Code formate

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.

.github/workflows/docs-ack.yml

@@ -12,8 +12,6 @@ jobs:
   docs-ack:
     name: Require docs PR URL or explicit "not needed"
     runs-on: ubuntu-latest
-    # Crowdin's translation-sync service PRs are auto-generated without the PR template.
-    if: github.event.pull_request.user.login != 'netbirddev'
 
     steps:
       - name: Read PR body

.github/workflows/pr-title-check.yml

@@ -7,8 +7,6 @@ on:
 jobs:
   check-title:
     runs-on: ubuntu-latest
-    # Crowdin's translation-sync service PRs are auto-generated with a fixed title.
-    if: github.event.pull_request.user.login != 'netbirddev'
     steps:
       - name: Validate PR title prefix
         uses: actions/github-script@3a2844b7e9c422d3c10d287c895573f7108da1b3 # v9.0.0

.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:
@@ -67,6 +65,10 @@ 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
@@ -79,8 +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:
@@ -92,6 +94,10 @@ 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)
@@ -111,32 +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.
-  #
-  # GoReleaser derives the credential env var from the upload name, so these
-  # would look for UPLOAD_DEBIAN-GTK3_SECRET / UPLOAD_YUM-GTK3_SECRET. The
-  # release workflow only exports UPLOAD_DEBIAN_SECRET / UPLOAD_YUM_SECRET, and
-  # a missing secret is a silent skip rather than a failure -- the packages
-  # reached the GitHub release but never the package repositories. Point
-  # `password` at the exported vars so both uploads authenticate.
-  - 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
-    password: "{{ .Env.UPLOAD_DEBIAN_SECRET }}"
     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
-    password: "{{ .Env.UPLOAD_YUM_SECRET }}"
     method: PUT

client/android/ssh_client.go

@@ -0,0 +1,829 @@
+//go:build android
+
+package android
+
+import (
+	"bufio"
+	"bytes"
+	"context"
+	"errors"
+	"fmt"
+	"io"
+	"net"
+	"os"
+	"strconv"
+	"strings"
+	"sync"
+	"time"
+
+	log "github.com/sirupsen/logrus"
+	gossh "golang.org/x/crypto/ssh"
+	"golang.org/x/crypto/ssh/knownhosts"
+
+	"github.com/netbirdio/netbird/client/internal"
+	"github.com/netbirdio/netbird/client/internal/auth"
+	"github.com/netbirdio/netbird/client/internal/profilemanager"
+	nbssh "github.com/netbirdio/netbird/client/ssh"
+	"github.com/netbirdio/netbird/client/ssh/detection"
+)
+
+const (
+	sshDialTimeout      = 30 * time.Second
+	sshDetectionTimeout = 5 * time.Second
+)
+
+// PasswordRequiredMarker tells Java to prompt for a password and retry. It is
+// a string because gomobile flattens errors to their message, so a sentinel
+// value would not survive the binding.
+const PasswordRequiredMarker = "netbird-ssh-password-required"
+
+// HostKeyUnknownMarker tells Java to show the fingerprint and, on confirmation,
+// retry with TrustHostKey set. The presented fingerprint is appended after the
+// marker so the prompt can display it and the retry can guard against a key
+// that changed between the two connects. Only regular (non-NetBird) servers
+// reach this: NetBird peers verify against the registry.
+const HostKeyUnknownMarker = "netbird-ssh-hostkey-unknown"
+
+var (
+	errPasswordRequired = errors.New(PasswordRequiredMarker)
+	errClientClosed     = errors.New("ssh client closed")
+)
+
+// errHostKeyUnknown carries the presented fingerprint so Connect can build the
+// marker message the Java side parses.
+type errHostKeyUnknown struct {
+	fingerprint string
+}
+
+func (e *errHostKeyUnknown) Error() string {
+	return HostKeyUnknownMarker + ":" + e.fingerprint
+}
+
+// engineHostKeyVerifier adapts *internal.Engine to nbssh.HostKeyVerifier.
