Merge remote-tracking branch 'origin/main' into components-impl-drop-indexes-use-xids

Signed-off-by: Dmitri Dolguikh <dmitri.external@netbird.io>

client/internal/auth/device_flow.go

@@ -259,12 +259,18 @@ func (d *DeviceAuthorizationFlow) WaitToken(ctx context.Context, info AuthFlowIn
 	ticker := time.NewTicker(interval)
 	defer ticker.Stop()
 
+	log.Infof("device flow: waiting for user authorization, polling token endpoint every %s, code expires in %s", interval, timeout)
+
+	start := time.Now()
+	polls := 0
+
 	for {
 		select {
 		case <-waitCtx.Done():
 			return TokenInfo{}, waitCtx.Err()
 		case <-ticker.C:
 
+			polls++
 			tokenResponse, err := d.requestToken(info)
 			if err != nil {
 				return TokenInfo{}, fmt.Errorf("parsing token response failed with error: %v", err)
@@ -272,10 +278,12 @@ func (d *DeviceAuthorizationFlow) WaitToken(ctx context.Context, info AuthFlowIn
 
 			if tokenResponse.Error != "" {
 				if tokenResponse.Error == "authorization_pending" {
+					log.Tracef("device flow: authorization still pending after poll %d", polls)
 					continue
 				} else if tokenResponse.Error == "slow_down" {
 					interval += (3 * time.Second)
 					ticker.Reset(interval)
+					log.Infof("device flow: IdP requested slow_down, polling interval increased to %s", interval)
 					continue
 				}
 
@@ -296,6 +304,7 @@ func (d *DeviceAuthorizationFlow) WaitToken(ctx context.Context, info AuthFlowIn
 				return TokenInfo{}, fmt.Errorf("validate access token failed with error: %v", err)
 			}
 
+			log.Infof("device flow: user authorization confirmed after %d polls in %s", polls, time.Since(start).Round(time.Second))
 			return tokenInfo, err
 		}
 	}

client/internal/auth/pkce_flow.go

@@ -188,6 +188,8 @@ func (p *PKCEAuthorizationFlow) WaitToken(ctx context.Context, info AuthFlowInfo
 	waitCtx, cancel := context.WithTimeout(ctx, timeout)
 	defer cancel()
 
+	log.Infof("pkce flow: waiting for authorization callback on %s, timeout %s", p.oAuthConfig.RedirectURL, timeout)
+
 	tokenChan := make(chan *oauth2.Token, 1)
 	errChan := make(chan error, 1)
 
@@ -221,6 +223,7 @@ func (p *PKCEAuthorizationFlow) WaitToken(ctx context.Context, info AuthFlowInfo
 func (p *PKCEAuthorizationFlow) startServer(server *http.Server, tokenChan chan<- *oauth2.Token, errChan chan<- error) {
 	mux := http.NewServeMux()
 	mux.HandleFunc("/", func(w http.ResponseWriter, req *http.Request) {
+		log.Infof("pkce flow: received authorization callback from IdP")
 		cert := p.providerConfig.ClientCertPair
 		if cert != nil {
 			tr := &http.Transport{
@@ -271,11 +274,18 @@ func (p *PKCEAuthorizationFlow) handleRequest(req *http.Request) (*oauth2.Token,
 		return nil, fmt.Errorf("authentication failed: missing code")
 	}
 
-	return p.oAuthConfig.Exchange(
+	exchangeStart := time.Now()
+	token, err := p.oAuthConfig.Exchange(
 		req.Context(),
 		code,
 		oauth2.SetAuthURLParam("code_verifier", p.codeVerifier),
 	)
+	if err != nil {
+		return nil, err
+	}
+
+	log.Infof("pkce flow: authorization code exchanged for token in %s", time.Since(exchangeStart).Round(time.Millisecond))
+	return token, nil
 }
 
 func (p *PKCEAuthorizationFlow) parseOAuthToken(token *oauth2.Token) (TokenInfo, error) {

client/internal/debug/debug.go

@@ -480,7 +480,6 @@ func (g *BundleGenerator) addStatus() error {
 
 		fullStatus := g.statusRecorder.GetFullStatus()
 		protoFullStatus := nbstatus.ToProtoFullStatus(fullStatus)
-		protoFullStatus.Events = g.statusRecorder.GetEventHistory()
 		overview := nbstatus.ConvertToStatusOutputOverview(protoFullStatus, nbstatus.ConvertOptions{
 			Anonymize:     g.anonymize,
 			ProfileName:   profName,

client/internal/engine.go

@@ -561,7 +561,7 @@ func (e *Engine) Start(netbirdConfig *mgmProto.NetbirdConfig, mgmtURL *url.URL)
 		} else {
 			log.Infof("running rosenpass in strict mode")
 		}
-		e.rpManager, err = rosenpass.NewManager(e.config.PreSharedKey, e.config.WgIfaceName)
+		e.rpManager, err = rosenpass.NewManager(e.config.PreSharedKey, e.config.WgIfaceName, publicKey)
 		if err != nil {
 			return fmt.Errorf("create rosenpass manager: %w", err)
 		}
@@ -2672,13 +2672,14 @@ func (e *Engine) updateForwardRules(rules []*mgmProto.ForwardingRule) ([]firewal
 
 func (e *Engine) toExcludedLazyPeers(rules []firewallManager.ForwardRule, peers []*mgmProto.RemotePeerConfig) map[string]bool {
 	excludedPeers := make(map[string]bool)
+
+	// Ingress forward targets: inbound forwarded traffic is initiated remotely and
+	// cannot wake a lazy connection, so the peer routing the target must stay
+	// permanently connected. AllowedIPs are already parsed on the peer conn, so
+	// reuse those typed prefixes instead of re-parsing the network map strings.
 	for _, r := range rules {
-		ip := r.TranslatedAddress
 		for _, p := range peers {
-			for _, allowedIP := range p.GetAllowedIps() {
-				if allowedIP != ip.String() {
-					continue
-				}
+			if e.peerRoutesAddr(p, r.TranslatedAddress) {
 				log.Infof("exclude forwarder peer from lazy connection: %s", p.GetWgPubKey())
 				excludedPeers[p.GetWgPubKey()] = true
 			}
@@ -2688,6 +2689,27 @@ func (e *Engine) toExcludedLazyPeers(rules []firewallManager.ForwardRule, peers
 	return excludedPeers
 }
 
+// peerRoutesAddr reports whether the peer is a router for addr, matched against
+// the peer's already-parsed AllowedIPs from the store (the same typed value the
+// lazy manager consumes) rather than re-parsing the network map strings.
+func (e *Engine) peerRoutesAddr(p *mgmProto.RemotePeerConfig, addr netip.Addr) bool {
+	prefixes, ok := e.peerStore.AllowedIPs(p.GetWgPubKey())
+	if !ok {
+		return false
+	}
+	return prefixesContain(prefixes, addr)
+}
+
+// prefixesContain reports whether addr falls within any of the prefixes.
+func prefixesContain(prefixes []netip.Prefix, addr netip.Addr) bool {
+	for _, prefix := range prefixes {
+		if prefix.Contains(addr) {
+			return true
+		}
+	}
+	return false
+}
+
 // isChecksEqual checks if two slices of checks are equal.
 func isChecksEqual(checks1, checks2 []*mgmProto.Checks) bool {
 	normalize := func(checks []*mgmProto.Checks) []string {

client/internal/engine_lazy_exclude_test.go

@@ -0,0 +1,87 @@
+package internal
+
+import (
+	"net/netip"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	firewallManager "github.com/netbirdio/netbird/client/firewall/manager"
+	"github.com/netbirdio/netbird/client/internal/peer"
+	"github.com/netbirdio/netbird/client/internal/peerstore"
+	mgmProto "github.com/netbirdio/netbird/shared/management/proto"
+)
+
+func TestPrefixesContain(t *testing.T) {
+	tests := []struct {
+		name     string
+		prefixes []string
+		addr     string
+		want     bool
+	}{
+		{name: "own overlay /32 matches", prefixes: []string{"100.110.8.145/32"}, addr: "100.110.8.145", want: true},
+		{name: "addr inside routed subnet", prefixes: []string{"10.121.0.0/16"}, addr: "10.121.208.4", want: true},
+		{name: "addr outside subnet", prefixes: []string{"10.121.0.0/16"}, addr: "10.122.0.1", want: false},
+		{name: "different /32", prefixes: []string{"100.110.8.145/32"}, addr: "100.110.8.146", want: false},
+		{name: "ipv6 /128 matches", prefixes: []string{"fd00::1/128"}, addr: "fd00::1", want: true},
+		{name: "no prefixes", prefixes: nil, addr: "10.121.208.4", want: false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			prefixes := make([]netip.Prefix, 0, len(tt.prefixes))
+			for _, p := range tt.prefixes {
+				prefixes = append(prefixes, netip.MustParsePrefix(p))
+			}
+			require.Equal(t, tt.want, prefixesContain(prefixes, netip.MustParseAddr(tt.addr)))
+		})
+	}
+}
+
+// TestToExcludedLazyPeers_ForwardTarget guards a regression: the forward-target
+// peer (the peer routing a ForwardRule.TranslatedAddress) must be excluded from
+// lazy connections, matched via the peer's already-parsed AllowedIPs.
+func TestToExcludedLazyPeers_ForwardTarget(t *testing.T) {
+	const targetPeerKey = "cccccccccccccccccccccccccccccccccccccccccc0="
+	const otherPeerKey = "dddddddddddddddddddddddddddddddddddddddddd0="
+
+	store := peerstore.NewConnStore()
+	store.AddPeerConn(targetPeerKey, newTestConn(t, targetPeerKey, "100.110.8.145/32"))
+	store.AddPeerConn(otherPeerKey, newTestConn(t, otherPeerKey, "100.110.9.10/32"))
+
+	e := &Engine{peerStore: store}
+
+	peers := []*mgmProto.RemotePeerConfig{
+		{WgPubKey: targetPeerKey, AllowedIps: []string{"100.110.8.145/32"}},
+		{WgPubKey: otherPeerKey, AllowedIps: []string{"100.110.9.10/32"}},
+	}
+	rules := []firewallManager.ForwardRule{
+		{TranslatedAddress: netip.MustParseAddr("100.110.8.145")},
+	}
+
+	excluded := e.toExcludedLazyPeers(rules, peers)
+
+	require.True(t, excluded[targetPeerKey], "forward-target peer must be excluded from lazy connections")
+	require.False(t, excluded[otherPeerKey], "non-target peer must not be excluded")
+	require.Len(t, excluded, 1)
+}
+
+func TestToExcludedLazyPeers_NoRules(t *testing.T) {
+	e := &Engine{peerStore: peerstore.NewConnStore()}
+
+	peers := []*mgmProto.RemotePeerConfig{
+		{WgPubKey: "peer-a", AllowedIps: []string{"100.110.8.145/32"}},
+	}
+
+	require.Empty(t, e.toExcludedLazyPeers(nil, peers))
+}
+
+func newTestConn(t *testing.T, key, allowedIP string) *peer.Conn {
+	t.Helper()
+	conn, err := peer.NewConn(peer.ConnConfig{
+		Key:      key,
+		WgConfig: peer.WgConfig{AllowedIps: []netip.Prefix{netip.MustParsePrefix(allowedIP)}},
+	}, peer.ServiceDependencies{})
+	require.NoError(t, err)
+	return conn
+}

client/internal/netflow/store/event_aggregation_test.go

@@ -175,7 +175,9 @@ func TestFlowAggregationOfUnknownProtocols(t *testing.T) {
 }
 
 func TestResetAggregationWindow(t *testing.T) {
-	store := NewAggregatingMemoryStore()
+	now := time.Now()
+	nowFunc := func() time.Time { return now }
+	store := NewAggregatingMemoryStoreWithTimeFunc(nowFunc)
 	store.StoreEvent(&types.Event{
 		ID:        uuid.New(),
 		Timestamp: time.Now(),
@@ -198,6 +200,7 @@ func TestResetAggregationWindow(t *testing.T) {
 		},
 	})
 
