DisableRouting drops both back to zero.
+func TestNftablesRouting_RepeatedEnableSingleReference(t *testing.T) {
+	m := newNftRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	require.NoError(t, m.EnableRouting(), "first enable")
+	require.NoError(t, m.EnableRouting(), "second enable")
+	require.NoError(t, m.EnableRouting(), "third enable")
+	v4, v6 := state.Counts()
+	assert.Equal(t, 1, v4, "repeated enable holds a single v4 reference")
+	assert.Equal(t, 1, v6, "repeated enable holds a single v6 reference")
+
+	require.NoError(t, m.DisableRouting(), "disable")
+	v4, v6 = state.Counts()
+	assert.Equal(t, 0, v4, "single disable releases the v4 reference")
+	assert.Equal(t, 0, v6, "single disable releases the v6 reference")
+}
+
+// TestNftablesRouting_DisableKeepsDNATReference verifies that an unpaired
+// DisableRouting does not release references held by active DNAT rules.
+func TestNftablesRouting_DisableKeepsDNATReference(t *testing.T) {
+	m := newNftRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(dnatV6(9095))
+	require.NoError(t, err, "add v6 dnat")
+
+	require.NoError(t, m.DisableRouting(), "unpaired disable")
+	_, v6 := state.Counts()
+	assert.Equal(t, 1, v6, "DNAT-held reference survives unpaired DisableRouting")
+
+	require.NoError(t, m.DeleteDNATRule(r1), "delete v6 dnat")
+	_, v6 = state.Counts()
+	assert.Equal(t, 0, v6, "delete releases the DNAT reference")
+}
+
+// TestNftablesDNAT_DoubleDeleteNoUnderflow verifies that deleting the same rule
+// twice does not underflow the refcount (the second delete is a no-op).
+func TestNftablesDNAT_DoubleDeleteNoUnderflow(t *testing.T) {
+	m := newNftRefcountManager(t, true)
+	state := m.router.ipFwdState
+
+	r1, err := m.AddDNATRule(dnatV6(9093))
+	require.NoError(t, err)
+	_, v6 := state.Counts()
+	assert.Equal(t, 1, v6)
+
+	require.NoError(t, m.DeleteDNATRule(r1), "first delete")
+	_, v6 = state.Counts()
+	assert.Equal(t, 0, v6)
+
+	require.NoError(t, m.DeleteDNATRule(r1), "second delete must be no-op")
+	_, v6 = state.Counts()
+	assert.Equal(t, 0, v6, "double delete must not underflow")
+}

client/firewall/nftables/manager_linux.go

@@ -105,8 +105,8 @@ func (m *Manager) createIPv6Components(tableName string, wgIface iFaceMapper, mt
 		return fmt.Errorf("create v6 router: %w", err)
 	}
 
-	// Share the same IP forwarding state with the v4 router, since
-	// EnableIPForwarding controls both v4 and v6 sysctls.
+	// Share the per-family forwarding refcounter with the v4 router so a v4
+	// rule and a v6 rule against the same state machine cooperate cleanly.
 	m.router6.ipFwdState = m.router.ipFwdState
 
 	m.aclManager6, err = newAclManager(workTable6, wgIface, chainNameRoutingFw)
@@ -530,17 +530,12 @@ func (m *Manager) SetLogLevel(log.Level) {
 }
 
 func (m *Manager) EnableRouting() error {
-	if err := m.router.ipFwdState.RequestForwarding(); err != nil {
-		return fmt.Errorf("enable IP forwarding: %w", err)
-	}
-	return nil
+	// v6 only when the overlay actually has v6.
+	return m.router.ipFwdState.RequestRouting(m.router6 != nil)
 }
 
 func (m *Manager) DisableRouting() error {
-	if err := m.router.ipFwdState.ReleaseForwarding(); err != nil {
-		return fmt.Errorf("disable IP forwarding: %w", err)
-	}
-	return nil
+	return m.router.ipFwdState.ReleaseRouting()
 }
 
 // Flush rule/chain/set operations from the buffer

client/firewall/nftables/router_linux.go

@@ -93,7 +93,7 @@ func newRouter(workTable *nftables.Table, wgIface iFaceMapper, mtu uint16) (*rou
 		rules:      make(map[string]*nftables.Rule),
 		af:         familyForAddr(workTable.Family == nftables.TableFamilyIPv4),
 		wgIface:    wgIface,
-		ipFwdState: ipfwdstate.NewIPForwardingState(),
+		ipFwdState: ipfwdstate.NewIPForwardingState(wgIface.Name()),
 		mtu:        mtu,
 	}
 
@@ -1553,10 +1553,6 @@ func (r *router) refreshRulesMap() error {
 }
 
 func (r *router) AddDNATRule(rule firewall.ForwardRule) (firewall.Rule, error) {
-	if err := r.ipFwdState.RequestForwarding(); err != nil {
-		return nil, err
-	}
-
 	ruleKey := rule.ID()
 	if _, exists := r.rules[ruleKey+dnatSuffix]; exists {
 		return rule, nil
@@ -1567,7 +1563,18 @@ func (r *router) AddDNATRule(rule firewall.ForwardRule) (firewall.Rule, error) {
 		return nil, fmt.Errorf("convert protocol to number: %w", err)
 	}
 
+	// Request forwarding before queueing rules: addDnatRedirect/addDnatMasq
+	// buffer netlink messages on r.conn that the next caller's Flush would
+	// commit if we returned without flushing them ourselves.
+	v6 := r.af.tableFamily == nftables.TableFamilyIPv6
+	if err := r.ipFwdState.RequestForwarding(v6); err != nil {
+		return nil, fmt.Errorf("enable forwarding: %w", err)
+	}
+
 	if err := r.addDnatRedirect(rule, protoNum, ruleKey); err != nil {
+		if rerr := r.ipFwdState.ReleaseForwarding(v6); rerr != nil {
+			log.Warnf("rollback forwarding refcount: %v", rerr)
+		}
 		return nil, err
 	}
 
@@ -1579,6 +1586,11 @@ func (r *router) AddDNATRule(rule firewall.ForwardRule) (firewall.Rule, error) {
 	// TODO: find chains with drop policies and add rules there
 
 	if err := r.conn.Flush(); err != nil {
+		if rerr := r.ipFwdState.ReleaseForwarding(v6); rerr != nil {
+			log.Warnf("rollback forwarding refcount: %v", rerr)
+		}
+		delete(r.rules, ruleKey+dnatSuffix)
+		delete(r.rules, ruleKey+snatSuffix)
 		return nil, fmt.Errorf("flush rules: %w", err)
 	}
 
@@ -1781,16 +1793,18 @@ func (r *router) addDnatMasq(rule firewall.ForwardRule, protoNum uint8, ruleKey
 }
 
 func (r *router) DeleteDNATRule(rule firewall.Rule) error {
-	if err := r.ipFwdState.ReleaseForwarding(); err != nil {
-		log.Errorf("%v", err)
-	}
-
 	ruleKey := rule.ID()
 
 	if err := r.refreshRulesMap(); err != nil {
 		return fmt.Errorf(refreshRulesMapError, err)
 	}
 
+	_, hadDNAT := r.rules[ruleKey+dnatSuffix]
+	_, hadSNAT := r.rules[ruleKey+snatSuffix]
+	if !hadDNAT && !hadSNAT {
+		return nil
+	}
+
 	var merr *multierror.Error
 	var needsFlush bool
 
@@ -1822,9 +1836,16 @@ func (r *router) DeleteDNATRule(rule firewall.Rule) error {
 		}
 	}
 
+	// Release the refcount only once the rules are gone from the kernel. On
+	// failure (including the refreshRulesMap error above) the rules and their
+	// map entries remain, keeping forwarding on until a retry removes them.
 	if merr == nil {
 		delete(r.rules, ruleKey+dnatSuffix)
 		delete(r.rules, ruleKey+snatSuffix)
+
+		if err := r.ipFwdState.ReleaseForwarding(r.af.tableFamily == nftables.TableFamilyIPv6); err != nil {
+			log.Errorf("%v", err)
+		}
 	}
 
 	return nberrors.FormatErrorOrNil(merr)

client/iface/bind/ice_bind.go

@@ -22,6 +22,16 @@ import (
 	nbnet "github.com/netbirdio/netbird/client/net"
 )
 
+const (
+	// wgMsgTypeHandshakeInitiation is the lowest WireGuard message type.
+	wgMsgTypeHandshakeInitiation uint32 = 1
+	// wgMsgTypeTransport is the highest WireGuard message type.
+	wgMsgTypeTransport uint32 = 4
+	// wgMinMsgSize is the smallest WireGuard message: transport data with an empty
+	// payload, which is what a keepalive is.
+	wgMinMsgSize = 32
+)
+
 type receiverCreator struct {
 	iceBind *ICEBind
 }
@@ -216,8 +226,15 @@ func (s *ICEBind) createReceiverFn(pc wgConn.BatchReader, conn *net.UDPConn, rxO
 		for i := 0; i < numMsgs; i++ {
 			msg := &(*msgs)[i]
 
-			// todo: handle err
-			if ok, _ := s.filterOutStunMessages(msg.Buffers, msg.N, msg.Addr); ok {
+			if ok, err := s.filterOutStunMessages(msg.Buffers, msg.N, msg.Addr); ok {
+				if err != nil {
+					log.Debugf("failed to handle STUN packet from %s: %v", msg.Addr, err)
+				}
+				// WireGuard reuses sizes and eps across reads and only skips a slot
+				// whose size is below the minimum message size. Leaving a consumed
+				// slot untouched makes it process this buffer again under the
+				// previous packet's length and endpoint.
+				sizes[i] = 0
 				continue
 			}
 			sizes[i] = msg.N
@@ -271,11 +288,16 @@ func (s *ICEBind) createOrUpdateMux() {
 
 func (s *ICEBind) filterOutStunMessages(buffers [][]byte, n int, addr net.Addr) (bool, error) {
 	for i := range buffers {
-		if !stun.IsMessage(buffers[i]) {
+		if n > len(buffers[i]) {
+			continue
+		}
+		pkt := buffers[i][:n]
+
+		if isWireGuardMsg(pkt) || !stun.IsMessage(pkt) {
 			continue
 		}
 
-		msg, err := s.parseSTUNMessage(buffers[i][:n])
+		msg, err := s.parseSTUNMessage(pkt)
 		if err != nil {
 			buffers[i] = []byte{}
 			return true, err
@@ -347,18 +369,34 @@ func putMessages(msgs *[]ipv6.Message, msgsPool *sync.Pool) {
 	msgsPool.Put(msgs)
 }
 
-func isTransportPkg(buffers [][]byte, n int) bool {
-	// The first buffer should contain at least 4 bytes for type
-	if len(buffers[0]) < 4 {
-		return true
+// isWireGuardMsg reports whether the packet carries a WireGuard message header: a
+// little-endian uint32 message type in the range 1..4, which leaves the three bytes
+// after the type byte zero, in a packet long enough to hold any WireGuard message.
+//
+// A well formed STUN message cannot take that shape. Its length field sits in the two
+// bytes the type must leave zero, and for a message of at least wgMinMsgSize bytes that
+// field holds at least 12, so the two framings do not overlap. The test has to be this
+// tight because stun.IsMessage only looks at the magic cookie, which in a WireGuard
+// message overlaps the receiver index: a session whose index happens to equal the cookie
+// would otherwise have all of its inbound data misrouted to the STUN handler until the
+// next rekey.
+func isWireGuardMsg(pkt []byte) bool {
+	if len(pkt) < wgMinMsgSize {
+		return false
 	}
 
-	// WireGuard packet type is a little-endian uint32 at start
-	packetType := binary.LittleEndian.Uint32(buffers[0][:4])
-
-	// Check if packetType matches known WireGuard message types
-	if packetType == 4 && n > 32 {
-		return true
-	}
-	return false
+	msgType := binary.LittleEndian.Uint32(pkt[:4])
+	return msgType >= wgMsgTypeHandshakeInitiation && msgType <= wgMsgTypeTransport
+}
+
+// isTransportPkg reports whether the packet is WireGuard transport data carrying a
+// payload, which is what counts as peer activity. A keepalive holds no payload and is
+// exactly wgMinMsgSize bytes.
+func isTransportPkg(buffers [][]byte, n int) bool {
+	if n < 4 || n > len(buffers[0]) {
+		return false
+	}
+
+	msgType := binary.LittleEndian.Uint32(buffers[0][:4])
+	return msgType == wgMsgTypeTransport && n > wgMinMsgSize
 }

client/iface/bind/stun_filter_test.go

@@ -0,0 +1,215 @@
+//go:build !js
+
+package bind
+
+import (
+	"encoding/binary"
+	"net"
+	"testing"
+	"time"
+
+	"github.com/pion/stun/v3"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"golang.org/x/net/ipv4"
+	wgConn "golang.zx2c4.com/wireguard/conn"
+)
+
+// magicCookieBytes is the STUN magic cookie as it appears on the wire. In a
+// WireGuard message the same offset holds the receiver (or sender) index, which is
+// a random uint32, so a session can draw exactly this value.
+var magicCookieBytes = []byte{0x21, 0x12, 0xA4, 0x42}
+
+const testBufSize = 1500
+
+// wgMsg builds a WireGuard message of the given type and size, with the index field
+// at bytes 4:8 set to index.
+func wgMsg(msgType uint32, size int, index []byte) []byte {
+	pkt := make([]byte, size)
+	binary.LittleEndian.PutUint32(pkt[:4], msgType)
+	copy(pkt[4:8], index)
+	return pkt
+}
+
+// intoBuffer copies pkt into a full-size receive buffer, the way the kernel read
+// does, so tests see the same buffer/length split as the hot path.
+func intoBuffer(pkt []byte) [][]byte {
+	buf := make([]byte, testBufSize)
+	copy(buf, pkt)
+	return [][]byte{buf}
+}
+
+func TestFilterOutStunMessages_PassesWireGuardWithCookieShapedIndex(t *testing.T) {
+	tests := []struct {
+		name    string
+		msgType uint32
+		size    int
+	}{
+		{"transport data", wgMsgTypeTransport, 128},
+		{"keepalive", wgMsgTypeTransport, wgMinMsgSize},
+		{"handshake initiation", wgMsgTypeHandshakeInitiation, 148},
+		{"handshake response", 2, 92},
+		{"cookie reply", 3, 64},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			pkt := wgMsg(tc.msgType, tc.size, magicCookieBytes)
+			require.True(t, stun.IsMessage(pkt), "precondition: pion sees this as STUN")
+
+			buffers := intoBuffer(pkt)
+			bind := &ICEBind{}
+
+			filtered, err := bind.filterOutStunMessages(buffers, tc.size, &net.UDPAddr{})
+			assert.NoError(t, err)
+			assert.False(t, filtered, "WireGuard message must be handed to WireGuard, not the STUN handler")
+			assert.Len(t, buffers[0], testBufSize, "buffer must be left intact for WireGuard")
+		})
+	}
+}
+
+func TestFilterOutStunMessages_FiltersRealSTUNMessage(t *testing.T) {
+	msg, err := stun.Build(stun.BindingRequest, stun.TransactionID, stun.Fingerprint)
+	require.NoError(t, err)
+
+	buffers := intoBuffer(msg.Raw)
+	bind := &ICEBind{}
+
+	filtered, err := bind.filterOutStunMessages(buffers, len(msg.Raw), &net.UDPAddr{})
+	assert.NoError(t, err)
+	assert.True(t, filtered, "STUN message must be consumed by the STUN handler")
+	assert.Empty(t, buffers[0], "consumed buffer must be emptied so WireGuard does not see it")
+}
+
+// TestIsWireGuardMsg_DisjointFromSTUN locks the invariant the filter relies on: a
+// well formed STUN message long enough to be a WireGuard message always has a
+// non-zero length field, so it cannot be mistaken for a WireGuard header.
+func TestIsWireGuardMsg_DisjointFromSTUN(t *testing.T) {
+	types := []stun.MessageType{
+		stun.BindingRequest,
+		stun.BindingSuccess,
+		stun.BindingError,
+		{Method: stun.MethodBinding, Class: stun.ClassIndication},
+	}
+
+	for _, msgType := range types {
+		// Long enough that the length guard is not what makes this pass.
+		msg, err := stun.Build(msgType, stun.TransactionID,
+			stun.NewUsername("remoteUfrag:localUfrag"), stun.Fingerprint)
+		require.NoError(t, err)
+		require.GreaterOrEqual(t, len(msg.Raw), wgMinMsgSize, "precondition: %s", msgType)
+		assert.False(t, isWireGuardMsg(msg.Raw),
+			"%s must not look like a WireGuard message", msgType)
+	}
+}
+
+func TestIsWireGuardMsg(t *testing.T) {
+	tests := []struct {
+		name string
+		pkt  []byte
+		want bool
+	}{
+		{"transport data", wgMsg(wgMsgTypeTransport, 128, nil), true},
+		{"handshake initiation", wgMsg(wgMsgTypeHandshakeInitiation, 148, nil), true},
+		{"unknown type 5", wgMsg(5, 128, nil), false},
+		{"type 0", wgMsg(0, 128, nil), false},
+		{"non-zero reserved byte", []byte{0x04, 0x00, 0x01, 0x00}, false},
+		{"too short", []byte{0x04, 0x00, 0x00}, false},
+		{"empty", nil, false},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			assert.Equal(t, tc.want, isWireGuardMsg(tc.pkt), "wrong classification for %s", tc.name)
+		})
+	}
+}
+
+// TestFilterOutStunMessages_IgnoresBytesBeyondPacket guards against classifying on
+// buffer contents left over from an earlier, longer packet.
+func TestFilterOutStunMessages_IgnoresBytesBeyondPacket(t *testing.T) {
+	buf := make([]byte, testBufSize)
+	copy(buf[4:8], magicCookieBytes)
+	buffers := [][]byte{buf}
+	bind := &ICEBind{}
+
+	filtered, err := bind.filterOutStunMessages(buffers, 2, &net.UDPAddr{})
+	assert.NoError(t, err)
+	assert.False(t, filtered, "a 2 byte packet must not be classified from stale buffer bytes")
+}
+
+// TestReceiveFn_ClearsSizeOfConsumedPacket covers the accounting WireGuard relies
+// on: sizes is reused across reads, so a slot whose packet was consumed as STUN must
+// be reported as empty. Otherwise WireGuard reprocesses the same buffer under the
+// previous packet's length, which for a WireGuard-shaped packet means it is handled
+// twice.
+func TestReceiveFn_ClearsSizeOfConsumedPacket(t *testing.T) {
+	conn := listenUDP(t, "udp4", "127.0.0.1:0")
+	defer conn.Close()
+
+	recvFn := receiverCreator{setupICEBind(t)}.CreateReceiverFn(
+		ipv4.NewPacketConn(conn), conn, false, createMsgPool(),
+	)
+
+	msg, err := stun.Build(stun.BindingRequest, stun.TransactionID, stun.Fingerprint)
+	require.NoError(t, err)
+
+	sender := listenUDP(t, "udp4", "127.0.0.1:0")
+	defer sender.Close()
+	_, err = sender.WriteTo(msg.Raw, conn.LocalAddr())
+	require.NoError(t, err)
+
+	require.NoError(t, conn.SetReadDeadline(time.Now().Add(3*time.Second)))
+
+	bufs := [][]byte{make([]byte, 1500)}
+	// A leftover size from an earlier read, which is what makes the missing reset
+	// observable.
+	sizes := []int{148}
+	eps := make([]wgConn.Endpoint, 1)
+
+	n, err := recvFn(bufs, sizes, eps)
+	require.NoError(t, err)
+	require.Equal(t, 1, n)
+	assert.Zero(t, sizes[0], "consumed STUN packet must not leave a size behind for WireGuard")
+}
+
+func TestIsTransportPkg(t *testing.T) {
+	tests := []struct {
+		name string
+		pkt  []byte
+		n    int
+		want bool
+	}{
+		{"transport data with payload", wgMsg(wgMsgTypeTransport, 128, nil), 128, true},
+		{"keepalive", wgMsg(wgMsgTypeTransport, wgMinMsgSize, nil), wgMinMsgSize, false},
+		{"handshake initiation", wgMsg(wgMsgTypeHandshakeInitiation, 148, nil), 148, false},
+		{"stale type bytes beyond packet", wgMsg(wgMsgTypeTransport, 128, nil), 2, false},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			assert.Equal(t, tc.want, isTransportPkg(intoBuffer(tc.pkt), tc.n),
+				"wrong activity classification for %s", tc.name)
+		})
+	}
+}
+
+// TestFilterOutStunMessages_ConsumesSTUNWithWireGuardShapedType covers the one STUN
+// encoding whose leading bytes collide with a WireGuard message type: method 0x080 as a
+// request encodes to 0x0200, so the type byte reads as a handshake response and the byte
+// after it is zero. Only the length check keeps such a message out of WireGuard's hands.
+// pion implements no method in that range, so this is a synthetic worst case rather than
+// traffic ICE produces.
+func TestFilterOutStunMessages_ConsumesSTUNWithWireGuardShapedType(t *testing.T) {
+	msg, err := stun.Build(stun.NewType(stun.Method(0x080), stun.ClassRequest), stun.TransactionID)
+	require.NoError(t, err)
+	require.Equal(t, []byte{0x02, 0x00, 0x00, 0x00}, msg.Raw[:4],
+		"precondition: the leading bytes read as a WireGuard message type")
+
+	buffers := intoBuffer(msg.Raw)
+	bind := &ICEBind{}
+
+	filtered, err := bind.filterOutStunMessages(buffers, len(msg.Raw), &net.UDPAddr{})
+	assert.NoError(t, err)
+	assert.True(t, filtered, "STUN message must be consumed despite its WireGuard-shaped type")
+}

client/internal/auth/auth.go

@@ -2,6 +2,7 @@ package auth
 
 import (
 	"context"
+	"errors"
 	"net/url"
 	"strings"
 	"sync"
@@ -140,25 +141,21 @@ func (a *Auth) IsSSOSupported(ctx context.Context) (bool, error) {
 // This avoids creating a new connection to the management server
 func (a *Auth) GetOAuthFlow(ctx context.Context, forceDeviceAuth bool) (OAuthFlow, error) {
 	var flow OAuthFlow
-	var err error
 
-	err = a.withRetry(ctx, func(client *mgm.GrpcClient) error {
-		if forceDeviceAuth {
-			flow, err = a.getDeviceFlow(client)
-			return err
-		}
+	// the connection is owned by a and outlives this call, so a later fallback reuses it
+	newAuth := func(context.Context) (*Auth, func(), error) {
+		return a, func() {}, nil
+	}
 
-		// Try PKCE flow first
-		flow, err = a.getPKCEFlow(client)
-		if err != nil {
-			// If PKCE not supported, try Device flow
-			if s, ok := status.FromError(err); ok && (s.Code() == codes.NotFound || s.Code() == codes.Unimplemented) {
-				flow, err = a.getDeviceFlow(client)
-				return err
-			}
-			return err
+	err := a.withRetry(ctx, func(client *mgm.GrpcClient) error {
+		var err error
+		flow, err = oauthFlowWithFallback(a, client, flowOrder(forceDeviceAuth), "", newAuth)
+
+		var ssoUnavailable *ssoUnavailableError
+		if errors.As(err, &ssoUnavailable) {
+			return backoff.Permanent(err)
 		}
-		return nil
+		return err
 	})
 
 	return flow, err

client/internal/auth/device_flow.go

@@ -48,8 +48,17 @@ type DeviceAuthProviderConfig struct {
 	LoginHint string
 }
 
-// validateDeviceAuthConfig validates device authorization provider configuration
+// validateDeviceAuthConfig validates device authorization provider configuration. A missing
+// value means management does not have this flow configured, so the error wraps
+// errFlowNotConfigured and the caller can fall back to the other flow.
 func validateDeviceAuthConfig(config *DeviceAuthProviderConfig) error {
+	if err := checkDeviceAuthConfig(config); err != nil {
+		return fmt.Errorf("%w: %w", errFlowNotConfigured, err)
+	}
+	return nil
+}
+
+func checkDeviceAuthConfig(config *DeviceAuthProviderConfig) error {
 	errorMsgFormat := "invalid provider configuration received from management: %s value is empty. Contact your NetBird administrator"
 
 	if config.Audience == "" {
@@ -161,8 +170,12 @@ func (d *DeviceAuthorizationFlow) RequestAuthInfo(ctx context.Context) (AuthFlow
 		return AuthFlowInfo{}, fmt.Errorf("reading body failed with error: %v", err)
 	}
 
-	if res.StatusCode != 200 {
-		return AuthFlowInfo{}, fmt.Errorf("request device code returned status %d error: %s", res.StatusCode, string(body))
+	if res.StatusCode != http.StatusOK {
+		reqErr := fmt.Errorf("request device code returned status %d error: %s", res.StatusCode, string(body))
+		if deviceGrantUnsupported(res.StatusCode, body) {
+			return AuthFlowInfo{}, fmt.Errorf("%w: %w", errFlowNotConfigured, reqErr)
+		}
+		return AuthFlowInfo{}, reqErr
 	}
 
 	deviceCode := AuthFlowInfo{}
@@ -186,6 +199,34 @@ func (d *DeviceAuthorizationFlow) RequestAuthInfo(ctx context.Context) (AuthFlow
 	return deviceCode, err
 }
 
+// deviceGrantUnsupported reports whether the IdP's answer to a device code request means it does
+// not serve the device authorization grant at all, rather than a transient or request-specific
+// failure. An IdP that does not route the endpoint answers 404/405/501; one that knows the
+// endpoint but has the grant disabled for this client answers with an OAuth 2.0 error code.
+func deviceGrantUnsupported(statusCode int, body []byte) bool {
+	switch statusCode {
+	case http.StatusNotFound, http.StatusMethodNotAllowed, http.StatusNotImplemented:
+		return true
+	case http.StatusBadRequest, http.StatusUnauthorized, http.StatusForbidden:
+	default:
+		return false
+	}
+
+	var oauthErr struct {
+		Error string `json:"error"`
+	}
+	if err := json.Unmarshal(body, &oauthErr); err != nil {
+		return false
+	}
+
+	switch oauthErr.Error {
+	case "unsupported_grant_type", "unauthorized_client", "invalid_client":
+		return true
+	default:
+		return false
+	}
+}
+
 func appendLoginHint(uri, loginHint string) string {
 	if uri == "" || loginHint == "" {
 		return uri

client/internal/auth/oauth.go

@@ -2,15 +2,19 @@ package auth
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"net/http"
+	"net/url"
 	"runtime"
+	"sync"
 
 	log "github.com/sirupsen/logrus"
 	"google.golang.org/grpc/codes"
 	gstatus "google.golang.org/grpc/status"
 
 	"github.com/netbirdio/netbird/client/internal/profilemanager"
+	mgm "github.com/netbirdio/netbird/shared/management/client"
 )
 
 // OAuthFlow represents an interface for authorization using different OAuth 2.0 flows
@@ -59,77 +63,278 @@ func (t TokenInfo) GetTokenToUse() string {
 	return t.AccessToken
 }
 
-func shouldUseDeviceFlow(force bool, isUnixDesktopClient bool) bool {
-	return force || (runtime.GOOS == "linux" || runtime.GOOS == "freebsd") && !isUnixDesktopClient
+// errFlowNotConfigured marks a flow this deployment does not offer: management returned no
+// configuration for it, the configuration it returned is incomplete, or the IdP refuses to serve
+// the grant. It is the only condition that makes the client try the other flow, so that a
+// transient failure keeps failing on the flow the user actually wants.
+var errFlowNotConfigured = errors.New("authorization flow is not configured")
+
+// ssoUnavailableError reports that the management server offers no usable SSO flow at all.
+// Retrying cannot help, so callers should surface it to the user instead of backing off.
+type ssoUnavailableError struct {
+	msg string
 }
 
-// NewOAuthFlow initializes and returns the appropriate OAuth flow based on the management configuration
-//
-// It starts by initializing the PKCE.If this process fails, it resorts to the Device Code Flow,
-// and if that also fails, the authentication process is deemed unsuccessful
-//
-// On Linux distros without desktop environment support, it only tries to initialize the Device Code Flow
-// forceDeviceCodeFlow can be used to skip PKCE and go directly to Device Code Flow (e.g., for Android TV)
-func NewOAuthFlow(ctx context.Context, config *profilemanager.Config, isUnixDesktopClient bool, forceDeviceCodeFlow bool, hint string) (OAuthFlow, error) {
-	if shouldUseDeviceFlow(forceDeviceCodeFlow, isUnixDesktopClient) {
-		return authenticateWithDeviceCodeFlow(ctx, config, hint)
-	}
-
-	pkceFlow, err := authenticateWithPKCEFlow(ctx, config, hint)
-	if err != nil {
-		log.Debugf("failed to initialize pkce authentication with error: %v\n", err)
-		log.Debug("falling back to device code flow")
-		return authenticateWithDeviceCodeFlow(ctx, config, hint)
-	}
-	return pkceFlow, nil
+func (e *ssoUnavailableError) Error() string {
+	return e.msg
 }
 
-// authenticateWithPKCEFlow initializes the Proof Key for Code Exchange flow auth flow
-func authenticateWithPKCEFlow(ctx context.Context, config *profilemanager.Config, hint string) (OAuthFlow, error) {
-	authClient, err := NewAuth(ctx, config.PrivateKey, config.ManagementURL, config)
-	if err != nil {
-		return nil, fmt.Errorf("failed to create auth client: %v", err)
-	}
-	defer authClient.Close()
+// oauthFlowInit names one of the OAuth flows and builds it from the management configuration.
+type oauthFlowInit struct {
+	name string
+	init func(a *Auth, client *mgm.GrpcClient, hint string) (OAuthFlow, error)
+}
 
-	pkceFlowInfo, err := authClient.getPKCEFlow(authClient.client)
+// authFactory hands out a management connection to build a flow with, plus the cleanup that
+// releases it. Callers that own a long-lived connection return it with a no-op cleanup.
+type authFactory func(ctx context.Context) (*Auth, func(), error)
+
+// fallbackFlow wraps the flow that was picked at initialization time with the flows that were
+// not tried. Whether the IdP actually serves a flow only shows up when the flow is run: an IdP
+// with the device grant disabled answers the device code request with 404 even though
+// management handed out a device flow configuration. When that happens the wrapper swaps in the
+// next flow instead of failing the login.
+type fallbackFlow struct {
+	mu        sync.Mutex
+	active    OAuthFlow
+	remaining []oauthFlowInit
+	hint      string
+	newAuth   authFactory
+}
+
+func (f *fallbackFlow) RequestAuthInfo(ctx context.Context) (AuthFlowInfo, error) {
+	info, err := f.current().RequestAuthInfo(ctx)
+	if err == nil || !isFlowUnavailable(err) {
+		return info, err
+	}
+
+	next, nextErr := f.initNext(ctx)
+	if nextErr != nil {
+		log.Debugf("failed to fall back to another authorization flow: %v", nextErr)
+		return AuthFlowInfo{}, err
+	}
+
+	return next.RequestAuthInfo(ctx)
+}
+
+func (f *fallbackFlow) WaitToken(ctx context.Context, info AuthFlowInfo) (TokenInfo, error) {
+	return f.current().WaitToken(ctx, info)
+}
+
+func (f *fallbackFlow) GetClientID(ctx context.Context) string {
+	return f.current().GetClientID(ctx)
+}
+
+func (f *fallbackFlow) current() OAuthFlow {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+
+	return f.active
+}
+
+// initNext initializes the next flow this deployment offers and makes it the active one.
+func (f *fallbackFlow) initNext(ctx context.Context) (OAuthFlow, error) {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+
+	if len(f.remaining) == 0 {
+		return nil, errors.New("no authorization flow left to try")
+	}
+
+	a, cleanup, err := f.newAuth(ctx)
 	if err != nil {
-		return nil, fmt.Errorf("getting pkce authorization flow info failed with error: %v", err)
+		return nil, err
+	}
+	defer cleanup()
+
+	flow, remaining, err := initFirstAvailableFlow(a, a.client, f.remaining, f.hint)
+	if err != nil {
+		return nil, err
+	}
+
+	log.Infof("the identity provider does not serve the selected authorization flow, continuing with the next one")
+	f.active = flow
+	f.remaining = remaining
+
+	return flow, nil
+}
+
+// preferDeviceFlow reports whether the device code flow should be tried before PKCE. PKCE needs
+// a browser on this host and a loopback listener to receive the redirect, neither of which
+// exists on a Unix host without a graphical session. The GOOS guard keeps a caller that reports
+// no graphical session on a platform that always has one from changing the preference.
+func preferDeviceFlow(force bool, hasGraphicalSession bool) bool {
+	return force || (runtime.GOOS == "linux" || runtime.GOOS == "freebsd") && !hasGraphicalSession
+}
+
+// flowOrder returns both flows in the order they should be attempted.
+func flowOrder(preferDevice bool) []oauthFlowInit {
+	pkce := oauthFlowInit{name: "pkce authorization flow", init: initPKCEFlow}
+	device := oauthFlowInit{name: "device code flow", init: initDeviceFlow}
+
+	if preferDevice {
+		return []oauthFlowInit{device, pkce}
+	}
+	return []oauthFlowInit{pkce, device}
+}
+
+func initPKCEFlow(a *Auth, client *mgm.GrpcClient, hint string) (OAuthFlow, error) {
+	flow, err := a.getPKCEFlow(client)
+	if err != nil {
+		return nil, err
 	}
 
 	if hint != "" {
-		pkceFlowInfo.SetLoginHint(hint)
+		flow.SetLoginHint(hint)
 	}
 
-	return pkceFlowInfo, nil
+	return flow, nil
 }
 
-// authenticateWithDeviceCodeFlow initializes the Device Code auth Flow
-func authenticateWithDeviceCodeFlow(ctx context.Context, config *profilemanager.Config, hint string) (OAuthFlow, error) {
+func initDeviceFlow(a *Auth, client *mgm.GrpcClient, hint string) (OAuthFlow, error) {
+	flow, err := a.getDeviceFlow(client)
+	if err != nil {
+		return nil, err
+	}
+
+	if hint != "" {
+		flow.SetLoginHint(hint)
+	}
+
+	return flow, nil
+}
+
+// NewOAuthFlow initializes and returns an OAuth flow based on the management configuration.
+//
+// Both flows are optional server side: management answers NotFound for a flow it has no
+// configuration for. The preferred flow is tried first and the other one is used as a fallback,
+// so a server that only offers one of them still works. forceDeviceCodeFlow prefers the device
+// code flow regardless of platform (e.g. for Android TV).
+func NewOAuthFlow(ctx context.Context, config *profilemanager.Config, hasGraphicalSession bool, forceDeviceCodeFlow bool, hint string) (OAuthFlow, error) {
 	authClient, err := NewAuth(ctx, config.PrivateKey, config.ManagementURL, config)
 	if err != nil {
-		return nil, fmt.Errorf("failed to create auth client: %v", err)
+		return nil, fmt.Errorf("create auth client: %w", err)
 	}
 	defer authClient.Close()
 