+type engineHostKeyVerifier struct {
+	engine *internal.Engine
+}
+
+func (v *engineHostKeyVerifier) VerifySSHHostKey(peerAddress string, presented []byte) error {
+	storedKey, found := v.engine.GetPeerSSHKey(peerAddress)
+	if !found {
+		return nbssh.ErrPeerNotFound
+	}
+	return nbssh.VerifyHostKey(storedKey, presented, peerAddress)
+}
+
+// SSHTerminalListener receives SSH session events. It is implemented in Java.
+//
+// All callbacks are invoked from goroutines and may run concurrently with each
+// other; the implementation must be safe to call from any thread.
+type SSHTerminalListener interface {
+	OnConnected()
+	OnData(data []byte)
+	OnClose(reason string)
+	OnError(message string)
+}
+
+// SSHClient is a NetBird-aware SSH client exposed to Java via gomobile.
+//
+// It dials through the running NetBird tunnel and runs a standard SSH session
+// on top with PTY enabled. Host-key verification uses the NetBird-provided
+// peer SSH host keys, identical to the desktop client.
+type SSHClient struct {
+	nb        *Client
+	mu        sync.Mutex
+	listener  SSHTerminalListener
+	urlOpener URLOpener
+
+	sshClient *gossh.Client
+	session   *gossh.Session
+	stdin     io.WriteCloser
+	closed    bool
+
+	// gen identifies the current connection attempt. Connect and Close bump it,
+	// so an in-flight dial or a reader left over from a previous connection
+	// finds itself stale and stays silent instead of publishing OnConnected or
+	// OnClose for a connection the caller already abandoned.
+	gen        uint64
+	dialCancel context.CancelFunc
+
+	// knownHostsPath is the TOFU store for regular SSH servers. Java supplies a
+	// per-profile path, since an overlay IP is a different host under a
+	// different profile. Empty until set: without it a regular server cannot be
+	// verified and Connect refuses one.
+	knownHostsPath string
+	// trustHostKey carries the fingerprint the user confirmed on a previous
+	// attempt, so the retry accepts exactly that key and persists it.
+	trustHostKey string
+}
+
+// NewSSHClient creates a new SSH client bound to the running NetBird Client.
+func NewSSHClient(c *Client) *SSHClient {
+	return &SSHClient{nb: c}
+}
+
+// SetListener registers the Java listener. Must be called before Connect to
+// receive any events.
+func (s *SSHClient) SetListener(l SSHTerminalListener) {
+	s.mu.Lock()
+	s.listener = l
+	s.mu.Unlock()
+}
+
+// SetURLOpener registers the Java URL opener used to display the device-code
+// authorization page in a Custom Tabs window when the target peer requires
+// JWT authentication. Must be set before Connect to be effective.
+func (s *SSHClient) SetURLOpener(opener URLOpener) {
+	s.mu.Lock()
+	s.urlOpener = opener
+	s.mu.Unlock()
+}
+
+// SetKnownHostsPath points the TOFU host-key store at a per-profile file. Must
+// be set before connecting to a regular SSH server; without it such a server
+// cannot be verified and Connect refuses one.
+func (s *SSHClient) SetKnownHostsPath(path string) {
+	s.mu.Lock()
+	s.knownHostsPath = path
+	s.mu.Unlock()
+}
+
+// TrustHostKey records the fingerprint the user confirmed for a regular server,
+// so the next Connect accepts that exact key and adds it to the known-hosts
+// store. Passing a fingerprint that no longer matches makes the connect fail
+// rather than trust a key that changed since the prompt.