+	now = now.Add(1 * time.Second)
 	reset := store.ResetAggregationWindow()
 	previousEvents, ok := reset.(*AggregatingMemory)
 	assert.True(t, ok)

client/internal/netflow/store/memory.go

@@ -29,6 +29,7 @@ type AggregatingMemory struct {
 	WindowStart time.Time
 	WindowEnd   time.Time
 	rnd         *v2.PCG
+	nowFunc     func() time.Time
 }
 
 func (m *Memory) StoreEvent(event *types.Event) {
@@ -62,14 +63,19 @@ func (m *Memory) DeleteEvents(ids []uuid.UUID) {
 }
 
 func NewAggregatingMemoryStore() *AggregatingMemory {
-	return &AggregatingMemory{WindowStart: time.Now(), Memory: Memory{events: make(map[uuid.UUID]*types.Event)}, rnd: v2.NewPCG(rand.Uint64(), rand.Uint64())}
+	return NewAggregatingMemoryStoreWithTimeFunc(defaultNowFunc)
+}
+
+// used in tests when deterministic (less random) time intervals are required
+func NewAggregatingMemoryStoreWithTimeFunc(nowFunc func() time.Time) *AggregatingMemory {
+	return &AggregatingMemory{WindowStart: nowFunc(), Memory: Memory{events: make(map[uuid.UUID]*types.Event)}, nowFunc: nowFunc, rnd: v2.NewPCG(rand.Uint64(), rand.Uint64())}
 }
 
 func (am *AggregatingMemory) ResetAggregationWindow() types.FlowEventAggregator {
 	am.mux.Lock()
 	defer am.mux.Unlock()
 
-	now := time.Now()
+	now := am.nowFunc()
 	toret := AggregatingMemory{WindowStart: am.WindowStart, WindowEnd: now, Memory: Memory{events: am.events}, rnd: v2.NewPCG(rand.Uint64(), rand.Uint64())}
 
 	am.events = make(map[uuid.UUID]*types.Event)
@@ -152,3 +158,7 @@ func (am *AggregatingMemory) GetAggregatedEvents() []*types.Event {
 
 	return slices.Collect(maps.Values(aggregated)) // could return an iterator instead here
 }
+
+func defaultNowFunc() time.Time {
+	return time.Now()
+}

client/internal/peer/conn.go

@@ -30,6 +30,11 @@ import (
 	relayClient "github.com/netbirdio/netbird/shared/relay/client"
 )
 
+// wgTimeoutEscalationThreshold is the number of consecutive WireGuard
+// handshake timeouts after which the rosenpass state for the peer is
+// considered desynced and gets reset.
+const wgTimeoutEscalationThreshold = 3
+
 // MetricsRecorder is an interface for recording peer connection metrics
 type MetricsRecorder interface {
 	RecordConnectionStages(
@@ -118,6 +123,9 @@ type Conn struct {
 	wgWatcher       *WGWatcher
 	wgWatcherWg     sync.WaitGroup
 	wgWatcherCancel context.CancelFunc
+	// wgTimeouts counts consecutive WireGuard handshake timeouts without a
+	// successful handshake in between. Guarded by mu.
+	wgTimeouts int
 
 	// used to store the remote Rosenpass key for Relayed connection in case of connection update from ice
 	rosenpassRemoteKey []byte
@@ -195,7 +203,6 @@ func NewConn(config ConnConfig, services ServiceDependencies) (*Conn, error) {
 		statusICE:          worker.NewAtomicStatus(),
 		dumpState:          dumpState,
 		endpointUpdater:    NewEndpointUpdater(connLog, config.WgConfig, isController(config)),
-		wgWatcher:          NewWGWatcher(connLog, config.WgConfig.WgInterface, config.Key, dumpState),
 		metricsRecorder:    services.MetricsRecorder,
 	}
 
@@ -663,11 +670,12 @@ func (conn *Conn) onGuardEvent() {
 	}
 }
 
-func (conn *Conn) onWGDisconnected() {
+func (conn *Conn) onWGDisconnected(watcherCtx context.Context) {
 	conn.mu.Lock()
 	defer conn.mu.Unlock()
 
-	if conn.ctx.Err() != nil {
+	// watcherCtx guards against a stale watcher tearing down a connection that already superseded it.
+	if conn.ctx.Err() != nil || watcherCtx.Err() != nil {
 		return
 	}
 
@@ -683,6 +691,29 @@ func (conn *Conn) onWGDisconnected() {
 	default:
 		conn.Log.Debugf("No active connection to close on WG timeout")
 	}
+
+	conn.escalateWGTimeoutLocked()
+}
+
+// escalateWGTimeoutLocked resets the peer's rosenpass state after repeated
+// handshake timeouts. With rosenpass enabled, persistent timeouts mean the
+// preshared keys have desynced; the renewal exchange runs over the dead
+// tunnel and cannot resync them. Reporting the peer disconnected drops its
+// rosenpass state, so the next connection configuration programs the
+// rendezvous key and the tunnel can bootstrap again. Callers must hold mu.
+func (conn *Conn) escalateWGTimeoutLocked() {
+	if conn.config.RosenpassConfig.PubKey == nil {
+		return
+	}
+
+	conn.wgTimeouts++
+	if conn.wgTimeouts < wgTimeoutEscalationThreshold || conn.onDisconnected == nil {
+		return
+	}
+	conn.wgTimeouts = 0
+
+	conn.Log.Warnf("%d consecutive WireGuard handshake timeouts, resetting rosenpass state for peer", wgTimeoutEscalationThreshold)
+	conn.onDisconnected(conn.config.WgConfig.RemoteKey)
 }
 
 func (conn *Conn) updateRelayStatus(relayServerAddr string, rosenpassPubKey []byte, updateTime time.Time) {
@@ -802,25 +833,39 @@ func (conn *Conn) isConnectedOnAllWay() (status guard.ConnStatus) {
 	})
 }
 
+// enableWgWatcherIfNeeded starts a fresh watcher instance per connection attempt, so its
+// lifecycle stays bound to conn.mu and enable/disable can't race an old goroutine's shutdown.
+// Caller must hold conn.mu.
 func (conn *Conn) enableWgWatcherIfNeeded(enabledTime time.Time) {
-	if !conn.wgWatcher.PrepareInitialHandshake() {
+	if conn.wgWatcher != nil {
 		return
 	}
 
+	watcher := NewWGWatcher(conn.Log, conn.config.WgConfig.WgInterface, conn.config.Key, conn.dumpState)
+	watcher.PrepareInitialHandshake()
+
 	wgWatcherCtx, wgWatcherCancel := context.WithCancel(conn.ctx)
+	conn.wgWatcher = watcher
 	conn.wgWatcherCancel = wgWatcherCancel
+
 	conn.wgWatcherWg.Add(1)
 	go func() {
 		defer conn.wgWatcherWg.Done()
-		conn.wgWatcher.EnableWgWatcher(wgWatcherCtx, enabledTime, conn.onWGDisconnected, conn.onWGHandshakeSuccess)
+		onDisconnected := func() { conn.onWGDisconnected(wgWatcherCtx) }
+		watcher.EnableWgWatcher(wgWatcherCtx, enabledTime, onDisconnected, conn.onWGHandshakeSuccess, conn.onWGCheckSuccess)
 	}()
 }
 
+// disableWgWatcherIfNeeded cancels and drops the watcher once no transport is active. It never
+// waits for the goroutine: the timeout path reentrantly calls back here under conn.mu, so
+// blocking would deadlock. Caller must hold conn.mu.
 func (conn *Conn) disableWgWatcherIfNeeded() {
-	if conn.currentConnPriority == conntype.None && conn.wgWatcherCancel != nil {
-		conn.wgWatcherCancel()
-		conn.wgWatcherCancel = nil
+	if conn.currentConnPriority != conntype.None || conn.wgWatcher == nil {
+		return
 	}
+	conn.wgWatcherCancel()
+	conn.wgWatcher = nil
+	conn.wgWatcherCancel = nil
 }
 
 func (conn *Conn) newProxy(remoteConn net.Conn) (wgproxy.Proxy, error) {
@@ -843,7 +888,9 @@ func (conn *Conn) resetEndpoint() {
 		return
 	}
 	conn.Log.Infof("reset wg endpoint")
-	conn.wgWatcher.Reset()
+	if conn.wgWatcher != nil {
+		conn.wgWatcher.Reset()
+	}
 	if err := conn.endpointUpdater.RemoveEndpointAddress(); err != nil {
 		conn.Log.Warnf("failed to remove endpoint address before update: %v", err)
 	}
@@ -892,6 +939,15 @@ func (conn *Conn) onWGHandshakeSuccess(when time.Time) {
 	conn.recordConnectionMetrics()
 }
 
+// onWGCheckSuccess is called for every watcher check that observed a fresh
+// handshake, including handshakes of connections that were already up when
+// the watcher started.
+func (conn *Conn) onWGCheckSuccess() {
+	conn.mu.Lock()
+	conn.wgTimeouts = 0
+	conn.mu.Unlock()
+}
+
 // recordConnectionMetrics records connection stage timestamps as metrics
 func (conn *Conn) recordConnectionMetrics() {
 	if conn.metricsRecorder == nil {

client/internal/peer/conn_test.go

@@ -7,6 +7,7 @@ import (
 	"testing"
 	"time"
 
+	log "github.com/sirupsen/logrus"
 	"github.com/stretchr/testify/assert"
 