-	deviceFlowInfo, err := authClient.getDeviceFlow(authClient.client)
+	// the connection above is closed on return, so a later fallback opens its own
+	newAuth := func(ctx context.Context) (*Auth, func(), error) {
+		a, err := NewAuth(ctx, config.PrivateKey, config.ManagementURL, config)
+		if err != nil {
+			return nil, nil, fmt.Errorf("create auth client: %w", err)
+		}
+		return a, func() {
+			if err := a.Close(); err != nil {
+				log.Debugf("failed to close auth client: %v", err)
+			}
+		}, nil
+	}
+
+	flows := flowOrder(preferDeviceFlow(forceDeviceCodeFlow, hasGraphicalSession))
+	return oauthFlowWithFallback(authClient, authClient.client, flows, hint, newAuth)
+}
+
+// oauthFlowWithFallback initializes the first flow this deployment offers, moving on to the next
+// one when a flow is not configured here. It only fails once every flow has been tried, and any
+// flow left untried is handed to the returned flow so it can still fall back if the IdP rejects
+// the flow that was picked.
+func oauthFlowWithFallback(a *Auth, client *mgm.GrpcClient, flows []oauthFlowInit, hint string, newAuth authFactory) (OAuthFlow, error) {
+	flow, remaining, err := initFirstAvailableFlow(a, client, flows, hint)
 	if err != nil {
-		switch s, ok := gstatus.FromError(err); {
-		case ok && s.Code() == codes.NotFound:
-			return nil, fmt.Errorf("no SSO provider returned from management. " +
-				"Please proceed with setting up this device using setup keys " +
-				"https://docs.netbird.io/how-to/register-machines-using-setup-keys")
-		case ok && s.Code() == codes.Unimplemented:
-			return nil, fmt.Errorf("the management server, %s, does not support SSO providers, "+
-				"please update your server or use Setup Keys to login", config.ManagementURL)
-		default:
-			return nil, fmt.Errorf("getting device authorization flow info failed with error: %v", err)
+		return nil, err
+	}
+
+	if len(remaining) == 0 {
+		return flow, nil
+	}
+
+	return &fallbackFlow{
+		active:    flow,
+		remaining: remaining,
+		hint:      hint,
+		newAuth:   newAuth,
+	}, nil
+}
+
+// initFirstAvailableFlow returns the first flow that could be initialized along with the flows
+// after it, which are still untried.
+func initFirstAvailableFlow(a *Auth, client *mgm.GrpcClient, flows []oauthFlowInit, hint string) (OAuthFlow, []oauthFlowInit, error) {
+	var errs []error
+	for i, f := range flows {
+		flow, err := f.init(a, client, hint)
+		if err == nil {
+			return flow, flows[i+1:], nil
+		}
+
+		errs = append(errs, fmt.Errorf("%s: %w", f.name, err))
+
+		// only a flow this deployment does not offer is worth replacing with another one
+		if !isFlowUnavailable(err) {
+			break
+		}
+		if i < len(flows)-1 {
+			log.Infof("%s is not configured (%v), falling back to %s", f.name, err, flows[i+1].name)
 		}
 	}
 
-	if hint != "" {
-		deviceFlowInfo.SetLoginHint(hint)
+	return nil, nil, flowInitError(a.mgmURL, errs)
+}
+
+// flowInitError turns the per-flow initialization errors into a single actionable error. The
+// message stays neutral about what to do instead: SSO is also how a peer extends its session and
+// authenticates SSH, where a setup key is no alternative. Callers that are enrolling a device add
+// that advice themselves, see IsSSOUnavailable.
+func flowInitError(mgmURL *url.URL, errs []error) error {
+	if allMatch(errs, isFlowUnimplemented) {
+		return &ssoUnavailableError{msg: fmt.Sprintf("the management server, %s, does not support SSO providers, "+
+			"please update your server", mgmURL)}
 	}
 
-	return deviceFlowInfo, nil
+	if allMatch(errs, isFlowUnavailable) {
+		return &ssoUnavailableError{msg: "the management server has no SSO provider configured: " +
+			"neither the pkce authorization flow nor the device code flow is available"}
+	}
+
+	return fmt.Errorf("initialize authorization flow: %w", errors.Join(errs...))
+}
+
+// IsSSOUnavailable reports whether err means the management server offers no usable SSO flow, so
+// no retry and no other flow can help. Enrollment paths use it to point the user at setup keys.
+func IsSSOUnavailable(err error) bool {
+	var ssoUnavailable *ssoUnavailableError
+	return errors.As(err, &ssoUnavailable)
+}
+
+func allMatch(errs []error, match func(error) bool) bool {
+	if len(errs) == 0 {
+		return false
+	}
+
+	for _, err := range errs {
+		if !match(err) {
+			return false
+		}
+	}
+	return true
+}
+
+// isFlowUnavailable reports whether the flow is not on offer here: management has no
+// configuration for it (NotFound), predates the RPC entirely (Unimplemented), returned an
+// incomplete configuration, or the IdP does not serve the grant.
+func isFlowUnavailable(err error) bool {
+	return errors.Is(err, errFlowNotConfigured) ||
+		hasStatusCode(err, codes.NotFound) ||
+		hasStatusCode(err, codes.Unimplemented)
+}
+
+func isFlowUnimplemented(err error) bool {
+	return hasStatusCode(err, codes.Unimplemented)
+}
+
+func hasStatusCode(err error, code codes.Code) bool {
+	s, ok := gstatus.FromError(err)
+	if !ok {
+		return false
+	}
+	return s.Code() == code
 }

client/internal/auth/oauth_test.go

@@ -0,0 +1,221 @@
+package auth
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net/url"
+	"runtime"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"google.golang.org/grpc/codes"
+	"google.golang.org/grpc/status"
+
+	mgm "github.com/netbirdio/netbird/shared/management/client"
+)
+
+// stubFlow is a minimal OAuthFlow returned by the fake initializers below. requestErr, when set,
+// is what its RequestAuthInfo returns, standing in for an IdP that rejects the flow.
+type stubFlow struct {
+	name       string
+	hint       string
+	requestErr error
+}
+
+func (s *stubFlow) RequestAuthInfo(context.Context) (AuthFlowInfo, error) {
+	if s.requestErr != nil {
+		return AuthFlowInfo{}, s.requestErr
+	}
+	return AuthFlowInfo{UserCode: s.name}, nil
+}
+
+func (s *stubFlow) WaitToken(context.Context, AuthFlowInfo) (TokenInfo, error) {
+	return TokenInfo{}, nil
+}
+
+func (s *stubFlow) GetClientID(context.Context) string {
+	return ""
+}
+
+// stubInit returns a flow initializer that yields a named stub flow, or err when err is non-nil.
+func stubInit(name string, err error) oauthFlowInit {
+	return stubInitFlow(name, err, nil)
+}
+
+// stubInitFlow is stubInit with control over what the resulting flow's RequestAuthInfo returns.
+func stubInitFlow(name string, initErr, requestErr error) oauthFlowInit {
+	return oauthFlowInit{
+		name: name,
+		init: func(_ *Auth, _ *mgm.GrpcClient, hint string) (OAuthFlow, error) {
+			if initErr != nil {
+				return nil, initErr
+			}
+			return &stubFlow{name: name, hint: hint, requestErr: requestErr}, nil
+		},
+	}
+}
+
+// stubAuthFactory hands out an Auth without a management connection, which the stub
+// initializers above never touch.
+func stubAuthFactory(a *Auth) authFactory {
+	return func(context.Context) (*Auth, func(), error) {
+		return a, func() {}, nil
+	}
+}
+
+func TestOAuthFlowWithFallback(t *testing.T) {
+	notFound := status.Error(codes.NotFound, "no device authorization flow information available")
+	unimplemented := status.Error(codes.Unimplemented, "unknown method")
+	incompleteConfig := fmt.Errorf("%w: Client ID value is empty", errFlowNotConfigured)
+	unreachable := status.Error(codes.Unavailable, "connection refused")
+
+	tests := []struct {
+		name          string
+		flows         []oauthFlowInit
+		expectedFlow  string
+		expectedErr   string
+		expectedNoSSO bool
+	}{
+		{
+			name:         "preferred flow is used",
+			flows:        []oauthFlowInit{stubInit("device", nil), stubInit("pkce", nil)},
+			expectedFlow: "device",
+		},
+		{
+			// the RedHat case: device code flow disabled on management, PKCE configured
+			name:         "falls back when preferred flow is not configured",
+			flows:        []oauthFlowInit{stubInit("device", notFound), stubInit("pkce", nil)},
+			expectedFlow: "pkce",
+		},
+		{
+			name:         "falls back on an incomplete flow configuration",
+			flows:        []oauthFlowInit{stubInit("pkce", incompleteConfig), stubInit("device", nil)},
+			expectedFlow: "device",
+		},
+		{
+			name:        "does not fall back when the preferred flow fails for another reason",
+			flows:       []oauthFlowInit{stubInit("pkce", unreachable), stubInit("device", nil)},
+			expectedErr: "connection refused",
+		},
+		{
+			// stays neutral about the remedy: --extend and SSH auth cannot use a setup key
+			name:          "neither flow configured reports no SSO provider",
+			flows:         []oauthFlowInit{stubInit("device", notFound), stubInit("pkce", notFound)},
+			expectedErr:   "no SSO provider configured",
+			expectedNoSSO: true,
+		},
+		{
+			name:          "old server without the flow RPCs asks for an update",
+			flows:         []oauthFlowInit{stubInit("device", unimplemented), stubInit("pkce", unimplemented)},
+			expectedErr:   "does not support SSO providers",
+			expectedNoSSO: true,
+		},
+	}
+
+	mgmURL, err := url.Parse("https://api.netbird.io:443")
+	require.NoError(t, err)
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			a := &Auth{mgmURL: mgmURL}
+			flow, err := oauthFlowWithFallback(a, nil, tt.flows, "user@example.com", stubAuthFactory(a))
+
+			if tt.expectedErr != "" {
+				require.Error(t, err)
+				assert.Contains(t, err.Error(), tt.expectedErr)
+
+				var ssoUnavailable *ssoUnavailableError
+				assert.Equal(t, tt.expectedNoSSO, errors.As(err, &ssoUnavailable),
+					"terminal SSO-unavailable classification mismatch for %v", err)
+				return
+			}
+
+			require.NoError(t, err)
+			stub := activeStub(t, flow)
+			assert.Equal(t, tt.expectedFlow, stub.name)
+			assert.Equal(t, "user@example.com", stub.hint, "login hint must be passed to the flow")
+		})
+	}
+}
+
+// activeStub unwraps the flow currently in use, which is behind a fallbackFlow whenever an
+// untried flow is left.
+func activeStub(t *testing.T, flow OAuthFlow) *stubFlow {
+	t.Helper()
+
+	if fallback, ok := flow.(*fallbackFlow); ok {
+		flow = fallback.current()
+	}
+
+	stub, ok := flow.(*stubFlow)
+	require.True(t, ok, "unexpected flow type %T", flow)
+	return stub
+}
+
+// TestFallbackFlowRequestAuthInfo covers the failure the RedHat report hit: management hands out
+// a device flow configuration, but the IdP does not serve the grant and only says so when the
+// device code is requested.
+func TestFallbackFlowRequestAuthInfo(t *testing.T) {
+	mgmURL, err := url.Parse("https://api.netbird.io:443")
+	require.NoError(t, err)
+	a := &Auth{mgmURL: mgmURL}
+
+	idpRejects := fmt.Errorf("%w: request device code returned status 404", errFlowNotConfigured)
+
+	t.Run("swaps in the untried flow", func(t *testing.T) {
+		flows := []oauthFlowInit{stubInitFlow("device", nil, idpRejects), stubInit("pkce", nil)}
+
+		flow, err := oauthFlowWithFallback(a, nil, flows, "", stubAuthFactory(a))
+		require.NoError(t, err)
+		require.Equal(t, "device", activeStub(t, flow).name)
+
+		info, err := flow.RequestAuthInfo(context.Background())
+		require.NoError(t, err)
+		assert.Equal(t, "pkce", info.UserCode, "the request must be served by the fallback flow")
+		assert.Equal(t, "pkce", activeStub(t, flow).name, "the fallback flow must stay active for WaitToken")
+	})
+
+	t.Run("keeps the original error when nothing else is configured", func(t *testing.T) {
+		flows := []oauthFlowInit{
+			stubInitFlow("device", nil, idpRejects),
+			stubInit("pkce", status.Error(codes.NotFound, "no pkce authorization flow information available")),
+		}
+
+		flow, err := oauthFlowWithFallback(a, nil, flows, "", stubAuthFactory(a))
+		require.NoError(t, err)
+
+		_, err = flow.RequestAuthInfo(context.Background())
+		require.Error(t, err)
+		assert.Contains(t, err.Error(), "status 404")
+	})
+
+	t.Run("does not swap flows on an unrelated failure", func(t *testing.T) {
+		flows := []oauthFlowInit{
+			stubInitFlow("device", nil, errors.New("timeout talking to the IdP")),
+			stubInit("pkce", nil),
+		}
+
+		flow, err := oauthFlowWithFallback(a, nil, flows, "", stubAuthFactory(a))
+		require.NoError(t, err)
+
+		_, err = flow.RequestAuthInfo(context.Background())
+		require.Error(t, err)
+		assert.Equal(t, "device", activeStub(t, flow).name, "the preferred flow must stay active")
+	})
+}
+
+func TestFlowOrder(t *testing.T) {
+	assert.Equal(t, "pkce authorization flow", flowOrder(false)[0].name)
+	assert.Equal(t, "device code flow", flowOrder(true)[0].name)
+	assert.Len(t, flowOrder(false), 2, "both flows must always be attempted")
+}
+
+func TestPreferDeviceFlow(t *testing.T) {
+	isUnix := runtime.GOOS == "linux" || runtime.GOOS == "freebsd"
+
+	assert.True(t, preferDeviceFlow(true, true), "forced device flow wins over a desktop session")
+	assert.Equal(t, isUnix, preferDeviceFlow(false, false), "headless unix hosts prefer the device flow")
+	assert.False(t, preferDeviceFlow(false, true), "desktop clients prefer PKCE")
+}

client/internal/auth/pkce_flow.go

@@ -62,8 +62,17 @@ type PKCEAuthProviderConfig struct {
 	LoginHint string
 }
 
-// validatePKCEConfig validates PKCE provider configuration
+// validatePKCEConfig validates PKCE provider configuration. A missing value means management
+// does not have this flow configured, so the error wraps errFlowNotConfigured and the caller can
+// fall back to the other flow.
 func validatePKCEConfig(config *PKCEAuthProviderConfig) error {
+	if err := checkPKCEConfig(config); err != nil {
+		return fmt.Errorf("%w: %w", errFlowNotConfigured, err)
+	}
+	return nil
+}
+
+func checkPKCEConfig(config *PKCEAuthProviderConfig) error {
 	errorMsgFormat := "invalid provider configuration received from management: %s value is empty. Contact your NetBird administrator"
 
 	if config.ClientID == "" {

client/internal/debug/debug.go

@@ -34,9 +34,8 @@ import (
 	"github.com/netbirdio/netbird/shared/netiputil"
 )
 
-const readmeContent = `Netbird debug bundle
-This debug bundle contains the following files.
-If the --anonymize flag is set, the files are anonymized to protect sensitive information.
+const readmeContent = `This debug bundle contains the following files.
+If anonymization is enabled (--anonymize / --anonymize-level), the files are anonymized to protect sensitive information.
 
 status.txt: Anonymized status information of the NetBird client.
 client.log: Most recent, anonymized client log file of the NetBird client.
@@ -70,21 +69,34 @@ capture.pcap: Packet capture in pcap format. Only present when capture was runni
 
 
 Anonymization Process
-The files in this bundle have been anonymized to protect sensitive information. Here's how the anonymization was applied:
+The files in this bundle have been anonymized to protect sensitive information. The level applied to this bundle is recorded at the top of this file. Here's how the anonymization was applied:
 
 IP Addresses
 
-IPv4 addresses are replaced with addresses starting from 198.51.100.0
-IPv6 addresses are replaced with addresses starting from 100::
+Default level:
+- Public IPv4 addresses are replaced with addresses starting from 198.51.100.0
+- Public IPv6 addresses are replaced with addresses starting from 2001:db8:ffff::
+- IPv6 unique local addresses (fc00::/7) are anonymized as well: their random global ID uniquely identifies the network.
+- IP addresses from internal IPv4 ranges and well-known addresses are not anonymized (e.g. 8.8.8.8, 100.64.0.0/10, addresses starting with 192.168., 172.16., 10., 169.254., fe80::).
+
+Strict level (--anonymize-level strict), in addition to the default level:
+- Private (RFC 1918), CGNAT (100.64.0.0/10), and link-local (169.254.0.0/16, fe80::/10) addresses are anonymized too.
+- Internal IPv4 addresses are replaced with addresses starting from 198.18.0.0 and internal IPv6 addresses with addresses starting from 2001:db8:1::, so internal addresses remain distinguishable from public ones.
+- Addresses are mapped in order of first appearance: subnet structure, allocation scheme, and gateway conventions are not preserved. Prefix lengths of networks are preserved.
+- Peer names in front of NetBird domains are replaced with numbered placeholders (e.g. peer-1.netbird.cloud), and subdomain labels of other domains with host-N placeholders.
+- WireGuard public keys are replaced with consistent placeholder keys.
 
-IP addresses from non public ranges and well known addresses are not anonymized (e.g. 8.8.8.8, 100.64.0.0/10, addresses starting with 192.168., 172.16., 10., etc.).
 Reoccuring IP addresses are replaced with the same anonymized address.
 
 Note: The anonymized IP addresses in the status file do not match those in the log and routes files. However, the anonymized IP addresses are consistent within the status file and across the routes and log files.
 
+MAC Addresses
+MAC addresses are replaced at every anonymization level with consistent placeholders counting up from 02:00:00:00:00:01. Broadcast, multicast, and all-zero addresses are kept. At the default level a preserved IPv6 link-local address may still embed a MAC address (EUI-64); the strict level anonymizes those addresses.
+
 Domains
 All domain names (except for the netbird domains) are replaced with randomly generated strings ending in ".domain". Anonymized domains are consistent across all files in the bundle.
 Reoccuring domain names are replaced with the same anonymized domain.
+At the strict level, the peer name labels in front of netbird domains are anonymized as well.
 
 Sync Response
 The network_map.json file contains the following anonymized information:
@@ -281,6 +293,7 @@ type BundleGenerator struct {
 	cliVersion     string
 
 	anonymize         bool
+	anonymizeLevel    anonymize.Level
 	includeSystemInfo bool
 	logFileCount      uint32
 
@@ -288,7 +301,10 @@ type BundleGenerator struct {
 }
 
 type BundleConfig struct {
-	Anonymize         bool
+	Anonymize bool
+	// AnonymizeLevel selects how much the anonymizer redacts.
+	// anonymize.LevelStrict implies Anonymize.
+	AnonymizeLevel    anonymize.Level
 	IncludeSystemInfo bool
 	LogFileCount      uint32
 }
@@ -327,8 +343,11 @@ func NewBundleGenerator(deps GeneratorDependencies, cfg BundleConfig) *BundleGen
 		uiLogOpener = openLogFile
 	}
 
+	anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+	anonymizer.SetLevel(cfg.AnonymizeLevel)
+
 	return &BundleGenerator{
-		anonymizer: anonymize.NewAnonymizer(anonymize.DefaultAddresses()),
+		anonymizer: anonymizer,
 
 		internalConfig: deps.InternalConfig,
 		statusRecorder: deps.StatusRecorder,
@@ -345,7 +364,8 @@ func NewBundleGenerator(deps GeneratorDependencies, cfg BundleConfig) *BundleGen
 		daemonVersion:  deps.DaemonVersion,
 		cliVersion:     deps.CliVersion,
 
-		anonymize:         cfg.Anonymize,
+		anonymize:         cfg.Anonymize || cfg.AnonymizeLevel >= anonymize.LevelStrict,
+		anonymizeLevel:    cfg.AnonymizeLevel,
 		includeSystemInfo: cfg.IncludeSystemInfo,
 		logFileCount:      logFileCount,
 	}
@@ -485,7 +505,13 @@ func (g *BundleGenerator) addSystemInfo() {
 }
 
 func (g *BundleGenerator) addReadme() error {
-	readmeReader := strings.NewReader(readmeContent)
+	level := "none (anonymization disabled)"
+	if g.anonymize {
+		level = g.anonymizeLevel.String()
+	}
+	header := fmt.Sprintf("Netbird debug bundle\nAnonymization level applied to this bundle: %s\n", level)
+
+	readmeReader := strings.NewReader(header + readmeContent)
 	if err := g.addFileToZip(readmeReader, "README.txt"); err != nil {
 		return fmt.Errorf("add README file to zip: %w", err)
 	}
@@ -507,9 +533,10 @@ func (g *BundleGenerator) addStatus() error {
 		fullStatus := g.statusRecorder.GetFullStatus()
 		protoFullStatus := nbstatus.ToProtoFullStatus(fullStatus)
 		overview := nbstatus.ConvertToStatusOutputOverview(protoFullStatus, nbstatus.ConvertOptions{
-			Anonymize:     g.anonymize,
-			ProfileName:   profName,
-			DaemonVersion: g.daemonVersion,
+			Anonymize:      g.anonymize,
+			AnonymizeLevel: g.anonymizeLevel,
+			ProfileName:    profName,
+			DaemonVersion:  g.daemonVersion,
 		})
 		overview.CliVersion = g.cliVersion
 		statusOutput := overview.FullDetailSummary()
@@ -662,7 +689,7 @@ func (g *BundleGenerator) addCommonConfigFields(configContent *strings.Builder)
 	configContent.WriteString("NetBird Client Configuration:\n\n")
 
 	if key, err := wgtypes.ParseKey(g.internalConfig.PrivateKey); err == nil {
-		configContent.WriteString(fmt.Sprintf("PublicKey: %s\n", key.PublicKey().String()))
+		configContent.WriteString(fmt.Sprintf("PublicKey: %s\n", g.anonymizer.AnonymizeWGKey(key.PublicKey().String())))
 	}
 	configContent.WriteString(fmt.Sprintf("WgIface: %s\n", g.internalConfig.WgIface))
 	configContent.WriteString(fmt.Sprintf("WgPort: %d\n", g.internalConfig.WgPort))
@@ -952,6 +979,11 @@ func (g *BundleGenerator) addUpdateLogs() error {
 		}
 
 		baseName := filepath.Base(logFile)
+		data, err = g.anonymizeBytes(data)
+		if err != nil {
+			log.Warnf("skipping update log file %s: %v", baseName, err)
+			continue
+		}
 		if err := g.addFileToZip(bytes.NewReader(data), filepath.Join("update-logs", baseName)); err != nil {
 			return fmt.Errorf("add update log file %s to zip: %w", baseName, err)
 		}
@@ -979,6 +1011,13 @@ func (g *BundleGenerator) addCorruptedStateFiles() error {
 		}
 
 		fileName := filepath.Base(match)
+		// Corrupted state files usually fail structured JSON anonymization,
+		// so run them through the string anonymizer instead.
+		data, err = g.anonymizeBytes(data)
+		if err != nil {
+			log.Warnf("skipping corrupted state file %s: %v", fileName, err)
+			continue
+		}
 		if err := g.addFileToZip(bytes.NewReader(data), "corrupted_states/"+fileName); err != nil {
 			log.Warnf("Failed to add corrupted state file %s to zip: %v", fileName, err)
 			continue
@@ -990,6 +1029,27 @@ func (g *BundleGenerator) addCorruptedStateFiles() error {
 	return nil
 }
 
+// anonymizeBytes runs raw file content through the string anonymizer line by
+// line when anonymization is enabled. It errors instead of returning partial
+// content, so a caller never adds an unanonymized fallback to the bundle.
+func (g *BundleGenerator) anonymizeBytes(data []byte) ([]byte, error) {
+	if !g.anonymize {
+		return data, nil
+	}
+
+	var buf bytes.Buffer
+	scanner := bufio.NewScanner(bytes.NewReader(data))
+	scanner.Buffer(make([]byte, 1024*1024), 1024*1024)
+	for scanner.Scan() {
+		buf.WriteString(g.anonymizer.AnonymizeString(scanner.Text()))
+		buf.WriteByte('\n')
+	}
+	if err := scanner.Err(); err != nil {
+		return nil, fmt.Errorf("anonymize content: %w", err)
+	}
+	return buf.Bytes(), nil
+}
+
 func (g *BundleGenerator) addMetrics() error {
 	if g.clientMetrics == nil {
 		log.Debugf("skipping metrics in debug bundle: no metrics collector")
@@ -1462,6 +1522,7 @@ func anonymizeRemotePeer(peer *mgmProto.RemotePeerConfig, anonymizer *anonymize.
 	}
 
 	peer.Fqdn = anonymizer.AnonymizeDomain(peer.Fqdn)
+	peer.WgPubKey = anonymizer.AnonymizeWGKey(peer.WgPubKey)
 
 	anonymizeSSHConfig(peer.SshConfig)
 }

client/internal/debug/debug_linux.go

@@ -844,6 +844,10 @@ func collectSysctls() string {
 		[]string{"net.ipv4.conf.all.src_valid_mark", "net.ipv4.conf.default.src_valid_mark"},
 		listInterfaceSysctls("ipv4", "src_valid_mark")...,
 	))
+	writeSysctlGroup(&builder, "accept_ra", append(
+		[]string{"net.ipv6.conf.all.accept_ra", "net.ipv6.conf.default.accept_ra"},
+		listInterfaceSysctls("ipv6", "accept_ra")...,
+	))
 	writeSysctlGroup(&builder, "conntrack", []string{
 		"net.netfilter.nf_conntrack_acct",
 		"net.netfilter.nf_conntrack_tcp_loose",

client/internal/debug/wgshow.go

@@ -35,14 +35,14 @@ func (g *BundleGenerator) toWGShowFormat(s *configurer.Stats) string {
 	var sb strings.Builder
 
 	sb.WriteString(fmt.Sprintf("interface: %s\n", s.DeviceName))
-	sb.WriteString(fmt.Sprintf("  public key: %s\n", s.PublicKey))
+	sb.WriteString(fmt.Sprintf("  public key: %s\n", g.anonymizer.AnonymizeWGKey(s.PublicKey)))
 	sb.WriteString(fmt.Sprintf("  listen port: %d\n", s.ListenPort))
 	if s.FWMark != 0 {
 		sb.WriteString(fmt.Sprintf("  fwmark: %#x\n", s.FWMark))
 	}
 
 	for _, peer := range s.Peers {
-		sb.WriteString(fmt.Sprintf("\npeer: %s\n", peer.PublicKey))
+		sb.WriteString(fmt.Sprintf("\npeer: %s\n", g.anonymizer.AnonymizeWGKey(peer.PublicKey)))
 		if peer.Endpoint.IP != nil {
 			if g.anonymize {
 				anonEndpoint := g.anonymizer.AnonymizeUDPAddr(peer.Endpoint)
@@ -54,7 +54,11 @@ func (g *BundleGenerator) toWGShowFormat(s *configurer.Stats) string {
 		if len(peer.AllowedIPs) > 0 {
 			var ipStrings []string
 			for _, ipnet := range peer.AllowedIPs {
-				ipStrings = append(ipStrings, ipnet.String())
+				ipStr := ipnet.String()
+				if g.anonymize {
+					ipStr = g.anonymizer.AnonymizeIPString(ipStr)
+				}
+				ipStrings = append(ipStrings, ipStr)
 			}
 			sb.WriteString(fmt.Sprintf("  allowed ips: %s\n", strings.Join(ipStrings, ", ")))
 		}

client/internal/dns/host_darwin.go

@@ -267,18 +267,38 @@ func (s *systemConfigurator) getSystemDNSSettings() (SystemDNSSettings, error) {
 		return SystemDNSSettings{}, fmt.Errorf("sending the command: %w", err)
 	}
 
-	var dnsSettings SystemDNSSettings
+	dnsSettings, serverAddresses, err := parseSystemDNSSettings(b)
+	if err != nil {
+		return dnsSettings, err
+	}
+
+	s.mu.Lock()
+	s.origNameservers = serverAddresses
+	s.mu.Unlock()
+
+	return dnsSettings, nil
+}
+
+// parseSystemDNSSettings parses the output of `scutil show State:/Network/Service/<id>/DNS`.
+// Lines that don't match the expected "index : value" shape are skipped: hosts with unusual
+// network services (e.g. orphaned hardware ports) can produce entries without a value.
+func parseSystemDNSSettings(out []byte) (SystemDNSSettings, []netip.Addr, error) {
+	// port is not exposed by scutil, default to 53
+	dnsSettings := SystemDNSSettings{ServerPort: DefaultPort}
 	var serverAddresses []netip.Addr
 	inSearchDomainsArray := false
 	inServerAddressesArray := false
 
-	scanner := bufio.NewScanner(bytes.NewReader(b))
+	scanner := bufio.NewScanner(bytes.NewReader(out))
 	for scanner.Scan() {
 		line := strings.TrimSpace(scanner.Text())
 		switch {
 		case strings.HasPrefix(line, "DomainName :"):
-			domainName := strings.TrimSpace(strings.Split(line, ":")[1])
-			dnsSettings.Domains = append(dnsSettings.Domains, domainName)
+			domainName := strings.TrimSpace(strings.TrimPrefix(line, "DomainName :"))
+			if domainName != "" {
+				dnsSettings.Domains = append(dnsSettings.Domains, domainName)
+			}
+			continue
 		case line == "SearchDomains : <array> {":
 			inSearchDomainsArray = true
 			continue
@@ -288,36 +308,45 @@ func (s *systemConfigurator) getSystemDNSSettings() (SystemDNSSettings, error) {
 		case line == "}":
 			inSearchDomainsArray = false
 			inServerAddressesArray = false
+			continue
+		}
+
+		if !inSearchDomainsArray && !inServerAddressesArray {
+			continue
+		}
+
+		parts := strings.SplitN(line, " : ", 2)
+		if len(parts) != 2 {
+			log.Debugf("skipping unexpected scutil DNS line %q", line)
+			continue
+		}
+		value := strings.TrimSpace(parts[1])
+		if value == "" {
+			continue
 		}
 
 		if inSearchDomainsArray {
-			searchDomain := strings.Split(line, " : ")[1]
-			dnsSettings.Domains = append(dnsSettings.Domains, searchDomain)
-		} else if inServerAddressesArray {
-			address := strings.Split(line, " : ")[1]
-			if ip, err := netip.ParseAddr(address); err == nil && !ip.IsUnspecified() {
-				ip = ip.Unmap()
-				serverAddresses = append(serverAddresses, ip)
-				// Prefer the first IPv4 server as ServerIP since our DNS listener is IPv4.
-				if !dnsSettings.ServerIP.IsValid() && ip.Is4() {
-					dnsSettings.ServerIP = ip
-				}
-			}
+			dnsSettings.Domains = append(dnsSettings.Domains, value)
+			continue
+		}
+
+		ip, err := netip.ParseAddr(value)
+		if err != nil || ip.IsUnspecified() {
+			continue
+		}
+		ip = ip.Unmap()
+		serverAddresses = append(serverAddresses, ip)
+		// Prefer the first IPv4 server as ServerIP since our DNS listener is IPv4.
+		if !dnsSettings.ServerIP.IsValid() && ip.Is4() {
+			dnsSettings.ServerIP = ip
 		}
 	}
 
 	if err := scanner.Err(); err != nil {
-		return dnsSettings, err
+		return dnsSettings, serverAddresses, err
 	}
 