+func (s *SSHClient) TrustHostKey(fingerprint string) {
+	s.mu.Lock()
+	s.trustHostKey = fingerprint
+	s.mu.Unlock()
+}
+
+// Connect dials the SSH server through the NetBird tunnel and performs the
+// SSH handshake. It auto-detects the server type via SSH banner inspection
+// and selects the appropriate authentication path:
+//
+//   - NetBird-SSH server requiring JWT: launches the OAuth 2.0 device-code
+//     flow, opens the verification URL through the registered URLOpener, and
+//     uses the resulting token as the SSH password. Host-key verification
+//     uses the NetBird peer registry.
+//   - NetBird-SSH server without JWT: authenticates with the NetBird SSH
+//     private key. Host-key verification uses the NetBird peer registry.
+//   - Regular SSH server (e.g. OpenSSH): authenticates with the NetBird key
+//     first (so a user-installed NetBird public key works), then falls back
+//     to the supplied password if non-empty. Host-key verification is
+//     trust-on-first-use against the per-profile known-hosts store.
+//
+// The password parameter is only consulted for regular SSH servers.
+func (s *SSHClient) Connect(host string, port int, user, password string) error {
+	if port < 1 || port > 65535 {
+		return fmt.Errorf("invalid port: %d", port)
+	}
+
+	cfg, _, cc := s.nb.stateSnapshot()
+	if cc == nil {
+		return errors.New("netbird client not running")
+	}
+	if cfg == nil {
+		return errors.New("netbird config not loaded")
+	}
+	engine := cc.Engine()
+	if engine == nil {
+		return errors.New("netbird engine not available")
+	}
+
+	s.mu.Lock()
+	s.gen++
+	gen := s.gen
+	s.mu.Unlock()
+
+	serverType := detectServerType(host, port)
+	log.Debugf("SSH server type: %s", serverType)
+
+	authMethods, hostKeyCallback, err := s.buildAuth(cfg, engine, serverType, password)
+	if err != nil {
+		return err
+	}
+
+	clientConfig := &gossh.ClientConfig{
+		User:            user,
+		Auth:            authMethods,
+		HostKeyCallback: hostKeyCallback,
+		Timeout:         sshDialTimeout,
+	}
+	err = s.dialAndHandshake(gen, host, port, clientConfig)
+
+	// An unknown host key is a prompt, not a failure: return the marker intact
+	// (rootCause would unwrap it) so Java can show the fingerprint and retry.
+	var unknownHost *errHostKeyUnknown
+	if errors.As(err, &unknownHost) {
+		return errors.New(unknownHost.Error())
+	}
+
+	// A regular server may still accept a password, so let the caller ask for
+	// one instead of failing. NetBird servers never use a password, so a
+	// failure there is genuine.
+	if err != nil && serverType != detection.ServerTypeNetBirdJWT &&
+		serverType != detection.ServerTypeNetBirdNoJWT && isAuthFailure(err) &&
+		passwordCouldHelp(err, password != "") {
+		return errPasswordRequired
+	}
+	if err != nil {
+		return rootCause(err)
+	}
+	return nil
+}
+
+// StartSession requests a PTY and starts an interactive shell. Output from
+// the session is forwarded to the listener via OnData.
+func (s *SSHClient) StartSession(cols, rows int) error {
+	err := s.startSession(cols, rows)
+	if err != nil {
+		log.Infof("SSH: start session failed: %v", err)
+		return rootCause(err)
+	}
+	return nil
+}
+
+// Write sends data to the SSH session stdin.
+func (s *SSHClient) Write(data []byte) error {
+	s.mu.Lock()
+	stdin := s.stdin
+	s.mu.Unlock()
+	if stdin == nil {
+		return errors.New("ssh session not started")
+	}
+	if _, err := stdin.Write(data); err != nil {
+		return fmt.Errorf("write stdin: %w", err)
+	}
+	return nil
+}
+
+// Resize updates the PTY window size.
+func (s *SSHClient) Resize(cols, rows int) error {
+	s.mu.Lock()
+	session := s.session
+	s.mu.Unlock()
+	if session == nil {
+		return errors.New("ssh session not started")
+	}
+	return session.WindowChange(rows, cols)
+}
+
+// Reset makes a closed client usable for another Connect: Close leaves the
+// one-shot guard set, and clearing it lets the same client back a reconnect.