 	"github.com/netbirdio/netbird/client/iface"
@@ -304,3 +305,84 @@ func TestConn_presharedKey_RosenpassManaged(t *testing.T) {
 		t.Fatalf("expected non-nil presharedKey before Rosenpass manages PSK")
 	}
 }
+
+func newWGTimeoutTestConn(rosenpassEnabled bool, disconnected *[]string) *Conn {
+	cfg := ConnConfig{
+		Key:      "LLHf3Ma6z6mdLbriAJbqhX7+nM/B71lgw2+91q3LfhU=",
+		LocalKey: "RRHf3Ma6z6mdLbriAJbqhX7+nM/B71lgw2+91q3LfhU=",
+		WgConfig: WgConfig{RemoteKey: "LLHf3Ma6z6mdLbriAJbqhX7+nM/B71lgw2+91q3LfhU="},
+	}
+	if rosenpassEnabled {
+		cfg.RosenpassConfig = RosenpassConfig{PubKey: []byte("dummykey")}
+	}
+
+	conn := &Conn{
+		ctx:           context.Background(),
+		config:        cfg,
+		Log:           log.WithField("peer", cfg.Key),
+		metricsStages: &MetricsStages{},
+	}
+	conn.SetOnDisconnected(func(remotePeer string) {
+		*disconnected = append(*disconnected, remotePeer)
+	})
+	return conn
+}
+
+// TestConn_onWGDisconnected_EscalatesToRosenpassReset: repeated handshake
+// timeouts with rosenpass enabled mean the preshared keys have desynced. The
+// renewal exchange runs over the dead tunnel and cannot resync them, so after
+// wgTimeoutEscalationThreshold consecutive timeouts the conn must report the
+// peer disconnected, dropping its rosenpass state so the next configuration
+// programs the rendezvous key.
+func TestConn_onWGDisconnected_EscalatesToRosenpassReset(t *testing.T) {
+	var disconnected []string
+	conn := newWGTimeoutTestConn(true, &disconnected)
+
+	for i := 0; i < wgTimeoutEscalationThreshold-1; i++ {
+		conn.onWGDisconnected(conn.ctx)
+	}
+	assert.Empty(t, disconnected, "escalation must not fire below the threshold")
+
+	conn.onWGDisconnected(conn.ctx)
+	assert.Equal(t, []string{conn.config.WgConfig.RemoteKey}, disconnected,
+		"reaching the threshold must report the peer disconnected once")
+
+	for i := 0; i < wgTimeoutEscalationThreshold-1; i++ {
+		conn.onWGDisconnected(conn.ctx)
+	}
+	assert.Len(t, disconnected, 1, "escalation must restart counting after firing")
+
+	conn.onWGDisconnected(conn.ctx)
+	assert.Len(t, disconnected, 2, "continued timeouts must escalate again")
+}
+
+// TestConn_onWGDisconnected_CheckSuccessResetsEscalation: a successful
+// handshake between timeouts means the tunnel recovered; the counter must
+// start over.
+func TestConn_onWGDisconnected_CheckSuccessResetsEscalation(t *testing.T) {
+	var disconnected []string
+	conn := newWGTimeoutTestConn(true, &disconnected)
+
+	for i := 0; i < wgTimeoutEscalationThreshold-1; i++ {
+		conn.onWGDisconnected(conn.ctx)
+	}
+	conn.onWGCheckSuccess()
+
+	for i := 0; i < wgTimeoutEscalationThreshold-1; i++ {
+		conn.onWGDisconnected(conn.ctx)
+	}
+	assert.Empty(t, disconnected, "handshake success must reset the timeout count")
+}
+
+// TestConn_onWGDisconnected_NoEscalationWithoutRosenpass: without rosenpass
+// there is no per-peer key state to reset; repeated timeouts must not report
+// disconnects.
+func TestConn_onWGDisconnected_NoEscalationWithoutRosenpass(t *testing.T) {
+	var disconnected []string
+	conn := newWGTimeoutTestConn(false, &disconnected)
+
+	for i := 0; i < wgTimeoutEscalationThreshold*3; i++ {
+		conn.onWGDisconnected(conn.ctx)
+	}
+	assert.Empty(t, disconnected, "escalation must be limited to rosenpass connections")
+}

client/internal/peer/wg_watcher.go

@@ -3,7 +3,6 @@ package peer
 import (
 	"context"
 	"fmt"
-	"sync"
 	"time"
 
 	log "github.com/sirupsen/logrus"
@@ -24,14 +23,14 @@ type WGInterfaceStater interface {
 	GetStats() (map[string]configurer.WGStats, error)
 }
 
+// WGWatcher is single-shot: one instance per connection attempt, run once, then discarded.
+// Lifecycle is owned by Conn under conn.mu, so it keeps no "enabled" state to go stale.
 type WGWatcher struct {
 	log           *log.Entry
 	wgIfaceStater WGInterfaceStater
 	peerKey       string
 	stateDump     *stateDump
 
-	enabled   bool
-	muEnabled sync.Mutex
 	// initialHandshake is not thread-safe; never call PrepareInitialHandshake and EnableWgWatcher concurrently.
 	initialHandshake time.Time
 
@@ -48,36 +47,23 @@ func NewWGWatcher(log *log.Entry, wgIfaceStater WGInterfaceStater, peerKey strin
 	}
 }
 
-// PrepareInitialHandshake reserves the watcher and reads the peer's current WireGuard
-// handshake time. It must be called before the peer is (re)configured on the WireGuard
-// interface, so the captured baseline reflects the state prior to this connection attempt
-// instead of racing with that configuration. Returns ok=false if the watcher is already
-// running, in which case EnableWgWatcher must not be called.
-func (w *WGWatcher) PrepareInitialHandshake() (ok bool) {
-	w.muEnabled.Lock()
-	if w.enabled {
-		w.muEnabled.Unlock()
-		return false
-	}
-
+// PrepareInitialHandshake reads the peer's current WireGuard handshake time. It must be
+// called before the peer is (re)configured on the WireGuard interface, so the captured
+// baseline reflects the state prior to this connection attempt instead of racing with
+// that configuration.
+func (w *WGWatcher) PrepareInitialHandshake() {
 	w.log.Debugf("enable WireGuard watcher")
-	w.enabled = true
-	w.muEnabled.Unlock()
-
 	handshake, _ := w.wgState()
 	w.initialHandshake = handshake
-	return true
 }
 
 // EnableWgWatcher runs the WireGuard watcher loop using the handshake baseline captured by
 // PrepareInitialHandshake. The watcher runs until ctx is cancelled. Caller is responsible
-// for context lifecycle management.
-func (w *WGWatcher) EnableWgWatcher(ctx context.Context, enabledTime time.Time, onDisconnectedFn func(), onHandshakeSuccessFn func(when time.Time)) {
-	w.periodicHandshakeCheck(ctx, onDisconnectedFn, onHandshakeSuccessFn, enabledTime, w.initialHandshake)
-
-	w.muEnabled.Lock()
-	w.enabled = false
-	w.muEnabled.Unlock()
+// for context lifecycle management. onHandshakeSuccessFn is called only for the first
+// handshake observed by this run, onCheckSuccessFn for every check that observed a fresh
+// handshake, including the first.
+func (w *WGWatcher) EnableWgWatcher(ctx context.Context, enabledTime time.Time, onDisconnectedFn func(), onHandshakeSuccessFn func(when time.Time), onCheckSuccessFn func()) {
+	w.periodicHandshakeCheck(ctx, onDisconnectedFn, onHandshakeSuccessFn, onCheckSuccessFn, enabledTime, w.initialHandshake)
 }
 
 // Reset signals the watcher that the WireGuard peer has been reset and a new
@@ -90,7 +76,7 @@ func (w *WGWatcher) Reset() {
 }
 
 // wgStateCheck help to check the state of the WireGuard handshake and relay connection
-func (w *WGWatcher) periodicHandshakeCheck(ctx context.Context, onDisconnectedFn func(), onHandshakeSuccessFn func(when time.Time), enabledTime time.Time, initialHandshake time.Time) {
+func (w *WGWatcher) periodicHandshakeCheck(ctx context.Context, onDisconnectedFn func(), onHandshakeSuccessFn func(when time.Time), onCheckSuccessFn func(), enabledTime time.Time, initialHandshake time.Time) {
 	w.log.Infof("WireGuard watcher started")
 
 	timer := time.NewTimer(wgHandshakeOvertime)
@@ -103,6 +89,7 @@ func (w *WGWatcher) periodicHandshakeCheck(ctx context.Context, onDisconnectedFn
 		case <-timer.C:
 			handshake, ok := w.handshakeCheck(lastHandshake)
 			if !ok {
+				// early ctx cancel check return
 				if ctx.Err() != nil {
 					return
 				}
@@ -117,6 +104,10 @@ func (w *WGWatcher) periodicHandshakeCheck(ctx context.Context, onDisconnectedFn
 				}
 			}
 
+			if onCheckSuccessFn != nil && ctx.Err() == nil {
+				onCheckSuccessFn()
+			}
+
 			lastHandshake = *handshake
 
 			resetTime := time.Until(handshake.Add(checkPeriod))
@@ -147,9 +138,9 @@ func (w *WGWatcher) handshakeCheck(lastHandshake time.Time) (*time.Time, bool) {
 
 	w.log.Tracef("previous handshake, handshake: %v, %v", lastHandshake, handshake)
 
-	// the current know handshake did not change
+	// the current known handshake did not change
 	if handshake.Equal(lastHandshake) {
-		w.log.Warnf("WireGuard handshake timed out: %v", handshake)
+		w.log.Warnf("WireGuard handshake not updated: %v", handshake)
 		return nil, false
 	}
 

client/internal/peer/wg_watcher_test.go

@@ -7,7 +7,6 @@ import (
 	"time"
 
 	log "github.com/sirupsen/logrus"
-	"github.com/stretchr/testify/require"
 
 	"github.com/netbirdio/netbird/client/iface/configurer"
 )
@@ -24,6 +23,72 @@ func (m *MocWgIface) disconnect() {
 	m.stop = true
 }
 
+type mockHandshakeStats struct {
+	mu        sync.Mutex
+	handshake time.Time
+}
+
+func (m *mockHandshakeStats) GetStats() (map[string]configurer.WGStats, error) {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+	return map[string]configurer.WGStats{"": {LastHandshake: m.handshake}}, nil
+}
+
+func (m *mockHandshakeStats) advance() {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+	m.handshake = time.Now()
+}
+
+// TestWGWatcher_CheckSuccessCallback: onCheckSuccessFn must fire for a fresh
+// handshake even when the watcher started with an existing handshake baseline,
+// the case where onHandshakeSuccessFn stays silent.
+func TestWGWatcher_CheckSuccessCallback(t *testing.T) {
+	// checkPeriod bounds how stale a handshake may be before the watcher treats it
+	// as a suspended-machine timeout. The first check fires after wgHandshakeOvertime,
+	// so keep checkPeriod well above any scheduling jitter to avoid a false timeout
+	// converting the expected success into a disconnect on a loaded runner.
+	checkPeriod = 1 * time.Minute
+	wgHandshakeOvertime = 1 * time.Second
+
+	mlog := log.WithField("peer", "tet")
+	// Use an old baseline so advance() yields a strictly newer handshake even on
+	// platforms with coarse clock resolution (Windows), where two time.Now() calls
+	// microseconds apart can return the same instant and read as a timed-out handshake.
+	stats := &mockHandshakeStats{handshake: time.Now().Add(-time.Hour)}
+	watcher := NewWGWatcher(mlog, stats, "", newStateDump("peer", mlog, &Status{}))
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	watcher.PrepareInitialHandshake()
+
+	firstHandshake := make(chan struct{}, 1)
+	checkSuccess := make(chan struct{}, 1)
+	go watcher.EnableWgWatcher(ctx, time.Now(), func() {}, func(when time.Time) {
+		firstHandshake <- struct{}{}
+	}, func() {
+		select {
+		case checkSuccess <- struct{}{}:
+		default:
+		}
+	})
+
+	stats.advance()
+
+	select {
+	case <-checkSuccess:
+	case <-time.After(10 * time.Second):
+		t.Errorf("timeout waiting for check success callback")
+	}
+
+	select {
+	case <-firstHandshake:
+		t.Errorf("first-handshake callback must not fire for a non-zero baseline")
+	default:
+	}
+}
+
 func TestWGWatcher_EnableWgWatcher(t *testing.T) {
 	checkPeriod = 5 * time.Second
 	wgHandshakeOvertime = 1 * time.Second
@@ -35,8 +100,7 @@ func TestWGWatcher_EnableWgWatcher(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
 