-	// default to 53 port
-	dnsSettings.ServerPort = DefaultPort
-
-	s.mu.Lock()
-	s.origNameservers = serverAddresses
-	s.mu.Unlock()
-
-	return dnsSettings, nil
+	return dnsSettings, serverAddresses, nil
 }
 
 func (s *systemConfigurator) getOriginalNameservers() []netip.Addr {
@@ -435,11 +464,15 @@ func (s *systemConfigurator) getPrimaryService() (string, string, error) {
 	router := ""
 	for scanner.Scan() {
 		text := scanner.Text()
+		parts := strings.SplitN(text, ":", 2)
+		if len(parts) != 2 {
+			continue
+		}
 		if strings.Contains(text, "PrimaryService") {
-			primaryService = strings.TrimSpace(strings.Split(text, ":")[1])
+			primaryService = strings.TrimSpace(parts[1])
 		}
 		if strings.Contains(text, "Router") {
-			router = strings.TrimSpace(strings.Split(text, ":")[1])
+			router = strings.TrimSpace(parts[1])
 		}
 	}
 	if err := scanner.Err(); err != nil && err != io.EOF {

client/internal/dns/host_darwin_test.go

@@ -328,6 +328,120 @@ func removeTestDNSKey(key string) error {
 	return err
 }
 
+func TestParseSystemDNSSettings(t *testing.T) {
+	tests := []struct {
+		name            string
+		output          string
+		expectedDomains []string
+		expectedServers []netip.Addr
+		expectedIP      netip.Addr
+	}{
+		{
+			name: "well_formed",
+			output: `<dictionary> {
+  DomainName : example.com
+  SearchDomains : <array> {
+    0 : example.com
+    1 : corp.example.com
+  }
+  ServerAddresses : <array> {
+    0 : 192.168.1.1
+    1 : fd00::53
+  }
+}
+`,
+			expectedDomains: []string{"example.com", "example.com", "corp.example.com"},
+			expectedServers: []netip.Addr{netip.MustParseAddr("192.168.1.1"), netip.MustParseAddr("fd00::53")},
+			expectedIP:      netip.MustParseAddr("192.168.1.1"),
+		},
+		{
+			// entries without a value after the separator used to panic with
+			// "index out of range [1] with length 1"
+			name: "malformed_array_entries_skipped",
+			output: `<dictionary> {
+  SearchDomains : <array> {
+    0 :
+    (null)
+
+    1 : corp.example.com
+  }
+  ServerAddresses : <array> {
+    0 :
+    1 : 192.168.1.1
+  }
+}
+`,
+			expectedDomains: []string{"corp.example.com"},
+			expectedServers: []netip.Addr{netip.MustParseAddr("192.168.1.1")},
+			expectedIP:      netip.MustParseAddr("192.168.1.1"),
+		},
+		{
+			name: "domain_name_without_value_skipped",
+			output: `<dictionary> {
+  DomainName :
+  ServerAddresses : <array> {
+    0 : 192.168.1.1
+  }
+}
+`,
+			expectedServers: []netip.Addr{netip.MustParseAddr("192.168.1.1")},
+			expectedIP:      netip.MustParseAddr("192.168.1.1"),
+		},
+		{
+			name: "ipv6_first_prefers_ipv4_server_ip",
+			output: `<dictionary> {
+  ServerAddresses : <array> {
+    0 : fd00::53
+    1 : 192.168.1.1
+  }
+}
+`,
+			expectedServers: []netip.Addr{netip.MustParseAddr("fd00::53"), netip.MustParseAddr("192.168.1.1")},
+			expectedIP:      netip.MustParseAddr("192.168.1.1"),
+		},
+		{
+			name: "invalid_and_unspecified_addresses_skipped",
+			output: `<dictionary> {
+  ServerAddresses : <array> {
+    0 : (null)
+    1 : 0.0.0.0
+    2 : 192.168.1.1
+  }
+}
+`,
+			expectedServers: []netip.Addr{netip.MustParseAddr("192.168.1.1")},
+			expectedIP:      netip.MustParseAddr("192.168.1.1"),
+		},
+		{
+			name: "v4_mapped_address_unmapped",
+			output: `<dictionary> {
+  ServerAddresses : <array> {
+    0 : ::ffff:192.168.1.1
+  }
+}
+`,
+			expectedServers: []netip.Addr{netip.MustParseAddr("192.168.1.1")},
+			expectedIP:      netip.MustParseAddr("192.168.1.1"),
+		},
+		{
+			name:   "empty_output",
+			output: "",
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			settings, servers, err := parseSystemDNSSettings([]byte(tc.output))
+			require.NoError(t, err, "parsing should not fail")
+
+			assert.Equal(t, tc.expectedDomains, settings.Domains, "domains should match")
+			assert.Equal(t, tc.expectedServers, servers, "server addresses should match")
+			assert.Equal(t, tc.expectedIP, settings.ServerIP, "server IP should match")
+			assert.Equal(t, DefaultPort, settings.ServerPort, "server port should default to 53")
+		})
+	}
+}
+
 func TestGetOriginalNameservers(t *testing.T) {
 	configurator := &systemConfigurator{
 		createdKeys: make(map[string]struct{}),

client/internal/engine.go

@@ -23,6 +23,7 @@ import (
 	"golang.zx2c4.com/wireguard/tun/netstack"
 	"golang.zx2c4.com/wireguard/wgctrl/wgtypes"
 
+	"github.com/netbirdio/netbird/client/anonymize"
 	nberrors "github.com/netbirdio/netbird/client/errors"
 	"github.com/netbirdio/netbird/client/firewall"
 	"github.com/netbirdio/netbird/client/firewall/firewalld"
@@ -1385,6 +1386,7 @@ func (e *Engine) handleBundle(params *mgmProto.BundleParameters) (*mgmProto.JobR
 
 	bundleJobParams := debug.BundleConfig{
 		Anonymize:         params.Anonymize,
+		AnonymizeLevel:    anonymize.ParseLevel(params.AnonymizeLevel),
 		IncludeSystemInfo: true,
 		LogFileCount:      uint32(params.LogFileCount),
 	}

client/internal/metrics/connection_type.go

@@ -4,11 +4,17 @@ package metrics
 type ConnectionType string
 
 const (
-	// ConnectionTypeICE represents a direct peer-to-peer connection using ICE
-	ConnectionTypeICE ConnectionType = "ice"
+	// ConnectionTypeICEP2P represents a direct peer-to-peer connection using ICE
+	ConnectionTypeICEP2P ConnectionType = "ice_p2p"
+
+	// ConnectionTypeICETurn represents an ICE connection through a TURN server
+	ConnectionTypeICETurn ConnectionType = "ice_turn"
 
 	// ConnectionTypeRelay represents a relayed connection
 	ConnectionTypeRelay ConnectionType = "relay"
+
+	// ConnectionTypeUnknown represents a connection with no active transport. It is not pushed.
+	ConnectionTypeUnknown ConnectionType = "unknown"
 )
 
 // String returns the string representation of the connection type

client/internal/metrics/influxdb_test.go

@@ -28,7 +28,7 @@ func TestInfluxDBMetrics_RecordAndExport(t *testing.T) {
 		WgHandshakeSuccess: time.Now().Add(-1 * time.Second),
 	}
 
-	m.RecordConnectionStages(context.Background(), agentInfo, "pair123", ConnectionTypeICE, false, ts)
+	m.RecordConnectionStages(context.Background(), agentInfo, "pair123", ConnectionTypeICEP2P, false, ts)
 
 	var buf bytes.Buffer
 	err := m.Export(&buf)
@@ -60,7 +60,7 @@ func TestInfluxDBMetrics_ExportDeterministicFieldOrder(t *testing.T) {
 
 	// Record multiple times and verify consistent field order
 	for i := 0; i < 10; i++ {
-		m.RecordConnectionStages(context.Background(), agentInfo, "pair123", ConnectionTypeICE, false, ts)
+		m.RecordConnectionStages(context.Background(), agentInfo, "pair123", ConnectionTypeICEP2P, false, ts)
 	}
 
 	var buf bytes.Buffer

client/internal/metrics/infra/README.md

@@ -56,14 +56,33 @@ Measurement: `netbird_peer_connection`
 
 Tags:
 - `deployment_type`: "cloud" | "selfhosted" | "unknown"
-- `connection_type`: "ice" | "relay"
+- `connection_type`: "ice_p2p" | "ice_turn" | "relay" (see below)
 - `attempt_type`: "initial" | "reconnection"
 - `version`: NetBird version string
 - `os`: Operating system (linux, darwin, windows, android, ios, etc.)
 - `arch`: CPU architecture (amd64, arm64, etc.)
+- `peer_id`: anonymised peer identifier (truncated SHA-256 of the WireGuard public key)
+- `connection_pair_id`: deterministic identifier for the peer pair, identical on both sides
 
 **Note:** `SignalingReceived` is set when the first offer or answer arrives from the remote peer (in both initial and reconnection paths). It excludes the potentially unbounded wait for the remote peer to come online.
 
+#### `connection_type` values
+
+Derived from the connection priority (`conntype.ConnPriority`) by `metricsConnType` in `client/internal/peer/conn.go`:
+
+| Value | Priority | Traffic is |
+|-------|----------|------------|
+| `ice_p2p` | `ICEP2P` | direct peer-to-peer |
+| `ice_turn` | `ICETurn` | relayed, through a TURN server |
+| `relay` | `Relay` | relayed, through a NetBird relay |
+| `unknown` | `None` or unrecognised | no active transport — **the sample is not pushed** |
+
+**Direct traffic is `ice_p2p` only.** `ice_turn` is relayed despite being negotiated by ICE, matching `Conn.isRelayed`.
+
+`None` means no transport is active: not established yet, or reset after a relay drop or a peer-state reset. Such a sample cannot be attributed to a transport, so `recordConnectionMetrics` drops it instead of pushing it — `unknown` therefore never appears in the bucket. Connection counts are counts of connections whose transport was known at sampling time.
+
+**Samples recorded before 0.77 used a single `ice` value** which covered `ICEP2P`, `ICETurn` *and* `None`, so historical `ice` samples overstate direct connections by an unknown amount and must not be compared with `ice_p2p`.
+
 ### Sync Duration
 
 Measurement: `netbird_sync`

client/internal/peer/conn.go

@@ -307,6 +307,8 @@ func (conn *Conn) Close(signalToRemote bool) {
 
 	if conn.wgWatcherCancel != nil {
 		conn.wgWatcherCancel()
+		conn.wgWatcher = nil
+		conn.wgWatcherCancel = nil
 	}
 	conn.workerRelay.CloseConn()
 	if conn.workerICE != nil {
@@ -959,12 +961,9 @@ func (conn *Conn) recordConnectionMetrics() {
 	priority := conn.currentConnPriority
 	conn.mu.Unlock()
 
-	var connType metrics.ConnectionType
-	switch priority {
-	case conntype.Relay:
-		connType = metrics.ConnectionTypeRelay
-	default:
-		connType = metrics.ConnectionTypeICE
+	connType := metricsConnType(priority)
+	if connType == metrics.ConnectionTypeUnknown {
+		return
 	}
 
 	// Record metrics with timestamps - duration calculation happens in metrics package
@@ -1065,3 +1064,16 @@ func boolToConnStatus(connected bool) guard.ConnStatus {
 	}
 	return guard.ConnStatusDisconnected
 }
+
+func metricsConnType(priority conntype.ConnPriority) metrics.ConnectionType {
+	switch priority {
+	case conntype.Relay:
+		return metrics.ConnectionTypeRelay
+	case conntype.ICETurn:
+		return metrics.ConnectionTypeICETurn
+	case conntype.ICEP2P:
+		return metrics.ConnectionTypeICEP2P
+	default:
+		return metrics.ConnectionTypeUnknown
+	}
+}

client/internal/peer/conn_test.go

@@ -11,6 +11,8 @@ import (
 	"github.com/stretchr/testify/assert"
 
 	"github.com/netbirdio/netbird/client/iface"
+	"github.com/netbirdio/netbird/client/internal/metrics"
+	"github.com/netbirdio/netbird/client/internal/peer/conntype"
 	"github.com/netbirdio/netbird/client/internal/peer/dispatcher"
 	"github.com/netbirdio/netbird/client/internal/peer/guard"
 	"github.com/netbirdio/netbird/client/internal/peer/ice"
@@ -386,3 +388,33 @@ func TestConn_onWGDisconnected_NoEscalationWithoutRosenpass(t *testing.T) {
 	}
 	assert.Empty(t, disconnected, "escalation must be limited to rosenpass connections")
 }
+
+func TestMetricsConnType(t *testing.T) {
+	tests := []struct {
+		name     string
+		priority conntype.ConnPriority
+		expected metrics.ConnectionType
+	}{
+		{"relay", conntype.Relay, metrics.ConnectionTypeRelay},
+		{"ice over turn is relayed, not p2p", conntype.ICETurn, metrics.ConnectionTypeICETurn},
+		{"direct p2p", conntype.ICEP2P, metrics.ConnectionTypeICEP2P},
+		{"unset priority is unknown, not p2p", conntype.None, metrics.ConnectionTypeUnknown},
+		{"unrecognised priority is unknown", conntype.ConnPriority(99), metrics.ConnectionTypeUnknown},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			assert.Equal(t, tc.expected, metricsConnType(tc.priority))
+		})
+	}
+}
+
+func TestMetricsConnType_RelayedMatchesIsRelayed(t *testing.T) {
+	for _, priority := range []conntype.ConnPriority{conntype.None, conntype.Relay, conntype.ICETurn, conntype.ICEP2P} {
+		conn := &Conn{currentConnPriority: priority}
+		tag := metricsConnType(priority)
+		relayedTag := tag == metrics.ConnectionTypeRelay || tag == metrics.ConnectionTypeICETurn
+		assert.Equal(t, conn.isRelayed(), relayedTag,
+			"priority %s: isRelayed and the %q metric tag must agree", priority, tag)
+	}
+}

client/internal/routemanager/ipfwdstate/ipfwdstate.go

@@ -2,54 +2,183 @@ package ipfwdstate
 
 import (
 	"fmt"
+	"sync"
 
 	log "github.com/sirupsen/logrus"
 
 	"github.com/netbirdio/netbird/client/internal/routemanager/systemops"
 )
 
-// IPForwardingState is a struct that keeps track of the IP forwarding state.
-// todo: read initial state of the IP forwarding from the system and reset the state based on it.
-// todo: separate v4/v6 forwarding state, since the sysctls are independent
-// (net.ipv4.ip_forward vs net.ipv6.conf.all.forwarding). Currently the nftables
-// manager shares one instance between both routers, which works only because
-// EnableIPForwarding enables both sysctls in a single call.
+// IPForwardingState tracks v4 and v6 IP-forwarding sysctl enables with
+// independent refcounts so a v4-only routing setup doesn't flip v6 sysctls.
 type IPForwardingState struct {
-	enabledCounter int
+	mu sync.Mutex
+
+	v4Count int
+	v6Count int
+
+	// routingV4/routingV6 track whether the routing path currently holds a
+	// reference, so repeated EnableRouting calls (one per network-map update)
+	// hold at most one reference per family and an unpaired DisableRouting
+	// can't release references held by DNAT rules.
+	routingV4 bool
+	routingV6 bool
+
+	wgIfaceName string
+	v6Saved     map[string]int
 }
 
-func NewIPForwardingState() *IPForwardingState {
-	return &IPForwardingState{}
+// NewIPForwardingState returns a state tracker for the IP-forwarding sysctls.
+// wgIfaceName is excluded from the per-interface accept_ra handling.
+func NewIPForwardingState(wgIfaceName string) *IPForwardingState {
+	return &IPForwardingState{wgIfaceName: wgIfaceName}
 }
 
-func (f *IPForwardingState) RequestForwarding() error {
-	if f.enabledCounter != 0 {
-		f.enabledCounter++
+// Counts returns the current v4 and v6 refcounts. Intended for diagnostics
+// and tests.
+func (f *IPForwardingState) Counts() (v4, v6 int) {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+	return f.v4Count, f.v6Count
+}
+
+// RequestRouting takes the forwarding references for the routing path. It is
+// idempotent: while routing already holds a reference, further calls don't
+// increment the refcounts, and a v4-only request releases a previously held v6
+// reference. A v6 sysctl failure is logged and not returned so it can't take
+// down v4 routing (the sysctl may be unwritable, e.g. read-only /proc/sys or
+// IPv6 disabled on the kernel command line); v6 is retried on the next call.
+func (f *IPForwardingState) RequestRouting(v6 bool) error {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+
+	if !f.routingV4 {
+		if err := f.requestV4(); err != nil {
+			return err
+		}
+		f.routingV4 = true
+	}
+
+	if !v6 {
+		if !f.routingV6 {
+			return nil
+		}
+		f.routingV6 = false
+		return f.releaseV6()
+	}
+
+	if f.routingV6 {
 		return nil
 	}
-
-	if err := systemops.EnableIPForwarding(); err != nil {
-		return fmt.Errorf("failed to enable IP forwarding with sysctl: %w", err)
+	if err := f.requestV6(); err != nil {
+		log.Warnf("enable IPv6 forwarding for routing: %v", err)
+		return nil
 	}
-	f.enabledCounter = 1
-	log.Info("IP forwarding enabled")
-
+	f.routingV6 = true
 	return nil
 }
 
-func (f *IPForwardingState) ReleaseForwarding() error {
-	if f.enabledCounter == 0 {
-		return nil
+// ReleaseRouting releases the references RequestRouting holds. Calls without a
+// held reference are no-ops.
+func (f *IPForwardingState) ReleaseRouting() error {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+
+	if f.routingV4 {
+		f.routingV4 = false
+		f.releaseV4()
 	}
-
-	if f.enabledCounter > 1 {
-		f.enabledCounter--
-		return nil
+	if f.routingV6 {
+		f.routingV6 = false
+		return f.releaseV6()
 	}
-
-	// if failed to disable IP forwarding we anyway decrement the counter
-	f.enabledCounter = 0
-
-	// todo call systemops.DisableIPForwarding()
+	return nil
+}
+
+// RequestForwarding enables the family's forwarding sysctl on first request.
+func (f *IPForwardingState) RequestForwarding(v6 bool) error {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+
+	if v6 {
+		return f.requestV6()
+	}
+	return f.requestV4()
+}
+
+// ReleaseForwarding decrements the family counter. The last v6 release restores
+// what enable captured. v4 stays on: net.ipv4.ip_forward is co-owned by other
+// tooling (docker, k8s, libvirt).
+func (f *IPForwardingState) ReleaseForwarding(v6 bool) error {
+	f.mu.Lock()
+	defer f.mu.Unlock()
+
+	if v6 {
+		return f.releaseV6()
+	}
+	f.releaseV4()
+	return nil
+}
+
+func (f *IPForwardingState) requestV4() error {
+	if f.v4Count == 0 {
+		if err := systemops.EnableV4IPForwarding(); err != nil {
+			return fmt.Errorf("enable IPv4 forwarding: %w", err)
+		}
+		log.Info("IPv4 forwarding enabled")
+	}
+	f.v4Count++
+	return nil
+}
+
+func (f *IPForwardingState) releaseV4() {
+	if f.v4Count > 0 {
+		f.v4Count--
+	}
+}
+
+func (f *IPForwardingState) requestV6() error {
+	if f.v6Count == 0 {
+		saved, err := systemops.EnableV6IPForwarding(f.wgIfaceName)
+		if err != nil {
+			if rerr := systemops.DisableV6IPForwarding(saved); rerr != nil {
+				log.Warnf("rollback partial v6 sysctls: %v", rerr)
+			}
+			return fmt.Errorf("enable IPv6 forwarding: %w", err)
+		}
+		// A failed restore on a previous release keeps its saved values; those
+		// are the true originals, so keep them over what this enable captured.
+		if f.v6Saved == nil {
+			f.v6Saved = saved
+		} else {
+			for k, v := range saved {
+				if _, ok := f.v6Saved[k]; !ok {
+					f.v6Saved[k] = v
+				}
+			}
+		}
+		log.Info("IPv6 forwarding enabled")
+	}
+	f.v6Count++
+	return nil
+}
+
+func (f *IPForwardingState) releaseV6() error {
+	if f.v6Count == 0 {
+		return nil
+	}
+	f.v6Count--
+	if f.v6Count > 0 {
+		return nil
+	}
+
+	// Keep the saved values on failure so a later release or enable/release
+	// cycle can still restore them; re-restoring an already-restored key is a
+	// no-op since the sysctl already holds the desired value.
+	if err := systemops.DisableV6IPForwarding(f.v6Saved); err != nil {
+		return fmt.Errorf("disable IPv6 forwarding: %w", err)
+	}
+	f.v6Saved = nil
+	log.Info("IPv6 forwarding disabled")
 	return nil
 }

client/internal/routemanager/ipfwdstate/ipfwdstate_privileged_linux_test.go

@@ -0,0 +1,39 @@
+//go:build privileged
+
+package ipfwdstate
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// TestRequestRoutingV6ToV4Transition verifies that a v4-only routing request
+// releases a previously held routing-owned v6 reference without touching
+// references held by DNAT rules.
+func TestRequestRoutingV6ToV4Transition(t *testing.T) {
+	f := NewIPForwardingState("wt-fwd-test")
+
+	require.NoError(t, f.RequestRouting(true), "request routing with v6")
+	v4, v6 := f.Counts()
+	assert.Equal(t, 1, v4, "v4 reference held")
+	assert.Equal(t, 1, v6, "v6 reference held")
+
+	require.NoError(t, f.RequestRouting(false), "request routing v4-only")
+	v4, v6 = f.Counts()
+	assert.Equal(t, 1, v4, "v4 reference kept")
+	assert.Equal(t, 0, v6, "routing-owned v6 reference released")
+
+	// A DNAT-held reference survives a v4-only routing request.
+	require.NoError(t, f.RequestForwarding(true), "dnat v6 reference")
+	require.NoError(t, f.RequestRouting(false), "repeat v4-only request")
+	_, v6 = f.Counts()
+	assert.Equal(t, 1, v6, "dnat-held v6 reference survives")
+	require.NoError(t, f.ReleaseForwarding(true), "release dnat v6 reference")
+
+	require.NoError(t, f.ReleaseRouting(), "release routing")
+	v4, v6 = f.Counts()
+	assert.Equal(t, 0, v4, "all v4 references released")
+	assert.Equal(t, 0, v6, "all v6 references released")
+}

client/internal/routemanager/sysctl/sysctl_linux.go

@@ -58,11 +58,7 @@ func Setup(wgIface iface) (map[string]int, error) {
 			continue
 		}
 
-		// Escape '%' and '.' so they survive the dot-to-slash conversion in Set()
-		safeName := strings.ReplaceAll(intf.Name, "%", percentEscape)
-		safeName = strings.ReplaceAll(safeName, ".", dotEscape)
-
-		i := fmt.Sprintf(rpFilterInterfacePath, safeName)
+		i := fmt.Sprintf(rpFilterInterfacePath, EscapeInterfaceName(intf.Name))
 		oldVal, err := Set(i, 2, true)
 		if err != nil {
 			result = multierror.Append(result, err)
@@ -74,6 +70,13 @@ func Setup(wgIface iface) (map[string]int, error) {
 	return keys, nberrors.FormatErrorOrNil(result)
 }
 
+// EscapeInterfaceName escapes '%' and '.' in an interface name (e.g. VLANs
+// like eth0.100) so the name survives the dot-to-slash conversion in Set.
+func EscapeInterfaceName(name string) string {
+	safe := strings.ReplaceAll(name, "%", percentEscape)
+	return strings.ReplaceAll(safe, ".", dotEscape)
+}
+
 // Set sets a sysctl configuration, if onlyIfOne is true it will only set the new value if it's set to 1
 func Set(key string, desiredValue int, onlyIfOne bool) (int, error) {
 	path := strings.ReplaceAll(key, ".", "/")

client/internal/routemanager/systemops/systemops_android.go

@@ -32,8 +32,17 @@ func (r *SysOps) removeFromRouteTable(netip.Prefix, Nexthop) error {
 	return nil
 }
 
-func EnableIPForwarding() error {
-	log.Infof("Enable IP forwarding is not implemented on %s", runtime.GOOS)
+func EnableV4IPForwarding() error {
+	log.Infof("Enable IPv4 forwarding is not implemented on %s", runtime.GOOS)
+	return nil
+}
+
+func EnableV6IPForwarding(string) (map[string]int, error) {
+	log.Infof("Enable IPv6 forwarding is not implemented on %s", runtime.GOOS)
+	return map[string]int{}, nil
+}
+
+func DisableV6IPForwarding(map[string]int) error {
 	return nil
 }
 

client/internal/routemanager/systemops/systemops_ios.go

@@ -58,8 +58,17 @@ func (r *SysOps) removeFromRouteTable(netip.Prefix, Nexthop) error {
 	return nil
 }
 
-func EnableIPForwarding() error {
-	log.Infof("Enable IP forwarding is not implemented on %s", runtime.GOOS)
+func EnableV4IPForwarding() error {
+	log.Infof("Enable IPv4 forwarding is not implemented on %s", runtime.GOOS)
+	return nil
+}
+
+func EnableV6IPForwarding(string) (map[string]int, error) {
+	log.Infof("Enable IPv6 forwarding is not implemented on %s", runtime.GOOS)
+	return map[string]int{}, nil
+}
+
+func DisableV6IPForwarding(map[string]int) error {
 	return nil
 }
 

client/internal/routemanager/systemops/systemops_linux.go

@@ -763,13 +763,10 @@ func flushRoutes(tableID, family int) error {
 	return nberrors.FormatErrorOrNil(result)
 }
 
-func EnableIPForwarding() error {
+func EnableV4IPForwarding() error {
 	if _, err := sysctl.Set(ipv4ForwardingPath, 1, false); err != nil {
 		return err
 	}
-	if _, err := sysctl.Set(ipv6ForwardingPath, 1, false); err != nil {
-		log.Warnf("failed to enable IPv6 forwarding: %v", err)
-	}
 	return nil
 }
 

client/internal/routemanager/systemops/systemops_nonlinux.go

@@ -43,8 +43,17 @@ func (r *SysOps) RemoveVPNRoute(prefix netip.Prefix, intf *net.Interface) error
 	return r.genericRemoveVPNRoute(prefix, intf)
 }
 
-func EnableIPForwarding() error {
-	log.Infof("Enable IP forwarding is not implemented on %s", runtime.GOOS)
+func EnableV4IPForwarding() error {
+	log.Infof("Enable IPv4 forwarding is not implemented on %s", runtime.GOOS)
+	return nil
+}
+
+func EnableV6IPForwarding(string) (map[string]int, error) {
+	log.Infof("Enable IPv6 forwarding is not implemented on %s", runtime.GOOS)
+	return map[string]int{}, nil
+}
+
+func DisableV6IPForwarding(map[string]int) error {
 	return nil
 }
 

client/internal/routemanager/systemops/v6forwarding_linux.go

@@ -0,0 +1,92 @@
+//go:build !android
+
+package systemops
+
+import (
+	"fmt"
+	"net"
+	"os"
+
+	"github.com/hashicorp/go-multierror"
+	log "github.com/sirupsen/logrus"
+
+	nberrors "github.com/netbirdio/netbird/client/errors"
+	"github.com/netbirdio/netbird/client/internal/routemanager/sysctl"
+)
+
+const (
+	// 1 (default) accepts RAs only while forwarding is off; 2 keeps RA
+	// acceptance on regardless, so RA-installed host defaults survive our
+	// v6 forwarding flip.
+	acceptRAInterfacePath  = "net.ipv6.conf.%s.accept_ra"
+	acceptRADefaultPath    = "net.ipv6.conf.default.accept_ra"
+	acceptRAProcPathFormat = "/proc/sys/net/ipv6/conf/%s/accept_ra"
+)
+
+// EnableV6IPForwarding bumps accept_ra=2 on host v6 interfaces before flipping
+// forwarding=1, so RA-installed host defaults survive. Returns the prior values
+// of sysctls we actually changed; entries already at the target are omitted.
+func EnableV6IPForwarding(wgIfaceName string) (map[string]int, error) {
+	saved := map[string]int{}
+	bumpAcceptRA(saved, wgIfaceName)
+
+	oldVal, err := sysctl.Set(ipv6ForwardingPath, 1, false)
+	if err != nil {
+		return saved, err
+	}
+	if oldVal != 1 {
+		saved[ipv6ForwardingPath] = oldVal
+	}
+	return saved, nil
+}
+
+// DisableV6IPForwarding restores what EnableV6IPForwarding captured.
+func DisableV6IPForwarding(saved map[string]int) error {
+	var result *multierror.Error
+	for key, value := range saved {
+		if _, err := sysctl.Set(key, value, false); err != nil {
+			result = multierror.Append(result, fmt.Errorf("restore %s: %w", key, err))
+		}
+	}
+	return nberrors.FormatErrorOrNil(result)
+}
+
+func bumpAcceptRA(saved map[string]int, wgIfaceName string) {
+	// Also bump conf.default so interfaces created while forwarding is on
+	// (hotplug, new Wi-Fi/dock) inherit accept_ra=2 and keep accepting RAs.
+	bumpAcceptRAKey(saved, acceptRADefaultPath)
+
+	interfaces, err := net.Interfaces()
+	if err != nil {
+		log.Warnf("list interfaces for accept_ra: %v", err)
+		return
+	}
+	for _, intf := range interfaces {
+		if intf.Name == "lo" || intf.Name == wgIfaceName {
+			continue
+		}
+		bumpAcceptRAForInterface(saved, intf.Name)
+	}
+}
+
+func bumpAcceptRAForInterface(saved map[string]int, name string) {
+	// Build procfs path from name, not the dotted key: VLAN names like eth0.100.
+	if _, err := os.Stat(fmt.Sprintf(acceptRAProcPathFormat, name)); err != nil {
+		return
+	}
+	bumpAcceptRAKey(saved, fmt.Sprintf(acceptRAInterfacePath, sysctl.EscapeInterfaceName(name)))
+}
+
+func bumpAcceptRAKey(saved map[string]int, key string) {
+	// onlyIfOne=true: leave admin overrides (0, 2) alone.
+	oldVal, err := sysctl.Set(key, 2, true)
+	if err != nil {
+		log.Warnf("bump %s: %v", key, err)
+		return
+	}
+	// With onlyIfOne, a write only happened when the old value was 1; values
+	// left untouched (0, 2) must not be recorded for restore.
+	if oldVal == 1 {
+		saved[key] = oldVal
+	}
+}

client/ios/NetBirdSDK/client.go

@@ -14,6 +14,7 @@ import (
 
 	log "github.com/sirupsen/logrus"
 
+	nbAnonymize "github.com/netbirdio/netbird/client/anonymize"
 	"github.com/netbirdio/netbird/client/internal"
 	"github.com/netbirdio/netbird/client/internal/auth"
 	"github.com/netbirdio/netbird/client/internal/debug"
@@ -28,6 +29,13 @@ import (
 	types "github.com/netbirdio/netbird/upload-server/types"
 )
 
+// AnonymizeLevelDefault and AnonymizeLevelStrict are the accepted
+// anonymizeLevel values for DebugBundle.
+const (
+	AnonymizeLevelDefault = nbAnonymize.LevelDefaultString
+	AnonymizeLevelStrict  = nbAnonymize.LevelStrictString
+)
+
 // ConnectionListener export internal Listener for mobile
 type ConnectionListener interface {
 	peer.Listener
@@ -200,8 +208,10 @@ func (c *Client) Stop() {
 // DebugBundle generates a debug bundle, uploads it and returns the upload key.
 // It works with or without a running engine: when the engine is up it reuses
 // the live config, sync response and client metrics; otherwise it loads the
-// config from disk (or the preloaded tvOS config).
-func (c *Client) DebugBundle(anonymize bool) (string, error) {
+// config from disk (or the preloaded tvOS config). anonymizeLevel is "default"
+// or "strict"; strict also anonymizes internal IP ranges, peer names, and
+// WireGuard public keys, and implies anonymize.
+func (c *Client) DebugBundle(anonymize bool, anonymizeLevel string) (string, error) {
 	cfg, cc := c.stateSnapshot()
 
 	// If the engine hasn't been started, load config so we can reach management.
@@ -251,6 +261,7 @@ func (c *Client) DebugBundle(anonymize bool) (string, error) {
 		deps,
 		debug.BundleConfig{
 			Anonymize:         anonymize,
+			AnonymizeLevel:    nbAnonymize.ParseLevel(anonymizeLevel),
 			IncludeSystemInfo: true,
 		},
 	)

client/proto/daemon.pb.go

@@ -2781,6 +2781,11 @@ type DebugBundleRequest struct {
 	// untrusted TLS certificate. Restricted to privileged callers; for
 	// self-hosted upload servers.
 	UploadInsecure bool `protobuf:"varint,7,opt,name=uploadInsecure,proto3" json:"uploadInsecure,omitempty"`
+	// anonymizeLevel selects how much the anonymizer redacts: "default"
+	// (or empty) keeps internal IP ranges, "strict" also anonymizes them.
+	// Unknown values are treated as "strict". Only meaningful with anonymize;
+	// "strict" implies it.
+	AnonymizeLevel string `protobuf:"bytes,8,opt,name=anonymizeLevel,proto3" json:"anonymizeLevel,omitempty"`
 	unknownFields  protoimpl.UnknownFields
 	sizeCache      protoimpl.SizeCache
 }
@@ -2857,6 +2862,13 @@ func (x *DebugBundleRequest) GetUploadInsecure() bool {
 	return false
 }
 
+func (x *DebugBundleRequest) GetAnonymizeLevel() string {
+	if x != nil {
+		return x.AnonymizeLevel
+	}
+	return ""
+}
+
 type DebugBundleResponse struct {
 	state               protoimpl.MessageState `protogen:"open.v1"`
 	Path                string                 `protobuf:"bytes,1,opt,name=path,proto3" json:"path,omitempty"`
@@ -5616,9 +5628,13 @@ func (x *GetPeerSSHHostKeyResponse) GetFound() bool {
 type RequestJWTAuthRequest struct {
 	state protoimpl.MessageState `protogen:"open.v1"`
 	// hint for OIDC login_hint parameter (typically email address)
-	Hint          *string `protobuf:"bytes,1,opt,name=hint,proto3,oneof" json:"hint,omitempty"`
-	unknownFields protoimpl.UnknownFields
-	sizeCache     protoimpl.SizeCache
+	Hint *string `protobuf:"bytes,1,opt,name=hint,proto3,oneof" json:"hint,omitempty"`
+	// hasGraphicalSession tells the daemon that the caller has a graphical session,
+	// which decides whether PKCE or the device code flow is preferred. The daemon
+	// cannot detect this itself: it does not inherit the session environment.
+	HasGraphicalSession bool `protobuf:"varint,2,opt,name=hasGraphicalSession,proto3" json:"hasGraphicalSession,omitempty"`
+	unknownFields       protoimpl.UnknownFields
+	sizeCache           protoimpl.SizeCache
 }
 
 func (x *RequestJWTAuthRequest) Reset() {
@@ -5658,6 +5674,13 @@ func (x *RequestJWTAuthRequest) GetHint() string {
 	return ""
 }
 
+func (x *RequestJWTAuthRequest) GetHasGraphicalSession() bool {
+	if x != nil {
+		return x.HasGraphicalSession
+	}
+	return false
+}
+
 // RequestJWTAuthResponse contains authentication flow information
 type RequestJWTAuthResponse struct {
 	state protoimpl.MessageState `protogen:"open.v1"`
@@ -5882,9 +5905,13 @@ type RequestExtendAuthSessionRequest struct {
 	state protoimpl.MessageState `protogen:"open.v1"`
 	// Optional OIDC login_hint (typically the user's email) to pre-fill the
 	// IdP login form.
-	Hint          *string `protobuf:"bytes,1,opt,name=hint,proto3,oneof" json:"hint,omitempty"`
-	unknownFields protoimpl.UnknownFields
-	sizeCache     protoimpl.SizeCache
+	Hint *string `protobuf:"bytes,1,opt,name=hint,proto3,oneof" json:"hint,omitempty"`
+	// hasGraphicalSession tells the daemon that the caller has a graphical session,
+	// which decides whether PKCE or the device code flow is preferred. The daemon
+	// cannot detect this itself: it does not inherit the session environment.
+	HasGraphicalSession bool `protobuf:"varint,2,opt,name=hasGraphicalSession,proto3" json:"hasGraphicalSession,omitempty"`
+	unknownFields       protoimpl.UnknownFields
+	sizeCache           protoimpl.SizeCache
 }
 
 func (x *RequestExtendAuthSessionRequest) Reset() {
@@ -5924,6 +5951,13 @@ func (x *RequestExtendAuthSessionRequest) GetHint() string {
 	return ""
 }
 