+func (s *SSHClient) Reset() {
+	s.mu.Lock()
+	defer s.mu.Unlock()
+	s.closed = false
+}
+
+// Close terminates the SSH session and underlying connection. Safe to call
+// multiple times.
+func (s *SSHClient) Close() error {
+	s.mu.Lock()
+	s.gen++
+	if s.dialCancel != nil {
+		s.dialCancel()
+		s.dialCancel = nil
+	}
+	sshClient := s.sshClient
+	session := s.session
+	stdin := s.stdin
+	s.sshClient = nil
+	s.session = nil
+	s.stdin = nil
+	notify := !s.closed
+	s.closed = true
+	listener := s.listener
+	s.mu.Unlock()
+
+	if stdin != nil {
+		if err := stdin.Close(); err != nil {
+			log.Debugf("ssh: stdin close: %v", err)
+		}
+	}
+	if session != nil {
+		if err := session.Close(); err != nil && !errors.Is(err, io.EOF) {
+			log.Debugf("ssh: session close: %v", err)
+		}
+	}
+	var firstErr error
+	if sshClient != nil {
+		if err := sshClient.Close(); err != nil {
+			firstErr = err
+		}
+	}
+	if notify && listener != nil {
+		listener.OnClose("closed by client")
+	}
+	return firstErr
+}
+
+func (s *SSHClient) startSession(cols, rows int) error {
+	log.Debugf("SSH: starting session %dx%d", cols, rows)
+	s.mu.Lock()
+	sshClient := s.sshClient
+	gen := s.gen
+	s.mu.Unlock()
+
+	if sshClient == nil {
+		return errors.New("ssh client not connected")
+	}
+
+	session, err := sshClient.NewSession()
+	if err != nil {
+		return fmt.Errorf("new session: %w", err)
+	}
+
+	modes := gossh.TerminalModes{
+		gossh.ECHO:          1,
+		gossh.TTY_OP_ISPEED: 14400,
+		gossh.TTY_OP_OSPEED: 14400,
+		gossh.VINTR:         3,
+		gossh.VQUIT:         28,
+		gossh.VERASE:        127,
+	}
+	if err := session.RequestPty("xterm-256color", rows, cols, modes); err != nil {
+		closeQuiet(session, "session after pty error")
+		return fmt.Errorf("request pty: %w", err)
+	}
+
+	stdin, err := session.StdinPipe()
+	if err != nil {
+		closeQuiet(session, "session after stdin error")
+		return fmt.Errorf("stdin pipe: %w", err)
+	}
+	stdout, err := session.StdoutPipe()
+	if err != nil {
+		closeQuiet(session, "session after stdout error")
+		return fmt.Errorf("stdout pipe: %w", err)
+	}
+	stderr, err := session.StderrPipe()
+	if err != nil {
+		closeQuiet(session, "session after stderr error")
+		return fmt.Errorf("stderr pipe: %w", err)
+	}
+
+	if err := session.Shell(); err != nil {
+		closeQuiet(session, "session after shell error")
+		return fmt.Errorf("start shell: %w", err)
+	}
+
+	s.mu.Lock()
+	if gen != s.gen {
+		s.mu.Unlock()
+		closeQuiet(session, "stale session")
+		return errClientClosed
+	}
+	s.session = session
+	s.stdin = stdin
+	s.mu.Unlock()
+
+	readerDone := make(chan string, 2)
+	go func() { readerDone <- s.readLoop(stdout, "stdout") }()
+	go func() { readerDone <- s.readLoop(stderr, "stderr") }()
+	go func() {
+		reason := <-readerDone
+		if second := <-readerDone; reason == "" {
+			reason = second
+		}
+		s.notifyClose(gen, reason)
+	}()
+	log.Debug("SSH: session started, shell running")
+	return nil
+}
+
+func (s *SSHClient) buildAuth(cfg *profilemanager.Config, engine *internal.Engine,
+	serverType detection.ServerType, password string) ([]gossh.AuthMethod, gossh.HostKeyCallback, error) {
+
+	switch serverType {