-	ok := watcher.PrepareInitialHandshake()
-	require.True(t, ok, "watcher should not be enabled yet")
+	watcher.PrepareInitialHandshake()
 
 	onDisconnected := make(chan struct{}, 1)
 	go watcher.EnableWgWatcher(ctx, time.Now(), func() {
@@ -44,7 +108,7 @@ func TestWGWatcher_EnableWgWatcher(t *testing.T) {
 		onDisconnected <- struct{}{}
 	}, func(when time.Time) {
 		mlog.Infof("onHandshakeSuccess: %v", when)
-	})
+	}, nil)
 
 	// wait for initial reading
 	time.Sleep(2 * time.Second)
@@ -66,14 +130,13 @@ func TestWGWatcher_ReEnable(t *testing.T) {
 	watcher := NewWGWatcher(mlog, mocWgIface, "", newStateDump("peer", mlog, &Status{}))
 
 	ctx, cancel := context.WithCancel(context.Background())
-	ok := watcher.PrepareInitialHandshake()
-	require.True(t, ok, "watcher should not be enabled yet")
+	watcher.PrepareInitialHandshake()
 
 	wg := &sync.WaitGroup{}
 	wg.Add(1)
 	go func() {
 		defer wg.Done()
-		watcher.EnableWgWatcher(ctx, time.Now(), func() {}, func(when time.Time) {})
+		watcher.EnableWgWatcher(ctx, time.Now(), func() {}, func(when time.Time) {}, nil)
 	}()
 	cancel()
 
@@ -83,13 +146,12 @@ func TestWGWatcher_ReEnable(t *testing.T) {
 	ctx, cancel = context.WithCancel(context.Background())
 	defer cancel()
 
-	ok = watcher.PrepareInitialHandshake()
-	require.True(t, ok, "watcher should be re-enabled after the previous run stopped")
+	watcher.PrepareInitialHandshake()
 
 	onDisconnected := make(chan struct{}, 1)
 	go watcher.EnableWgWatcher(ctx, time.Now(), func() {
 		onDisconnected <- struct{}{}
-	}, func(when time.Time) {})
+	}, func(when time.Time) {}, nil)
 
 	time.Sleep(2 * time.Second)
 	mocWgIface.disconnect()

client/internal/rosenpass/manager.go

@@ -39,6 +39,7 @@ type rpServer interface {
 
 type Manager struct {
 	ifaceName    string
+	localWgKey   wgtypes.Key
 	spk          []byte
 	ssk          []byte
 	rpKeyHash    string
@@ -51,8 +52,9 @@ type Manager struct {
 	wgIface      PresharedKeySetter
 }
 
-// NewManager creates a new Rosenpass manager
-func NewManager(preSharedKey *wgtypes.Key, wgIfaceName string) (*Manager, error) {
+// NewManager creates a new Rosenpass manager. localWgKey is the local
+// WireGuard public key, used to derive the per-peer rendezvous key.
+func NewManager(preSharedKey *wgtypes.Key, wgIfaceName string, localWgKey wgtypes.Key) (*Manager, error) {
 	public, secret, err := rp.GenerateKeyPair()
 	if err != nil {
 		return nil, err
@@ -62,6 +64,7 @@ func NewManager(preSharedKey *wgtypes.Key, wgIfaceName string) (*Manager, error)
 	log.Tracef("generated new rosenpass key pair with public key %s", rpKeyHash)
 	return &Manager{
 		ifaceName:    wgIfaceName,
+		localWgKey:   localWgKey,
 		rpKeyHash:    rpKeyHash,
 		spk:          public,
 		ssk:          secret,
@@ -73,7 +76,7 @@ func NewManager(preSharedKey *wgtypes.Key, wgIfaceName string) (*Manager, error)
 		// nil receiver in addPeer -> m.rpWgHandler.AddPeer. generateConfig will
 		// replace it with a fresh handler on each Run() to clear stale peer
 		// state from previous engine sessions.
-		rpWgHandler: NewNetbirdHandler(),
+		rpWgHandler: NewNetbirdHandler((*[32]byte)(preSharedKey), localWgKey),
 		lock:        sync.Mutex{},
 	}, nil
 }
@@ -161,7 +164,7 @@ func (m *Manager) generateConfig() (rp.Config, error) {
 	cfg.Peers = []rp.PeerConfig{}
 
 	m.lock.Lock()
-	m.rpWgHandler = NewNetbirdHandler()
+	m.rpWgHandler = NewNetbirdHandler(m.preSharedKey, m.localWgKey)
 	if m.wgIface != nil {
 		m.rpWgHandler.SetInterface(m.wgIface)
 	}

client/internal/rosenpass/manager_test.go

@@ -85,7 +85,7 @@ func newTestManager(spkFirstByte byte, mock *mockServer) *Manager {
 		ssk:         make([]byte, 32),
 		rpKeyHash:   "test-hash",
 		rpPeerIDs:   make(map[string]*rp.PeerID),
-		rpWgHandler: NewNetbirdHandler(),
+		rpWgHandler: NewNetbirdHandler(nil, wgtypes.Key{0x01}),
 		server:      mock,
 	}
 }
@@ -255,7 +255,7 @@ func TestAddPeer_NilServer_ReturnsErrorNoCrash(t *testing.T) {
 // issue #4341 cannot occur in the window between NewManager and Run().
 func TestNewManager_PreInitializesHandler(t *testing.T) {
 	psk := wgtypes.Key{}
-	m, err := NewManager(&psk, "wt0")
+	m, err := NewManager(&psk, "wt0", wgtypes.Key{0x01})
 	require.NoError(t, err)
 	require.NotNil(t, m.rpWgHandler, "rpWgHandler must be initialized in NewManager")
 }
@@ -329,10 +329,10 @@ func TestIsPresharedKeyInitialized_AddedButNotHandshaken_ReturnsFalse(t *testing
 	require.False(t, m.IsPresharedKeyInitialized(wgKey))
 }
 
-// --- NetbirdHandler.outputKey ----------------------------------------------
+// --- NetbirdHandler.applyKey ----------------------------------------------
 
-func TestHandler_OutputKey_FirstCallUsesUpdateOnlyFalse(t *testing.T) {
-	h := NewNetbirdHandler()
+func TestHandler_ApplyKey_FirstCallUsesUpdateOnlyFalse(t *testing.T) {
+	h := NewNetbirdHandler(nil, wgtypes.Key{0x01})
 	iface := &mockIface{}
 	h.SetInterface(iface)
 
@@ -348,8 +348,8 @@ func TestHandler_OutputKey_FirstCallUsesUpdateOnlyFalse(t *testing.T) {
 	require.Equal(t, wgKey.String(), iface.calls[0].peerKey)
 }
 
-func TestHandler_OutputKey_SubsequentCallsUseUpdateOnlyTrue(t *testing.T) {
-	h := NewNetbirdHandler()
+func TestHandler_ApplyKey_SubsequentCallsUseUpdateOnlyTrue(t *testing.T) {
+	h := NewNetbirdHandler(nil, wgtypes.Key{0x01})
 	iface := &mockIface{}
 	h.SetInterface(iface)
 
@@ -364,8 +364,8 @@ func TestHandler_OutputKey_SubsequentCallsUseUpdateOnlyTrue(t *testing.T) {
 	require.True(t, iface.calls[1].updateOnly, "subsequent rotations must use updateOnly=true")
 }
 
-func TestHandler_OutputKey_NilInterface_NoCrashNoCall(t *testing.T) {
-	h := NewNetbirdHandler()
+func TestHandler_ApplyKey_NilInterface_NoCrashNoCall(t *testing.T) {
+	h := NewNetbirdHandler(nil, wgtypes.Key{0x01})
 	// no SetInterface — iface remains nil
 	pid := rp.PeerID{0x03}
 	h.AddPeer(pid, "wt0", rp.Key(wgtypes.Key{}))
@@ -374,8 +374,8 @@ func TestHandler_OutputKey_NilInterface_NoCrashNoCall(t *testing.T) {
 	h.HandshakeCompleted(pid, rp.Key{})
 }
 
-func TestHandler_OutputKey_UnknownPeer_NoCall(t *testing.T) {
-	h := NewNetbirdHandler()
+func TestHandler_ApplyKey_UnknownPeer_NoCall(t *testing.T) {
+	h := NewNetbirdHandler(nil, wgtypes.Key{0x01})
 	iface := &mockIface{}
 	h.SetInterface(iface)
 
@@ -384,7 +384,7 @@ func TestHandler_OutputKey_UnknownPeer_NoCall(t *testing.T) {
 }
 
 func TestHandler_RemovePeer_ClearsInitializedState(t *testing.T) {
-	h := NewNetbirdHandler()
+	h := NewNetbirdHandler(nil, wgtypes.Key{0x01})
 	iface := &mockIface{}
 	h.SetInterface(iface)
 
@@ -398,7 +398,7 @@ func TestHandler_RemovePeer_ClearsInitializedState(t *testing.T) {
 }
 
 func TestHandler_SetInterfaceAfterAddPeer_StillReceivesKey(t *testing.T) {
-	h := NewNetbirdHandler()
+	h := NewNetbirdHandler(nil, wgtypes.Key{0x01})
 	pid := rp.PeerID{0x05}
 	wgKey := wgtypes.Key{0xEE}
 	h.AddPeer(pid, "wt0", rp.Key(wgKey))

client/internal/rosenpass/netbird_handler.go

@@ -18,19 +18,34 @@ type PresharedKeySetter interface {
 type wireGuardPeer struct {
 	Interface string
 	PublicKey rp.Key
+	// initialized is true once a completed exchange has set a
+	// Rosenpass-managed PSK for this peer.
+	initialized bool
+	// chainKey is the key output by the last completed exchange, advanced by
+	// one ratchet step on expiry. Nil until the first exchange completes and
+	// after the peer has fallen back to the rendezvous key.
+	chainKey *wgtypes.Key
+	// expiries counts failed renewals since the last completed exchange.
+	expiries int
 }
 
 type NetbirdHandler struct {
-	mu               sync.Mutex
-	iface            PresharedKeySetter
-	peers            map[rp.PeerID]wireGuardPeer
-	initializedPeers map[rp.PeerID]bool
+	mu    sync.Mutex
+	iface PresharedKeySetter
+	// preSharedKey is the account-level preshared key, used as the rendezvous
+	// key when set. Nil means the deterministic seed key is used instead.
+	preSharedKey *[32]byte
+	// localWgKey is the local WireGuard public key, one of the two inputs to
+	// the deterministic seed key.
+	localWgKey wgtypes.Key
+	peers      map[rp.PeerID]*wireGuardPeer
 }
 