+func (x *RequestExtendAuthSessionRequest) GetHasGraphicalSession() bool {
+	if x != nil {
+		return x.HasGraphicalSession
+	}
+	return false
+}
+
 // RequestExtendAuthSessionResponse carries the verification URI the UI
 // should open in a browser. The daemon retains the flow state and resolves
 // it via WaitExtendAuthSession.
@@ -7253,7 +7287,7 @@ const file_daemon_proto_rawDesc = "" +
 	"\x12translatedHostname\x18\x04 \x01(\tR\x12translatedHostname\x128\n" +
 	"\x0etranslatedPort\x18\x05 \x01(\v2\x10.daemon.PortInfoR\x0etranslatedPort\"G\n" +
 	"\x17ForwardingRulesResponse\x12,\n" +
-	"\x05rules\x18\x01 \x03(\v2\x16.daemon.ForwardingRuleR\x05rules\"\xdc\x01\n" +
+	"\x05rules\x18\x01 \x03(\v2\x16.daemon.ForwardingRuleR\x05rules\"\x84\x02\n" +
 	"\x12DebugBundleRequest\x12\x1c\n" +
 	"\tanonymize\x18\x01 \x01(\bR\tanonymize\x12\x1e\n" +
 	"\n" +
@@ -7264,7 +7298,8 @@ const file_daemon_proto_rawDesc = "" +
 	"\n" +
 	"cliVersion\x18\x06 \x01(\tR\n" +
 	"cliVersion\x12&\n" +
-	"\x0euploadInsecure\x18\a \x01(\bR\x0euploadInsecure\"}\n" +
+	"\x0euploadInsecure\x18\a \x01(\bR\x0euploadInsecure\x12&\n" +
+	"\x0eanonymizeLevel\x18\b \x01(\tR\x0eanonymizeLevel\"}\n" +
 	"\x13DebugBundleResponse\x12\x12\n" +
 	"\x04path\x18\x01 \x01(\tR\x04path\x12 \n" +
 	"\vuploadedKey\x18\x02 \x01(\tR\vuploadedKey\x120\n" +
@@ -7490,9 +7525,10 @@ const file_daemon_proto_rawDesc = "" +
 	"sshHostKey\x12\x16\n" +
 	"\x06peerIP\x18\x02 \x01(\tR\x06peerIP\x12\x1a\n" +
 	"\bpeerFQDN\x18\x03 \x01(\tR\bpeerFQDN\x12\x14\n" +
-	"\x05found\x18\x04 \x01(\bR\x05found\"9\n" +
+	"\x05found\x18\x04 \x01(\bR\x05found\"k\n" +
 	"\x15RequestJWTAuthRequest\x12\x17\n" +
-	"\x04hint\x18\x01 \x01(\tH\x00R\x04hint\x88\x01\x01B\a\n" +
+	"\x04hint\x18\x01 \x01(\tH\x00R\x04hint\x88\x01\x01\x120\n" +
+	"\x13hasGraphicalSession\x18\x02 \x01(\bR\x13hasGraphicalSessionB\a\n" +
 	"\x05_hint\"\x9a\x02\n" +
 	"\x16RequestJWTAuthResponse\x12(\n" +
 	"\x0fverificationURI\x18\x01 \x01(\tR\x0fverificationURI\x128\n" +
@@ -7512,9 +7548,10 @@ const file_daemon_proto_rawDesc = "" +
 	"\x14WaitJWTTokenResponse\x12\x14\n" +
 	"\x05token\x18\x01 \x01(\tR\x05token\x12\x1c\n" +
 	"\ttokenType\x18\x02 \x01(\tR\ttokenType\x12\x1c\n" +
-	"\texpiresIn\x18\x03 \x01(\x03R\texpiresIn\"C\n" +
+	"\texpiresIn\x18\x03 \x01(\x03R\texpiresIn\"u\n" +
 	"\x1fRequestExtendAuthSessionRequest\x12\x17\n" +
-	"\x04hint\x18\x01 \x01(\tH\x00R\x04hint\x88\x01\x01B\a\n" +
+	"\x04hint\x18\x01 \x01(\tH\x00R\x04hint\x88\x01\x01\x120\n" +
+	"\x13hasGraphicalSession\x18\x02 \x01(\bR\x13hasGraphicalSessionB\a\n" +
 	"\x05_hint\"\xe0\x01\n" +
 	" RequestExtendAuthSessionResponse\x12(\n" +
 	"\x0fverificationURI\x18\x01 \x01(\tR\x0fverificationURI\x128\n" +

client/proto/daemon.proto

@@ -540,6 +540,11 @@ message DebugBundleRequest {
   // untrusted TLS certificate. Restricted to privileged callers; for
   // self-hosted upload servers.
   bool uploadInsecure = 7;
+  // anonymizeLevel selects how much the anonymizer redacts: "default"
+  // (or empty) keeps internal IP ranges, "strict" also anonymizes them.
+  // Unknown values are treated as "strict". Only meaningful with anonymize;
+  // "strict" implies it.
+  string anonymizeLevel = 8;
 }
 
 message DebugBundleResponse {
@@ -889,6 +894,10 @@ message GetPeerSSHHostKeyResponse {
 message RequestJWTAuthRequest {
   // hint for OIDC login_hint parameter (typically email address)
   optional string hint = 1;
+  // hasGraphicalSession tells the daemon that the caller has a graphical session,
+  // which decides whether PKCE or the device code flow is preferred. The daemon
+  // cannot detect this itself: it does not inherit the session environment.
+  bool hasGraphicalSession = 2;
 }
 
 // RequestJWTAuthResponse contains authentication flow information
@@ -932,6 +941,10 @@ message RequestExtendAuthSessionRequest {
   // Optional OIDC login_hint (typically the user's email) to pre-fill the
   // IdP login form.
   optional string hint = 1;
+  // hasGraphicalSession tells the daemon that the caller has a graphical session,
+  // which decides whether PKCE or the device code flow is preferred. The daemon
+  // cannot detect this itself: it does not inherit the session environment.
+  bool hasGraphicalSession = 2;
 }
 
 // RequestExtendAuthSessionResponse carries the verification URI the UI

client/server/debug.go

@@ -16,6 +16,7 @@ import (
 	"google.golang.org/grpc/codes"
 	gstatus "google.golang.org/grpc/status"
 
+	"github.com/netbirdio/netbird/client/anonymize"
 	"github.com/netbirdio/netbird/client/internal/debug"
 	"github.com/netbirdio/netbird/client/internal/ipcauth"
 	"github.com/netbirdio/netbird/client/proto"
@@ -122,6 +123,7 @@ func (s *Server) generateDebugBundle(req *proto.DebugBundleRequest, uiOpener deb
 		},
 		debug.BundleConfig{
 			Anonymize:         req.GetAnonymize(),
+			AnonymizeLevel:    anonymize.ParseLevel(req.GetAnonymizeLevel()),
 			IncludeSystemInfo: req.GetSystemInfo(),
 			LogFileCount:      req.GetLogFileCount(),
 		},

client/server/server.go

@@ -682,6 +682,11 @@ func (s *Server) Login(callerCtx context.Context, msg *proto.LoginRequest) (*pro
 		oAuthFlow, err := auth.NewOAuthFlow(ctx, config, msg.IsUnixDesktopClient, false, hint)
 		if err != nil {
 			state.Set(internal.StatusLoginFailed)
+			// enrolling a device is the one flow a setup key can replace
+			if auth.IsSSOUnavailable(err) {
+				return nil, fmt.Errorf("%w. Set this device up with a setup key instead: "+
+					"https://docs.netbird.io/how-to/register-machines-using-setup-keys", err)
+			}
 			return nil, err
 		}
 
@@ -1723,8 +1728,8 @@ func (s *Server) RequestJWTAuth(
 		hint = profilemanager.GetLoginHint()
 	}
 
-	isDesktop := isUnixRunningDesktop()
-	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, isDesktop, false, hint)
+	// the daemon has no graphical session of its own, only the caller can answer this
+	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, msg.GetHasGraphicalSession(), false, hint)
 	if err != nil {
 		return nil, gstatus.Errorf(codes.Internal, "failed to create OAuth flow: %v", err)
 	}
@@ -1827,8 +1832,8 @@ func (s *Server) RequestExtendAuthSession(
 		hint = profilemanager.GetLoginHint()
 	}
 
-	isDesktop := isUnixRunningDesktop()
-	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, isDesktop, false, hint)
+	// the daemon has no graphical session of its own, only the caller can answer this
+	oAuthFlow, err := auth.NewOAuthFlow(ctx, config, msg.GetHasGraphicalSession(), false, hint)
 	if err != nil {
 		return nil, gstatus.Errorf(codes.Internal, "failed to create OAuth flow: %v", err)
 	}
@@ -2000,13 +2005,6 @@ func (s *Server) ExposeService(req *proto.ExposeServiceRequest, srv proto.Daemon
 	return nil
 }
 
-func isUnixRunningDesktop() bool {
-	if runtime.GOOS != "linux" && runtime.GOOS != "freebsd" {
-		return false
-	}
-	return os.Getenv("DESKTOP_SESSION") != "" || os.Getenv("XDG_CURRENT_DESKTOP") != ""
-}
-
 func (s *Server) runProbes(ctx context.Context, waitForProbeResult bool) {
 	if s.connectClient == nil {
 		return

client/ssh/common.go

@@ -13,6 +13,7 @@ import (
 	"golang.org/x/crypto/ssh"
 
 	"github.com/netbirdio/netbird/client/proto"
+	"github.com/netbirdio/netbird/util"
 )
 
 const (
@@ -92,7 +93,8 @@ func printAuthInstructions(stderr io.Writer, authResponse *proto.RequestJWTAuthR
 
 // RequestJWTToken requests or retrieves a JWT token for SSH authentication
 func RequestJWTToken(ctx context.Context, client proto.DaemonServiceClient, stdout, stderr io.Writer, useCache bool, hint string, openBrowser func(string) error) (string, error) {
-	req := &proto.RequestJWTAuthRequest{}
+	// the ssh client runs in the user's session, the daemon does not: tell it what we can see
+	req := &proto.RequestJWTAuthRequest{HasGraphicalSession: util.HasGraphicalSession()}
 	if hint != "" {
 		req.Hint = &hint
 	}
@@ -193,4 +195,3 @@ func buildAddressList(hostname string, remote net.Addr) []string {
 	}
 	return addresses
 }
-

client/ssh/server/command_execution_windows.go

@@ -243,7 +243,7 @@ func (s *Server) setUserEnvironmentVariables(envMap map[string]string, userProfi
 
 // prepareCommandEnv prepares environment variables for command execution on Windows
 func (s *Server) prepareCommandEnv(logger *log.Entry, localUser *user.User, session ssh.Session) []string {
-	username, domain := s.parseUsername(localUser.Username)
+	username, domain := parseUsername(localUser.Username)
 	userEnv, err := s.getUserEnvironment(logger, username, domain)
 	if err != nil {
 		log.Debugf("failed to get user environment for %s\\%s, using fallback: %v", domain, username, err)
@@ -383,7 +383,7 @@ func (s *Server) executeCommandWithPty(logger *log.Entry, session ssh.Session, _
 		return false
 	}
 
-	username, domain := s.parseUsername(localUser.Username)
+	username, domain := parseUsername(localUser.Username)
 	shell := getUserShell(localUser.Uid)
 
 	req := PtyExecutionRequest{

client/ssh/server/port_forwarding.go

@@ -133,7 +133,12 @@ func (s *Server) checkPrivilegedPortAccess(forwardType string, port uint32, resu
 		return nil
 	}
 
-	if result.User != nil && isPrivilegedUsername(result.User.Username) {
+	// Only uid 0 may bind below the threshold, which is the kernel's own rule and
+	// is asked directly rather than through isPrivilegedOrUnknown: that helper
+	// reports an account it cannot evaluate as privileged, which is safe for a
+	// refusal and unsafe for a grant such as this one. Windows has returned
+	// above, so Uid here is a Unix uid and never a SID.
+	if result.User != nil && result.User.Uid == "0" {
 		return nil
 	}
 

client/ssh/server/privileges_other.go

@@ -0,0 +1,16 @@
+//go:build !windows
+
+package server
+
+// isProcessElevated is only meaningful on Windows; other platforms use the
+// effective UID check in isCurrentProcessPrivileged.
+func isProcessElevated() bool {
+	return false
+}
+
+// isWindowsAccountPrivilegedOrUnknown is only reachable on Windows. Report
+// privileged on other platforms so a caller refusing privileged accounts fails
+// closed.
+func isWindowsAccountPrivilegedOrUnknown(string) bool {
+	return true
+}

client/ssh/server/privileges_windows.go

@@ -0,0 +1,228 @@
+//go:build windows
+
+package server
+
+import (
+	"fmt"
+	"strings"
+	"unsafe"
+
+	log "github.com/sirupsen/logrus"
+	"golang.org/x/sys/windows"
+)
+
+var (
+	netapi32                  = windows.NewLazySystemDLL("netapi32.dll")
+	procNetUserGetLocalGroups = netapi32.NewProc("NetUserGetLocalGroups")
+)
+
+const (
+	// lgIncludeIndirect makes NetUserGetLocalGroups also return local groups
+	// the user belongs to through a global group.
+	lgIncludeIndirect  = 0x1
+	maxPreferredLength = 0xFFFFFFFF
+)
+
+// localGroupUsersInfo0 mirrors LOCALGROUP_USERS_INFO_0.
+type localGroupUsersInfo0 struct {
+	name *uint16
+}
+
+// isProcessElevated reports whether the current process token is elevated
+// (TokenElevation): true for elevated administrators, the built-in
+// Administrator, administrators with UAC disabled, and SYSTEM; false for
+// standard users and administrators running with a UAC-filtered token.
+func isProcessElevated() bool {
+	return windows.GetCurrentProcessToken().IsElevated()
+}
+
+// isWindowsAccountPrivilegedOrUnknown reports whether the account is privileged
+// on this machine: a well-known service account, a built-in Administrator
+// (RID 500), or a member of the local Administrators group, directly or through
+// nested groups.
+//
+// An account whose privilege cannot be determined counts as privileged, which
+// is why the name says "or unknown". That is fail-closed for a caller that
+// refuses privileged accounts, and fail-open for a caller that grants something
+// to them, so only the former may use this.
+func isWindowsAccountPrivilegedOrUnknown(username string) bool {
+	sid, _, _, err := windows.LookupSID("", username)
+	if err != nil {
+		log.Warnf("privilege check: SID lookup for %q failed, treating as privileged: %v", username, err)
+		return true
+	}
+
+	if isPrivilegedUserSID(sid) {
+		return true
+	}
+
+	member, err := isLocalAdminsMember(username)
+	if err != nil {
+		log.Warnf("privilege check: cannot determine Administrators membership for %q, treating as privileged: %v", username, err)
+		return true
+	}
+	return member
+}
+
+// isPrivilegedUserSID reports whether the SID itself identifies a privileged
+// principal, without consulting group membership.
+func isPrivilegedUserSID(sid *windows.SID) bool {
+	wellKnown := []windows.WELL_KNOWN_SID_TYPE{
+		windows.WinLocalSystemSid,
+		windows.WinLocalServiceSid,
+		windows.WinNetworkServiceSid,
+		windows.WinBuiltinAdministratorsSid,
+	}
+	for _, sidType := range wellKnown {
+		if sid.IsWellKnown(sidType) {
+			return true
+		}
+	}
+	return isBuiltinAdministratorSID(sid)
+}
+
+// isBuiltinAdministratorSID reports whether the SID is a machine or domain
+// built-in Administrator account (S-1-5-21-...-500). RID 500 is reserved for
+// that account; it can be renamed but cannot be removed from the
+// Administrators group.
+func isBuiltinAdministratorSID(sid *windows.SID) bool {
+	if sid.IdentifierAuthority() != windows.SECURITY_NT_AUTHORITY {
+		return false
+	}
+	count := sid.SubAuthorityCount()
+	if count < 2 || sid.SubAuthority(0) != 21 {
+		return false
+	}
+	return sid.SubAuthority(uint32(count-1)) == 500
+}
+
+// isLocalAdminsMember reports whether the account is a member of the local
+// Administrators group.
+//
+// Local accounts are checked against the local SAM, which is authoritative for
+// them and, unlike a token, cannot under-report: UAC filters the tokens of
+// local administrators, and a filtered token carries Administrators as
+// deny-only, which a membership check on the token would read as "not a
+// member". Domain accounts are exempt from that filtering, so for them an S4U
+// token is preferred because its group list is LSA's transitive expansion and
+// therefore covers nested and universal groups plus the machine's own local
+// groups. NetUserGetLocalGroups expands only one global-group hop but needs no
+// logon, so it serves as the fallback when no token can be obtained.
+func isLocalAdminsMember(username string) (bool, error) {
+	adminSid, err := windows.CreateWellKnownSid(windows.WinBuiltinAdministratorsSid)
+	if err != nil {
+		return false, fmt.Errorf("create Administrators SID: %w", err)
+	}
+
+	account, domain := parseUsername(username)
+	if NewPrivilegeDropper().isLocalUser(domain) {
+		return localGroupsContainSID(account, adminSid)
+	}
+
+	member, s4uErr := s4uTokenIsMember(account, domain, adminSid)
+	if s4uErr == nil {
+		return member, nil
+	}
+	log.Debugf("privilege check: S4U membership check for %q failed, falling back to local group enumeration: %v", username, s4uErr)
+
+	member, err = localGroupsContainSID(buildUserCpn(account, domain), adminSid)
+	if err != nil {
+		return false, fmt.Errorf("S4U check: %w; local group enumeration: %w", s4uErr, err)
+	}
+	return member, nil
+}
+
+// s4uTokenIsMember obtains an S4U token for the account and checks whether the
+// given SID is enabled in it.
+func s4uTokenIsMember(account, domain string, sid *windows.SID) (bool, error) {
+	token, err := generateS4UUserToken(log.NewEntry(log.StandardLogger()), account, domain)
+	if err != nil {
+		return false, err
+	}
+	defer func() {
+		if err := windows.CloseHandle(token); err != nil {
+			log.Debugf("close S4U token: %v", err)
+		}
+	}()
+	return windows.Token(token).IsMember(sid)
+}
+
+// localGroupsContainSID reports whether the wanted group is among the local
+// groups the account belongs to, directly or through a global group.
+//
+// The wanted SID is resolved to its group name once and compared against the
+// enumerated names. Well-known SIDs resolve from a static table, so that lookup
+// needs no domain controller, and it keeps the comparison correct for a renamed
+// or localized group because both sides then carry the new name. Resolving each
+// enumerated name back to a SID instead would add a lookup per group that can
+// block until it times out while a domain controller is unreachable, and cannot
+// change the outcome: the names enumerated here are local groups of this
+// machine, whose names are unique, so a name match identifies the group.
+//
+// A failure to resolve the wanted SID is returned rather than reported as
+// "not a member", so a privilege check built on this fails closed.
+func localGroupsContainSID(username string, want *windows.SID) (bool, error) {
+	wantName, _, _, err := want.LookupAccount("")
+	if err != nil {
+		return false, fmt.Errorf("resolve group SID %s to a name: %w", want, err)
+	}
+
+	groups, err := netUserGetLocalGroups(username)
+	if err != nil {
+		return false, err
+	}
+
+	for _, group := range groups {
+		if strings.EqualFold(group, wantName) {
+			return true, nil
+		}
+	}
+	return false, nil
+}
+
+// netUserGetLocalGroups returns the names of the local groups the account is a
+// member of, including indirect membership through global groups.
+func netUserGetLocalGroups(username string) ([]string, error) {
+	name16, err := windows.UTF16PtrFromString(username)
+	if err != nil {
+		return nil, fmt.Errorf("convert username: %w", err)
+	}
+
+	var buf *byte
+	var entriesRead, totalEntries uint32
+	status, _, _ := procNetUserGetLocalGroups.Call(
+		0, // local server
+		uintptr(unsafe.Pointer(name16)),
+		0, // level 0: LOCALGROUP_USERS_INFO_0
+		lgIncludeIndirect,
+		uintptr(unsafe.Pointer(&buf)),
+		maxPreferredLength,
+		uintptr(unsafe.Pointer(&entriesRead)),
+		uintptr(unsafe.Pointer(&totalEntries)),
+	)
+	if status != 0 {
+		return nil, fmt.Errorf("NetUserGetLocalGroups for %q: status %d", username, status)
+	}
+	if buf == nil {
+		return nil, nil
+	}
+	defer func() {
+		if err := windows.NetApiBufferFree(buf); err != nil {
+			log.Debugf("free NetApi buffer: %v", err)
+		}
+	}()
+
+	// MAX_PREFERRED_LENGTH makes the API allocate as much as it needs, so a
+	// short read is not expected. Report it rather than silently returning a
+	// subset of the account's groups.
+	if entriesRead != totalEntries {
+		return nil, fmt.Errorf("NetUserGetLocalGroups for %q returned %d of %d groups", username, entriesRead, totalEntries)
+	}
+
+	entries := unsafe.Slice((*localGroupUsersInfo0)(unsafe.Pointer(buf)), entriesRead)
+	groups := make([]string, 0, entriesRead)
+	for _, entry := range entries {
+		groups = append(groups, windows.UTF16PtrToString(entry.name))
+	}
+	return groups, nil
+}

client/ssh/server/privileges_windows_test.go

@@ -0,0 +1,293 @@
+//go:build windows
+
+package server
+
+import (
+	"os/user"
+	"testing"
+	"unsafe"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"golang.org/x/sys/windows"
+)
+
+// filterNormalAccount limits NetUserEnum to normal user accounts.
+const filterNormalAccount = 0x2
+
+// TOKEN_ELEVATION_TYPE values.
+const (
+	tokenElevationTypeDefault = 1
+	tokenElevationTypeFull    = 2
+	tokenElevationTypeLimited = 3
+)
+
+// tokenElevationType reads TokenElevationType from a token.
+func tokenElevationType(token windows.Token) (uint32, error) {
+	var elevationType, returnedLen uint32
+	err := windows.GetTokenInformation(token, windows.TokenElevationType,
+		(*byte)(unsafe.Pointer(&elevationType)), uint32(unsafe.Sizeof(elevationType)), &returnedLen)
+	if err != nil {
+		return 0, err
+	}
+	return elevationType, nil
+}
+
+// userInfo0 mirrors USER_INFO_0.
+type userInfo0 struct {
+	name *uint16
+}
+
+func mustParseSID(t *testing.T, s string) *windows.SID {
+	t.Helper()
+	sid, err := windows.StringToSid(s)
+	require.NoError(t, err, "parse SID %s", s)
+	return sid
+}
+
+// localAccountNames returns the names of the local user accounts.
+func localAccountNames(t *testing.T) []string {
+	t.Helper()
+
+	var buf *byte
+	var entriesRead, totalEntries, resume uint32
+	err := windows.NetUserEnum(nil, 0, filterNormalAccount, &buf, maxPreferredLength,
+		&entriesRead, &totalEntries, &resume)
+	require.NoError(t, err, "enumerate local users")
+	t.Cleanup(func() {
+		require.NoError(t, windows.NetApiBufferFree(buf), "free NetApi buffer")
+	})
+
+	entries := unsafe.Slice((*userInfo0)(unsafe.Pointer(buf)), entriesRead)
+	names := make([]string, 0, entriesRead)
+	for _, entry := range entries {
+		names = append(names, windows.UTF16PtrToString(entry.name))
+	}
+	return names
+}
+
+// localAccountNameByRID returns the name of the local account carrying the
+// given RID. Accounts such as Administrator and Guest can be renamed and are
+// localized, so tests must not name them literally.
+func localAccountNameByRID(t *testing.T, rid uint32) string {
+	t.Helper()
+
+	for _, name := range localAccountNames(t) {
+		sid, _, _, err := windows.LookupSID("", name)
+		if err != nil {
+			continue
+		}
+		if sid.IdentifierAuthority() != windows.SECURITY_NT_AUTHORITY {
+			continue
+		}
+		count := sid.SubAuthorityCount()
+		if count < 2 || sid.SubAuthority(0) != 21 {
+			continue
+		}
+		if sid.SubAuthority(uint32(count-1)) == rid {
+			return name
+		}
+	}
+
+	t.Fatalf("no local account with RID %d", rid)
+	return ""
+}
+
+// wellKnownAccountName resolves a well-known SID to the qualified account name
+// the local system uses for it, which is localized.
+func wellKnownAccountName(t *testing.T, sidType windows.WELL_KNOWN_SID_TYPE) string {
+	t.Helper()
+
+	sid, err := windows.CreateWellKnownSid(sidType)
+	require.NoError(t, err, "create well-known SID")
+	name, domain, _, err := sid.LookupAccount("")
+	require.NoError(t, err, "resolve %s to an account name", sid)
+	if domain == "" {
+		return name
+	}
+	return domain + `\` + name
+}
+
+func TestIsBuiltinAdministratorSID(t *testing.T) {
+	tests := []struct {
+		name string
+		sid  string
+		want bool
+	}{
+		{"machine_administrator", "S-1-5-21-1111111111-2222222222-3333333333-500", true},
+		{"domain_administrator", "S-1-5-21-3390233681-4087452608-412898826-500", true},
+		{"regular_user", "S-1-5-21-1111111111-2222222222-3333333333-1001", false},
+		{"guest_account", "S-1-5-21-1111111111-2222222222-3333333333-501", false},
+		{"domain_admins_group", "S-1-5-21-1111111111-2222222222-3333333333-512", false},
+		{"system", "S-1-5-18", false},
+		{"administrators_group", "S-1-5-32-544", false},
+		{"non_nt_authority", "S-1-1-0", false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := isBuiltinAdministratorSID(mustParseSID(t, tt.sid))
+			assert.Equal(t, tt.want, result, "RID 500 detection for %s", tt.sid)
+		})
+	}
+}
+
+func TestIsPrivilegedUserSID(t *testing.T) {
+	tests := []struct {
+		name string
+		sid  string
+		want bool
+	}{
+		{"local_system", "S-1-5-18", true},
+		{"local_service", "S-1-5-19", true},
+		{"network_service", "S-1-5-20", true},
+		{"administrators_group", "S-1-5-32-544", true},
+		{"builtin_administrator", "S-1-5-21-1111111111-2222222222-3333333333-500", true},
+		{"regular_user", "S-1-5-21-1111111111-2222222222-3333333333-1001", false},
+		{"users_group", "S-1-5-32-545", false},
+		{"everyone", "S-1-1-0", false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := isPrivilegedUserSID(mustParseSID(t, tt.sid))
+			assert.Equal(t, tt.want, result, "SID privilege classification for %s", tt.sid)
+		})
+	}
+}
+
+func TestIsWindowsAccountPrivilegedOrUnknown(t *testing.T) {
+	tests := []struct {
+		name     string
+		username string
+		want     bool
+	}{
+		{"system", wellKnownAccountName(t, windows.WinLocalSystemSid), true},
+		{"local_service", wellKnownAccountName(t, windows.WinLocalServiceSid), true},
+		{"network_service", wellKnownAccountName(t, windows.WinNetworkServiceSid), true},
+		{"administrators_group", wellKnownAccountName(t, windows.WinBuiltinAdministratorsSid), true},
+		// The built-in Administrator (RID 500) and Guest (RID 501) accounts
+		// exist on every Windows installation, though they may be disabled.
+		{"builtin_administrator", localAccountNameByRID(t, 500), true},
+		{"guest", localAccountNameByRID(t, 501), false},
+		// Unresolvable accounts fail closed.
+		{"nonexistent_user", "netbird-no-such-user", true},
+		{"empty_username", "", true},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result := isWindowsAccountPrivilegedOrUnknown(tt.username)
+			assert.Equal(t, tt.want, result, "account privilege classification for %q", tt.username)
+		})
+	}
+}
+
+func TestIsProcessElevated(t *testing.T) {
+	elevated := isProcessElevated()
+
+	// TokenElevationType is a second, independent view of the same token:
+	// Full means elevated and Limited means a filtered administrator, while
+	// Default covers both a standard user and an administrator with no linked
+	// token (UAC off, the built-in Administrator, SYSTEM), so it implies nothing.
+	elevationType, err := tokenElevationType(windows.GetCurrentProcessToken())
+	require.NoError(t, err, "read token elevation type")
+
+	adminSid, err := windows.CreateWellKnownSid(windows.WinBuiltinAdministratorsSid)
+	require.NoError(t, err, "create Administrators SID")
+
+	// Token(0) makes CheckTokenMembership evaluate the caller's own token. It
+	// counts only enabled SIDs, so a filtered administrator reports false here.
+	member, err := windows.Token(0).IsMember(adminSid)
+	require.NoError(t, err, "check own Administrators membership")
+
+	t.Logf("elevated=%v elevationType=%d memberOfAdministrators=%v", elevated, elevationType, member)
+
+	switch elevationType {
+	case tokenElevationTypeFull:
+		assert.True(t, elevated, "a token of elevation type Full must report elevated")
+	case tokenElevationTypeLimited:
+		assert.False(t, elevated, "a filtered administrator token must not report elevated")
+	}
+
+	// Administrators enabled in the token means the token wields administrative
+	// rights, which is what elevation reports.
+	if member {
+		assert.True(t, elevated, "token with enabled Administrators membership must report elevated")
+	}
+}
+
+// TestS4UMembershipAgreesWithLocalGroups exercises the S4U token path used
+// for domain accounts. S4U logons need the TCB privilege, so the test runs
+// only as SYSTEM (which is how CI executes the suite). For local accounts the
+// token's Administrators membership must agree with the SAM enumeration.
+func TestS4UMembershipAgreesWithLocalGroups(t *testing.T) {
+	system, err := windows.CreateWellKnownSid(windows.WinLocalSystemSid)
+	require.NoError(t, err, "create SYSTEM SID")
+	current, err := user.Current()
+	require.NoError(t, err, "get current user")
+	if current.Uid != system.String() {
+		t.Skipf("S4U logon requires SYSTEM (running as %s)", current.Username)
+	}
+
+	adminSid, err := windows.CreateWellKnownSid(windows.WinBuiltinAdministratorsSid)
+	require.NoError(t, err, "create Administrators SID")
+
+	checked := 0
+	for _, name := range localAccountNames(t) {
+		viaToken, err := s4uTokenIsMember(name, ".", adminSid)
+		if err != nil {
+			// Disabled or logon-restricted accounts cannot get an S4U logon.
+			t.Logf("skipping %s: %v", name, err)
+			continue
+		}
+		viaSAM, err := localGroupsContainSID(name, adminSid)
+		require.NoError(t, err, "enumerate local groups for %s", name)
+
+		assert.Equal(t, viaSAM, viaToken, "S4U token and SAM enumeration must agree on Administrators membership for %s", name)
+		checked++
+	}
+	// Ineligible accounts are skipped, so without this the test could report
+	// success while comparing nothing at all.
+	require.Positive(t, checked, "no local account completed an S4U logon, so nothing was compared")
+	t.Logf("checked %d local accounts via S4U", checked)
+}
+
+// TestLocalGroupsContainSID_Administrator checks the positive case against the
+// built-in Administrator, a member of Administrators on every installation.
+func TestLocalGroupsContainSID_Administrator(t *testing.T) {
+	adminSid, err := windows.CreateWellKnownSid(windows.WinBuiltinAdministratorsSid)
+	require.NoError(t, err, "create Administrators SID")
+
+	administrator := localAccountNameByRID(t, 500)
+	member, err := localGroupsContainSID(administrator, adminSid)
+	require.NoError(t, err, "enumerate local groups for %s", administrator)
+	assert.True(t, member, "%s is a member of the Administrators group", administrator)
+}
+
+// TestLocalGroupsContainSID_UnresolvableGroupFailsClosed covers a wanted SID
+// that resolves to no group: the error must surface rather than being reported
+// as "not a member", so the privilege check treats the account as privileged.
+func TestLocalGroupsContainSID_UnresolvableGroupFailsClosed(t *testing.T) {
+	unknown := mustParseSID(t, "S-1-5-21-1111111111-2222222222-3333333333-4444")
+
+	_, err := localGroupsContainSID(localAccountNameByRID(t, 500), unknown)
+	require.Error(t, err, "must report an error when the wanted group cannot be identified")
+}
+
+func TestLocalGroupsContainSID_Guest(t *testing.T) {
+	guestsSid, err := windows.CreateWellKnownSid(windows.WinBuiltinGuestsSid)
+	require.NoError(t, err, "create Guests SID")
+	adminsSid, err := windows.CreateWellKnownSid(windows.WinBuiltinAdministratorsSid)
+	require.NoError(t, err, "create Administrators SID")
+
+	guest := localAccountNameByRID(t, 501)
+
+	inGuests, err := localGroupsContainSID(guest, guestsSid)
+	require.NoError(t, err, "enumerate local groups for %s", guest)
+	assert.True(t, inGuests, "%s is a member of the Guests group", guest)
+
+	inAdmins, err := localGroupsContainSID(guest, adminsSid)
+	require.NoError(t, err, "enumerate local groups for %s", guest)
+	assert.False(t, inAdmins, "%s is not a member of the Administrators group", guest)
+}

client/ssh/server/server_config_test.go

@@ -239,6 +239,7 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 		forwardType   string
 		port          uint32
 		username      string
+		uid           string
 		expectError   bool
 		errorMsg      string
 		skipOnWindows bool
@@ -248,6 +249,7 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 			forwardType:   "remote",
 			port:          80,
 			username:      "testuser",
+			uid:           "1000",
 			expectError:   true,
 			errorMsg:      "cannot bind to privileged port",
 			skipOnWindows: true,
@@ -257,6 +259,7 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 			forwardType:   "tcpip-forward",
 			port:          443,
 			username:      "testuser",
+			uid:           "1000",
 			expectError:   true,
 			errorMsg:      "cannot bind to privileged port",
 			skipOnWindows: true,
@@ -266,6 +269,7 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 			forwardType: "remote",
 			port:        8080,
 			username:    "testuser",
+			uid:         "1000",
 			expectError: false,
 		},
 		{
@@ -273,6 +277,7 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 			forwardType: "remote",
 			port:        0,
 			username:    "testuser",
+			uid:         "1000",
 			expectError: false,
 		},
 		{
@@ -280,13 +285,35 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 			forwardType: "remote",
 			port:        22,
 			username:    "root",
+			uid:         "0",
 			expectError: false,
 		},
+		{
+			// Only uid 0 is privileged, whatever the account is called.
+			name:          "uid 0 under another name may bind a privileged port",
+			forwardType:   "remote",
+			port:          22,
+			username:      "toor",
+			uid:           "0",
+			expectError:   false,
+			skipOnWindows: true,
+		},
+		{
+			name:          "account named root without uid 0 may not",
+			forwardType:   "remote",
+			port:          22,
+			username:      "root",
+			uid:           "1000",
+			expectError:   true,
+			errorMsg:      "cannot bind to privileged port",
+			skipOnWindows: true,
+		},
 		{
 			name:        "local forward privileged port allowed for non-root",
 			forwardType: "local",
 			port:        80,
 			username:    "testuser",
+			uid:         "1000",
 			expectError: false,
 		},
 	}
@@ -299,7 +326,7 @@ func TestServer_PrivilegedPortAccess(t *testing.T) {
 
 			result := PrivilegeCheckResult{
 				Allowed: true,
-				User:    &user.User{Username: tt.username},
+				User:    &user.User{Username: tt.username, Uid: tt.uid},
 			}
 
 			err := server.checkPrivilegedPortAccess(tt.forwardType, tt.port, result)
@@ -420,6 +447,13 @@ func TestServer_PortConflictHandling(t *testing.T) {
 
 func TestServer_IsPrivilegedUser(t *testing.T) {
 
+	// Windows classification depends on account SIDs and group membership, and
+	// the accounts involved carry localized, renameable names. It is covered by
+	// TestIsWindowsAccountPrivileged, which resolves them from well-known SIDs.
+	if runtime.GOOS == "windows" {
+		t.Skip("covered by TestIsWindowsAccountPrivileged")
+	}
+
 	tests := []struct {
 		username    string
 		expected    bool
@@ -440,44 +474,16 @@ func TestServer_IsPrivilegedUser(t *testing.T) {
 			expected:    false,
 			description: "empty username should not be privileged",
 		},
-	}
-
-	// Add Windows-specific tests
-	if runtime.GOOS == "windows" {
-		tests = append(tests, []struct {
-			username    string
-			expected    bool
-			description string
-		}{
-			{
-				username:    "Administrator",
-				expected:    true,
-				description: "Administrator should be considered privileged on Windows",
-			},
-			{
-				username:    "administrator",
-				expected:    true,
-				description: "administrator should be considered privileged on Windows (case insensitive)",
-			},
-		}...)
-	} else {
-		// On non-Windows systems, Administrator should not be privileged
-		tests = append(tests, []struct {
-			username    string
-			expected    bool
-			description string
-		}{
-			{
-				username:    "Administrator",
-				expected:    false,
-				description: "Administrator should not be privileged on non-Windows systems",
-			},
-		}...)
+		{
+			username:    "Administrator",
+			expected:    false,
+			description: "Administrator should not be privileged on non-Windows systems",
+		},
 	}
 
 	for _, tt := range tests {
 		t.Run(tt.description, func(t *testing.T) {
-			result := isPrivilegedUsername(tt.username)
+			result := isPrivilegedOrUnknown(tt.username)
 			assert.Equal(t, tt.expected, result, tt.description)
 		})
 	}

client/ssh/server/sftp_windows.go

@@ -17,7 +17,7 @@ import (
 // createSftpCommand creates a Windows SFTP command with user switching.
 // The caller must close the returned token handle after starting the process.
 func (s *Server) createSftpCommand(targetUser *user.User, sess ssh.Session) (*exec.Cmd, windows.Token, error) {
-	username, domain := s.parseUsername(targetUser.Username)
+	username, domain := parseUsername(targetUser.Username)
 
 	netbirdPath, err := os.Executable()
 	if err != nil {

client/ssh/server/user_utils.go

@@ -16,11 +16,6 @@ var (
 	ErrPrivilegedUserSwitch = errors.New("cannot switch to privileged user - current user lacks required privileges")
 )
 