+	case detection.ServerTypeNetBirdJWT:
+		token, err := s.requestJWTToken(cfg)
+		if err != nil {
+			return nil, nil, fmt.Errorf("jwt: %w", err)
+		}
+		auths := []gossh.AuthMethod{gossh.Password(token)}
+		return auths, nbssh.CreateHostKeyCallback(&engineHostKeyVerifier{engine: engine}), nil
+
+	case detection.ServerTypeNetBirdNoJWT:
+		if cfg.SSHKey == "" {
+			return nil, nil, errors.New("no NetBird SSH key available")
+		}
+		signer, err := gossh.ParsePrivateKey([]byte(cfg.SSHKey))
+		if err != nil {
+			return nil, nil, fmt.Errorf("parse netbird ssh key: %w", err)
+		}
+		auths := []gossh.AuthMethod{gossh.PublicKeys(signer)}
+		return auths, nbssh.CreateHostKeyCallback(&engineHostKeyVerifier{engine: engine}), nil
+
+	case detection.ServerTypeRegular:
+		var auths []gossh.AuthMethod
+		if cfg.SSHKey != "" {
+			if signer, err := gossh.ParsePrivateKey([]byte(cfg.SSHKey)); err == nil {
+				auths = append(auths, gossh.PublicKeys(signer))
+			} else {
+				log.Debugf("ssh: parse netbird key for regular auth: %v", err)
+			}
+		}
+		if password != "" {
+			pw := password
+			auths = append(auths, gossh.Password(pw))
+			auths = append(auths, gossh.KeyboardInteractive(func(_, _ string, questions []string, _ []bool) ([]string, error) {
+				answers := make([]string, len(questions))
+				for i := range questions {
+					answers[i] = pw
+				}
+				return answers, nil
+			}))
+		}
+		if len(auths) == 0 {
+			// Nothing to offer at all: ask for a password rather than failing,
+			// so the caller can retry once the user supplies one.
+			return nil, nil, errPasswordRequired
+		}
+		callback, err := s.tofuHostKeyCallback()
+		if err != nil {
+			return nil, nil, err
+		}
+		return auths, callback, nil
+
+	default:
+		return nil, nil, fmt.Errorf("unsupported SSH server type: %v", serverType)
+	}
+}
+
+// tofuHostKeyCallback verifies a regular server's host key against the
+// per-profile known-hosts file. An unknown host returns errHostKeyUnknown so
+// Java can show the fingerprint and, once confirmed, retry with the key
+// trusted; a changed key is rejected outright, as OpenSSH does. When the user
+// has confirmed a fingerprint, the callback accepts exactly that key and
+// appends it to the store.
+func (s *SSHClient) tofuHostKeyCallback() (gossh.HostKeyCallback, error) {
+	s.mu.Lock()
+	path := s.knownHostsPath
+	trusted := s.trustHostKey
+	s.mu.Unlock()
+
+	if path == "" {
+		return nil, errors.New("no known-hosts store configured for regular SSH")
+	}
+
+	if err := ensureFileExists(path); err != nil {
+		return nil, fmt.Errorf("prepare known-hosts store: %w", err)
+	}
+
+	known, err := knownhosts.New(path)
+	if err != nil {
+		return nil, fmt.Errorf("load known-hosts store: %w", err)
+	}
+
+	return func(hostname string, remote net.Addr, key gossh.PublicKey) error {
+		err := known(hostname, remote, key)
+		if err == nil {
+			return nil
+		}
+
+		var keyErr *knownhosts.KeyError
+		if !errors.As(err, &keyErr) {
+			return err
+		}
+		// Want holds the keys already stored for this host: non-empty means the
+		// presented key replaced a known one, which TOFU must never accept
+		// silently.