-func NewNetbirdHandler() *NetbirdHandler {
+func NewNetbirdHandler(preSharedKey *[32]byte, localWgKey wgtypes.Key) *NetbirdHandler {
 	return &NetbirdHandler{
-		peers:            map[rp.PeerID]wireGuardPeer{},
-		initializedPeers: map[rp.PeerID]bool{},
+		preSharedKey: preSharedKey,
+		localWgKey:   localWgKey,
+		peers:        map[rp.PeerID]*wireGuardPeer{},
 	}
 }
 
@@ -42,10 +57,16 @@ func (h *NetbirdHandler) SetInterface(iface PresharedKeySetter) {
 	h.iface = iface
 }
 
+// AddPeer registers a peer with the handler. Re-adding a known peer (every
+// reconnection does) keeps its key recovery state.
 func (h *NetbirdHandler) AddPeer(pid rp.PeerID, intf string, pk rp.Key) {
 	h.mu.Lock()
 	defer h.mu.Unlock()
-	h.peers[pid] = wireGuardPeer{
+	if existing, ok := h.peers[pid]; ok && existing.PublicKey == pk {
+		existing.Interface = intf
+		return
+	}
+	h.peers[pid] = &wireGuardPeer{
 		Interface: intf,
 		PublicKey: pk,
 	}
@@ -55,7 +76,6 @@ func (h *NetbirdHandler) RemovePeer(pid rp.PeerID) {
 	h.mu.Lock()
 	defer h.mu.Unlock()
 	delete(h.peers, pid)
-	delete(h.initializedPeers, pid)
 }
 
 // IsPeerInitialized returns true if Rosenpass has completed a handshake
@@ -63,50 +83,120 @@ func (h *NetbirdHandler) RemovePeer(pid rp.PeerID) {
 func (h *NetbirdHandler) IsPeerInitialized(pid rp.PeerID) bool {
 	h.mu.Lock()
 	defer h.mu.Unlock()
-	return h.initializedPeers[pid]
+	peer, ok := h.peers[pid]
+	return ok && peer.initialized
 }
 
+// HandshakeCompleted programs the freshly exchanged output key and resets the
+// peer's key recovery state.
 func (h *NetbirdHandler) HandshakeCompleted(pid rp.PeerID, key rp.Key) {
-	h.outputKey(rp.KeyOutputReasonStale, pid, key)
-}
+	psk := wgtypes.Key(key)
 
-func (h *NetbirdHandler) HandshakeExpired(pid rp.PeerID) {
-	key, _ := rp.GeneratePresharedKey()
-	h.outputKey(rp.KeyOutputReasonStale, pid, key)
-}
-
-func (h *NetbirdHandler) outputKey(_ rp.KeyOutputReason, pid rp.PeerID, psk rp.Key) {
 	h.mu.Lock()
-	iface := h.iface
-	wg, ok := h.peers[pid]
-	isInitialized := h.initializedPeers[pid]
-	h.mu.Unlock()
+	defer h.mu.Unlock()
 
-	if iface == nil {
-		log.Warn("rosenpass: interface not set, cannot update preshared key")
+	peer, ok := h.peers[pid]
+	if !ok {
 		return
 	}
+	if peer.expiries > 0 {
+		log.Infof("rosenpass exchange completed for peer %s after %d expired renewals", wgtypes.Key(peer.PublicKey), peer.expiries)
+	}
+	// chainKey tracks the shared exchange output regardless of the local write
+	// outcome, so both ends still converge on the next expiry.
+	peer.chainKey = &psk
+	peer.expiries = 0
+	if !h.applyKeyLocked(pid, psk, peer.initialized) {
+		return
+	}
+	peer.initialized = true
+}
 
+// HandshakeExpired replaces the expired key. The renewal exchange runs over
+// the tunnel keyed by the PSK itself, so the replacement must be derivable on
+// both ends without communication: the first expiry ratchets the last shared
+// key forward, repeated expiries (and expiries without a completed exchange)
+// fall back to the rendezvous key and drop the peer out of the initialized
+// state so connection reconfigurations reprogram the rendezvous key as well.
+func (h *NetbirdHandler) HandshakeExpired(pid rp.PeerID) {
+	h.mu.Lock()
+	defer h.mu.Unlock()
+
+	peer, ok := h.peers[pid]
 	if !ok {
 		return
 	}
 
-	peerKey := wgtypes.Key(wg.PublicKey).String()
-	pskKey := wgtypes.Key(psk)
+	peer.expiries++
 
-	// Use updateOnly=true for later rotations (peer already has Rosenpass PSK)
-	// Use updateOnly=false for first rotation (peer has original/empty PSK)
-	if err := iface.SetPresharedKey(peerKey, pskKey, isInitialized); err != nil {
+	var psk wgtypes.Key
+	if peer.chainKey != nil && peer.expiries == 1 {
+		log.Infof("rosenpass key for peer %s expired without renewal, advancing to ratcheted key", wgtypes.Key(peer.PublicKey))
+		psk = RatchetKey(*peer.chainKey)
+		peer.chainKey = &psk
+	} else {
+		rendezvous, err := h.rendezvousKey(peer)
+		if err != nil {
+			// Fail closed: without a rendezvous key the expired key must
+			// still be rotated out, even if the replacement is unusable.
+			log.Errorf("failed to derive rendezvous key, replacing expired key with a random one: %v", err)
+			h.applyRandomKeyLocked(pid)
+			return
+		}
+		log.Warnf("rosenpass key for peer %s expired %d times without renewal, falling back to the rendezvous key", wgtypes.Key(peer.PublicKey), peer.expiries)
+		psk = rendezvous
+		peer.chainKey = nil
+		peer.initialized = false
+	}
+
+	h.applyKeyLocked(pid, psk, true)
+}
+
+// rendezvousKey returns the key both ends converge on without communication:
+// the account-level preshared key when configured, the deterministic seed key
+// otherwise. It mirrors the key that peer connections program when Rosenpass
+// does not manage the peer yet.
+func (h *NetbirdHandler) rendezvousKey(peer *wireGuardPeer) (wgtypes.Key, error) {
+	if h.preSharedKey != nil {
+		return *h.preSharedKey, nil
+	}
+
+	seed, err := DeterministicSeedKey(h.localWgKey.String(), wgtypes.Key(peer.PublicKey).String())
+	if err != nil {
+		return wgtypes.Key{}, err
+	}
+	return *seed, nil
+}
+
+// applyKeyLocked writes the preshared key for the peer to the WireGuard
+// interface and reports whether the write succeeded. Callers must hold h.mu
+// for the whole state-mutation-plus-write so that a concurrent completion and
+// expiry cannot reorder their writes relative to the in-memory chain key.
+func (h *NetbirdHandler) applyKeyLocked(pid rp.PeerID, psk wgtypes.Key, updateOnly bool) bool {
+	peer, ok := h.peers[pid]
+	if !ok {
+		return false
+	}
+
+	if h.iface == nil {
+		log.Warn("rosenpass: interface not set, cannot update preshared key")
+		return false
+	}
+
+	peerKey := wgtypes.Key(peer.PublicKey).String()
+	if err := h.iface.SetPresharedKey(peerKey, psk, updateOnly); err != nil {
 		log.Errorf("Failed to apply rosenpass key: %v", err)
+		return false
+	}
+
+	return true
+}
+
+func (h *NetbirdHandler) applyRandomKeyLocked(pid rp.PeerID) {
+	key, err := rp.GeneratePresharedKey()
+	if err != nil {
+		log.Errorf("failed to generate random preshared key: %v", err)
 		return
 	}
-
-	// Mark peer as isInitialized after the successful first rotation
-	if !isInitialized {
-		h.mu.Lock()
-		if _, exists := h.peers[pid]; exists {
-			h.initializedPeers[pid] = true
-		}
-		h.mu.Unlock()
-	}
+	h.applyKeyLocked(pid, wgtypes.Key(key), true)
 }