-// isPlatformUnix returns true for Unix-like platforms (Linux, macOS, etc.)
-func isPlatformUnix() bool {
-	return getCurrentOS() != "windows"
-}
-
 // Dependency injection variables for testing - allows mocking dynamic runtime checks
 var (
 	getCurrentUser         = currentUserWithGetent
@@ -29,6 +24,9 @@ var (
 	getIsProcessPrivileged = isCurrentProcessPrivileged
 
 	getEuid = os.Geteuid
+
+	getProcessElevated                   = isProcessElevated
+	getWindowsAccountPrivilegedOrUnknown = isWindowsAccountPrivilegedOrUnknown
 )
 
 const (
@@ -65,6 +63,13 @@ type PrivilegeCheckResult struct {
 	RequiresUserSwitching bool
 }
 
+// privilegeCheckContext holds all context needed for privilege checking
+type privilegeCheckContext struct {
+	currentUser           *user.User
+	currentUserPrivileged bool
+	allowRoot             bool
+}
+
 // CheckPrivileges performs comprehensive privilege checking for all SSH features.
 // This is the single source of truth for privilege decisions across the SSH server.
 func (s *Server) CheckPrivileges(req PrivilegeCheckRequest) PrivilegeCheckResult {
@@ -75,7 +80,7 @@ func (s *Server) CheckPrivileges(req PrivilegeCheckRequest) PrivilegeCheckResult
 
 	// Handle empty username case - but still check root access controls
 	if req.RequestedUsername == "" {
-		if isPrivilegedUsername(context.currentUser.Username) && !context.allowRoot {
+		if isPrivilegedOrUnknown(context.currentUser.Username) && !context.allowRoot {
 			return PrivilegeCheckResult{
 				Allowed: false,
 				Error:   &PrivilegedUserError{Username: context.currentUser.Username},
@@ -135,7 +140,7 @@ func (s *Server) checkUserRequest(ctx *privilegeCheckContext, req PrivilegeCheck
 
 	needsUserSwitching := !isSameResolvedUser(resolvedUser, ctx.currentUser)
 
-	if isPrivilegedUsername(resolvedUser.Username) && !ctx.allowRoot {
+	if isPrivilegedOrUnknown(resolvedUser.Username) && !ctx.allowRoot {
 		return PrivilegeCheckResult{
 			Allowed:               false,
 			Error:                 &PrivilegedUserError{Username: resolvedUser.Username},
@@ -175,6 +180,42 @@ func (s *Server) resolveRequestedUser(requestedUsername string) (*user.User, err
 	return u, nil
 }
 
+// SetAllowRootLogin configures root login access
+func (s *Server) SetAllowRootLogin(allow bool) {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+	s.allowRootLogin = allow
+}
+
+// userNameLookup performs user lookup with root login permission check
+func (s *Server) userNameLookup(username string) (*user.User, error) {
+	result, err := s.userPrivilegeCheck(username)
+	if err != nil {
+		return nil, err
+	}
+	return result.User, nil
+}
+
+// userPrivilegeCheck performs user lookup with full privilege check result
+func (s *Server) userPrivilegeCheck(username string) (PrivilegeCheckResult, error) {
+	result := s.CheckPrivileges(PrivilegeCheckRequest{
+		RequestedUsername:         username,
+		FeatureSupportsUserSwitch: true,
+		FeatureName:               FeatureSSHLogin,
+	})
+
+	if !result.Allowed {
+		return result, result.Error
+	}
+
+	return result, nil
+}
+
+// isPlatformUnix returns true for Unix-like platforms (Linux, macOS, etc.)
+func isPlatformUnix() bool {
+	return getCurrentOS() != "windows"
+}
+
 // isSameResolvedUser compares two resolved user identities
 func isSameResolvedUser(user1, user2 *user.User) bool {
 	if user1 == nil || user2 == nil {
@@ -183,13 +224,6 @@ func isSameResolvedUser(user1, user2 *user.User) bool {
 	return user1.Uid == user2.Uid
 }
 
-// privilegeCheckContext holds all context needed for privilege checking
-type privilegeCheckContext struct {
-	currentUser           *user.User
-	currentUserPrivileged bool
-	allowRoot             bool
-}
-
 // isSameUser checks if two usernames refer to the same user
 // SECURITY: This function must be conservative - it should only return true
 // when we're certain both usernames refer to the exact same user identity
@@ -253,159 +287,30 @@ func isWindowsSameUser(requestedUsername, currentUsername string) bool {
 	return strings.EqualFold(reqDomain, curDomain)
 }
 
-// SetAllowRootLogin configures root login access
-func (s *Server) SetAllowRootLogin(allow bool) {
-	s.mu.Lock()
-	defer s.mu.Unlock()
-	s.allowRootLogin = allow
-}
-
-// userNameLookup performs user lookup with root login permission check
-func (s *Server) userNameLookup(username string) (*user.User, error) {
-	result := s.CheckPrivileges(PrivilegeCheckRequest{
-		RequestedUsername:         username,
-		FeatureSupportsUserSwitch: true,
-		FeatureName:               FeatureSSHLogin,
-	})
-
-	if !result.Allowed {
-		return nil, result.Error
-	}
-
-	return result.User, nil
-}
-
-// userPrivilegeCheck performs user lookup with full privilege check result
-func (s *Server) userPrivilegeCheck(username string) (PrivilegeCheckResult, error) {
-	result := s.CheckPrivileges(PrivilegeCheckRequest{
-		RequestedUsername:         username,
-		FeatureSupportsUserSwitch: true,
-		FeatureName:               FeatureSSHLogin,
-	})
-
-	if !result.Allowed {
-		return result, result.Error
-	}
-
-	return result, nil
-}
-
-// isPrivilegedUsername checks if the given username represents a privileged user across platforms.
-// On Unix: root
-// On Windows: Administrator, SYSTEM (case-insensitive)
-// Handles domain-qualified usernames like "DOMAIN\Administrator" or "user@domain.com"
-func isPrivilegedUsername(username string) bool {
+// isPrivilegedOrUnknown reports whether the given username represents a
+// privileged user, or on Windows an account whose privilege could not be
+// determined.
+// On Unix: root.
+// On Windows: well-known service accounts, built-in Administrator accounts,
+// and members of the local Administrators group; handles domain-qualified
+// usernames like "DOMAIN\user" or "user@domain.com". An account that cannot be
+// resolved or evaluated is reported as privileged.
+//
+// Use this to refuse privileged accounts, never to grant them anything: the
+// undetermined case is safe for a refusal and unsafe for a grant.
+func isPrivilegedOrUnknown(username string) bool {
 	if getCurrentOS() != "windows" {
 		return username == "root"
 	}
-
-	bareUsername := username
-	// Handle Windows domain format: DOMAIN\username
-	if idx := strings.LastIndex(username, `\`); idx != -1 {
-		bareUsername = username[idx+1:]
-	}
-	// Handle email-style format: username@domain.com
-	if idx := strings.Index(bareUsername, "@"); idx != -1 {
-		bareUsername = bareUsername[:idx]
-	}
-
-	return isWindowsPrivilegedUser(bareUsername)
-}
-
-// isWindowsPrivilegedUser checks if a bare username (domain already stripped) represents a Windows privileged account
-func isWindowsPrivilegedUser(bareUsername string) bool {
-	// common privileged usernames (case insensitive)
-	privilegedNames := []string{
-		"administrator",
-		"admin",
-		"root",
-		"system",
-		"localsystem",
-		"networkservice",
-		"localservice",
-	}
-
-	usernameLower := strings.ToLower(bareUsername)
-	for _, privilegedName := range privilegedNames {
-		if usernameLower == privilegedName {
-			return true
-		}
-	}
-
-	// computer accounts (ending with $) are not privileged by themselves
-	// They only gain privileges through group membership or specific SIDs
-
-	if targetUser, err := lookupUser(bareUsername); err == nil {
-		return isWindowsPrivilegedSID(targetUser.Uid)
-	}
-
-	return false
-}
-
-// isWindowsPrivilegedSID checks if a Windows SID represents a privileged account
-func isWindowsPrivilegedSID(sid string) bool {
-	privilegedSIDs := []string{
-		"S-1-5-18",     // Local System (SYSTEM)
-		"S-1-5-19",     // Local Service (NT AUTHORITY\LOCAL SERVICE)
-		"S-1-5-20",     // Network Service (NT AUTHORITY\NETWORK SERVICE)
-		"S-1-5-32-544", // Administrators group (BUILTIN\Administrators)
-		"S-1-5-500",    // Built-in Administrator account (local machine RID 500)
-	}
-
-	for _, privilegedSID := range privilegedSIDs {
-		if sid == privilegedSID {
-			return true
-		}
-	}
-
-	// Check for domain administrator accounts (RID 500 in any domain)
-	// Format: S-1-5-21-domain-domain-domain-500
-	// This is reliable as RID 500 is reserved for the domain Administrator account
-	if strings.HasPrefix(sid, "S-1-5-21-") && strings.HasSuffix(sid, "-500") {
-		return true
-	}
-
-	// Check for other well-known privileged RIDs in domain contexts
-	// RID 512 = Domain Admins group, RID 516 = Domain Controllers group
-	if strings.HasPrefix(sid, "S-1-5-21-") {
-		if strings.HasSuffix(sid, "-512") || // Domain Admins group
-			strings.HasSuffix(sid, "-516") || // Domain Controllers group
-			strings.HasSuffix(sid, "-519") { // Enterprise Admins group
-			return true
-		}
-	}
-
-	return false
+	return getWindowsAccountPrivilegedOrUnknown(username)
 }
 
 // isCurrentProcessPrivileged checks if the current process is running with elevated privileges.
 // On Unix systems, this means running as root (UID 0).
-// On Windows, this means running as Administrator or SYSTEM.
+// On Windows, this means the process token is elevated (administrators, SYSTEM).
 func isCurrentProcessPrivileged() bool {
 	if getCurrentOS() == "windows" {
-		return isWindowsElevated()
+		return getProcessElevated()
 	}
 	return getEuid() == 0
 }
-
-// isWindowsElevated checks if the current process is running with elevated privileges on Windows
-func isWindowsElevated() bool {
-	currentUser, err := getCurrentUser()
-	if err != nil {
-		log.Errorf("failed to get current user for privilege check, assuming non-privileged: %v", err)
-		return false
-	}
-
-	if isWindowsPrivilegedSID(currentUser.Uid) {
-		log.Debugf("Windows user switching supported: running as privileged SID %s", currentUser.Uid)
-		return true
-	}
-
-	if isPrivilegedUsername(currentUser.Username) {
-		log.Debugf("Windows user switching supported: running as privileged username %s", currentUser.Username)
-		return true
-	}
-
-	log.Debugf("Windows user switching not supported: not running as privileged user (current: %s)", currentUser.Uid)
-	return false
-}

client/ssh/server/user_utils_test.go

@@ -4,6 +4,7 @@ import (
 	"errors"
 	"os/user"
 	"runtime"
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -27,8 +28,8 @@ func setupTestDependencies(currentUser *user.User, currentUserErr error, os stri
 	originalLookupUser := lookupUser
 	originalGetCurrentOS := getCurrentOS
 	originalGetEuid := getEuid
-
-	// Reset caches to ensure clean test state
+	originalGetProcessElevated := getProcessElevated
+	originalGetWindowsAccountPrivilegedOrUnknown := getWindowsAccountPrivilegedOrUnknown
 
 	// Set test values - inject platform dependencies
 	getCurrentUser = func() (*user.User, error) {
@@ -53,16 +54,31 @@ func setupTestDependencies(currentUser *user.User, currentUserErr error, os stri
 		return euid
 	}
 
-	// Mock privilege detection based on the test user
-	getIsProcessPrivileged = func() bool {
+	// Simulate the Windows token elevation check based on the fixture user:
+	// the built-in Administrator (RID 500) and SYSTEM run elevated.
+	getProcessElevated = func() bool {
 		if currentUser == nil {
 			return false
 		}
-		// Check both username and SID for Windows systems
-		if os == "windows" && isWindowsPrivilegedSID(currentUser.Uid) {
+		return currentUser.Uid == "S-1-5-18" || strings.HasSuffix(currentUser.Uid, "-500")
+	}
+
+	// Simulate the Windows account classifier for the fixture accounts.
+	// "root" does not exist on Windows; the real classifier fails closed on
+	// unresolvable accounts, so it counts as privileged here too.
+	getWindowsAccountPrivilegedOrUnknown = func(username string) bool {
+		bare := username
+		if idx := strings.LastIndex(bare, `\`); idx != -1 {
+			bare = bare[idx+1:]
+		}
+		if idx := strings.Index(bare, "@"); idx != -1 {
+			bare = bare[:idx]
+		}
+		switch strings.ToLower(bare) {
+		case "administrator", "system", "root":
 			return true
 		}
-		return isPrivilegedUsername(currentUser.Username)
+		return false
 	}
 
 	// Return cleanup function
@@ -71,10 +87,8 @@ func setupTestDependencies(currentUser *user.User, currentUserErr error, os stri
 		lookupUser = originalLookupUser
 		getCurrentOS = originalGetCurrentOS
 		getEuid = originalGetEuid
-
-		getIsProcessPrivileged = isCurrentProcessPrivileged
-
-		// Reset caches after test
+		getProcessElevated = originalGetProcessElevated
+		getWindowsAccountPrivilegedOrUnknown = originalGetWindowsAccountPrivilegedOrUnknown
 	}
 }
 
@@ -421,6 +435,9 @@ func TestUsedFallback_MeansNoPrivilegeDropping(t *testing.T) {
 }
 
 func TestPrivilegedUsernameDetection(t *testing.T) {
+	// Windows classification is syscall-backed (SID resolution, group
+	// membership) and is covered by privileges_windows_test.go; here only the
+	// Unix logic and the platform dispatch are exercised.
 	tests := []struct {
 		name       string
 		username   string
@@ -432,25 +449,9 @@ func TestPrivilegedUsernameDetection(t *testing.T) {
 		{"unix_regular_user", "alice", "linux", false},
 		{"unix_root_capital", "Root", "linux", false}, // Case-sensitive
 
-		// Windows tests
+		// Windows dispatch to the (mocked) account classifier
 		{"windows_administrator", "Administrator", "windows", true},
-		{"windows_system", "SYSTEM", "windows", true},
-		{"windows_admin", "admin", "windows", true},
-		{"windows_admin_lowercase", "administrator", "windows", true}, // Case-insensitive
-		{"windows_domain_admin", "DOMAIN\\Administrator", "windows", true},
-		{"windows_email_admin", "admin@domain.com", "windows", true},
 		{"windows_regular_user", "alice", "windows", false},
-		{"windows_domain_user", "DOMAIN\\alice", "windows", false},
-		{"windows_localsystem", "localsystem", "windows", true},
-		{"windows_networkservice", "networkservice", "windows", true},
-		{"windows_localservice", "localservice", "windows", true},
-
-		// Computer accounts (these depend on current user context in real implementation)
-		{"windows_computer_account", "WIN2K19-C2$", "windows", false},      // Computer account by itself not privileged
-		{"windows_domain_computer", "DOMAIN\\COMPUTER$", "windows", false}, // Domain computer account
-
-		// Cross-platform
-		{"root_on_windows", "root", "windows", true}, // Root should be privileged everywhere
 	}
 
 	for _, tt := range tests {
@@ -459,50 +460,8 @@ func TestPrivilegedUsernameDetection(t *testing.T) {
 			cleanup := setupTestDependencies(nil, nil, tt.platform, 1000, nil, nil)
 			defer cleanup()
 
-			result := isPrivilegedUsername(tt.username)
-			assert.Equal(t, tt.privileged, result)
-		})
-	}
-}
-
-func TestWindowsPrivilegedSIDDetection(t *testing.T) {
-	tests := []struct {
-		name        string
-		sid         string
-		privileged  bool
-		description string
-	}{
-		// Well-known system accounts
-		{"system_account", "S-1-5-18", true, "Local System (SYSTEM)"},
-		{"local_service", "S-1-5-19", true, "Local Service"},
-		{"network_service", "S-1-5-20", true, "Network Service"},
-		{"administrators_group", "S-1-5-32-544", true, "Administrators group"},
-		{"builtin_administrator", "S-1-5-500", true, "Built-in Administrator"},
-
-		// Domain accounts
-		{"domain_administrator", "S-1-5-21-1234567890-1234567890-1234567890-500", true, "Domain Administrator (RID 500)"},
-		{"domain_admins_group", "S-1-5-21-1234567890-1234567890-1234567890-512", true, "Domain Admins group"},
-		{"domain_controllers_group", "S-1-5-21-1234567890-1234567890-1234567890-516", true, "Domain Controllers group"},
-		{"enterprise_admins_group", "S-1-5-21-1234567890-1234567890-1234567890-519", true, "Enterprise Admins group"},
-
-		// Regular users
-		{"regular_user", "S-1-5-21-1234567890-1234567890-1234567890-1001", false, "Regular domain user"},
-		{"another_regular_user", "S-1-5-21-1234567890-1234567890-1234567890-1234", false, "Another regular user"},
-		{"local_user", "S-1-5-21-1234567890-1234567890-1234567890-1000", false, "Local regular user"},
-
-		// Groups that are not privileged
-		{"domain_users", "S-1-5-21-1234567890-1234567890-1234567890-513", false, "Domain Users group"},
-		{"power_users", "S-1-5-32-547", false, "Power Users group"},
-
-		// Invalid SIDs
-		{"malformed_sid", "S-1-5-invalid", false, "Malformed SID"},
-		{"empty_sid", "", false, "Empty SID"},
-	}
-
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			result := isWindowsPrivilegedSID(tt.sid)
-			assert.Equal(t, tt.privileged, result, "Failed for %s: %s", tt.description, tt.sid)
+			result := isPrivilegedOrUnknown(tt.username)
+			assert.Equal(t, tt.privileged, result, "privilege classification for %s on %s", tt.username, tt.platform)
 		})
 	}
 }

client/ssh/server/userswitching_windows.go

@@ -91,7 +91,7 @@ func validateUsernameFormat(username string) error {
 func (s *Server) createExecutorCommand(logger *log.Entry, session ssh.Session, localUser *user.User, hasPty bool) (*exec.Cmd, func(), error) {
 	logger.Debugf("creating Windows executor command for user %s (Pty: %v)", localUser.Username, hasPty)
 
-	username, _ := s.parseUsername(localUser.Username)
+	username, _ := parseUsername(localUser.Username)
 	if err := validateUsername(username); err != nil {
 		return nil, nil, fmt.Errorf("invalid username %q: %w", username, err)
 	}
@@ -102,7 +102,7 @@ func (s *Server) createExecutorCommand(logger *log.Entry, session ssh.Session, l
 // createUserSwitchCommand creates a command with Windows user switching.
 // Returns the command and a cleanup function that must be called after starting the process.
 func (s *Server) createUserSwitchCommand(logger *log.Entry, session ssh.Session, localUser *user.User) (*exec.Cmd, func(), error) {
-	username, domain := s.parseUsername(localUser.Username)
+	username, domain := parseUsername(localUser.Username)
 
 	shell := getUserShell(localUser.Uid)
 
@@ -138,7 +138,7 @@ func (s *Server) createUserSwitchCommand(logger *log.Entry, session ssh.Session,
 }
 
 // parseUsername extracts username and domain from a Windows username
-func (s *Server) parseUsername(fullUsername string) (username, domain string) {
+func parseUsername(fullUsername string) (username, domain string) {
 	// Handle DOMAIN\username format
 	if idx := strings.LastIndex(fullUsername, `\`); idx != -1 {
 		domain = fullUsername[:idx]

client/status/status.go

@@ -46,7 +46,10 @@ func ParseDaemonStatus(s string) DaemonStatus {
 
 // ConvertOptions holds parameters for ConvertToStatusOutputOverview.
 type ConvertOptions struct {
-	Anonymize            bool
+	Anonymize bool
+	// AnonymizeLevel selects how much the anonymizer redacts. Only
+	// meaningful when Anonymize is set.
+	AnonymizeLevel       anonymize.Level
 	DaemonVersion        string
 	DaemonStatus         DaemonStatus
 	StatusFilter         string
@@ -217,6 +220,7 @@ func ConvertToStatusOutputOverview(pbFullStatus *proto.FullStatus, opts ConvertO
 
 	if opts.Anonymize {
 		anonymizer := anonymize.NewAnonymizer(anonymize.DefaultAddresses())
+		anonymizer.SetLevel(opts.AnonymizeLevel)
 		anonymizeOverview(anonymizer, &overview)
 	}
 
@@ -976,6 +980,7 @@ func timeAgo(t time.Time) string {
 
 func anonymizePeerDetail(a *anonymize.Anonymizer, peer *PeerStateDetailOutput) {
 	peer.FQDN = a.AnonymizeDomain(peer.FQDN)
+	peer.PubKey = a.AnonymizeWGKey(peer.PubKey)
 	if localIP, port, err := net.SplitHostPort(peer.IceCandidateEndpoint.Local); err == nil {
 		peer.IceCandidateEndpoint.Local = fmt.Sprintf("%s:%s", a.AnonymizeIPString(localIP), port)
 	}
@@ -1007,6 +1012,7 @@ func anonymizeOverview(a *anonymize.Anonymizer, overview *OutputOverview) {
 	overview.SignalState.URL = a.AnonymizeURI(overview.SignalState.URL)
 	overview.SignalState.Error = a.AnonymizeString(overview.SignalState.Error)
 
+	overview.PubKey = a.AnonymizeWGKey(overview.PubKey)
 	overview.IP = a.AnonymizeIPString(overview.IP)
 	overview.IPv6 = a.AnonymizeIPString(overview.IPv6)
 	for i, detail := range overview.Relays.Details {

client/ui/authsession/service.go

@@ -58,7 +58,8 @@ func (s *Session) RequestExtend(ctx context.Context, p ExtendStartParams) (Exten
 		return ExtendStartResult{}, err
 	}
 
-	req := &proto.RequestExtendAuthSessionRequest{}
+	// a request from the UI implies a graphical session, which the daemon cannot detect itself
+	req := &proto.RequestExtendAuthSessionRequest{HasGraphicalSession: true}
 	if p.Hint != "" {
 		h := p.Hint
 		req.Hint = &h

client/ui/frontend/src/contexts/DebugBundleContext.tsx

@@ -71,10 +71,12 @@ type BundleOptions = {
     hasWindow: boolean;
     totalSec: number;
     uploadUrl: string;
-    anonymize: boolean;
+    anonymizeLevel: AnonymizeLevel;
     systemInfo: boolean;
 };
 
+export type AnonymizeLevel = "none" | "default" | "strict";
+
 const startCaptureBestEffort = async (totalSec: number, pcap: CaptureState) => {
     try {
         // Mirror the CLI's safety margin: window + 30s, server caps at 10m.
@@ -187,7 +189,10 @@ const runBundleFlow = async (
 
     if (opts.uploadUrl) setStage({ kind: "uploading" });
     const result = await DebugSvc.Bundle({
-        anonymize: opts.anonymize,
+        anonymize: opts.anonymizeLevel !== "none",
+        // The daemon only knows "default" and "strict"; "none" is expressed
+        // through the anonymize flag being off.
+        anonymizeLevel: opts.anonymizeLevel === "strict" ? "strict" : "default",
         systemInfo: opts.systemInfo,
         uploadUrl: opts.uploadUrl,
         logFileCount,
@@ -198,7 +203,7 @@ const runBundleFlow = async (
 };
 
 const useDebugBundle = () => {
-    const [anonymize, setAnonymize] = useState(false);
+    const [anonymizeLevel, setAnonymizeLevel] = useState<AnonymizeLevel>("none");
     const [systemInfo, setSystemInfo] = useState(true);
     const [upload, setUpload] = useState(true);
     const [trace, setTrace] = useState(true);
@@ -240,7 +245,7 @@ const useDebugBundle = () => {
             hasWindow: capture && totalSec > 0,
             totalSec,
             uploadUrl: upload ? NETBIRD_UPLOAD_URL : "",
-            anonymize,
+            anonymizeLevel,
             systemInfo,
         };
 
@@ -272,8 +277,8 @@ const useDebugBundle = () => {
     };
 
     return {
-        anonymize,
-        setAnonymize,
+        anonymizeLevel,
+        setAnonymizeLevel,
         systemInfo,
         setSystemInfo,
         upload,

client/ui/frontend/src/modules/settings/SettingsTroubleshooting.tsx

@@ -1,6 +1,6 @@
 import { useId, type ReactNode } from "react";
 import { Trans, useTranslation } from "react-i18next";
-import { CircleCheckBig, FolderOpen, Loader2 } from "lucide-react";
+import { ChevronDown, CircleCheckBig, FolderOpen, Info, Loader2 } from "lucide-react";
 import { Browser } from "@wailsio/runtime";
 import { Debug as DebugSvc } from "@bindings/services";
 import type { DebugBundleResult } from "@bindings/services/models.js";
@@ -8,13 +8,22 @@ import { Button } from "@/components/buttons/Button";
 import { DialogActions } from "@/components/dialog/DialogActions";
 import { DialogDescription } from "@/components/dialog/DialogDescription";
 import { DialogHeading } from "@/components/dialog/DialogHeading";
+import {
+    DropdownMenu,
+    DropdownMenuContent,
+    DropdownMenuRadioGroup,
+    DropdownMenuRadioItem,
+    DropdownMenuTrigger,
+} from "@/components/DropdownMenu";
 import FancyToggleSwitch from "@/components/switches/FancyToggleSwitch";
 import HelpText from "@/components/typography/HelpText.tsx";
 import { Input } from "@/components/inputs/Input";
 import { Label } from "@/components/typography/Label";
 import { SquareIcon } from "@/components/SquareIcon";
+import { Tooltip } from "@/components/Tooltip";
+import { cn } from "@/lib/cn";
 import { formatRemaining } from "@/lib/formatters";
-import type { DebugStage } from "@/contexts/DebugBundleContext";
+import type { AnonymizeLevel, DebugStage } from "@/contexts/DebugBundleContext";
 import { useDebugBundleContext } from "@/contexts/DebugBundleContext";
 import { SectionGroup, SettingsBottomBar } from "@/modules/settings/SettingsSection.tsx";
 
@@ -24,8 +33,8 @@ export function SettingsTroubleshooting() {
     const { t } = useTranslation();
     const durationId = useId();
     const {
-        anonymize,
-        setAnonymize,
+        anonymizeLevel,
+        setAnonymizeLevel,
         systemInfo,
         setSystemInfo,
         upload,
@@ -55,12 +64,71 @@ export function SettingsTroubleshooting() {
 
     return (
         <SectionGroup title={t("settings.troubleshooting.section.title")}>
-            <FancyToggleSwitch
-                value={anonymize}
-                onChange={setAnonymize}
-                label={t("settings.troubleshooting.anonymize.label")}
-                helpText={t("settings.troubleshooting.anonymize.help")}
-            />
+            <div className={"flex items-center justify-between gap-6"}>
+                <div className={"max-w-md flex-1"}>
+                    <Label as={"div"}>
+                        <span className={"inline-flex items-center gap-1.5"}>
+                            {t("settings.troubleshooting.anonymize.label")}
+                            <Tooltip
+                                content={
+                                    <div className={"max-w-xs whitespace-normal leading-relaxed"}>
+                                        {t("settings.troubleshooting.anonymize.info")}
+                                    </div>
+                                }
+                            >
+                                <Info
+                                    size={14}
+                                    aria-label={t("settings.troubleshooting.anonymize.label")}
+                                    className={"shrink-0 cursor-default text-nb-gray-400"}
+                                />
+                            </Tooltip>
+                        </span>
+                    </Label>
+                    <HelpText margin={false}>
+                        {t("settings.troubleshooting.anonymize.help")}
+                    </HelpText>
+                </div>
+                <div className={"shrink-0"}>
+                    <DropdownMenu>
+                        <DropdownMenuTrigger asChild>
+                            <button
+                                type={"button"}
+                                aria-label={t("settings.troubleshooting.anonymize.label")}
+                                className={cn(
+                                    "inline-flex h-[40px] min-w-[160px] items-center justify-between gap-2 px-3",
+                                    "rounded-md border bg-white dark:bg-nb-gray-900",
+                                    "border-neutral-200 dark:border-nb-gray-700",
+                                    "cursor-default text-xs font-semibold text-nb-gray-100 outline-none",
+                                    "hover:border-nb-gray-600 data-[state=open]:border-nb-gray-600",
+                                )}
+                            >
+                                {t(`settings.troubleshooting.anonymize.${anonymizeLevel}`)}
+                                <ChevronDown
+                                    size={16}
+                                    aria-hidden={"true"}
+                                    className={"shrink-0 text-nb-gray-200"}
+                                />
+                            </button>
+                        </DropdownMenuTrigger>
+                        <DropdownMenuContent align={"end"} className={"min-w-[160px]"}>
+                            <DropdownMenuRadioGroup
+                                value={anonymizeLevel}
+                                onValueChange={(v) => setAnonymizeLevel(v as AnonymizeLevel)}
+                            >
+                                <DropdownMenuRadioItem value={"none"}>
+                                    {t("settings.troubleshooting.anonymize.none")}
+                                </DropdownMenuRadioItem>
+                                <DropdownMenuRadioItem value={"default"}>
+                                    {t("settings.troubleshooting.anonymize.default")}
+                                </DropdownMenuRadioItem>
+                                <DropdownMenuRadioItem value={"strict"}>
+                                    {t("settings.troubleshooting.anonymize.strict")}
+                                </DropdownMenuRadioItem>
+                            </DropdownMenuRadioGroup>
+                        </DropdownMenuContent>
+                    </DropdownMenu>
+                </div>
+            </div>
             <FancyToggleSwitch
                 value={systemInfo}
                 onChange={setSystemInfo}

client/ui/i18n/TRANSLATING.md

@@ -2,9 +2,24 @@
 
 A short brief for translating the desktop UI — for any translator, human or AI agent (*"you"* = whoever's translating).
 
-**Drive an agent with:** *"Read `i18n/TRANSLATING.md` and translate the UI to Russian"* — or *"…and review the existing German translation."*
+**Translations are managed on Crowdin: <https://crowdin.com/project/netbird>.** Join the project, pick your language, and translate in the editor. Each string carries a context note (the `description` from the source file) telling you what it is and where it shows up, and the project's glossary, style guide, and QA checks mirror this document.
 
-> 💡 **The one habit that matters most:** read each key's `description` before translating it. Labels are terse and ambiguous on their own; the `description` tells you what the string is, where it shows up, what to keep verbatim, and what it actually means.
+> 💡 **The one habit that matters most:** read each string's context before translating it. Labels are terse and ambiguous on their own; the context tells you what the string is, where it shows up, what to keep verbatim, and what it actually means.
+
+---
+
+## How contributions flow
+
+```text
+i18n/locales/en/common.json ──sync──▶ Crowdin ──service PR──▶ i18n/locales/<code>/common.json
+```
+
+- `i18n/locales/en/common.json` is the source of truth. New and changed strings sync to Crowdin automatically (see `crowdin.yml` in the repository root).
+- Crowdin opens and updates a service pull request with the translated bundles, keeping the source's file shape and key order. Keys nobody has translated yet are left out of the export; the app falls back to English for them at runtime. Maintainers review and merge that PR.
+- Don't hand-edit `i18n/locales/<code>/common.json` in your own PRs: the next sync would conflict with or overwrite your changes. Translate on Crowdin instead.
+- Missing your language? Request it on the Crowdin project page or in a [GitHub discussion](https://github.com/netbirdio/netbird/discussions). When a language first ships, a maintainer adds its row to `i18n/locales/_index.json` with `code`, `displayName` (the native name), and `englishName`, which puts it in the app's language picker.
+
+**Prefer translating with an AI agent?** That still works: drive it with *"Read `i18n/TRANSLATING.md` and translate the UI to Russian"* as before, but deliver the result to Crowdin instead of a pull request. Download your language's file from the Crowdin editor, let the agent translate it, and upload it back (the editor's offline translation flow). Crowdin runs its QA checks on upload, and the next service PR carries the strings into the repo.
 