+		if len(keyErr.Want) > 0 {
+			return fmt.Errorf("SSH host key changed for %s (possible attack)", hostname)
+		}
+
+		fingerprint := gossh.FingerprintSHA256(key)
+		if trusted == "" {
+			return &errHostKeyUnknown{fingerprint: fingerprint}
+		}
+		if trusted != fingerprint {
+			return fmt.Errorf("SSH host key changed since it was confirmed for %s", hostname)
+		}
+		if err := appendKnownHost(path, hostname, remote, key); err != nil {
+			return fmt.Errorf("persist trusted host key: %w", err)
+		}
+		// The confirmation is spent: now that the key is stored, a later
+		// reconnect must verify against the file, not re-accept this fingerprint.
+		s.mu.Lock()
+		s.trustHostKey = ""
+		s.mu.Unlock()
+		return nil
+	}, nil
+}
+
+func (s *SSHClient) requestJWTToken(cfg *profilemanager.Config) (string, error) {
+	s.mu.Lock()
+	urlOpener := s.urlOpener
+	s.mu.Unlock()
+	if urlOpener == nil {
+		return "", errors.New("URL opener not configured for JWT auth")
+	}
+
+	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Minute)
+	defer cancel()
+
+	flow, err := auth.NewOAuthFlow(ctx, cfg, false, true, profilemanager.GetLoginHint())
+	if err != nil {
+		return "", fmt.Errorf("create oauth flow: %w", err)
+	}
+
+	flowInfo, err := flow.RequestAuthInfo(ctx)
+	if err != nil {
+		return "", fmt.Errorf("request auth info: %w", err)
+	}
+
+	// Called synchronously: Open is what marks the surface as opened on the
+	// client side, and OnLoginSuccess below is a no-op until it has. Starting
+	// both in their own goroutines let them race, so a fast token left the
+	// browser in front of the terminal.
+	urlOpener.Open(flowInfo.VerificationURIComplete, flowInfo.UserCode)
+
+	// WaitToken blocks for as long as the browser round-trip takes, so say so
+	// rather than leaving the terminal blank.
+	s.notifyStatus("Waiting for browser authentication...")
+
+	tokenInfo, err := flow.WaitToken(ctx, flowInfo)
+	if err != nil {
+		return "", fmt.Errorf("wait for token: %w", err)
+	}
+
+	token := tokenInfo.GetTokenToUse()
+	if token == "" {
+		return "", errors.New("empty token returned by IdP")
+	}
+
+	// Tells the client the browser round-trip is over so it can dismiss the
+	// surface it opened, the same way the login and session-extend flows do.
+	// Without it the Custom Tab stays in front of the terminal even though the
+	// token has already been collected.
+	urlOpener.OnLoginSuccess()
+
+	return token, nil
+}
+
+func (s *SSHClient) dialAndHandshake(gen uint64, host string, port int, clientConfig *gossh.ClientConfig) error {
+	addr := net.JoinHostPort(host, strconv.Itoa(port))
+	ctx, cancel := context.WithTimeout(context.Background(), sshDialTimeout)
+	defer cancel()
+
+	s.mu.Lock()
+	if gen != s.gen {
+		s.mu.Unlock()
+		return errClientClosed
+	}
+	s.dialCancel = cancel
+	s.mu.Unlock()
+
+	var dialer net.Dialer
+	conn, err := dialer.DialContext(ctx, "tcp", addr)
+	if err != nil {
+		return fmt.Errorf("dial %s: %w", addr, err)
+	}
+
+	// DialContext bounds only the TCP establishment; without a deadline on the
+	// socket a peer that accepts and then goes silent blocks the handshake
+	// forever.