client/internal/rosenpass/netbird_handler_test.go

@@ -0,0 +1,250 @@
+package rosenpass
+
+import (
+	"testing"
+
+	rp "cunicu.li/go-rosenpass"
+	"github.com/stretchr/testify/require"
+	"golang.zx2c4.com/wireguard/wgctrl/wgtypes"
+)
+
+// handlerTestLink wires two NetbirdHandlers as the two ends of a single
+// tunnel: handler A manages the rosenpass peer B and vice versa, the way two
+// NetBird clients see each other.
+type handlerTestLink struct {
+	handlerA, handlerB *NetbirdHandler
+	ifaceA, ifaceB     *mockIface
+	pidA, pidB         rp.PeerID
+	wgKeyA, wgKeyB     wgtypes.Key
+}
+
+func newHandlerTestLink(t *testing.T, preSharedKey *[32]byte) *handlerTestLink {
+	t.Helper()
+
+	link := &handlerTestLink{
+		ifaceA: &mockIface{},
+		ifaceB: &mockIface{},
+	}
+	link.pidA[0] = 0xaa
+	link.pidB[0] = 0xbb
+	link.wgKeyA[31] = 1
+	link.wgKeyB[31] = 2
+
+	link.handlerA = NewNetbirdHandler(preSharedKey, link.wgKeyA)
+	link.handlerB = NewNetbirdHandler(preSharedKey, link.wgKeyB)
+
+	link.handlerA.SetInterface(link.ifaceA)
+	link.handlerB.SetInterface(link.ifaceB)
+
+	link.handlerA.AddPeer(link.pidB, "wt0", rp.Key(link.wgKeyB))
+	link.handlerB.AddPeer(link.pidA, "wt0", rp.Key(link.wgKeyA))
+
+	return link
+}
+
+// complete simulates a completed rosenpass exchange: both ends derive the
+// same output key.
+func (l *handlerTestLink) complete(osk rp.Key) {
+	l.handlerA.HandshakeCompleted(l.pidB, osk)
+	l.handlerB.HandshakeCompleted(l.pidA, osk)
+}
+
+// expire simulates a failed key renewal on both ends.
+func (l *handlerTestLink) expire() {
+	l.handlerA.HandshakeExpired(l.pidB)
+	l.handlerB.HandshakeExpired(l.pidA)
+}
+
+func lastPSK(t *testing.T, m *mockIface) wgtypes.Key {
+	t.Helper()
+	m.mu.Lock()
+	defer m.mu.Unlock()
+	require.NotEmpty(t, m.calls, "expected at least one SetPresharedKey call")
+	return m.calls[len(m.calls)-1].psk
+}
+
+func TestHandshakeCompleted_SetsKeyAndInitializes(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	require.Equal(t, wgtypes.Key(osk), lastPSK(t, link.ifaceA), "completed exchange must program the osk")
+	require.False(t, link.ifaceA.calls[0].updateOnly, "first rotation must not be update-only")
+	require.True(t, link.handlerA.IsPeerInitialized(link.pidB), "peer must be initialized after first completed exchange")
+
+	link.complete(osk)
+	require.True(t, link.ifaceA.calls[1].updateOnly, "later rotations must be update-only")
+}
+
+// TestHandshakeExpired_BothSidesConverge encodes the core recovery invariant:
+// rosenpass renewals run over the tunnel that the PSK itself keys, so when a
+// renewal fails on both ends, both ends must fall back to the same key or the
+// tunnel can never handshake again.
+func TestHandshakeExpired_BothSidesConverge(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	link.expire()
+	keyA := lastPSK(t, link.ifaceA)
+	keyB := lastPSK(t, link.ifaceB)
+	require.NotEqual(t, wgtypes.Key(osk), keyA, "expired key must be rotated out")
+	require.Equal(t, keyA, keyB, "both ends must converge on the same key after expiry")
+
+	link.expire()
+	require.Equal(t, lastPSK(t, link.ifaceA), lastPSK(t, link.ifaceB),
+		"both ends must still converge after repeated expiries")
+}
+
+// TestHandshakeExpired_ExpiryWithoutCompletionConverges covers the bootstrap
+// case: the initial exchange never completed (the tunnel ran on the rendezvous
+// key), so an expiry must not replace the working key with an unrecoverable
+// one on either end.
+func TestHandshakeExpired_ExpiryWithoutCompletionConverges(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	link.expire()
+	require.Equal(t, lastPSK(t, link.ifaceA), lastPSK(t, link.ifaceB),
+		"both ends must converge when the exchange never completed")
+}
+
+// TestHandshakeExpired_RepeatedExpiryClearsInitialized: once renewals keep
+// failing, the peer must drop out of the initialized state so the next
+// connection reconfiguration reprograms the rendezvous key instead of
+// preserving a poisoned rosenpass-managed key.
+func TestHandshakeExpired_RepeatedExpiryClearsInitialized(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	link.expire()
+	link.expire()
+
+	require.False(t, link.handlerA.IsPeerInitialized(link.pidB),
+		"repeated expiries must clear the initialized state")
+	require.False(t, link.handlerB.IsPeerInitialized(link.pidA),
+		"repeated expiries must clear the initialized state")
+}
+
+// TestHandshakeCompleted_AfterExpiryRecovers: a completed exchange after a
+// desync must fully reset the recovery state.
+func TestHandshakeCompleted_AfterExpiryRecovers(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk1, osk2 rp.Key
+	osk1[0] = 1
+	osk2[0] = 2
+
+	link.complete(osk1)
+	link.expire()
+	link.expire()
+
+	link.complete(osk2)
+	require.Equal(t, wgtypes.Key(osk2), lastPSK(t, link.ifaceA), "new exchange must program the fresh osk")
+	require.True(t, link.handlerA.IsPeerInitialized(link.pidB), "peer must be initialized again after recovery")
+
+	link.expire()
+	require.Equal(t, lastPSK(t, link.ifaceA), lastPSK(t, link.ifaceB),
+		"recovered link must converge again on the next expiry")
+	require.NotEqual(t, wgtypes.Key(osk2), lastPSK(t, link.ifaceA), "expired key must be rotated out")
+}
+
+// TestHandshakeExpired_FirstExpiryRatchetsLastKey: the first expiry must
+// derive the replacement from the last shared key, so an attacker who only
+// blocks the renewal exchange gains nothing over the previous key.
+func TestHandshakeExpired_FirstExpiryRatchetsLastKey(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	link.expire()
+	require.Equal(t, RatchetKey(wgtypes.Key(osk)), lastPSK(t, link.ifaceA),
+		"first expiry must program the ratcheted key")
+	require.True(t, link.handlerA.IsPeerInitialized(link.pidB),
+		"ratchet step must keep the peer initialized so reconfigurations preserve the key")
+}
+
+// TestHandshakeExpired_RepeatedExpiryFallsBackToSeed: once the ratchet key
+// also fails, both ends must land on the same key that peer connections
+// program for uninitialized peers, so a reconnect completes the recovery.
+func TestHandshakeExpired_RepeatedExpiryFallsBackToSeed(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	link.expire()
+	link.expire()
+
+	seed, err := DeterministicSeedKey(link.wgKeyA.String(), link.wgKeyB.String())
+	require.NoError(t, err)
+	require.Equal(t, *seed, lastPSK(t, link.ifaceA), "repeated expiry must fall back to the seed key")
+	require.Equal(t, *seed, lastPSK(t, link.ifaceB), "repeated expiry must fall back to the seed key")
+}
+
+// TestHandshakeExpired_ConfiguredPSKUsedAsRendezvous: with an account-level
+// preshared key configured, the fallback must be that key, matching what peer
+// connections program for uninitialized peers.
+func TestHandshakeExpired_ConfiguredPSKUsedAsRendezvous(t *testing.T) {
+	psk := &[32]byte{0x77}
+	link := newHandlerTestLink(t, psk)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	link.expire()
+	link.expire()
+
+	require.Equal(t, wgtypes.Key(*psk), lastPSK(t, link.ifaceA),
+		"fallback must be the configured preshared key")
+	require.Equal(t, wgtypes.Key(*psk), lastPSK(t, link.ifaceB),
+		"fallback must be the configured preshared key on both ends")
+}
+
+// TestHandshakeExpired_ExpiryWritesAreUpdateOnly: expiry replacements must
+// never create a WireGuard peer that connection management has removed.
+func TestHandshakeExpired_ExpiryWritesAreUpdateOnly(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+
+	link.expire()
+	link.expire()
+
+	for _, call := range link.ifaceA.calls[1:] {
+		require.True(t, call.updateOnly, "expiry writes must be update-only")
+	}
+}
+
+// TestAddPeer_ReAddKeepsRecoveryState: reconnections re-add the peer on every
+// OnConnected; that must not reset the expiry chain state.
+func TestAddPeer_ReAddKeepsRecoveryState(t *testing.T) {
+	link := newHandlerTestLink(t, nil)
+
+	var osk rp.Key
+	osk[0] = 0x42
+	link.complete(osk)
+	link.expire()
+
+	link.handlerA.AddPeer(link.pidB, "wt0", rp.Key(link.wgKeyB))
+	require.True(t, link.handlerA.IsPeerInitialized(link.pidB),
+		"re-adding a known peer must keep its state")
+
+	link.expire()
+	seed, err := DeterministicSeedKey(link.wgKeyA.String(), link.wgKeyB.String())
+	require.NoError(t, err)
+	require.Equal(t, *seed, lastPSK(t, link.ifaceA),
+		"second expiry after re-add must continue to the seed fallback")
+}

client/internal/rosenpass/seed.go

@@ -1,11 +1,28 @@
 package rosenpass
 
 import (
+	"crypto/sha256"
 	"fmt"
 
 	"golang.zx2c4.com/wireguard/wgctrl/wgtypes"
 )
 
+// ratchetLabel domain-separates the expiry ratchet from other uses of the
+// rosenpass output key.
+const ratchetLabel = "netbird-rosenpass-expiry-ratchet"
+
+// RatchetKey derives the successor preshared key from the previous Rosenpass
+// output key. When a key expires without a completed renewal, both peers
+// advance their last shared key by one ratchet step: the expired key is
+// rotated out while both ends still converge on an identical, non-public
+// replacement without communicating.
+func RatchetKey(prev wgtypes.Key) wgtypes.Key {
+	input := make([]byte, 0, len(ratchetLabel)+len(prev))
+	input = append(input, ratchetLabel...)
+	input = append(input, prev[:]...)
+	return sha256.Sum256(input)
+}
+
 // DeterministicSeedKey derives a 32-byte WireGuard preshared key from a pair
 // of peer public keys. Both peers, given the same key pair, produce the same
 // output regardless of which side runs the function: the inputs are ordered

client/mdm/canonical_loaders.go

@@ -22,6 +22,7 @@ var allKeys = []string{
 	KeyDisableMetricsCollection,
 	KeyAllowServerSSH,
 	KeyDisableAutoConnect,
+	KeyDisableAutostart,
 	KeyPreSharedKey,
 	KeyRosenpassEnabled,
 	KeyRosenpassPermissive,

client/mdm/policy.go

@@ -20,10 +20,10 @@ import (
 // names (lowerCamelCase) so the daemon can map a Policy key directly to a
 // configuration field.
 const (
-	KeyManagementURL            = "managementURL"
-	KeyDisableUpdateSettings    = "disableUpdateSettings"
-	KeyDisableProfiles          = "disableProfiles"
-	KeyDisableNetworks          = "disableNetworks"
+	KeyManagementURL         = "managementURL"
+	KeyDisableUpdateSettings = "disableUpdateSettings"
+	KeyDisableProfiles       = "disableProfiles"
+	KeyDisableNetworks       = "disableNetworks"
 	// KeyDisableAdvancedView gates the advanced-view section in the
 	// upcoming UI revision. UI-only: NOT stored on Config, not
 	// applied by applyMDMPolicy, not rejectable via SetConfig. The
@@ -37,10 +37,16 @@ const (
 	KeyDisableMetricsCollection = "disableMetricsCollection"
 	KeyAllowServerSSH           = "allowServerSSH"
 	KeyDisableAutoConnect       = "disableAutoConnect"
-	KeyPreSharedKey             = "preSharedKey"
-	KeyRosenpassEnabled         = "rosenpassEnabled"
-	KeyRosenpassPermissive      = "rosenpassPermissive"
-	KeyWireguardPort            = "wireguardPort"
+	// KeyDisableAutostart suppresses the GUI's fresh-install
+	// launch-on-login default and marks the Settings toggle as
+	// MDM-managed. UI-only: NOT stored on Config and not applied by
+	// applyMDMPolicy; the GUI reads it directly and it appears in
+	// GetConfigResponse.mDMManagedFields when set.
+	KeyDisableAutostart    = "disableAutostart"
+	KeyPreSharedKey        = "preSharedKey"
+	KeyRosenpassEnabled    = "rosenpassEnabled"
+	KeyRosenpassPermissive = "rosenpassPermissive"
+	KeyWireguardPort       = "wireguardPort"
 
 	// Split tunnel is modeled as a single conceptual policy with two
 	// registry/plist values. KeySplitTunnelMode is the discriminator

client/server/server.go

@@ -828,6 +828,7 @@ func (s *Server) WaitSSOLogin(callerCtx context.Context, msg *proto.WaitSSOLogin
 		return nil, err
 	}
 
+	log.Infof("SSO login flow finished, returning success to caller")
 	return &proto.WaitSSOLoginResponse{
 		Email: tokenInfo.Email,
 	}, nil
@@ -835,6 +836,7 @@ func (s *Server) WaitSSOLogin(callerCtx context.Context, msg *proto.WaitSSOLogin
 
 // Up starts engine work in the daemon.
 func (s *Server) Up(callerCtx context.Context, msg *proto.UpRequest) (*proto.UpResponse, error) {
+	log.Infof("up request received")
 	s.mutex.Lock()
 	// clientRunning is the daemon-intent flag (set by previous Up/Start, cleared
 	// by Down). connectionGoroutineRunning() reports whether the previous retry-loop

client/status/status.go

@@ -746,6 +746,8 @@ func ToProtoFullStatus(fullStatus peer.FullStatus) *proto.FullStatus {
 		pbFullStatus.DnsServers = append(pbFullStatus.DnsServers, pbDnsState)
 	}
 