 ---
 
@@ -30,25 +45,6 @@ A **business zero-trust VPN** — an encrypted **overlay mesh** between a compan
 
 ---
 
-## The files
-
-```
-i18n/locales/_index.json         shipped-language list
-i18n/locales/en/common.json      source of truth — message + description
-i18n/locales/<code>/common.json  a target — message only
-```
-
-Chrome-extension JSON, each key → `{ "message", "description" }`. You translate the **`message`**.
-
-| ✅ Do | ❌ Don't |
-|---|---|
-| Keep **every key** from `en`, in the same order | Translate, rename, reorder, drop, or add keys (they're identifiers; the set grows over time) |
-| Put **only `message`** in target bundles | Copy `description` into a target bundle |
-| Give every key a non-empty `message` | Leave keys missing or empty |
-| Save valid UTF-8 JSON, no BOM | Add trailing commas or break the JSON |
-
----
-
 ## Hard rules — get these exactly right
 
 These are the usual ways a translation *breaks the app*, not just reads oddly.
@@ -58,7 +54,7 @@ These are the usual ways a translation *breaks the app*, not just reads oddly.
 | Copy `{placeholders}` verbatim — `{version}`, `{count}`, `{name}`… | Translate the word inside the braces (`{verbleibend}` breaks it) |
 | Reposition a placeholder so the sentence flows | Drop or duplicate a placeholder |
 | Preserve every `\n`, leading/trailing space, and trailing `...` | Trim "invisible" spaces or the `...` (they're load-bearing) |
-| Keep `®` in WireGuard® and quotes around `{name}` | Strip punctuation the description flags |
+| Keep `®` in WireGuard® and quotes around `{name}` | Strip punctuation the context flags |
 
 **Plurals:** the app has only a *one / other* split — the singular key fires only when `count == 1`; the `{count}` key covers everything else (0, 2, 5, 100…). Languages with more than two forms (ru, pl, uk) can't be fully correct here — use the form that fits the widest range (Russian genitive plural: `минут` / `часов` / `дней`). Don't invent extra keys or cram multiple forms into one string. When no single form fits every value — a unit label after a number field, say — reach for a number-agnostic form (an abbreviation, or wording that reads the same for 1 and 100) instead of forcing a plural the *one / other* split can't supply.
 
@@ -78,13 +74,15 @@ When a brand sits beside a common noun, keep its exact spelling but join them th
 
 > **Use the word that language's IT users actually say.** Translate when a natural, common term exists; keep the English term *only* when the literal translation would be awkward or no one in that field really uses it.
 
-Apply each term **consistently** — same English term → same translation everywhere — and keep a term once you've settled it. Whether a term stays English or takes a native word is **language-dependent**: a technical loanword (e.g. *Daemon*, *Handshake*) often stays, an everyday word (e.g. *Latency*, *Public key*) usually localizes, and some (*Exit Node*, *Peer*) go either way depending on the language. Decide per term with the rule above — a foreign origin alone is no reason to keep English. **Your main reference is the existing bundles:** match how a term was already rendered for your language rather than re-deciding it.
+Apply each term **consistently** — same English term → same translation everywhere — and keep a term once you've settled it. Whether a term stays English or takes a native word is **language-dependent**: a technical loanword (e.g. *Daemon*, *Handshake*) often stays, an everyday word (e.g. *Latency*, *Public key*) usually localizes, and some (*Exit Node*, *Peer*) go either way depending on the language. Decide per term with the rule above — a foreign origin alone is no reason to keep English. **Your main reference is the existing translation:** match how a term was already rendered for your language rather than re-deciding it.
 
 Two checks before you commit a term:
 
 - **Prefer established localized wording.** If a widely used tool in this space (for example WireGuard) ships your language, its wording for a shared term such as *handshake* is what users already expect — look at the translated app, not just English docs. For generic UI verbs and formal address, follow your OS vendor's style guide (Microsoft / Apple / Google).
 - **Watch for false friends.** A literal translation can collide with a *different* established term in your field — confirm your word doesn't already mean something else in this domain before using it.
 
+These tiers are mirrored in the Crowdin project glossary, so the editor highlights them inline. When you settle a new Tier C term for your language, add its translation to the glossary entry so it sticks for everyone who comes after you.
+
 ---
 
 ## Style
@@ -98,7 +96,7 @@ Two checks before you commit a term:
 
 Where it reads naturally, aim to keep each string **roughly the same length** as the English — the UI is tight and over-long strings can wrap or truncate. It's a soft preference, not a rule: if your language simply needs more words, use them.
 
-A few habits that keep a bundle reading like one product rather than a word-for-word port:
+A few habits that keep a translation reading like one product rather than a word-for-word port:
 
 - **Translate meaning, not words.** Render what a string *does*. An idiom or an awkward source phrase should become natural in your language, not a literal calque.
 - **Keep one voice within a family.** Sibling strings — the connection states, every settings *help* caption, every "… Failed" title — should share a grammatical form. If one member sounds wrong in that form, re-voice the whole family rather than leave one odd sibling.
@@ -107,27 +105,26 @@ A few habits that keep a bundle reading like one product rather than a word-for-
 
 ---
 
-## Procedure
+## Reviewing a language
 
-**New language** — read `en/common.json` *with* descriptions → settle your Tier C terms → write `i18n/locales/<code>/common.json` (same keys and order as `en`, `message` only, placeholders & brands preserved) → add a row to `_index.json` (`{"code","displayName"` = native name`,"englishName"}`) → run the QA list. Use the locale-code style the existing entries use (e.g. `fr`, `pt`, `zh-CN`).
+**On Crowdin:** proofread in the editor — context, glossary highlights, and QA flags sit inline next to each string.
 
-**Review (de / hu / …)** — read source and target side by side; for each key check glossary conformance (e.g. de `Exit-Node` → `Exit Node`, hu `Kilépő csomópont` → `Exit Node`), placeholder/`\n` integrity, consistency, tone, and that the meaning matches the English `description`. Fix in place, then report what you changed (especially term standardizations) so a native speaker can sanity-check.
+**In the repo** — e.g. driving an AI agent with *"Read `i18n/TRANSLATING.md` and review the existing German translation"* — read source and target side by side; for each key check glossary conformance (e.g. de `Exit-Node` → `Exit Node`, hu `Kilépő csomópont` → `Exit Node`), placeholder/`\n` integrity, consistency, tone, and that the meaning matches the English `description`. Report what you found, and apply the fixes **on Crowdin** — direct edits to the locale files are overwritten by the next sync.
 
 ---
 
 ## QA before you finish
 
-- [ ] Valid JSON · **every `en` key** present, same order · **no `description`** fields
 - [ ] Every `{placeholder}`, `\n`, and intentional space preserved · `...` / `… Failed` / `{name}` quotes kept
-- [ ] Tier A/B left intact · Tier C applied consistently (and matching the existing bundle for your language)
+- [ ] Tier A/B left intact · Tier C applied consistently (and matching the existing translation for your language)
 - [ ] Buttons & tray short · locale punctuation and capitalization applied
-- [ ] New language added to `_index.json`
+- [ ] Crowdin QA flags resolved (variables, glossary terms, punctuation)
 - [ ] **Tested in the running app** ↓
 
 ---
 
 ## Test it in the app
 
-A bundle can pass every check above and still read wrong on screen. **Run the app, switch to your language, and click through the real surfaces** — tray menu, main window, every Settings tab, the dialogs. Watch for text overflow or truncation, labels that are technically right but wrong *for what the control does*, leaked placeholders, and terms that drift between screens.
+A translation can pass every check above and still read wrong on screen. **Run the app, switch to your language, and click through the real surfaces** — tray menu, main window, every Settings tab, the dialogs. Watch for text overflow or truncation, labels that are technically right but wrong *for what the control does*, leaked placeholders, and terms that drift between screens.
 
 How to run the app and switch language: see the project README. Can't run it (e.g. a headless agent)? Say so in your summary — don't silently skip this step.

client/ui/i18n/locales/en/common.json

@@ -1013,11 +1013,27 @@
     },
     "settings.troubleshooting.anonymize.label": {
         "message": "Anonymize Sensitive Information",
-        "description": "Toggle label: anonymize sensitive information in the bundle."
+        "description": "Label for the anonymization level dropdown (None, Default, Strict)."
     },
     "settings.troubleshooting.anonymize.help": {
-        "message": "Hides public IP addresses and non-NetBird domains from logs.",
-        "description": "Helper text for anonymizing logs (hides public IPs and non-NetBird domains)."
+        "message": "Hides IP addresses, domains, and other sensitive values.",
+        "description": "Helper text under the anonymization dropdown. The level details live in the info tooltip."
+    },
+    "settings.troubleshooting.anonymize.info": {
+        "message": "Default keeps internal IPv4 addresses and peer names readable for support. Strict additionally anonymizes private (RFC 1918), CGNAT, and link-local IP addresses, peer names, and WireGuard public keys. Recurring values map to the same placeholder, so peers stay distinguishable. Use Strict when sharing the bundle outside your organization.",
+        "description": "Info tooltip explaining the anonymization levels. 'RFC 1918', 'CGNAT', 'link-local', and 'WireGuard' are technical terms — keep them."
+    },
+    "settings.troubleshooting.anonymize.none": {
+        "message": "None",
+        "description": "Dropdown option: no anonymization."
+    },
+    "settings.troubleshooting.anonymize.default": {
+        "message": "Default",
+        "description": "Dropdown option: default anonymization level."
+    },
+    "settings.troubleshooting.anonymize.strict": {
+        "message": "Strict",
+        "description": "Dropdown option: strict anonymization level."
     },
     "settings.troubleshooting.systemInfo.label": {
         "message": "Include System Information",

client/ui/services/connection.go

@@ -108,10 +108,11 @@ func (s *Connection) Login(ctx context.Context, p LoginParams) (LoginResult, err
 	}
 
 	req := &proto.LoginRequest{
-		ManagementUrl:       p.ManagementURL,
-		SetupKey:            p.SetupKey,
-		Hostname:            p.Hostname,
-		IsUnixDesktopClient: runtime.GOOS == "linux",
+		ManagementUrl: p.ManagementURL,
+		SetupKey:      p.SetupKey,
+		Hostname:      p.Hostname,
+		// a login driven by the UI always has a graphical session available
+		IsUnixDesktopClient: true,
 	}
 	if profileName != "" {
 		req.ProfileName = ptrStr(profileName)

client/ui/services/debug.go

@@ -15,10 +15,13 @@ import (
 )
 
 type DebugBundleParams struct {
-	Anonymize    bool   `json:"anonymize"`
-	SystemInfo   bool   `json:"systemInfo"`
-	UploadURL    string `json:"uploadUrl"`
-	LogFileCount uint32 `json:"logFileCount"`
+	Anonymize bool `json:"anonymize"`
+	// AnonymizeLevel is "default" or "strict"; strict also anonymizes
+	// private IP ranges, peer names, and WireGuard public keys.
+	AnonymizeLevel string `json:"anonymizeLevel"`
+	SystemInfo     bool   `json:"systemInfo"`
+	UploadURL      string `json:"uploadUrl"`
+	LogFileCount   uint32 `json:"logFileCount"`
 }
 
 // DebugBundleResult: Path is set for local-only bundles, UploadedKey on upload
@@ -48,11 +51,12 @@ func (s *Debug) Bundle(ctx context.Context, p DebugBundleParams) (DebugBundleRes
 		return DebugBundleResult{}, err
 	}
 	resp, err := cli.DebugBundle(ctx, &proto.DebugBundleRequest{
-		Anonymize:    p.Anonymize,
-		SystemInfo:   p.SystemInfo,
-		UploadURL:    p.UploadURL,
-		LogFileCount: p.LogFileCount,
-		CliVersion:   version.NetbirdVersion(),
+		Anonymize:      p.Anonymize,
+		AnonymizeLevel: p.AnonymizeLevel,
+		SystemInfo:     p.SystemInfo,
+		UploadURL:      p.UploadURL,
+		LogFileCount:   p.LogFileCount,
+		CliVersion:     version.NetbirdVersion(),
 	})
 	if err != nil {
 		return DebugBundleResult{}, err

crowdin.yml

@@ -0,0 +1,11 @@
+skip_untranslated_strings: true
+skip_untranslated_files: true
+import_eq_suggestions: true
+
+files:
+  - source: /client/ui/i18n/locales/en/common.json
+    translation: /client/ui/i18n/locales/%two_letters_code%/common.json
+    type: chrome
+    languages_mapping:
+      two_letters_code:
+        zh-CN: zh-CN

e2e/agentnetwork/chat_test.go

@@ -438,14 +438,10 @@ func TestProvidersMatrix(t *testing.T) {
 	// Create every provider, all enabled, each with a unique model string so the
 	// proxy's connect-time snapshot carries them all and model→provider routing
 	// is unambiguous (provider toggles after connect don't reconcile to the
-	// proxy, so we enable everything up front). The first create bootstraps the
-	// cluster.
+	// proxy, so we enable everything up front).
 	ids := make([]string, 0, len(matrix))
-	for i, pc := range matrix {
+	for _, pc := range matrix {
 		req := providerRequest(pc)
-		if i == 0 {
-			req.BootstrapCluster = ptr(harness.AgentNetworkCluster)
-		}
 		prov, perr := srv.CreateProvider(ctx, req)
 		require.NoError(t, perr, "create provider %s", pc.name)
 		ids = append(ids, prov.Id)

e2e/agentnetwork/custom_pricing_test.go

@@ -82,13 +82,12 @@ func provisionPricedProvider(t *testing.T, ctx context.Context, name string, mod
 	// need NOT be in the catalog — the operator names it and prices it here.
 	dummyKey := "sk-price-e2e"
 	prov, err := srv.CreateProvider(ctx, api.AgentNetworkProviderRequest{
-		Name:             name,
-		ProviderId:       "openai_api",
-		UpstreamUrl:      vllm.URL,
-		ApiKey:           &dummyKey,
-		Enabled:          ptr(true),
-		BootstrapCluster: ptr(harness.AgentNetworkCluster),
-		Models:           &models,
+		Name:        name,
+		ProviderId:  "openai_api",
+		UpstreamUrl: vllm.URL,
+		ApiKey:      &dummyKey,
+		Enabled:     ptr(true),
+		Models:      &models,
 	})
 	require.NoError(t, err, "create provider")
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), prov.Id) })

e2e/agentnetwork/guardrail_block_test.go

@@ -113,15 +113,14 @@ func runPathRoutedGuardrailCase(t *testing.T, tc pathRoutedGuardrailCase) {
 
 	// Catch-all provider (no models) so the router forwards any model; a static
 	// bearer key means the router injects a static auth header instead of minting
-	// a GCP token. Bootstraps the cluster if it isn't already.
+	// a GCP token.
 	staticKey := "static-e2e-token"
 	prov, err := srv.CreateProvider(ctx, api.AgentNetworkProviderRequest{
-		Name:             tc.name,
-		ProviderId:       tc.catalogID,
-		UpstreamUrl:      vllm.URL,
-		ApiKey:           &staticKey,
-		Enabled:          ptr(true),
-		BootstrapCluster: ptr(harness.AgentNetworkCluster),
+		Name:        tc.name,
+		ProviderId:  tc.catalogID,
+		UpstreamUrl: vllm.URL,
+		ApiKey:      &staticKey,
+		Enabled:     ptr(true),
 	})
 	require.NoError(t, err, "create %s provider", tc.name)
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), prov.Id) })

e2e/agentnetwork/guardrail_groupswitch_test.go

@@ -73,7 +73,6 @@ func TestGuardrailGroupSwitchTakesEffectAfterTTL(t *testing.T) {
 			{Id: modelA, InputPer1k: 0.001, OutputPer1k: 0.001},
 			{Id: modelB, InputPer1k: 0.001, OutputPer1k: 0.001},
 		},
-		BootstrapCluster: ptr(harness.AgentNetworkCluster),
 	})
 	require.NoError(t, err, "create provider")
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), prov.Id) })

e2e/agentnetwork/guardrail_multipolicy_test.go

@@ -61,15 +61,14 @@ func TestGuardrailMultiPolicyModelAllowlist(t *testing.T) {
 	}
 
 	// pRestricted declares the two guardrailed models so routing is deterministic
-	// (model -> provider). Created first, so it carries the bootstrap cluster.
+	// (model -> provider).
 	pRestricted, err := srv.CreateProvider(ctx, api.AgentNetworkProviderRequest{
-		Name:             "restricted",
-		ProviderId:       "openai_api",
-		UpstreamUrl:      vllm.URL,
-		ApiKey:           &staticKey,
-		Enabled:          ptr(true),
-		Models:           models(modelSelected, modelOther),
-		BootstrapCluster: ptr(harness.AgentNetworkCluster),
+		Name:        "restricted",
+		ProviderId:  "openai_api",
+		UpstreamUrl: vllm.URL,
+		ApiKey:      &staticKey,
+		Enabled:     ptr(true),
+		Models:      models(modelSelected, modelOther),
 	})
 	require.NoError(t, err, "create restricted provider")
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), pRestricted.Id) })

e2e/agentnetwork/guardrail_pergroup_providers_test.go

@@ -115,7 +115,7 @@ func TestGuardrailPerGroupAllowlist_AllProviders(t *testing.T) {
 	staticKey := "static-e2e-token"
 	enabled := true
 
-	for i, c := range cases {
+	for _, c := range cases {
 		req := api.AgentNetworkProviderRequest{
 			Name:        "e2e-pergroup-" + c.name,
 			ProviderId:  c.catalogID,
@@ -124,9 +124,6 @@ func TestGuardrailPerGroupAllowlist_AllProviders(t *testing.T) {
 			Enabled:     ptr(true),
 			Models:      c.models,
 		}
-		if i == 0 {
-			req.BootstrapCluster = ptr(harness.AgentNetworkCluster)
-		}
 		prov, perr := srv.CreateProvider(ctx, req)
 		require.NoError(t, perr, "create provider %s", c.name)
 		c.providerID = prov.Id
@@ -283,13 +280,12 @@ func TestGuardrailMultiGroupUser(t *testing.T) {
 
 	// P1 — union scenario: two restricting policies, one per group.
 	p1, err := srv.CreateProvider(ctx, api.AgentNetworkProviderRequest{
-		Name:             "e2e-mg-union",
-		ProviderId:       "openai_api",
-		UpstreamUrl:      vllm.URL,
-		ApiKey:           &staticKey,
-		Enabled:          ptr(true),
-		Models:           priced(unionA, unionB, unionC),
-		BootstrapCluster: ptr(harness.AgentNetworkCluster),
+		Name:        "e2e-mg-union",
+		ProviderId:  "openai_api",
+		UpstreamUrl: vllm.URL,
+		ApiKey:      &staticKey,
+		Enabled:     ptr(true),
+		Models:      priced(unionA, unionB, unionC),
 	})
 	require.NoError(t, err, "create union provider")
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), p1.Id) })

e2e/agentnetwork/guardrail_test.go

@@ -115,14 +115,11 @@ func TestModelAllowlistEnforced(t *testing.T) {
 	})
 	require.NoError(t, err, "mint setup key")
 
-	// Providers with their configured (allowed) models; the first bootstraps the cluster.
+	// Providers with their configured (allowed) models
 	ids := make([]string, 0, len(providers))
 	allowed := make([]string, 0, len(providers))
-	for i, pc := range providers {
+	for _, pc := range providers {
 		req := providerRequest(pc)
-		if i == 0 {
-			req.BootstrapCluster = ptr(harness.AgentNetworkCluster)
-		}
 		prov, perr := srv.CreateProvider(ctx, req)
 		require.NoError(t, perr, "create provider %s", pc.name)
 		id := prov.Id

e2e/agentnetwork/main_test.go

@@ -14,6 +14,7 @@ import (
 	"time"
 
 	"github.com/netbirdio/netbird/e2e/harness"
+	"github.com/netbirdio/netbird/shared/management/http/api"
 )
 
 // srv is the shared combined server for the package, ready (PAT-authenticated)
@@ -42,5 +43,14 @@ func run(m *testing.M) int {
 		return 1
 	}
 
+	// Bootstrap the account's agent-network endpoint once for the package:
+	// providers no longer have settings side effects, and every data-plane
+	// test expects the shared account pinned to the combined proxy cluster.
+	cluster := harness.AgentNetworkCluster
+	if _, err := srv.CreateSettings(ctx, api.AgentNetworkSettingsCreateRequest{ProxyAddress: &cluster}); err != nil {
+		fmt.Fprintf(os.Stderr, "e2e: bootstrap agent-network endpoint: %v\n", err)
+		return 1
+	}
+
 	return m.Run()
 }

e2e/agentnetwork/management_test.go

@@ -21,11 +21,10 @@ func ptr[T any](v T) *T { return &v }
 func newProvider(t *testing.T, ctx context.Context, name string) api.AgentNetworkProvider {
 	t.Helper()
 	prov, err := srv.CreateProvider(ctx, api.AgentNetworkProviderRequest{
-		Name:             name,
-		ProviderId:       "openai_api",
-		UpstreamUrl:      "https://api.openai.com",
-		ApiKey:           ptr("sk-dummy-e2e-key"),
-		BootstrapCluster: ptr("eu.proxy.netbird.test"),
+		Name:        name,
+		ProviderId:  "openai_api",
+		UpstreamUrl: "https://api.openai.com",
+		ApiKey:      ptr("sk-dummy-e2e-key"),
 	})
 	require.NoError(t, err, "create provider %q", name)
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), prov.Id) })
@@ -57,17 +56,11 @@ func TestProviderLifecycle(t *testing.T) {
 		}}
 	}
 
-	for i, pc := range cases {
-		i, pc := i, pc
+	for _, pc := range cases {
+		pc := pc
 		t.Run(pc.name, func(t *testing.T) {
 			req := providerRequest(pc)
 			req.Name = "lc-" + pc.name
-			// Bootstrap the cluster on the first create in case the matrix has
-			// not run (e.g. no provider keys → settings not yet bootstrapped).
-			if i == 0 {
-				req.BootstrapCluster = ptr(harness.AgentNetworkCluster)
-			}
-
 			prov, err := srv.CreateProvider(ctx, req)
 			require.NoError(t, err, "create %s provider", pc.name)
 			t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), prov.Id) })
@@ -137,45 +130,65 @@ func TestProviderValidation(t *testing.T) {
 	requireClientError(t, err)
 }
 
-// TestSettingsRoundTrip flips the collection toggles and confirms cluster /
-// subdomain stay immutable, then restores the original state.
+// TestSettingsRoundTrip flips the collection toggles and confirms the
+// endpoint and proxy address stay immutable, then restores the original
+// state. A second bootstrap attempt must be rejected as a conflict.
 func TestSettingsRoundTrip(t *testing.T) {
 	ctx := context.Background()
 
-	// Settings are bootstrapped on first provider create.
-	newProvider(t, ctx, "Settings Bootstrap")
-
+	// The package's TestMain bootstrapped the shared account's endpoint.
 	before, err := srv.GetSettings(ctx)
 	require.NoError(t, err, "get settings")
-	require.NotEmpty(t, before.Cluster, "settings must carry an assigned cluster")
+	require.NotEmpty(t, before.Endpoint, "settings must carry the bootstrapped endpoint")
+	require.NotEmpty(t, before.ProxyAddress, "settings must carry the bootstrapped proxy address")
+
+	require.NotNil(t, before.AccessLogRetentionDays, "bootstrapped settings must carry a retention")
+	beforeRetention := *before.AccessLogRetentionDays
 
 	flipped, err := srv.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
+		Endpoint:               before.Endpoint,
+		ProxyAddress:           before.ProxyAddress,
 		EnableLogCollection:    !before.EnableLogCollection,
 		EnablePromptCollection: !before.EnablePromptCollection,
 		RedactPii:              !before.RedactPii,
+		AccessLogRetentionDays: beforeRetention,
 	})
 	require.NoError(t, err, "update settings")
 	assert.Equal(t, !before.EnableLogCollection, flipped.EnableLogCollection, "log collection toggle must flip")
 	assert.Equal(t, !before.EnablePromptCollection, flipped.EnablePromptCollection, "prompt collection toggle must flip")
-	assert.Equal(t, before.Cluster, flipped.Cluster, "cluster must be immutable across updates")
-	assert.Equal(t, before.Subdomain, flipped.Subdomain, "subdomain must be immutable across updates")
+	require.NotNil(t, flipped.AccessLogRetentionDays)
+	assert.Equal(t, beforeRetention, *flipped.AccessLogRetentionDays,
+		"retention sent unchanged must round-trip, not reset to the zero value")
+	assert.Equal(t, before.Endpoint, flipped.Endpoint, "endpoint must be immutable across updates")
+	assert.Equal(t, before.ProxyAddress, flipped.ProxyAddress, "proxy address must be immutable across updates")
 
-	// A cluster different from the pinned one must be rejected; echoing the
-	// pinned one back is valid.
+	// The account is already bootstrapped: a second bootstrap is a conflict,
+	// whatever shape it asks for.
+	_, err = srv.CreateSettings(ctx, api.AgentNetworkSettingsCreateRequest{
+		Endpoint: ptr("attacker.cluster.invalid"),
+	})
+	requireClientError(t, err)
+
+	// The identity fields ride along on the PUT as a required echo: a request
+	// carrying a different endpoint is rejected without applying anything.
 	_, err = srv.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
-		Cluster:                ptr("attacker.cluster.invalid"),
+		Endpoint:               "other.cluster.invalid",
+		ProxyAddress:           before.ProxyAddress,
 		EnableLogCollection:    before.EnableLogCollection,
 		EnablePromptCollection: before.EnablePromptCollection,
 		RedactPii:              before.RedactPii,
+		AccessLogRetentionDays: beforeRetention,
 	})
 	requireClientError(t, err)
 
 	// Restore the original toggles.
 	_, err = srv.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
-		Cluster:                ptr(before.Cluster),
+		Endpoint:               before.Endpoint,
+		ProxyAddress:           before.ProxyAddress,
 		EnableLogCollection:    before.EnableLogCollection,
 		EnablePromptCollection: before.EnablePromptCollection,
 		RedactPii:              before.RedactPii,
+		AccessLogRetentionDays: beforeRetention,
 	})
 	require.NoError(t, err, "restore settings")
 }

e2e/agentnetwork/settings_bootstrap_test.go

@@ -4,6 +4,7 @@ package agentnetwork
 
 import (
 	"context"
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -14,7 +15,8 @@ import (
 )
 
 // harnessStartFresh boots a dedicated combined server with its own fresh
-// account and registers its teardown on t.
+// account and registers its teardown on t. Unlike the shared srv, the fresh
+// account has NOT had its agent-network endpoint bootstrapped.
 func harnessStartFresh(ctx context.Context, t *testing.T) (*harness.Combined, error) {
 	t.Helper()
 	fresh, err := harness.StartCombined(ctx)
@@ -28,16 +30,16 @@ func harnessStartFresh(ctx context.Context, t *testing.T) (*harness.Combined, er
 	return fresh, nil
 }
 
-// TestSettingsBootstrapViaPut covers the settings-first bootstrap path on an
+// TestSettingsBootstrapViaPost covers the explicit bootstrap contract on an
 // account that has never been bootstrapped: the GET reads as the defaults
-// with an empty cluster/subdomain/endpoint, a PUT without a cluster has
-// nothing to pin and fails, and a PUT carrying a cluster creates the row and
-// pins it immutably. The shared srv cannot provide that starting state (any
-// provider-creating test bootstraps it, and test order is deliberately not
-// relied on), so this boots a dedicated combined server — the image is
-// already built and cached by TestMain's StartCombined, so the extra cost is
-// one container start.
-func TestSettingsBootstrapViaPut(t *testing.T) {
+// with an empty endpoint/proxy_address, a PUT has no row to update and fails,
+// and a POST creates the row and assigns the immutable endpoint — labeled
+// beneath a proxy address here, with the toggle overrides from the same
+// request applied. The shared srv cannot provide that starting state
+// (TestMain bootstraps it), so this boots a dedicated combined server — the
+// image is already built and cached by TestMain's StartCombined, so the extra
+// cost is one container start.
+func TestSettingsBootstrapViaPost(t *testing.T) {
 	ctx := context.Background()
 
 	fresh, err := harnessStartFresh(ctx, t)
@@ -47,32 +49,35 @@ func TestSettingsBootstrapViaPut(t *testing.T) {
 	// as an error and not as a null body.
 	before, err := fresh.GetSettings(ctx)
 	require.NoError(t, err, "get settings on a fresh account must succeed")
-	assert.Empty(t, before.Cluster, "cluster must be empty before bootstrap")
-	assert.Empty(t, before.Subdomain, "subdomain must be empty before bootstrap")
-	assert.Empty(t, before.Endpoint, "endpoint must be empty before bootstrap, not a bare dot")
+	assert.Empty(t, before.Endpoint, "endpoint must be empty before bootstrap")
+	assert.Empty(t, before.ProxyAddress, "proxy address must be empty before bootstrap")
+	assert.False(t, before.Dedicated, "an unbootstrapped account has no serving shape")
 	assert.True(t, before.EnableLogCollection, "defaults must show log collection on, matching bootstrap")
 	assert.False(t, before.EnablePromptCollection, "defaults must show prompt collection off")
 
-	// A PUT without a cluster has nothing to pin the account to.
+	// A PUT has no row to update yet — bootstrap is the explicit POST.
 	_, err = fresh.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
-		EnableLogCollection: true,
+		EnableLogCollection:    true,
+		AccessLogRetentionDays: 30,
 	})
 	requireClientError(t, err)
 
-	// A PUT carrying a cluster bootstraps the account and applies the
-	// mutable fields from the same request. Every toggle is set away from
-	// its bootstrap default so each assertion can actually fail.
+	// A POST with a proxy address bootstraps a labeled endpoint and applies
+	// the toggles from the same request. Every toggle is set away from its
+	// bootstrap default so each assertion can actually fail.
 	const cluster = "e2e.bootstrap.netbird.selfhosted"
-	bootstrapped, err := fresh.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
-		Cluster:                ptr(cluster),
-		EnableLogCollection:    false,
-		EnablePromptCollection: true,
-		RedactPii:              true,
+	bootstrapped, err := fresh.CreateSettings(ctx, api.AgentNetworkSettingsCreateRequest{
+		ProxyAddress:           ptr(cluster),
+		EnableLogCollection:    ptr(false),
+		EnablePromptCollection: ptr(true),
+		RedactPii:              ptr(true),
 	})
-	require.NoError(t, err, "bootstrap settings via PUT must succeed")
-	assert.Equal(t, cluster, bootstrapped.Cluster, "cluster must be pinned from the request")
-	require.NotEmpty(t, bootstrapped.Subdomain, "subdomain must be assigned at bootstrap")
-	assert.Equal(t, bootstrapped.Subdomain+"."+cluster, bootstrapped.Endpoint, "endpoint must combine subdomain and cluster")
+	require.NoError(t, err, "bootstrap settings via POST must succeed")
+	assert.Equal(t, cluster, bootstrapped.ProxyAddress, "proxy address must be pinned from the request")
+	require.NotEmpty(t, bootstrapped.Endpoint, "endpoint must be assigned at bootstrap")
+	assert.True(t, strings.HasSuffix(bootstrapped.Endpoint, "."+cluster),
+		"labeled endpoint must hang one label beneath the proxy address: %s", bootstrapped.Endpoint)
+	assert.False(t, bootstrapped.Dedicated, "a labeled pin is not dedicated")
 	assert.False(t, bootstrapped.EnableLogCollection, "log collection from the bootstrap request must override the default")
 	assert.True(t, bootstrapped.EnablePromptCollection, "prompt collection from the bootstrap request must apply")
 	assert.True(t, bootstrapped.RedactPii, "redact toggle from the bootstrap request must apply")
@@ -85,30 +90,90 @@ func TestSettingsBootstrapViaPut(t *testing.T) {
 	assert.Equal(t, bootstrapped.EnablePromptCollection, after.EnablePromptCollection, "prompt collection must persist")
 	assert.Equal(t, bootstrapped.RedactPii, after.RedactPii, "redact toggle must persist")
 
-	// Once bootstrapped, later updates may omit the cluster entirely.
+	// Once bootstrapped, PUT updates the toggles. The identity fields ride
+	// along as a required echo of the assigned values; a matching echo is
+	// accepted and never written.
 	persisted, err := fresh.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
+		Endpoint:               bootstrapped.Endpoint,
+		ProxyAddress:           bootstrapped.ProxyAddress,
 		EnableLogCollection:    true,
 		EnablePromptCollection: false,
 		RedactPii:              true,
+		AccessLogRetentionDays: 21,
 	})
-	require.NoError(t, err, "post-bootstrap update without cluster must succeed")
-	assert.Equal(t, cluster, persisted.Cluster, "omitted cluster must keep the pinned value")
+	require.NoError(t, err, "post-bootstrap update must succeed")
+	require.NotNil(t, persisted.AccessLogRetentionDays)
+	assert.Equal(t, 21, *persisted.AccessLogRetentionDays, "retention from the update must apply")
+	assert.Equal(t, bootstrapped.Endpoint, persisted.Endpoint, "endpoint must survive updates untouched")
+	assert.Equal(t, cluster, persisted.ProxyAddress, "proxy address must survive updates untouched")
 	assert.True(t, persisted.EnableLogCollection, "post-bootstrap toggle must apply")
 	assert.False(t, persisted.EnablePromptCollection, "post-bootstrap toggle must apply")
 