+	if deadline, ok := ctx.Deadline(); ok {
+		if err := conn.SetDeadline(deadline); err != nil {
+			closeQuiet(conn, "conn after deadline error")
+			return fmt.Errorf("set handshake deadline: %w", err)
+		}
+	}
+
+	sshConn, chans, reqs, err := gossh.NewClientConn(conn, addr, clientConfig)
+	if err != nil {
+		if cerr := conn.Close(); cerr != nil {
+			log.Debugf("ssh: close after handshake error: %v", cerr)
+		}
+		return fmt.Errorf("ssh handshake: %w", err)
+	}
+
+	if err := conn.SetDeadline(time.Time{}); err != nil {
+		closeQuiet(sshConn, "ssh conn after deadline clear error")
+		return fmt.Errorf("clear handshake deadline: %w", err)
+	}
+
+	client := gossh.NewClient(sshConn, chans, reqs)
+	s.mu.Lock()
+	if gen != s.gen {
+		s.mu.Unlock()
+		closeQuiet(client, "stale ssh client")
+		return errClientClosed
+	}
+	s.sshClient = client
+	listener := s.listener
+	s.mu.Unlock()
+
+	if listener != nil {
+		listener.OnConnected()
+	}
+	return nil
+}
+
+func (s *SSHClient) readLoop(r io.Reader, name string) string {
+	buf := make([]byte, 4096)
+	for {
+		n, err := r.Read(buf)
+		if n > 0 {
+			s.mu.Lock()
+			listener := s.listener
+			s.mu.Unlock()
+			if listener != nil {
+				chunk := make([]byte, n)
+				copy(chunk, buf[:n])
+				listener.OnData(chunk)
+			}
+		}
+		if err != nil {
+			// EOF is a normal shell exit, so report it without a reason.
+			if errors.Is(err, io.EOF) {
+				return ""
+			}
+			log.Debugf("ssh %s read: %v", name, err)
+			return rootCause(err).Error()
+		}
+	}
+}
+
+// notifyStatus writes a progress line to the terminal through the normal
+// output path, so long steps are visible while nothing else is arriving.
+func (s *SSHClient) notifyStatus(text string) {
+	s.mu.Lock()
+	listener := s.listener
+	s.mu.Unlock()
+	if listener != nil {
+		listener.OnData([]byte("\r\n\x1b[33m" + text + "\x1b[0m\r\n"))
+	}
+}
+
+func (s *SSHClient) notifyClose(gen uint64, reason string) {
+	s.mu.Lock()
+	if gen != s.gen || s.closed {
+		s.mu.Unlock()
+		return
+	}
+	s.closed = true
+	listener := s.listener
+	s.mu.Unlock()
+	if listener != nil {
+		listener.OnClose(reason)
+	}
+}
+
+// RemoveKnownHost deletes every known_hosts entry for host:port from the store,
+// so a host trusted for a session that is being deleted does not linger. Java
+// calls this only once no session targets that host, so a shared host stays
+// trusted. Missing file or entry is not an error: the goal state is "absent".
+func RemoveKnownHost(path, host string, port int) error {
+	target := knownhosts.Normalize(net.JoinHostPort(host, strconv.Itoa(port)))
+
+	data, err := os.ReadFile(path)
+	if err != nil {
+		if os.IsNotExist(err) {
+			return nil
+		}
+		return err
+	}
+
+	var kept []string
+	changed := false
+	scanner := bufio.NewScanner(bytes.NewReader(data))
+	for scanner.Scan() {
+		line := scanner.Text()
+		if knownHostsLineMatches(line, target) {
+			changed = true
+			continue
+		}
+		kept = append(kept, line)
+	}
+	if err := scanner.Err(); err != nil {
+		return err
+	}
+	if !changed {
+		return nil
+	}
+
+	out := strings.Join(kept, "\n")
+	if len(kept) > 0 {
+		out += "\n"
+	}
+	return os.WriteFile(path, []byte(out), 0o600)
+}
+
+func closeQuiet(c io.Closer, label string) {
+	if c == nil {
+		return
+	}
+	if err := c.Close(); err != nil && !errors.Is(err, io.EOF) {
+		log.Debugf("ssh: close %s: %v", label, err)
+	}
+}
+
+func detectServerType(host string, port int) detection.ServerType {
+	ctx, cancel := context.WithTimeout(context.Background(), sshDetectionTimeout)
+	defer cancel()
+
+	dialer := &net.Dialer{}
+	serverType, err := detection.DetectSSHServerType(ctx, dialer, host, port)
+	if err != nil {
+		log.Debugf("ssh: server detection failed: %v (assuming regular SSH)", err)
+		return detection.ServerTypeRegular
+	}
+	return serverType
+}
+
+// rootCause returns the innermost error of a %w chain, so the terminal shows
+// "i/o timeout" rather than every layer that added context on the way up.