+	pbFullStatus.Events = fullStatus.Events
+
 	return &pbFullStatus
 }
 

client/ui/autostart_default.go

@@ -0,0 +1,107 @@
+//go:build !android && !ios && !freebsd && !js
+
+package main
+
+import (
+	"context"
+	"os"
+	"path/filepath"
+
+	log "github.com/sirupsen/logrus"
+
+	"github.com/netbirdio/netbird/client/internal/profilemanager"
+	"github.com/netbirdio/netbird/client/mdm"
+	"github.com/netbirdio/netbird/client/ui/preferences"
+	"github.com/netbirdio/netbird/client/ui/services"
+)
+
+// autostartDefaultState carries the guard inputs of the one-time autostart
+// default decision so the decision itself stays a pure, testable function.
+type autostartDefaultState struct {
+	supported    bool
+	mdmDisabled  bool
+	priorInstall bool
+}
+
+// shouldEnableAutostartDefault applies the first-run guards in order and
+// returns whether autostart may be enabled, plus the reason when it may not.
+func shouldEnableAutostartDefault(s autostartDefaultState) (bool, string) {
+	switch {
+	case !s.supported:
+		return false, "autostart not supported on this platform"
+	case s.mdmDisabled:
+		return false, "autostart disabled by MDM policy"
+	case s.priorInstall:
+		return false, "existing NetBird installation"
+	}
+	return true, ""
+}
+
+// autostartDisabledByMDM reports whether the MDM policy manages the
+// disableAutostart key in a way that must suppress the default. An
+// unparseable managed value is treated as disabled to stay on the safe side.
+func autostartDisabledByMDM(policy *mdm.Policy) bool {
+	if !policy.HasKey(mdm.KeyDisableAutostart) {
+		return false
+	}
+	disabled, ok := policy.GetBool(mdm.KeyDisableAutostart)
+	return !ok || disabled
+}
+
+// netbirdFootprintExists reports whether the machine already carries NetBird
+// daemon config or state, meaning this is not a genuinely fresh install. It is
+// the update-safety gate for the autostart default: upgrading users always
+// have a footprint, so an update can never trigger a login-item write.
+func netbirdFootprintExists() bool {
+	candidates := []string{
+		profilemanager.DefaultConfigPath,
+		filepath.Join(profilemanager.DefaultConfigPathDir, "config.json"),
+		filepath.Join(profilemanager.DefaultConfigPathDir, "state.json"),
+	}
+	for _, path := range candidates {
+		if path != "" && fileExists(path) {
+			return true
+		}
+	}
+	return false
+}
+
+// applyAutostartDefault runs the one-time launch-on-login default for genuinely
+// fresh installs. The autostartInitialized marker is persisted before any
+// enable attempt so a crash mid-flow degrades to "never enabled" instead of
+// retrying login-item writes on every launch. A user's later disable in
+// Settings is never overridden: the marker guarantees at-most-once, ever.
+func applyAutostartDefault(ctx context.Context, autostart *services.Autostart, prefs *preferences.Store, prefsFileExisted bool) {
+	priorFootprint := netbirdFootprintExists() || prefsFileExisted
+
+	if prefs.Get().AutostartInitialized {
+		return
+	}
+	if err := prefs.SetAutostartInitialized(true); err != nil {
+		log.Warnf("persist autostart marker, skipping autostart default: %v", err)
+		return
+	}
+
+	state := autostartDefaultState{
+		supported:    autostart.Supported(ctx),
+		mdmDisabled:  autostartDisabledByMDM(mdm.LoadPolicy()),
+		priorInstall: priorFootprint,
+	}
+	enable, reason := shouldEnableAutostartDefault(state)
+	if !enable {
+		log.Debugf("skipping autostart default: %s", reason)
+		return
+	}
+
+	if err := autostart.SetEnabled(ctx, true); err != nil {
+		log.Warnf("enable autostart on fresh install: %v", err)
+		return
+	}
+	log.Info("autostart enabled by default on fresh install")
+}
+
+// fileExists reports whether path exists.
+func fileExists(path string) bool {
+	_, err := os.Stat(path)
+	return err == nil
+}

client/ui/autostart_default_test.go

@@ -0,0 +1,125 @@
+//go:build !android && !ios && !freebsd && !js
+
+package main
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+
+	"github.com/netbirdio/netbird/client/mdm"
+)
+
+func TestShouldEnableAutostartDefault(t *testing.T) {
+	allPass := autostartDefaultState{
+		supported:    true,
+		mdmDisabled:  false,
+		priorInstall: false,
+	}
+
+	tests := []struct {
+		name       string
+		mutate     func(*autostartDefaultState)
+		wantEnable bool
+		wantReason string
+	}{
+		{
+			name:       "fresh install with all guards passing enables",
+			mutate:     func(*autostartDefaultState) {},
+			wantEnable: true,
+		},
+		{
+			name:       "unsupported platform skips",
+			mutate:     func(s *autostartDefaultState) { s.supported = false },
+			wantReason: "autostart not supported on this platform",
+		},
+		{
+			name:       "MDM disable skips",
+			mutate:     func(s *autostartDefaultState) { s.mdmDisabled = true },
+			wantReason: "autostart disabled by MDM policy",
+		},
+		{
+			name:       "existing installation (upgrade) skips",
+			mutate:     func(s *autostartDefaultState) { s.priorInstall = true },
+			wantReason: "existing NetBird installation",
+		},
+		{
+			name: "unsupported wins over every other guard",
+			mutate: func(s *autostartDefaultState) {
+				s.supported = false
+				s.mdmDisabled = true
+				s.priorInstall = true
+			},
+			wantReason: "autostart not supported on this platform",
+		},
+		{
+			name: "MDM disable wins over prior install",
+			mutate: func(s *autostartDefaultState) {
+				s.mdmDisabled = true
+				s.priorInstall = true
+			},
+			wantReason: "autostart disabled by MDM policy",
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			state := allPass
+			tc.mutate(&state)
+			enable, reason := shouldEnableAutostartDefault(state)
+			assert.Equal(t, tc.wantEnable, enable, "enable decision should match for state %+v", state)
+			assert.Equal(t, tc.wantReason, reason, "skip reason should identify the failing guard")
+		})
+	}
+}
+
+func TestAutostartDisabledByMDM(t *testing.T) {
+	tests := []struct {
+		name   string
+		values map[string]any
+		want   bool
+	}{
+		{
+			name:   "empty policy does not disable",
+			values: nil,
+			want:   false,
+		},
+		{
+			name:   "unrelated managed keys do not disable",
+			values: map[string]any{mdm.KeyDisableAutoConnect: true},
+			want:   false,
+		},
+		{
+			name:   "disableAutostart true disables",
+			values: map[string]any{mdm.KeyDisableAutostart: true},
+			want:   true,
+		},
+		{
+			name:   "disableAutostart registry DWORD 1 disables",
+			values: map[string]any{mdm.KeyDisableAutostart: int64(1)},
+			want:   true,
+		},
+		{
+			name:   "disableAutostart string true disables",
+			values: map[string]any{mdm.KeyDisableAutostart: "true"},
+			want:   true,
+		},
+		{
+			name:   "disableAutostart explicit false allows",
+			values: map[string]any{mdm.KeyDisableAutostart: false},
+			want:   false,
+		},
+		{
+			name:   "unparseable managed value is treated as disabled",
+			values: map[string]any{mdm.KeyDisableAutostart: "not-a-bool"},
+			want:   true,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			got := autostartDisabledByMDM(mdm.NewPolicy(tc.values))
+			assert.Equal(t, tc.want, got, "MDM disable decision should match for values %v", tc.values)
+		})
+	}
+}

client/ui/frontend/src/app.tsx

@@ -16,10 +16,13 @@ import LoginWaitingForBrowserDialog from "@/modules/login/LoginWaitingForBrowser
 import { initI18n } from "@/lib/i18n";
 import { initPlatform } from "@/lib/platform";
 import { initLogForwarding } from "@/lib/logs";
+import { initStallWatch } from "@/lib/stallwatch";
 
 // Must run first so even init-time logs reach the Go log pipeline.
 initLogForwarding();
 
+initStallWatch();
+
 welcome();
 
 Promise.all([

client/ui/frontend/src/lib/connection.ts

@@ -51,7 +51,14 @@ async function runSsoLogin(
     if (uri) await openBrowserLoginUri(uri);
 
     const cancelPromise = buildSsoCancelPromise(state, signal);
-    const waitPromise = Connection.WaitSSOLogin({ userCode: result.userCode, hostname: "" });
+    // Combine wait + up in Go so the connection comes up the moment SSO
+    // completes. During SSO the tray window is hidden and the webview is
+    // suspended, so a frontend-driven Up (a promise continuation) would not
+    // fire until the user woke the window (e.g. hovering the tray icon).
+    const waitPromise = Connection.WaitSSOLoginAndUp(
+        { userCode: result.userCode, hostname: "" },
+        { profileName: "", username: "" },
+    );
 
     try {
         await Promise.race([waitPromise, cancelPromise]);
@@ -89,13 +96,13 @@ export async function startConnection(onSettled?: () => void, signal?: AbortSign
         if (signal?.aborted) state.cancelled = true;
 
         if (!state.cancelled && result.needsSsoLogin) {
+            // runSsoLogin brings the connection up in Go once SSO completes.
             await runSsoLogin(result, state, signal);
-        }
-
-        if (!state.cancelled && signal?.aborted) state.cancelled = true;
-
-        if (!state.cancelled) {
-            await Connection.Up({ profileName: "", username: "" });
+        } else {
+            if (!state.cancelled && signal?.aborted) state.cancelled = true;
+            if (!state.cancelled) {
+                await Connection.Up({ profileName: "", username: "" });
+            }
         }
     } catch (e) {
         WindowManager.CloseBrowserLogin().catch(console.error);

client/ui/frontend/src/lib/stallwatch.ts

@@ -0,0 +1,31 @@
+// Detects webview suspension (macOS App Nap / hidden-window timer throttling).
+// While the webview is suspended no JS runs at all, so detection happens on
+// resume: a 1s interval measures wall-clock drift and reports how long timers
+// were frozen. Silent unless a stall actually occurred; a stalled webview is
+// what delays promise continuations such as the WaitSSOLogin → Up handoff.
+
+const INTERVAL_MS = 1000;
+const STALL_THRESHOLD_MS = 5000;
+const REPORT_COOLDOWN_MS = 60_000;
+
+let started = false;
+
+export function initStallWatch() {
+    if (started) return;
+    started = true;
+
+    let last = Date.now();
+    let lastReport = 0;
+    setInterval(() => {
+        const now = Date.now();
+        const stall = now - last - INTERVAL_MS;
+        last = now;
+        if (stall < STALL_THRESHOLD_MS) return;
+        if (now - lastReport < REPORT_COOLDOWN_MS) return;
+        lastReport = now;
+        console.warn(
+            `webview timers were suspended for ${(stall / 1000).toFixed(1)}s ` +
+                `(App Nap / hidden-window throttling); pending UI work ran late`,
+        );
+    }, INTERVAL_MS);
+}

client/ui/main.go

@@ -197,6 +197,9 @@ func main() {
 		// daemon may keep the main window from showing, so the OS toast is the
 		// only reliable signal the user gets.
 		go notifyIfDaemonOutdated(compat, notifier, localizer)
+		// One-time launch-on-login default for fresh installs; gated by the
+		// NetBird footprint check, MDM policy, and the persisted marker.
+		go applyAutostartDefault(context.Background(), services.NewAutostart(app.Autostart), prefStore, prefStore.ExistedAtLoad())
 	})
 
 	if err := app.Run(); err != nil {

client/ui/preferences/store.go

@@ -54,6 +54,10 @@ type UIPreferences struct {
 	Language            i18n.LanguageCode `json:"language"`
 	ViewMode            ViewMode          `json:"viewMode"`
 	OnboardingCompleted bool              `json:"onboardingCompleted"`
+	// AutostartInitialized records that the one-time autostart default
+	// decision has run for this OS user. It only ever transitions to true
+	// and is never reset, so the default-on flow runs at most once, ever.
+	AutostartInitialized bool `json:"autostartInitialized"`
 }
 