-	// The cluster is immutable: a different value is rejected rather than
-	// silently ignored, and the rejected update must not disturb anything.
+	// The endpoint is immutable: a PUT carrying a different endpoint is
+	// rejected, and a second bootstrap is rejected as a conflict. Neither
+	// rejected write may disturb anything.
 	_, err = fresh.UpdateSettings(ctx, api.AgentNetworkSettingsRequest{
-		Cluster:             ptr("other.cluster.invalid"),
-		EnableLogCollection: false,
+		Endpoint:               "other.cluster.invalid",
+		ProxyAddress:           persisted.ProxyAddress,
+		EnableLogCollection:    persisted.EnableLogCollection,
+		EnablePromptCollection: persisted.EnablePromptCollection,
+		RedactPii:              persisted.RedactPii,
+		AccessLogRetentionDays: 21,
+	})
+	requireClientError(t, err)
+
+	_, err = fresh.CreateSettings(ctx, api.AgentNetworkSettingsCreateRequest{
+		Endpoint: ptr("other.cluster.invalid"),
 	})
 	requireClientError(t, err)
 
 	final, err := fresh.GetSettings(ctx)
-	require.NoError(t, err, "get settings after the rejected cluster change must succeed")
-	assert.Equal(t, persisted.Cluster, final.Cluster, "rejected update must not change the cluster")
-	assert.Equal(t, persisted.Endpoint, final.Endpoint, "rejected update must not change the endpoint")
-	assert.Equal(t, persisted.EnableLogCollection, final.EnableLogCollection, "rejected update must not apply its toggles")
-	assert.Equal(t, persisted.EnablePromptCollection, final.EnablePromptCollection, "rejected update must not apply its toggles")
-	assert.Equal(t, persisted.RedactPii, final.RedactPii, "rejected update must not apply its toggles")
+	require.NoError(t, err, "get settings after the rejected bootstrap must succeed")
+	assert.Equal(t, persisted.Endpoint, final.Endpoint, "rejected bootstrap must not change the endpoint")
+	assert.Equal(t, persisted.ProxyAddress, final.ProxyAddress, "rejected bootstrap must not change the proxy address")
+	assert.Equal(t, persisted.EnableLogCollection, final.EnableLogCollection, "rejected bootstrap must not apply its toggles")
+	assert.Equal(t, persisted.EnablePromptCollection, final.EnablePromptCollection, "rejected bootstrap must not apply its toggles")
+	assert.Equal(t, persisted.RedactPii, final.RedactPii, "rejected bootstrap must not apply its toggles")
+}
+
+// TestSettingsBootstrapSelfAddressed covers the dedicated shape end to end:
+// a POST carrying an endpoint claims the hostname verbatim, the proxy address
+// equals it, and the pin reads as dedicated — the address-first flow a
+// self-hosted operator uses before deploying the proxy that will declare it.
+// The tail covers the recovery path the guarded DELETE exists for: with no
+// providers and no proxy at the address, the claim can be released and a
+// fresh bootstrap succeeds — the fix for a typo'd immutable endpoint.
+func TestSettingsBootstrapSelfAddressed(t *testing.T) {
+	ctx := context.Background()
+
+	fresh, err := harnessStartFresh(ctx, t)
+	require.NoError(t, err, "start dedicated combined server")
+
+	created, err := fresh.CreateSettings(ctx, api.AgentNetworkSettingsCreateRequest{
+		Endpoint: ptr("gw.e2e.netbird.selfhosted"),
+	})
+	require.NoError(t, err, "self-addressed bootstrap must succeed")
+	assert.Equal(t, "gw.e2e.netbird.selfhosted", created.Endpoint, "endpoint must be claimed verbatim")
+	assert.Equal(t, created.Endpoint, created.ProxyAddress, "self-addressed: proxy address is the endpoint")
+	assert.True(t, created.Dedicated, "a self-addressed pin is dedicated")
+
+	// No providers exist and no proxy declares the address, so both delete
+	// guards are clear: the delete releases the claim and the account reads
+	// as unbootstrapped defaults again.
+	require.NoError(t, fresh.DeleteSettings(ctx), "guarded delete with both guards clear must succeed")
+
+	after, err := fresh.GetSettings(ctx)
+	require.NoError(t, err, "get settings after delete must succeed")
+	assert.Empty(t, after.Endpoint, "a deleted account must read as unbootstrapped")
+
+	// A second delete has nothing to remove.
+	requireClientError(t, fresh.DeleteSettings(ctx))
+
+	// Re-creating is a fresh bootstrap — the released hostname is free to be
+	// claimed again, or a different one chosen.
+	recreated, err := fresh.CreateSettings(ctx, api.AgentNetworkSettingsCreateRequest{
+		Endpoint: ptr("gw2.e2e.netbird.selfhosted"),
+	})
+	require.NoError(t, err, "bootstrap after delete must succeed")
+	assert.Equal(t, "gw2.e2e.netbird.selfhosted", recreated.Endpoint, "the fresh bootstrap claims the new hostname")
 }

e2e/agentnetwork/skiptls_test.go

@@ -66,9 +66,7 @@ func TestProviderSkipTLSVerification(t *testing.T) {
 		}
 	}
 
-	// First create bootstraps the account cluster.
 	insecureReq := newReq("skip-tls", insecureModel, true)
-	insecureReq.BootstrapCluster = ptr(harness.AgentNetworkCluster)
 	insecureProv, err := srv.CreateProvider(ctx, insecureReq)
 	require.NoError(t, err, "create skip-tls provider")
 	t.Cleanup(func() { _ = srv.DeleteProvider(context.Background(), insecureProv.Id) })

e2e/agentnetwork/vllm_test.go

@@ -57,12 +57,11 @@ func TestVLLMProvider(t *testing.T) {
 	// is enumerated so the router dispatches this model string to this provider.
 	dummyKey := "sk-vllm-e2e"
 	prov, err := srv.CreateProvider(ctx, api.AgentNetworkProviderRequest{
-		Name:             "vllm",
-		ProviderId:       "vllm",
-		UpstreamUrl:      vllm.URL,
-		ApiKey:           &dummyKey,
-		Enabled:          ptr(true),
-		BootstrapCluster: ptr(harness.AgentNetworkCluster),
+		Name:        "vllm",
+		ProviderId:  "vllm",
+		UpstreamUrl: vllm.URL,
+		ApiKey:      &dummyKey,
+		Enabled:     ptr(true),
 		Models: &[]api.AgentNetworkProviderModel{
 			{Id: harness.VLLMModel, InputPer1k: 0.001, OutputPer1k: 0.002},
 		},

e2e/harness/Dockerfile.client

@@ -20,5 +20,9 @@ ENV NETBIRD_BIN="/usr/local/bin/netbird" \
     NB_ENABLE_CAPTURE="false" \
     NB_ENTRYPOINT_SERVICE_TIMEOUT="30"
 ENTRYPOINT [ "/usr/local/bin/netbird-entrypoint.sh" ]
-COPY client/netbird-entrypoint.sh /usr/local/bin/netbird-entrypoint.sh
+# --chmod because the build context is not always a git checkout. A suite in
+# another module builds from this module's extracted copy in the module cache,
+# where every file is 0444 — the cache drops the executable bit git records — and
+# a bare COPY then produces an entrypoint the runtime cannot exec.
+COPY --chmod=0755 client/netbird-entrypoint.sh /usr/local/bin/netbird-entrypoint.sh
 COPY --from=builder /out/netbird /usr/local/bin/netbird

e2e/harness/agentnetwork.go

@@ -126,17 +126,33 @@ func (c *Combined) DeleteGuardrail(ctx context.Context, id string) error {
 	return anDelete(ctx, c, "/api/agent-network/guardrails/"+id)
 }
 
-// GetSettings returns the account's agent-network settings row. It exists only
-// after the first provider create bootstraps it.
+// CreateSettings bootstraps the account's agent-network settings row,
+// assigning the immutable endpoint. Exactly one of req.ProxyAddress (labeled
+// endpoint beneath that cluster) and req.Endpoint (self-addressed dedicated
+// endpoint) must be set; a second bootstrap returns a conflict.
+func (c *Combined) CreateSettings(ctx context.Context, req api.AgentNetworkSettingsCreateRequest) (api.AgentNetworkSettings, error) {
+	return anRequest[api.AgentNetworkSettings](ctx, c, http.MethodPost, "/api/agent-network/settings", req)
+}
+
+// GetSettings returns the account's agent-network settings row. Before the
+// CreateSettings bootstrap it reads as the defaults with an empty endpoint.
 func (c *Combined) GetSettings(ctx context.Context) (api.AgentNetworkSettings, error) {
 	return anRequest[api.AgentNetworkSettings](ctx, c, http.MethodGet, "/api/agent-network/settings", nil)
 }
 
-// UpdateSettings applies the mutable collection toggles.
+// UpdateSettings applies the mutable collection toggles. The request must
+// echo the assigned endpoint and proxy address unchanged — the server rejects
+// a PUT that tries to change them.
 func (c *Combined) UpdateSettings(ctx context.Context, req api.AgentNetworkSettingsRequest) (api.AgentNetworkSettings, error) {
 	return anRequest[api.AgentNetworkSettings](ctx, c, http.MethodPut, "/api/agent-network/settings", req)
 }
 
+// DeleteSettings removes the account's settings row, releasing the endpoint.
+// Refused while providers exist or a proxy is actively serving the endpoint.
+func (c *Combined) DeleteSettings(ctx context.Context) error {
+	return anDelete(ctx, c, "/api/agent-network/settings")
+}
+
 // ListConsumption returns the account's consumption rows (possibly empty).
 func (c *Combined) ListConsumption(ctx context.Context) ([]api.AgentNetworkConsumption, error) {
 	return anRequest[[]api.AgentNetworkConsumption](ctx, c, http.MethodGet, "/api/agent-network/consumption", nil)

e2e/harness/client.go

@@ -32,12 +32,36 @@ type Client struct {
 	container testcontainers.Container
 }
 
+// clientOptions is what the ClientOption values assemble.
+type clientOptions struct {
+	name string
+}
+
+// ClientOption adjusts how StartClient runs the agent.
+type ClientOption func(*clientOptions)
+
+// WithClientName names the agent, which sets both its network alias and its
+// container hostname. The hostname matters beyond addressing: the agent reports
+// it to management at registration, so it is the name the peer appears under in
+// the API.
+//
+// Required to run more than one agent against the same server — the default name
+// is shared, and two containers cannot hold the same alias on one network.
+func WithClientName(name string) ClientOption {
+	return func(o *clientOptions) { o.name = name }
+}
+
 // StartClient builds the client image and runs it on the combined server's
 // network, joining via the given setup key. The image entrypoint brings the
 // daemon up automatically; callers wait for connectivity with WaitConnected /
 // WaitProxyPeer.
-func StartClient(ctx context.Context, c *Combined, setupKey string) (*Client, error) {
-	root, err := repoRoot()
+func StartClient(ctx context.Context, c *Combined, setupKey string, opts ...ClientOption) (*Client, error) {
+	o := clientOptions{name: clientAlias}
+	for _, opt := range opts {
+		opt(&o)
+	}
+
+	root, err := repoRoot(ctx)
 	if err != nil {
 		return nil, err
 	}
@@ -47,9 +71,13 @@ func StartClient(ctx context.Context, c *Combined, setupKey string) (*Client, er
 	}
 
 	req := testcontainers.ContainerRequest{
-		Image:          clientImage,
+		Image: clientImage,
+		// The agent reports the container's hostname to management, so this is
+		// the name the peer is addressable by in the API as well as on the
+		// network. The entrypoint takes no hostname flag of its own.
+		Hostname:       o.name,
 		Networks:       []string{c.network.Name},
-		NetworkAliases: map[string][]string{c.network.Name: {clientAlias}},
+		NetworkAliases: map[string][]string{c.network.Name: {o.name}},
 		Env: map[string]string{
 			"NB_MANAGEMENT_URL": combinedExposedURL,
 			"NB_SETUP_KEY":      setupKey,

e2e/harness/combined.go

@@ -61,11 +61,68 @@ type Combined struct {
 	workDir string
 }
 
+// combinedOptions is what the CombinedOption values assemble.
+type combinedOptions struct {
+	geolocation bool
+	env         map[string]string
+}
+
+// CombinedOption adjusts how StartCombined boots the server. The defaults suit a
+// suite that only drives the API; the options exist for the ones that need more
+// of the product than that.
+type CombinedOption func(*combinedOptions)
+
+// WithGeolocation leaves the GeoLite database download enabled. It is off by
+// default because the download adds startup latency that most suites get nothing
+// for. A suite asserting on location-based posture checks needs it: management
+// evaluates those rules against the database, and without it the rule fails
+// instead of passing without having been checked.
+func WithGeolocation() CombinedOption {
+	return func(o *combinedOptions) { o.geolocation = true }
+}
+
+// WithServerEnv adds environment variables to the combined container, overriding
+// the defaults on a key collision. For settings this harness does not model
+// directly, so a suite needing one does not have to fork the harness to get it.
+func WithServerEnv(env map[string]string) CombinedOption {
+	return func(o *combinedOptions) {
+		if o.env == nil {
+			o.env = map[string]string{}
+		}
+		for k, v := range env {
+			o.env[k] = v
+		}
+	}
+}
+
+// combinedEnv is the combined container's environment: setup-PAT enabled so the
+// caller can mint an admin token through /api/setup, geolocation off unless the
+// suite asked for it, and whatever the suite added on top.
+func combinedEnv(o combinedOptions) map[string]string {
+	env := map[string]string{
+		"NB_SETUP_PAT_ENABLED": "true",
+	}
+	if !o.geolocation {
+		// Skip the GeoLite DB download — it blocks startup and agent-network
+		// ingest doesn't use geolocation.
+		env["NB_DISABLE_GEOLOCATION"] = "true"
+	}
+	for k, v := range o.env {
+		env[k] = v
+	}
+	return env
+}
+
 // StartCombined builds the combined server from its multistage Dockerfile and
 // boots it with setup-PAT enabled on a fresh shared network, returning once the
 // API is serving. The caller still owns minting the admin PAT via Bootstrap.
-func StartCombined(ctx context.Context) (*Combined, error) {
-	root, err := repoRoot()
+func StartCombined(ctx context.Context, opts ...CombinedOption) (*Combined, error) {
+	var o combinedOptions
+	for _, opt := range opts {
+		opt(&o)
+	}
+
+	root, err := repoRoot(ctx)
 	if err != nil {
 		return nil, err
 	}
@@ -88,7 +145,7 @@ func StartCombined(ctx context.Context) (*Combined, error) {
 		return nil, fmt.Errorf("create work dir: %w", err)
 	}
 
-	cfg := fmt.Sprintf(combinedConfigYAML, combinedExposedURL, containerIssuer)
+	cfg := fmt.Sprintf(combinedConfigYAML, combinedExposedURL, !o.geolocation, containerIssuer)
 	if err := os.WriteFile(filepath.Join(workDir, "config.yaml"), []byte(cfg), 0o644); err != nil { //nolint:gosec // non-secret config, bind-mounted and read by the container
 		_ = net.Remove(ctx)
 		return nil, fmt.Errorf("write combined config: %w", err)
@@ -112,13 +169,8 @@ func StartCombined(ctx context.Context) (*Combined, error) {
 		ExposedPorts:   []string{combinedHTTPPort},
 		Networks:       []string{net.Name},
 		NetworkAliases: map[string][]string{net.Name: {combinedAlias}},
-		Env: map[string]string{
-			"NB_SETUP_PAT_ENABLED": "true",
-			// Skip the GeoLite DB download — it blocks startup and agent-network
-			// ingest doesn't use geolocation.
-			"NB_DISABLE_GEOLOCATION": "true",
-		},
-		Cmd: []string{"--config", "/nb/config.yaml"},
+		Env:            combinedEnv(o),
+		Cmd:            []string{"--config", "/nb/config.yaml"},
 		HostConfigModifier: func(hc *container.HostConfig) {
 			hc.Binds = append(hc.Binds, workDir+":/nb")
 		},

e2e/harness/config.go

@@ -15,6 +15,11 @@ package harness
 // server is required to load it — a broken path or malformed file fails startup
 // rather than silently falling back to the compiled-in rates, and TestMain then
 // fails with the container logs.
+//
+// disableGeoliteUpdate is a parameter rather than a fixed true because a suite
+// that exercises geolocation needs the database: management can only evaluate a
+// location rule with GeoLite loaded, and a rule it cannot evaluate fails rather
+// than passing vacuously. See WithGeolocation.
 const combinedConfigYAML = `server:
   listenAddress: ":8080"
   exposedAddress: "%s"
@@ -25,7 +30,7 @@ const combinedConfigYAML = `server:
   authSecret: "e2e-relay-secret"
   dataDir: "/nb/data"
   disableAnonymousMetrics: true
-  disableGeoliteUpdate: true
+  disableGeoliteUpdate: %t
   auth:
     issuer: "%s"
   store:

e2e/harness/options_test.go

@@ -0,0 +1,161 @@
+//go:build e2e
+
+package harness
+
+import (
+	"context"
+	"fmt"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// The options exist so a suite can ask for a deployment this harness would not
+// otherwise give it. What they configure is a container environment and a config
+// file, both assembled before anything is started, so they are checkable without
+// Docker — which is the point: a wiring mistake here would otherwise only show up
+// as a puzzling failure minutes into a container run.
+
+func TestCombinedEnvGeolocation(t *testing.T) {
+	var off combinedOptions
+	assert.Equal(t, "true", combinedEnv(off)["NB_DISABLE_GEOLOCATION"],
+		"geolocation should be off by default")
+
+	var on combinedOptions
+	WithGeolocation()(&on)
+	assert.NotContains(t, combinedEnv(on), "NB_DISABLE_GEOLOCATION",
+		"WithGeolocation must leave NB_DISABLE_GEOLOCATION unset, so the server downloads the database")
+	assert.Equal(t, "true", combinedEnv(on)["NB_SETUP_PAT_ENABLED"],
+		"the setup PAT must stay enabled whatever else is configured; Bootstrap depends on it")
+}
+
+// The config file carries the same decision as the environment variable, and the
+// server needs both to agree: disableGeoliteUpdate suppresses the download even
+// when geolocation itself is enabled.
+func TestCombinedConfigGeolocation(t *testing.T) {
+	for _, tc := range []struct {
+		name string
+		opts []CombinedOption
+		want string
+	}{
+		{name: "default", want: "disableGeoliteUpdate: true"},
+		{name: "with geolocation", opts: []CombinedOption{WithGeolocation()}, want: "disableGeoliteUpdate: false"},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			var o combinedOptions
+			for _, opt := range tc.opts {
+				opt(&o)
+			}
+			cfg := fmt.Sprintf(combinedConfigYAML, combinedExposedURL, !o.geolocation, containerIssuer)
+			assert.Contains(t, cfg, tc.want, "geolocation not rendered as expected")
+			// The issuer is the last verb; a mis-ordered argument list would put
+			// the boolean here instead and the server would fail to start.
+			assert.Contains(t, cfg, `issuer: "`+containerIssuer+`"`, "issuer not rendered")
+		})
+	}
+}
+
+func TestWithServerEnvOverrides(t *testing.T) {
+	var o combinedOptions
+	WithServerEnv(map[string]string{"NB_LOG_LEVEL": "debug"})(&o)
+	WithServerEnv(map[string]string{"NB_SETUP_PAT_ENABLED": "false"})(&o)
+
+	env := combinedEnv(o)
+	assert.Equal(t, "debug", env["NB_LOG_LEVEL"], "added variable missing")
+	assert.Equal(t, "false", env["NB_SETUP_PAT_ENABLED"], "a suite must be able to override a default")
+}
+
+// Two agents on one network cannot share an alias, so the name has to reach both
+// the alias and the hostname. The hostname is the one management records, so it is
+// also what the peer is addressable by through the API.
+func TestWithClientName(t *testing.T) {
+	o := clientOptions{name: clientAlias}
+	require.Equal(t, "client", o.name, "unexpected default client name")
+
+	WithClientName("peer2")(&o)
+	assert.Equal(t, "peer2", o.name, "WithClientName did not take")
+}
+
+// repoRoot has to recognise this module rather than merely finding a go.mod, or a
+// suite in another module gets its own root and a build context without the
+// component Dockerfiles in it.
+func TestIsModule(t *testing.T) {
+	dir := t.TempDir()
+
+	other := filepath.Join(dir, "go.mod")
+	require.NoError(t, os.WriteFile(other, []byte("module example.com/other\n\ngo 1.25\n"), 0o600))
+	assert.False(t, isModule(other, modulePath), "another module's go.mod must not be taken for this repo")
+
+	ours := filepath.Join(dir, "ours.mod")
+	require.NoError(t, os.WriteFile(ours, []byte("// a comment\n\nmodule "+modulePath+"\n\ngo 1.25\n"), 0o600))
+	assert.True(t, isModule(ours, modulePath), "this repo's go.mod was not recognised")
+
+	assert.False(t, isModule(filepath.Join(dir, "absent.mod"), modulePath),
+		"a missing go.mod must not report a match")
+}
+
+// Running from inside the repo, repoRoot finds it by walking up — the module
+// lookup is only the fallback, and this asserts the walk still wins so an in-repo
+// run never depends on the module cache.
+func TestRepoRootFindsThisRepo(t *testing.T) {
+	root, err := repoRoot(context.Background())
+	require.NoError(t, err)
+	assert.True(t, isModule(filepath.Join(root, "go.mod"), modulePath),
+		"repoRoot returned %s, which is not this module", root)
+
+	for _, f := range []string{combinedDockerfile, clientDockerfile} {
+		_, err := os.Stat(filepath.Join(root, f))
+		assert.NoError(t, err, "%s is not present under the reported root %s", f, root)
+	}
+}
+
+// A caller that vendors its dependencies puts the go command in automatic vendor
+// mode, where `go list -m -f {{.Dir}}` succeeds and reports an EMPTY directory:
+// vendor/ holds packages, not module source. Without -mod=readonly the lookup
+// would come back empty and the harness would report a missing module for a
+// dependency that is present.
+func TestModuleDirResolvesUnderVendorMode(t *testing.T) {
+	if _, err := exec.LookPath("go"); err != nil {
+		t.Skip("no go tool on PATH")
+	}
+	ctx := context.Background()
+
+	base := t.TempDir()
+	dep := filepath.Join(base, "dep")
+	main := filepath.Join(base, "main")
+	require.NoError(t, os.MkdirAll(dep, 0o750))
+	require.NoError(t, os.MkdirAll(main, 0o750))
+
+	// A local replacement rather than a real dependency, so this needs no network.
+	require.NoError(t, os.WriteFile(filepath.Join(dep, "go.mod"),
+		[]byte("module example.com/dep\n\ngo 1.25\n"), 0o600))
+	require.NoError(t, os.WriteFile(filepath.Join(dep, "dep.go"),
+		[]byte("package dep\n"), 0o600))
+	require.NoError(t, os.WriteFile(filepath.Join(main, "go.mod"),
+		[]byte("module example.com/main\n\ngo 1.25\n\nrequire example.com/dep v0.0.0\n\nreplace example.com/dep v0.0.0 => ../dep\n"), 0o600))
+	require.NoError(t, os.WriteFile(filepath.Join(main, "main.go"),
+		[]byte("package main\n\nimport _ \"example.com/dep\"\n\nfunc main() {}\n"), 0o600))
+
+	t.Chdir(main)
+	vendor := exec.CommandContext(ctx, "go", "mod", "vendor")
+	out, err := vendor.CombinedOutput()
+	require.NoError(t, err, "go mod vendor: %s", out)
+
+	dir, err := moduleDir(ctx, "example.com/dep")
+	require.NoError(t, err, "the module must still resolve with a vendor directory present")
+	assert.Equal(t, dep, dir, "resolved the wrong directory")
+}
+
+// A cancelled context has to stop the lookup rather than leaving the caller
+// waiting on a subprocess it has already given up on.
+func TestModuleDirHonoursContext(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	cancel()
+
+	_, err := moduleDir(ctx, modulePath)
+	assert.ErrorIs(t, err, context.Canceled, "a cancelled context must stop the lookup")
+}

e2e/harness/paths.go

@@ -3,27 +3,82 @@
 package harness
 
 import (
+	"context"
 	"fmt"
 	"os"
+	"os/exec"
 	"path/filepath"
+	"strings"
 )
 
-// repoRoot walks up from the working directory to the module root (the
-// directory holding go.mod), so the Docker build context is correct no matter
-// which package the test runs from.
-func repoRoot() (string, error) {
+// modulePath is this module, used both to recognise the repo when walking up
+// from the working directory and to locate it when the suite lives elsewhere.
+const modulePath = "github.com/netbirdio/netbird"
+
+// repoRoot returns the directory the component Dockerfiles are built from.
+//
+// Walking up from the working directory finds it for any test inside this repo,
+// no matter which package it runs from. A suite in another module gets a
+// different answer that way — its own module root, where combined/Dockerfile
+// does not exist — so the ancestor has to be this module and not merely some
+// module. When it is not, the build context is the extracted module directory of
+// whichever version that suite depends on, which is the right one: the server it
+// tests against is then built from the same revision as the client library it
+// was compiled with.
+func repoRoot(ctx context.Context) (string, error) {
 	dir, err := os.Getwd()
 	if err != nil {
 		return "", err
 	}
 	for {
-		if _, statErr := os.Stat(filepath.Join(dir, "go.mod")); statErr == nil {
+		if isModule(filepath.Join(dir, "go.mod"), modulePath) {
 			return dir, nil
 		}
 		parent := filepath.Dir(dir)
 		if parent == dir {
-			return "", fmt.Errorf("go.mod not found above %s", dir)
+			break
 		}
 		dir = parent
 	}
+	return moduleDir(ctx, modulePath)
+}
+
+// isModule reports whether the go.mod at path declares the given module.
+func isModule(path, want string) bool {
+	b, err := os.ReadFile(path)
+	if err != nil {
+		return false
+	}
+	for _, line := range strings.Split(string(b), "\n") {
+		if rest, ok := strings.CutPrefix(strings.TrimSpace(line), "module "); ok {
+			return strings.TrimSpace(rest) == want
+		}
+	}
+	return false
+}
+
+// moduleDir asks the go tool where a module's source is, which for a dependent
+// module is its extracted copy in the module cache. The cache is read-only, and
+// a Docker build context is only ever read.
+//
+// -mod=readonly is required rather than cosmetic. A caller that vendors its
+// dependencies puts the go command in automatic vendor mode, where this lookup
+// succeeds with an EMPTY directory — vendor/ holds packages, not module source,
+// so there is nothing to report. Asking in readonly mode resolves against the
+// module graph instead, which answers for both a cached module and a local
+// replacement, and neither writes to go.mod.
+func moduleDir(ctx context.Context, module string) (string, error) {
+	cmd := exec.CommandContext(ctx, "go", "list", "-mod=readonly", "-m", "-f", "{{.Dir}}", module)
+	out, err := cmd.Output()
+	if err != nil {
+		return "", fmt.Errorf("locate %s: %w", module, err)
+	}
+	dir := strings.TrimSpace(string(out))
+	if dir == "" {
+		return "", fmt.Errorf("locate %s: the go tool reported no directory; run `go mod download %s`", module, module)
+	}
+	if _, err := os.Stat(dir); err != nil {
+		return "", fmt.Errorf("locate %s: %w", module, err)
+	}
+	return dir, nil
 }

e2e/harness/proxy.go

@@ -43,7 +43,7 @@ type Proxy struct {
 // or override any NB_PROXY_* var (e.g. NB_PROXY_TUNNEL_CACHE_TTL for tests that
 // need a short authorization-cache window).
 func StartProxy(ctx context.Context, c *Combined, proxyToken string, envOverrides ...map[string]string) (*Proxy, error) {
-	root, err := repoRoot()
+	root, err := repoRoot(ctx)
 	if err != nil {
 		return nil, err
 	}

go.mod

@@ -99,7 +99,7 @@ require (
 	github.com/pires/go-proxyproto v0.11.0
 	github.com/pkg/sftp v1.13.9
 	github.com/prometheus/client_golang v1.23.2
-	github.com/quic-go/quic-go v0.55.0
+	github.com/quic-go/quic-go v0.59.1
 	github.com/redis/go-redis/v9 v9.7.3
 	github.com/rs/xid v1.3.0
 	github.com/shirou/gopsutil/v4 v4.25.8
@@ -239,7 +239,6 @@ require (
 	github.com/jackc/pgservicefile v0.0.0-20221227161230-091c0ba34f0a // indirect
 	github.com/jackc/puddle/v2 v2.2.1 // indirect
 	github.com/jackpal/go-nat-pmp v1.0.2 // indirect
-	github.com/jchv/go-winloader v0.0.0-20250406163304-c1995be93bd1 // indirect
 	github.com/jinzhu/inflection v1.0.0 // indirect
 	github.com/jinzhu/now v1.1.5 // indirect
 	github.com/jmespath/go-jmespath v0.4.0 // indirect
@@ -340,4 +339,4 @@ replace github.com/dexidp/dex/api/v2 => github.com/netbirdio/dex/api/v2 v2.0.0-2
 
 replace github.com/mailru/easyjson => github.com/netbirdio/easyjson v0.9.0
 
-replace github.com/wailsapp/wails/v3 => github.com/netbirdio/wails/v3 v3.0.0-beta.3.0.20260803205919-ad21e92381f4
+replace github.com/wailsapp/wails/v3 => github.com/netbirdio/wails/v3 v3.0.0-beta.3.0.20260810103952-24e716aea4db

go.sum

@@ -349,8 +349,6 @@ github.com/jackc/puddle/v2 v2.2.1 h1:RhxXJtFG022u4ibrCSMSiu5aOq1i77R3OHKNJj77OAk
 github.com/jackc/puddle/v2 v2.2.1/go.mod h1:vriiEXHvEE654aYKXXjOvZM39qJ0q+azkZFrfEOc3H4=
 github.com/jackpal/go-nat-pmp v1.0.2 h1:KzKSgb7qkJvOUTqYl9/Hg/me3pWgBmERKrTGD7BdWus=
 github.com/jackpal/go-nat-pmp v1.0.2/go.mod h1:QPH045xvCAeXUZOxsnwmrtiCoxIr9eob+4orBN1SBKc=
-github.com/jchv/go-winloader v0.0.0-20250406163304-c1995be93bd1 h1:njuLRcjAuMKr7kI3D85AXWkw6/+v9PwtV6M6o11sWHQ=
-github.com/jchv/go-winloader v0.0.0-20250406163304-c1995be93bd1/go.mod h1:alcuEEnZsY1WQsagKhZDsoPCRoOijYqhZvPwLG0kzVs=
 github.com/jcmturner/aescts/v2 v2.0.0 h1:9YKLH6ey7H4eDBXW8khjYslgyqG2xZikXP0EQFKrle8=
 github.com/jcmturner/aescts/v2 v2.0.0/go.mod h1:AiaICIRyfYg35RUkr8yESTqvSy7csK90qZ5xfvvsoNs=
 github.com/jcmturner/dnsutils/v2 v2.0.0 h1:lltnkeZGL0wILNvrNiVCR6Ro5PGU/SeBvVO/8c/iPbo=
@@ -490,8 +488,8 @@ github.com/netbirdio/service v0.0.0-20240911161631-f62744f42502 h1:3tHlFmhTdX9ax
 github.com/netbirdio/service v0.0.0-20240911161631-f62744f42502/go.mod h1:CIMRFEJVL+0DS1a3Nx06NaMn4Dz63Ng6O7dl0qH0zVM=
 github.com/netbirdio/signal-dispatcher/dispatcher v0.0.0-20250805121659-6b4ac470ca45 h1:ujgviVYmx243Ksy7NdSwrdGPSRNE3pb8kEDSpH0QuAQ=
 github.com/netbirdio/signal-dispatcher/dispatcher v0.0.0-20250805121659-6b4ac470ca45/go.mod h1:5/sjFmLb8O96B5737VCqhHyGRzNFIaN/Bu7ZodXc3qQ=
-github.com/netbirdio/wails/v3 v3.0.0-beta.3.0.20260803205919-ad21e92381f4 h1:UKztc3QjWvzU5DZk+uYaOWN0x62NSe/pkxuPvzqZIy4=
-github.com/netbirdio/wails/v3 v3.0.0-beta.3.0.20260803205919-ad21e92381f4/go.mod h1:BzATbK71VFikMMMCo434wAi0QcaI03P+xeaWgDvQvjw=
+github.com/netbirdio/wails/v3 v3.0.0-beta.3.0.20260810103952-24e716aea4db h1:gBOE2r4AW1soSmpYJC5/n9/1L8UQ8+HLjed8CY/TzZY=
+github.com/netbirdio/wails/v3 v3.0.0-beta.3.0.20260810103952-24e716aea4db/go.mod h1:bsdahLwBQxXjlmdPPeQyrTcDJfcqAr/ymFj0RXhwtWI=
 github.com/netbirdio/wireguard-go v0.0.0-20260628102922-2834bebf6c1a h1:3CWK+yTvRKOcC0Q8VCTGy4l60TEb27CQVS7LkMxwjmw=
 github.com/netbirdio/wireguard-go v0.0.0-20260628102922-2834bebf6c1a/go.mod h1:rpwXGsirqLqN2L0JDJQlwOboGHmptD5ZD6T2VmcqhTw=
 github.com/nxadm/tail v1.4.4/go.mod h1:kenIhsEOeOJmVchQTgglprH7qJGnHDVpk1VPCcaMI8A=
@@ -582,8 +580,8 @@ github.com/prometheus/otlptranslator v1.0.0 h1:s0LJW/iN9dkIH+EnhiD3BlkkP5QVIUVEo
 github.com/prometheus/otlptranslator v1.0.0/go.mod h1:vRYWnXvI6aWGpsdY/mOT/cbeVRBlPWtBNDb7kGR3uKM=
 github.com/prometheus/procfs v0.19.2 h1:zUMhqEW66Ex7OXIiDkll3tl9a1ZdilUOd/F6ZXw4Vws=
 github.com/prometheus/procfs v0.19.2/go.mod h1:M0aotyiemPhBCM0z5w87kL22CxfcH05ZpYlu+b4J7mw=
-github.com/quic-go/quic-go v0.55.0 h1:zccPQIqYCXDt5NmcEabyYvOnomjs8Tlwl7tISjJh9Mk=
-github.com/quic-go/quic-go v0.55.0/go.mod h1:DR51ilwU1uE164KuWXhinFcKWGlEjzys2l8zUl5Ss1U=
+github.com/quic-go/quic-go v0.59.1 h1:0Gmua0HW1Tv7ANR7hUYwRyD0MG5OJfgvYSZasGZzBic=
+github.com/quic-go/quic-go v0.59.1/go.mod h1:upnsH4Ju1YkqpLXC305eW3yDZ4NfnNbmQRCMWS58IKU=
 github.com/redis/go-redis/v9 v9.7.3 h1:YpPyAayJV+XErNsatSElgRZZVCwXX9QzkKYNvO7x0wM=
 github.com/redis/go-redis/v9 v9.7.3/go.mod h1:bGUrSggJ9X9GUmZpZNEOQKaANxSGgOEBRltRTZHSvrA=
 github.com/rogpeppe/go-internal v1.14.1 h1:UQB4HGPB6osV0SQTLymcB4TgvyWu6ZyliaW0tI/otEQ=
@@ -793,7 +791,6 @@ golang.org/x/sys v0.0.0-20190916202348-b4ddaad3f8a3/go.mod h1:h1NjWce9XRLGQEsW7w
 golang.org/x/sys v0.0.0-20191005200804-aed5e4c7ecf9/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20191120155948-bd437916bb0e/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20200323222414-85ca7c5b95cd/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
-golang.org/x/sys v0.0.0-20200810151505-1b9f1253b3ed/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20200930185726-fdedc70b468f/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20201015000850-e3ed0017c211/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20201119102817-f84b799fce68/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=

infrastructure_files/migrate-to-enterprise.sh

@@ -173,11 +173,11 @@ EOF
 # ---------------------------------------------------------------------------
 
 detect_combined_service() {
-  yq eval '.services | to_entries | map(select(.value.image | test("^netbirdio/netbird-server"))) | .[0].key // ""' "$COMPOSE_FILE"
+  yq eval '.services | to_entries | map(select(.value.image | test("^(ghcr\\.io/)?netbirdio/netbird-server([:@]|$)"))) | .[0].key // ""' "$COMPOSE_FILE"
 }
 
 detect_dashboard_service() {
-  yq eval '.services | to_entries | map(select(.value.image | test("^netbirdio/dashboard"))) | .[0].key // ""' "$COMPOSE_FILE"
+  yq eval '.services | to_entries | map(select(.value.image | test("^(ghcr\\.io/)?netbirdio/dashboard([:@]|$)"))) | .[0].key // ""' "$COMPOSE_FILE"
 }
 
 detect_config_yaml_host_path() {
@@ -661,12 +661,12 @@ init_migration() {
   COMPOSE_NETWORK=$(detect_compose_network)
 
   if [[ -z "$COMBINED_SERVICE" ]]; then
-    echo "Could not find a service running netbirdio/netbird-server* in $COMPOSE_FILE." > /dev/stderr
+    echo "Could not find a service running netbirdio/netbird-server or ghcr.io/netbirdio/netbird-server in $COMPOSE_FILE." > /dev/stderr
     echo "This script targets the community combined-server deployment." > /dev/stderr
     exit 1
   fi
   if [[ -z "$DASHBOARD_SERVICE" ]]; then
-    echo "Could not find a service running netbirdio/dashboard* in $COMPOSE_FILE." > /dev/stderr
+    echo "Could not find a service running netbirdio/dashboard or ghcr.io/netbirdio/dashboard in $COMPOSE_FILE." > /dev/stderr
     exit 1
   fi
   if [[ -z "$CONFIG_YAML_HOST" ]]; then

management/internals/controllers/network_map/controller/controller.go

@@ -176,6 +176,7 @@ func (c *Controller) sendUpdateAccountPeers(ctx context.Context, accountID strin
 	semaphore := make(chan struct{}, 10)
 
 	c.injectAllProxyPolicies(ctx, account)
+	account.PrecomputePostureValidation(ctx)
 	dnsCache := &cache.DNSConfigCache{}
 	dnsDomain := c.GetDNSDomain(account.Settings)
 	peersCustomZone := account.GetPeersCustomZone(ctx, dnsDomain)
@@ -357,6 +358,7 @@ func (c *Controller) sendUpdateForAffectedPeers(ctx context.Context, accountID s
 	// network map that omitted the synth DNS zone, and the agent kept
 	// resolving against the stale or absent record.
 	c.injectAllProxyPolicies(ctx, account)
+	account.PrecomputePostureValidation(ctx)
 	dnsCache := &cache.DNSConfigCache{}
 	dnsDomain := c.GetDNSDomain(account.Settings)
 	peersCustomZone := account.GetPeersCustomZone(ctx, dnsDomain)

management/internals/modules/agentnetwork/handlers/budget_handler_test.go

@@ -102,8 +102,8 @@ func TestSettingsHandler_GetExposesCollectionToggles(t *testing.T) {
 
 	require.NoError(t, f.store.SaveAgentNetworkSettings(context.Background(), &agentNetworkTypes.Settings{
 		AccountID:              testAccountID,
-		Cluster:                "eu.proxy.netbird.io",
-		Subdomain:              "violet",
+		Domain:                 "violet.eu.proxy.netbird.io",
+		ProxyAddress:           "eu.proxy.netbird.io",
 		EnableLogCollection:    true,
 		EnablePromptCollection: true,
 		RedactPii:              false,

management/internals/modules/agentnetwork/handlers/providers_handler.go

@@ -155,12 +155,7 @@ func (h *handler) createProvider(w http.ResponseWriter, r *http.Request) {
 	provider := types.NewProvider(userAuth.AccountId)
 	provider.FromAPIRequest(&req)
 