+func rootCause(err error) error {
+	for {
+		// A joined error has no single root, so keep it as-is.
+		if _, ok := err.(interface{ Unwrap() []error }); ok {
+			return err
+		}
+		next := errors.Unwrap(err)
+		if next == nil {
+			return err
+		}
+		err = next
+	}
+}
+
+// ensureFileExists creates an empty known-hosts file when none exists yet, so
+// knownhosts.New has something to parse on the first connection to any host.
+func ensureFileExists(path string) error {
+	f, err := os.OpenFile(path, os.O_CREATE|os.O_WRONLY, 0o600)
+	if err != nil {
+		return err
+	}
+	return f.Close()
+}
+
+// appendKnownHost adds the confirmed key to the store in the standard
+// known_hosts format, so it verifies silently on later connections and can be
+// inspected or edited like any OpenSSH known_hosts file.
+func appendKnownHost(path, hostname string, remote net.Addr, key gossh.PublicKey) error {
+	addresses := []string{knownhosts.Normalize(hostname)}
+	if remote != nil {
+		if normalized := knownhosts.Normalize(remote.String()); normalized != addresses[0] {
+			addresses = append(addresses, normalized)
+		}
+	}
+	line := knownhosts.Line(addresses, key)
+
+	f, err := os.OpenFile(path, os.O_APPEND|os.O_WRONLY, 0o600)
+	if err != nil {
+		return err
+	}
+	defer func() {
+		if cerr := f.Close(); cerr != nil {
+			log.Debugf("ssh: close known-hosts after append: %v", cerr)
+		}
+	}()
+	_, err = f.WriteString(line + "\n")
+	return err
+}
+
+// knownHostsLineMatches reports whether a known_hosts line's address list
+// contains the normalized target. Comment and blank lines never match.
+func knownHostsLineMatches(line, target string) bool {
+	trimmed := strings.TrimSpace(line)
+	if trimmed == "" || strings.HasPrefix(trimmed, "#") {
+		return false
+	}
+	fields := strings.Fields(trimmed)
+	if len(fields) == 0 {
+		return false
+	}
+	for _, addr := range strings.Split(fields[0], ",") {
+		if addr == target {
+			return true
+		}
+	}
+	return false
+}
+
+// isAuthFailure distinguishes credential rejection from dial, timeout and
+// host-key errors, which retrying with a password would not fix.
+func isAuthFailure(err error) bool {
+	if errors.Is(err, errPasswordRequired) {
+		return true
+	}
+	var partial *gossh.PartialSuccessError
+	if errors.As(err, &partial) {
+		return true
+	}
+	return strings.Contains(err.Error(), "unable to authenticate")
+}
+
+// passwordCouldHelp reports whether prompting for a password again can change
+// the outcome. gossh lists a method under "attempted methods" only when the
+// server offered it, so a supplied password that was never attempted means the
+// server does not accept passwords and the real error should surface instead.
+func passwordCouldHelp(err error, passwordOffered bool) bool {
+	if !passwordOffered {
+		return true
+	}
+	msg := err.Error()
+	return strings.Contains(msg, "password") || strings.Contains(msg, "keyboard-interactive")
+}

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]

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/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
 	}