 // LanguageValidator rejects SetLanguage inputs with no shipped bundle.
@@ -72,8 +76,9 @@ type Emitter interface {
 type Store struct {
 	path string
 
-	mu      sync.RWMutex
-	current UIPreferences
+	mu            sync.RWMutex
+	current       UIPreferences
+	existedAtLoad bool
 
 	subsMu sync.Mutex
 	subs   []chan UIPreferences
@@ -157,6 +162,27 @@ func (s *Store) SetOnboardingCompleted(done bool) error {
 	return nil
 }
 
+// SetAutostartInitialized persists the one-time autostart decision marker.
+// No-op if unchanged.
+func (s *Store) SetAutostartInitialized(done bool) error {
+	s.mu.Lock()
+	if s.current.AutostartInitialized == done {
+		s.mu.Unlock()
+		return nil
+	}
+	next := s.current
+	next.AutostartInitialized = done
+	if err := s.persistLocked(next); err != nil {
+		s.mu.Unlock()
+		return fmt.Errorf("persist preferences: %w", err)
+	}
+	s.current = next
+	s.mu.Unlock()
+
+	s.broadcast(next)
+	return nil
+}
+
 // SetLanguage validates, persists, and broadcasts. No-op if unchanged.
 func (s *Store) SetLanguage(lang i18n.LanguageCode) error {
 	if lang == "" {
@@ -206,13 +232,29 @@ func (s *Store) Subscribe() (<-chan UIPreferences, func()) {
 	return ch, unsubscribe
 }
 
+// ExistedAtLoad reports whether the backing preferences file was present on
+// disk when the store loaded. It distinguishes a user who ran a prior GUI
+// version from a brand-new OS user with no preferences yet.
+func (s *Store) ExistedAtLoad() bool {
+	s.mu.RLock()
+	defer s.mu.RUnlock()
+	return s.existedAtLoad
+}
+
 // load reads the file into current. A missing file is not an error (the
 // in-memory default stands); malformed contents return an error.
 func (s *Store) load() error {
-	if _, err := os.Stat(s.path); errors.Is(err, os.ErrNotExist) {
-		return nil
+	if _, err := os.Stat(s.path); err != nil {
+		if errors.Is(err, os.ErrNotExist) {
+			return nil
+		}
+		return fmt.Errorf("stat preferences: %w", err)
 	}
 
+	s.mu.Lock()
+	s.existedAtLoad = true
+	s.mu.Unlock()
+
 	var loaded UIPreferences
 	if _, err := util.ReadJson(s.path, &loaded); err != nil {
 		return err

client/ui/preferences/store_test.go

@@ -215,6 +215,46 @@ func TestStore_FileShapeIsJSON(t *testing.T) {
 	assert.Equal(t, i18n.LanguageCode("hu"), parsed.Language)
 }
 
+func TestStore_SetAutostartInitializedPersistsAcrossReload(t *testing.T) {
+	withTempConfigDir(t)
+	emitter := &recordingEmitter{}
+	s, err := NewStore(nil, emitter)
+	require.NoError(t, err)
+
+	assert.False(t, s.Get().AutostartInitialized, "marker must default to false when no file is on disk")
+
+	require.NoError(t, s.SetAutostartInitialized(true))
+	assert.True(t, s.Get().AutostartInitialized, "Get should reflect the persisted marker")
+	require.Len(t, emitter.calledWith(EventPreferencesChanged), 1, "first marker write should broadcast")
+
+	// Re-setting the same value must be a no-op: no disk write, no broadcast.
+	require.NoError(t, s.SetAutostartInitialized(true))
+	assert.Len(t, emitter.calledWith(EventPreferencesChanged), 1, "idempotent marker write should not broadcast again")
+
+	// A fresh Store (new GUI launch) must see the marker so the autostart
+	// default decision never runs twice.
+	reloaded, err := NewStore(nil, nil)
+	require.NoError(t, err)
+	assert.True(t, reloaded.Get().AutostartInitialized, "marker must survive a reload from disk")
+}
+
+func TestStore_ExistedAtLoad(t *testing.T) {
+	withTempConfigDir(t)
+
+	// Brand-new OS user: no preferences file on disk yet.
+	fresh, err := NewStore(nil, nil)
+	require.NoError(t, err)
+	assert.False(t, fresh.ExistedAtLoad(), "ExistedAtLoad must be false when no file is on disk")
+
+	// Persisting a value writes the file to disk.
+	require.NoError(t, fresh.SetLanguage("en"))
+
+	// A subsequent GUI launch reopens the now-present file.
+	reopened, err := NewStore(nil, nil)
+	require.NoError(t, err)
+	assert.True(t, reopened.ExistedAtLoad(), "ExistedAtLoad must be true after the store has persisted and is reopened")
+}
+
 func TestStore_ErrUnsupportedSentinel(t *testing.T) {
 	// Verifies callers can match on the sentinel error rather than parsing
 	// strings — protects against accidental %v -> %w changes that would

client/ui/services/connection.go

@@ -35,7 +35,7 @@ type LoginResult struct {
 	VerificationURIComplete string `json:"verificationUriComplete"`
 }
 
-// WaitSSOParams are the inputs to WaitSSOLogin.
+// WaitSSOParams are the inputs to waitSSOLogin.
 type WaitSSOParams struct {
 	UserCode string `json:"userCode"`
 	Hostname string `json:"hostname"`
@@ -116,6 +116,7 @@ func (s *Connection) Login(ctx context.Context, p LoginParams) (LoginResult, err
 	if err != nil {
 		return LoginResult{}, s.classifyDaemonError(err)
 	}
+	log.Infof("daemon login response received, needs SSO login: %v", resp.GetNeedsSSOLogin())
 	return LoginResult{
 		NeedsSSOLogin:           resp.GetNeedsSSOLogin(),
 		UserCode:                resp.GetUserCode(),
@@ -124,26 +125,12 @@ func (s *Connection) Login(ctx context.Context, p LoginParams) (LoginResult, err
 	}, nil
 }
 
-func (s *Connection) WaitSSOLogin(ctx context.Context, p WaitSSOParams) (string, error) {
-	cli, err := s.conn.Client()
-	if err != nil {
-		return "", err
-	}
-	resp, err := cli.WaitSSOLogin(ctx, &proto.WaitSSOLoginRequest{
-		UserCode: p.UserCode,
-		Hostname: p.Hostname,
-	})
-	if err != nil {
-		return "", s.classifyDaemonError(err)
-	}
-	return resp.GetEmail(), nil
-}
-
 func (s *Connection) Up(ctx context.Context, p UpParams) error {
 	cli, err := s.conn.Client()
 	if err != nil {
 		return err
 	}
+	log.Infof("sending up request to daemon")
 	// Always async: status updates flow via SubscribeStatus.
 	req := &proto.UpRequest{Async: true}
 	if p.ProfileName != "" {
@@ -158,6 +145,27 @@ func (s *Connection) Up(ctx context.Context, p UpParams) error {
 	return nil
 }
 
+// WaitSSOLoginAndUp blocks until the SSO login completes and then brings the
+// connection up, both from the Go side. Keeping the post-login Up here rather
+// than as a frontend continuation is deliberate: during SSO the tray window is
+// hidden and the webview is suspended (macOS App Nap / hidden-window timer
+// throttling), so a frontend-driven Up would not run until the user woke the
+// window (e.g. by hovering the tray icon). Doing it in Go connects the moment
+// the daemon reports SSO success. Returns the authenticated user's email.
+func (s *Connection) WaitSSOLoginAndUp(ctx context.Context, wait WaitSSOParams, up UpParams) (string, error) {
+	email, err := s.waitSSOLogin(ctx, wait)
+	if err != nil {
+		return "", err
+	}
+	if err := ctx.Err(); err != nil {
+		return "", err
+	}
+	if err := s.Up(ctx, up); err != nil {
+		return "", err
+	}
+	return email, nil
+}
+
 func (s *Connection) Down(ctx context.Context) error {
 	cli, err := s.conn.Client()
 	if err != nil {
@@ -217,6 +225,26 @@ func (s *Connection) Logout(ctx context.Context, p LogoutParams) error {
 	return nil
 }
 
+// waitSSOLogin blocks until the daemon reports the SSO login result and returns
+// the authenticated user's email. It is unexported because the frontend drives
+// SSO through the exported WaitSSOLoginAndUp.
+func (s *Connection) waitSSOLogin(ctx context.Context, p WaitSSOParams) (string, error) {
+	cli, err := s.conn.Client()
+	if err != nil {
+		return "", err
+	}
+	log.Infof("waiting for SSO login to complete")
+	resp, err := cli.WaitSSOLogin(ctx, &proto.WaitSSOLoginRequest{
+		UserCode: p.UserCode,
+		Hostname: p.Hostname,
+	})
+	if err != nil {
+		return "", s.classifyDaemonError(err)
+	}
+	log.Infof("SSO login completed, daemon reported success")
+	return resp.GetEmail(), nil
+}
+
 // classifyDaemonError maps a gRPC error to a localised ClientError.
 func (s *Connection) classifyDaemonError(err error) *ClientError {
 	return s.classifier.classify(err)

client/ui/services/settings.go

@@ -20,11 +20,12 @@ type MDMFields struct {
 	DisableServerRoutes      bool   `json:"disableServerRoutes"`
 	AllowServerSSH           *bool  `json:"allowServerSSH"`
 	DisableAutoConnect       bool   `json:"disableAutoConnect"`
+	DisableAutostart         bool   `json:"disableAutostart"`
 	BlockInbound             bool   `json:"blockInbound"`
 	DisableMetricsCollection bool   `json:"disableMetricsCollection"`
 	SplitTunnelMode          bool   `json:"splitTunnelMode"`
 	SplitTunnelApps          bool   `json:"splitTunnelApps"`
-	DisableAdvancedView bool `json:"disableAdvancedView"`
+	DisableAdvancedView      bool   `json:"disableAdvancedView"`
 }
 
 type Features struct {