-	bootstrapCluster := ""
-	if req.BootstrapCluster != nil {
-		bootstrapCluster = *req.BootstrapCluster
-	}
-
-	created, err := h.manager.CreateProvider(r.Context(), userAuth.UserId, provider, bootstrapCluster)
+	created, err := h.manager.CreateProvider(r.Context(), userAuth.UserId, provider)
 	if err != nil {
 		util.WriteError(r.Context(), err, w)
 		return

management/internals/modules/agentnetwork/handlers/settings_handler.go

@@ -12,13 +12,55 @@ import (
 	"github.com/netbirdio/netbird/shared/management/http/util"
 )
 
-// addSettingsEndpoints registers the Agent Network settings routes. The
-// settings row is bootstrapped server-side on first provider create or on the
-// first PUT carrying a cluster; GET reads it and PUT applies a partial update
-// of the mutable collection toggles (cluster/subdomain stay immutable).
+// addSettingsEndpoints registers the Agent Network settings routes. POST
+// bootstraps the settings row, assigning the account's immutable endpoint;
+// GET reads it (defaults with an empty endpoint before bootstrap); PUT
+// carries every field, replacing the mutable collection toggles and rejecting
+// any change to the identity fields; DELETE removes the row — guarded so it
+// stays a bootstrap-repair operation — releasing the endpoint for a fresh
+// bootstrap.
 func (h *handler) addSettingsEndpoints(router *mux.Router) {
 	router.HandleFunc("/agent-network/settings", h.getSettings).Methods("GET", "OPTIONS")
+	router.HandleFunc("/agent-network/settings", h.createSettings).Methods("POST", "OPTIONS")
 	router.HandleFunc("/agent-network/settings", h.updateSettings).Methods("PUT", "OPTIONS")
+	router.HandleFunc("/agent-network/settings", h.deleteSettings).Methods("DELETE", "OPTIONS")
+}
+
+// createSettings bootstraps the account's settings row. Exactly one of
+// proxy_address (labeled endpoint; the server allocates the label) and
+// endpoint (self-addressed, claimed verbatim) must be provided; optional
+// collection toggles ride along with defaults for omitted fields.
+func (h *handler) createSettings(w http.ResponseWriter, r *http.Request) {
+	userAuth, err := nbcontext.GetUserAuthFromContext(r.Context())
+	if err != nil {
+		util.WriteError(r.Context(), err, w)
+		return
+	}
+
+	var req api.AgentNetworkSettingsCreateRequest
+	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
+		util.WriteErrorResponse("couldn't parse JSON request", http.StatusBadRequest, w)
+		return
+	}
+
+	settings := types.DefaultSettings(userAuth.AccountId)
+	settings.FromAPICreateRequest(&req)
+
+	proxyAddress := ""
+	if req.ProxyAddress != nil {
+		proxyAddress = *req.ProxyAddress
+	}
+	endpoint := ""
+	if req.Endpoint != nil {
+		endpoint = *req.Endpoint
+	}
+
+	created, err := h.manager.CreateSettings(r.Context(), userAuth.UserId, settings, proxyAddress, endpoint)
+	if err != nil {
+		util.WriteError(r.Context(), err, w)
+		return
+	}
+	util.WriteJSONObject(r.Context(), w, created.ToAPIResponse())
 }
 
 // updateSettings replaces the mutable settings fields on the account's row.
@@ -48,6 +90,24 @@ func (h *handler) updateSettings(w http.ResponseWriter, r *http.Request) {
 	util.WriteJSONObject(r.Context(), w, updated.ToAPIResponse())
 }
 
+// deleteSettings removes the account's settings row, releasing the endpoint.
+// The manager refuses (412) while providers exist or a proxy is actively
+// serving the endpoint; a later POST bootstraps fresh, allocating a new
+// endpoint.
+func (h *handler) deleteSettings(w http.ResponseWriter, r *http.Request) {
+	userAuth, err := nbcontext.GetUserAuthFromContext(r.Context())
+	if err != nil {
+		util.WriteError(r.Context(), err, w)
+		return
+	}
+
+	if err := h.manager.DeleteSettings(r.Context(), userAuth.AccountId, userAuth.UserId); err != nil {
+		util.WriteError(r.Context(), err, w)
+		return
+	}
+	util.WriteJSONObject(r.Context(), w, util.EmptyObject{})
+}
+
 // getSettings returns the account's agent-network settings. Accounts that
 // haven't been bootstrapped yet read as the defaults with an empty cluster,
 // subdomain and endpoint; the manager synthesises that view.

management/internals/modules/agentnetwork/handlers/settings_handler_test.go

@@ -1,20 +1,25 @@
 package handlers
 
 import (
+	"context"
 	"encoding/json"
+	"fmt"
 	"net/http"
+	"strings"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
+	rpproxy "github.com/netbirdio/netbird/management/internals/modules/reverseproxy/proxy"
 	"github.com/netbirdio/netbird/shared/management/http/api"
 )
 
 // TestSettingsHandler_GetUnbootstrappedReturnsDefaults pins the settings-read
 // convention shared with the account and DNS settings endpoints: settings
 // always read as a JSON object. Before bootstrap that object carries the
-// defaults with an empty cluster/subdomain/endpoint (the "not bootstrapped"
+// defaults with an empty endpoint/proxy_address (the "not bootstrapped"
 // signal) and no timestamps — never a 404 and never the legacy null body.
 func TestSettingsHandler_GetUnbootstrappedReturnsDefaults(t *testing.T) {
 	f := newAgentNetworkHandlerFixture(t)
@@ -27,9 +32,9 @@ func TestSettingsHandler_GetUnbootstrappedReturnsDefaults(t *testing.T) {
 
 	var got api.AgentNetworkSettings
 	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
-	assert.Empty(t, got.Cluster, "cluster must be empty until bootstrapped")
-	assert.Empty(t, got.Subdomain, "subdomain must be empty until bootstrapped")
-	assert.Empty(t, got.Endpoint, "endpoint must be empty until bootstrapped, not a bare dot")
+	assert.Empty(t, got.Endpoint, "endpoint must be empty until bootstrapped")
+	assert.Empty(t, got.ProxyAddress, "proxy address must be empty until bootstrapped")
+	assert.False(t, got.Dedicated, "an unbootstrapped account has no serving shape")
 	assert.True(t, got.EnableLogCollection, "defaults must show log collection on, matching bootstrap")
 	assert.False(t, got.EnablePromptCollection, "defaults must show prompt collection off")
 	assert.False(t, got.RedactPii, "defaults must show redaction off")
@@ -39,62 +44,149 @@ func TestSettingsHandler_GetUnbootstrappedReturnsDefaults(t *testing.T) {
 	assert.Nil(t, got.UpdatedAt, "no timestamps before a row exists")
 }
 
-// TestSettingsHandler_PutBootstrapsWithCluster covers the settings-first
-// bootstrap path: a PUT carrying a cluster on an unbootstrapped account
-// creates the row (cluster pinned, subdomain assigned) and applies the
-// mutable fields from the same request.
-func TestSettingsHandler_PutBootstrapsWithCluster(t *testing.T) {
+// TestSettingsHandler_PostBootstrapsLabeled covers the labeled bootstrap
+// shape: a POST carrying a proxy_address allocates a label beneath it, so the
+// endpoint hangs one label under the shared cluster's address and the pin is
+// not dedicated. Toggles riding along apply; omitted ones keep defaults.
+func TestSettingsHandler_PostBootstrapsLabeled(t *testing.T) {
 	f := newAgentNetworkHandlerFixture(t)
 
-	rec := f.do(t, http.MethodPut, "/agent-network/settings",
-		`{"cluster": "eu.proxy.netbird.io", "enable_log_collection": true, "enable_prompt_collection": true, "redact_pii": false, "access_log_retention_days": 30}`)
-	require.Equal(t, http.StatusOK, rec.Code, "bootstrap PUT must succeed: %s", rec.Body.String())
+	rec := f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"proxy_address": "eu.proxy.netbird.io", "enable_prompt_collection": true, "access_log_retention_days": 14}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
 
 	var got api.AgentNetworkSettings
 	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
-	assert.Equal(t, "eu.proxy.netbird.io", got.Cluster, "cluster must be pinned from the request")
-	assert.NotEmpty(t, got.Subdomain, "subdomain must be assigned at bootstrap")
-	assert.Equal(t, got.Subdomain+".eu.proxy.netbird.io", got.Endpoint, "endpoint must combine subdomain and cluster")
-	assert.True(t, got.EnableLogCollection, "toggle from the bootstrap request must apply")
+	assert.Equal(t, "eu.proxy.netbird.io", got.ProxyAddress, "proxy address must be pinned from the request")
+	require.NotEmpty(t, got.Endpoint, "endpoint must be allocated at bootstrap")
+	assert.True(t, strings.HasSuffix(got.Endpoint, ".eu.proxy.netbird.io"),
+		"labeled endpoint must hang off the proxy address: %s", got.Endpoint)
+	label := strings.TrimSuffix(got.Endpoint, ".eu.proxy.netbird.io")
+	assert.NotContains(t, label, ".", "the allocated label must be a single DNS label: %s", label)
+	assert.False(t, got.Dedicated, "a labeled pin is not dedicated")
+	assert.True(t, got.EnableLogCollection, "omitted toggle must keep its default")
 	assert.True(t, got.EnablePromptCollection, "toggle from the bootstrap request must apply")
 	require.NotNil(t, got.AccessLogRetentionDays)
-	assert.Equal(t, 30, *got.AccessLogRetentionDays, "retention from the bootstrap request must apply")
+	assert.Equal(t, 14, *got.AccessLogRetentionDays, "retention from the bootstrap request must apply")
+	assert.NotNil(t, got.CreatedAt, "a persisted row carries timestamps")
 
 	// The row is now readable via GET.
 	rec = f.do(t, http.MethodGet, "/agent-network/settings", "")
 	require.Equal(t, http.StatusOK, rec.Code, "GET after bootstrap must succeed")
+	var read api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &read))
+	assert.Equal(t, got.Endpoint, read.Endpoint, "GET must return the bootstrapped endpoint")
 }
 
-// TestSettingsHandler_PutWithoutClusterOnUnbootstrapped pins that a PUT
-// without a cluster cannot conjure a settings row out of nothing — there is
-// no cluster to pin — and surfaces as 404 like the GET.
-func TestSettingsHandler_PutWithoutClusterOnUnbootstrapped(t *testing.T) {
+// TestSettingsHandler_PostBootstrapsSelfAddressed covers the dedicated shape:
+// a POST carrying an endpoint claims the hostname verbatim, the proxy address
+// equals it, and the pin reads as dedicated. The claim is legitimate before
+// any proxy declares the address (address-first).
+func TestSettingsHandler_PostBootstrapsSelfAddressed(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"endpoint": "Brave-Otter.Gateway.Example.com"}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
+
+	var got api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
+	assert.Equal(t, "brave-otter.gateway.example.com", got.Endpoint,
+		"endpoint must be claimed verbatim, lowercased")
+	assert.Equal(t, got.Endpoint, got.ProxyAddress, "self-addressed: the proxy address is the endpoint")
+	assert.True(t, got.Dedicated, "a self-addressed pin is dedicated")
+	assert.True(t, got.EnableLogCollection, "omitted toggles must keep their defaults")
+}
+
+// TestSettingsHandler_PostRequiresExactlyOneIdentityField pins the request
+// contract: proxy_address and endpoint are mutually exclusive and one is
+// required — both or neither is a validation error, not a guess.
+func TestSettingsHandler_PostRequiresExactlyOneIdentityField(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodPost, "/agent-network/settings", `{}`)
+	assert.Equal(t, http.StatusUnprocessableEntity, rec.Code,
+		"empty POST must be rejected: got %d body=%s", rec.Code, rec.Body.String())
+
+	rec = f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"proxy_address": "eu.proxy.netbird.io", "endpoint": "brave-otter.gateway.example.com"}`)
+	assert.Equal(t, http.StatusUnprocessableEntity, rec.Code,
+		"POST with both identity fields must be rejected: got %d body=%s", rec.Code, rec.Body.String())
+}
+
+// TestSettingsHandler_PostRejectsMalformedHostnames pins per-write input
+// validation: shapes canonicalization cannot repair — trailing dots, embedded
+// whitespace, empty labels — are rejected with a validation error instead of
+// landing in an immutable column.
+func TestSettingsHandler_PostRejectsMalformedHostnames(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	for name, body := range map[string]string{
+		"trailing dot":     `{"endpoint": "gateway.example.com."}`,
+		"leading dot":      `{"endpoint": ".gateway.example.com"}`,
+		"inner whitespace": `{"endpoint": "gate way.example.com"}`,
+		"empty label":      `{"proxy_address": "eu..proxy.netbird.io"}`,
+	} {
+		rec := f.do(t, http.MethodPost, "/agent-network/settings", body)
+		assert.Equal(t, http.StatusUnprocessableEntity, rec.Code,
+			"%s must be rejected: got %d body=%s", name, rec.Code, rec.Body.String())
+	}
+}
+
+// TestSettingsHandler_PostConflictsOnSecondBootstrap pins that bootstrap is a
+// one-time create: a second POST returns 409 and leaves the row untouched.
+func TestSettingsHandler_PostConflictsOnSecondBootstrap(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodPost, "/agent-network/settings", `{"proxy_address": "eu.proxy.netbird.io"}`)
+	require.Equal(t, http.StatusOK, rec.Code, "first bootstrap must succeed: %s", rec.Body.String())
+	var first api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &first))
+
+	rec = f.do(t, http.MethodPost, "/agent-network/settings", `{"proxy_address": "us.proxy.netbird.io"}`)
+	assert.Equal(t, http.StatusConflict, rec.Code,
+		"second bootstrap must 409: got %d body=%s", rec.Code, rec.Body.String())
+
+	rec = f.do(t, http.MethodGet, "/agent-network/settings", "")
+	require.Equal(t, http.StatusOK, rec.Code)
+	var got api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
+	assert.Equal(t, first.Endpoint, got.Endpoint, "the original endpoint must survive the rejected bootstrap")
+	assert.Equal(t, first.ProxyAddress, got.ProxyAddress, "the original proxy address must survive")
+}
+
+// TestSettingsHandler_PutBeforeBootstrapIs404 pins that a PUT cannot conjure a
+// settings row out of nothing — bootstrap is the explicit POST — and the
+// error points the caller there.
+func TestSettingsHandler_PutBeforeBootstrapIs404(t *testing.T) {
 	f := newAgentNetworkHandlerFixture(t)
 
 	rec := f.do(t, http.MethodPut, "/agent-network/settings",
 		`{"enable_log_collection": false, "enable_prompt_collection": false, "redact_pii": false}`)
 	assert.Equal(t, http.StatusNotFound, rec.Code,
-		"cluster-less PUT on an unbootstrapped account must 404: got %d body=%s", rec.Code, rec.Body.String())
-	assert.Contains(t, rec.Body.String(), "cluster",
-		"the error must point the caller at the bootstrap paths: %s", rec.Body.String())
+		"PUT on an unbootstrapped account must 404: got %d body=%s", rec.Code, rec.Body.String())
+	assert.Contains(t, rec.Body.String(), "/api/agent-network/settings",
+		"the error must point the caller at the bootstrap POST: %s", rec.Body.String())
 }
 
 // TestSettingsHandler_PutReplacesMutableFields pins the update contract shared
-// with the other PUT endpoints: the request replaces every mutable field, so a
-// toggle absent from the JSON lands as its zero value rather than being
-// preserved. Cluster and subdomain survive untouched.
+// with the other PUT endpoints: the request carries every field, replacing the
+// mutable ones. The identity fields ride along as a required echo of the
+// assigned values — compared, never written — so the endpoint and proxy
+// address survive every accepted update.
 func TestSettingsHandler_PutReplacesMutableFields(t *testing.T) {
 	f := newAgentNetworkHandlerFixture(t)
 
-	rec := f.do(t, http.MethodPut, "/agent-network/settings",
-		`{"cluster": "eu.proxy.netbird.io", "enable_log_collection": true, "enable_prompt_collection": true, "redact_pii": true, "access_log_retention_days": 14}`)
-	require.Equal(t, http.StatusOK, rec.Code, "bootstrap PUT must succeed: %s", rec.Body.String())
+	rec := f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"proxy_address": "eu.proxy.netbird.io", "enable_prompt_collection": true, "redact_pii": true, "access_log_retention_days": 14}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
 
 	var before api.AgentNetworkSettings
 	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &before))
 
-	rec = f.do(t, http.MethodPut, "/agent-network/settings",
-		`{"enable_log_collection": true, "enable_prompt_collection": false, "redact_pii": false}`)
+	rec = f.do(t, http.MethodPut, "/agent-network/settings", fmt.Sprintf(
+		`{"endpoint": %q, "proxy_address": %q, "enable_log_collection": true, "enable_prompt_collection": false, "redact_pii": false, "access_log_retention_days": 7}`,
+		before.Endpoint, before.ProxyAddress))
 	require.Equal(t, http.StatusOK, rec.Code, "update PUT must succeed: %s", rec.Body.String())
 
 	var got api.AgentNetworkSettings
@@ -103,35 +195,201 @@ func TestSettingsHandler_PutReplacesMutableFields(t *testing.T) {
 	assert.False(t, got.EnablePromptCollection, "sent toggle must apply")
 	assert.False(t, got.RedactPii, "sent toggle must apply")
 	require.NotNil(t, got.AccessLogRetentionDays)
-	assert.Equal(t, 0, *got.AccessLogRetentionDays,
-		"retention absent from the request must land as the zero value — PUT replaces all mutable fields")
-	assert.Equal(t, before.Cluster, got.Cluster, "cluster must survive updates untouched")
-	assert.Equal(t, before.Subdomain, got.Subdomain, "subdomain must survive updates untouched")
+	assert.Equal(t, 7, *got.AccessLogRetentionDays, "sent retention must apply")
+	assert.Equal(t, before.Endpoint, got.Endpoint, "endpoint must survive updates untouched")
+	assert.Equal(t, before.ProxyAddress, got.ProxyAddress, "proxy address must survive updates untouched")
 }
 
-// TestSettingsHandler_PutRejectsClusterChange pins cluster immutability: once
-// assigned, a differing cluster is rejected as a validation error instead of
-// being silently ignored, so callers never observe a value other than the one
-// they sent. Echoing the assigned cluster back stays valid, which lets
-// declarative clients send their full desired state idempotently.
-func TestSettingsHandler_PutRejectsClusterChange(t *testing.T) {
+// TestSettingsHandler_PutRejectsChangedIdentity pins the immutability contract:
+// the PUT carries the identity fields like every other field, but they are an
+// echo — a request carrying a different endpoint or proxy address is rejected
+// as a validation error and the row is left untouched. The comparison is
+// lenient about casing (the stored values are normalized lowercase), so a
+// client replaying a GET response with different casing is not rejected.
+func TestSettingsHandler_PutRejectsChangedIdentity(t *testing.T) {
 	f := newAgentNetworkHandlerFixture(t)
 
-	rec := f.do(t, http.MethodPut, "/agent-network/settings",
-		`{"cluster": "eu.proxy.netbird.io", "enable_log_collection": true, "enable_prompt_collection": false, "redact_pii": false}`)
-	require.Equal(t, http.StatusOK, rec.Code, "bootstrap PUT must succeed: %s", rec.Body.String())
+	rec := f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"proxy_address": "eu.proxy.netbird.io", "enable_prompt_collection": true}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
+	var before api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &before))
 
-	rec = f.do(t, http.MethodPut, "/agent-network/settings",
-		`{"cluster": "us.proxy.netbird.io", "enable_log_collection": true, "enable_prompt_collection": false, "redact_pii": false}`)
-	assert.Equal(t, http.StatusUnprocessableEntity, rec.Code,
-		"cluster change must be rejected as a validation error: got %d body=%s", rec.Code, rec.Body.String())
+	for name, body := range map[string]string{
+		"changed endpoint": fmt.Sprintf(
+			`{"endpoint": "other.gateway.example.com", "proxy_address": %q, "enable_log_collection": false, "enable_prompt_collection": false, "redact_pii": false, "access_log_retention_days": 30}`,
+			before.ProxyAddress),
+		"changed proxy_address": fmt.Sprintf(
+			`{"endpoint": %q, "proxy_address": "us.proxy.netbird.io", "enable_log_collection": false, "enable_prompt_collection": false, "redact_pii": false, "access_log_retention_days": 30}`,
+			before.Endpoint),
+		"omitted identity": `{"enable_log_collection": false, "enable_prompt_collection": false, "redact_pii": false, "access_log_retention_days": 30}`,
+	} {
+		rec = f.do(t, http.MethodPut, "/agent-network/settings", body)
+		assert.Equal(t, http.StatusUnprocessableEntity, rec.Code,
+			"%s must be rejected: got %d body=%s", name, rec.Code, rec.Body.String())
+	}
 
-	rec = f.do(t, http.MethodPut, "/agent-network/settings",
-		`{"cluster": "eu.proxy.netbird.io", "enable_log_collection": true, "enable_prompt_collection": false, "redact_pii": true}`)
-	require.Equal(t, http.StatusOK, rec.Code, "echoing the assigned cluster must stay valid: %s", rec.Body.String())
+	// The rejected updates must not have applied anything — toggles included.
+	rec = f.do(t, http.MethodGet, "/agent-network/settings", "")
+	require.Equal(t, http.StatusOK, rec.Code)
+	var got api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
+	assert.Equal(t, before.Endpoint, got.Endpoint, "rejected PUT must not change the endpoint")
+	assert.Equal(t, before.ProxyAddress, got.ProxyAddress, "rejected PUT must not change the proxy address")
+	assert.True(t, got.EnablePromptCollection, "rejected PUT must not apply its toggles")
+
+	// An uppercased echo of the assigned values still names the same host and
+	// must be accepted.
+	rec = f.do(t, http.MethodPut, "/agent-network/settings", fmt.Sprintf(
+		`{"endpoint": %q, "proxy_address": %q, "enable_log_collection": true, "enable_prompt_collection": true, "redact_pii": false, "access_log_retention_days": 30}`,
+		strings.ToUpper(before.Endpoint), strings.ToUpper(before.ProxyAddress)))
+	assert.Equal(t, http.StatusOK, rec.Code,
+		"an uppercased identity echo must be accepted: got %d body=%s", rec.Code, rec.Body.String())
+}
+
+// TestSettingsHandler_PutOmittedRetentionLandsAsZero documents a residual the
+// required-ness of access_log_retention_days does not remove. Marking the field
+// required changes the generated client type from *int to int, so a generated
+// client cannot omit it — but nothing validates OpenAPI required-ness at
+// runtime, so a hand-rolled body without the field still decodes as 0, which
+// the API documents as "keep indefinitely".
+//
+// That is the same latitude the three booleans already have, so it is left
+// consistent rather than special-cased. This test exists to make the gap
+// explicit: if request validation is ever added, this expectation is what
+// changes.
+func TestSettingsHandler_PutOmittedRetentionLandsAsZero(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"proxy_address": "eu.proxy.netbird.io", "access_log_retention_days": 14}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
+	var before api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &before))
+
+	rec = f.do(t, http.MethodPut, "/agent-network/settings", fmt.Sprintf(
+		`{"endpoint": %q, "proxy_address": %q, "enable_log_collection": true, "enable_prompt_collection": false, "redact_pii": false}`,
+		before.Endpoint, before.ProxyAddress))
+	require.Equal(t, http.StatusOK, rec.Code, "update PUT must succeed: %s", rec.Body.String())
 
 	var got api.AgentNetworkSettings
 	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
-	assert.Equal(t, "eu.proxy.netbird.io", got.Cluster, "cluster must be unchanged")
-	assert.True(t, got.RedactPii, "toggle sent alongside the echoed cluster must apply")
+	require.NotNil(t, got.AccessLogRetentionDays)
+	assert.Equal(t, 0, *got.AccessLogRetentionDays,
+		"a non-conforming body that omits retention still replaces it with the zero value")
+}
+
+// TestSettingsHandler_DeleteBeforeBootstrapIs404 pins that DELETE on an
+// account with no settings row is a 404, mirroring the PUT.
+func TestSettingsHandler_DeleteBeforeBootstrapIs404(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodDelete, "/agent-network/settings", "")
+	assert.Equal(t, http.StatusNotFound, rec.Code,
+		"DELETE on an unbootstrapped account must 404: got %d body=%s", rec.Code, rec.Body.String())
+}
+
+// TestSettingsHandler_DeleteBlockedByProviders pins the first delete guard:
+// while any provider exists for the account, the delete is refused with 412
+// and the row survives. Providers route through the endpoint — the guard
+// keeps DELETE a bootstrap-repair operation rather than a way to abandon a
+// configured gateway.
+func TestSettingsHandler_DeleteBlockedByProviders(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodPost, "/agent-network/settings", `{"proxy_address": "eu.proxy.netbird.io"}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
+	var before api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &before))
+
+	f.seedProvider(t, "prov-guard")
+
+	rec = f.do(t, http.MethodDelete, "/agent-network/settings", "")
+	assert.Equal(t, http.StatusPreconditionFailed, rec.Code,
+		"delete with a provider present must be refused: got %d body=%s", rec.Code, rec.Body.String())
+
+	rec = f.do(t, http.MethodGet, "/agent-network/settings", "")
+	require.Equal(t, http.StatusOK, rec.Code)
+	var got api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &got))
+	assert.Equal(t, before.Endpoint, got.Endpoint, "the refused delete must leave the row intact")
+}
+
+// TestSettingsHandler_DeleteBlockedByActiveProxy pins the second delete
+// guard: while a proxy is actively serving the endpoint — an active proxy
+// row declaring the endpoint hostname as its cluster address, the dedicated
+// shape — the delete is refused with 412. A proxy that has disconnected no
+// longer blocks: the guard is about a live serving path, not history.
+//
+// The proxy declares its address with mixed casing on purpose: Connect
+// stores the declared address verbatim while the settings row is normalized
+// lowercase, and hostnames are case-insensitive, so the guard must match
+// across the casing difference rather than be sidestepped by it.
+func TestSettingsHandler_DeleteBlockedByActiveProxy(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	const endpoint = "gw.dedicated.example.com"
+	rec := f.do(t, http.MethodPost, "/agent-network/settings", fmt.Sprintf(`{"endpoint": %q}`, endpoint))
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
+
+	now := time.Now()
+	accountID := testAccountID
+	proxyRow := &rpproxy.Proxy{
+		ID:             "proxy-guard",
+		SessionID:      "sess-1",
+		ClusterAddress: "GW.Dedicated.Example.Com",
+		AccountID:      &accountID,
+		LastSeen:       now,
+		ConnectedAt:    &now,
+		Status:         rpproxy.StatusConnected,
+	}
+	require.NoError(t, f.store.SaveProxy(context.Background(), proxyRow))
+
+	rec = f.do(t, http.MethodDelete, "/agent-network/settings", "")
+	assert.Equal(t, http.StatusPreconditionFailed, rec.Code,
+		"delete with an active proxy at the endpoint must be refused: got %d body=%s", rec.Code, rec.Body.String())
+
+	// Once the proxy disconnects it no longer serves the endpoint, so the
+	// delete goes through.
+	require.NoError(t, f.store.DisconnectProxy(context.Background(), proxyRow.ID, proxyRow.SessionID))
+	rec = f.do(t, http.MethodDelete, "/agent-network/settings", "")
+	assert.Equal(t, http.StatusOK, rec.Code,
+		"delete after the proxy disconnected must succeed: got %d body=%s", rec.Code, rec.Body.String())
+}
+
+// TestSettingsHandler_DeleteReleasesEndpointForFreshBootstrap pins the
+// full-reset semantic that gives replace-on-change clients (e.g. Terraform's
+// RequiresReplace) a real path: with both guards clear the delete succeeds,
+// the account reads as the defaults again, and a fresh bootstrap draws a
+// fresh label. The released hostname is not reserved — a fresh draw may even
+// legitimately re-pick it — so the assertions check the new row's shape, not
+// that the label differs.
+func TestSettingsHandler_DeleteReleasesEndpointForFreshBootstrap(t *testing.T) {
+	f := newAgentNetworkHandlerFixture(t)
+
+	rec := f.do(t, http.MethodPost, "/agent-network/settings",
+		`{"proxy_address": "eu.proxy.netbird.io", "enable_prompt_collection": true}`)
+	require.Equal(t, http.StatusOK, rec.Code, "bootstrap POST must succeed: %s", rec.Body.String())
+
+	rec = f.do(t, http.MethodDelete, "/agent-network/settings", "")
+	require.Equal(t, http.StatusOK, rec.Code,
+		"delete with both guards clear must succeed: got %d body=%s", rec.Code, rec.Body.String())
+
+	rec = f.do(t, http.MethodGet, "/agent-network/settings", "")
+	require.Equal(t, http.StatusOK, rec.Code)
+	var after api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &after))
+	assert.Empty(t, after.Endpoint, "a deleted account must read as unbootstrapped defaults")
+	assert.False(t, after.EnablePromptCollection, "the deleted row's toggles must not linger")
+
+	rec = f.do(t, http.MethodPost, "/agent-network/settings", `{"proxy_address": "eu.proxy.netbird.io"}`)
+	require.Equal(t, http.StatusOK, rec.Code, "re-bootstrap after delete must succeed: %s", rec.Body.String())
+	var second api.AgentNetworkSettings
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &second))
+	require.NotEmpty(t, second.Endpoint, "the fresh bootstrap must allocate an endpoint")
+	assert.True(t, strings.HasSuffix(second.Endpoint, ".eu.proxy.netbird.io"),
+		"the fresh endpoint must hang beneath the requested proxy address: %s", second.Endpoint)
+	assert.False(t, second.EnablePromptCollection,
+		"the fresh row must carry bootstrap defaults, not the deleted row's toggles")
+	assert.NotNil(t, second.CreatedAt, "the fresh row is persisted and carries timestamps")
 }