fix: validate pf state before stabilization

cmd/cli/dns_intercept_darwin_test.go

@@ -3,9 +3,16 @@
 package cli
 
 import (
+	"context"
 	"errors"
+	"fmt"
+	"os"
+	"path/filepath"
 	"strings"
 	"testing"
+	"time"
+
+	"tailscale.com/net/netmon"
 
 	"github.com/Control-D-Inc/ctrld"
 )
@@ -215,3 +222,609 @@ func TestIsResourceExhaustion(t *testing.T) {
 		})
 	}
 }
+
+func stubPFAnchorCheckCommand(t *testing.T, outputs map[string]string) {
+	t.Helper()
+	original := runPFAnchorCheckCommand
+	runPFAnchorCheckCommand = func(args ...string) ([]byte, error) {
+		key := strings.Join(args, " ")
+		output, ok := outputs[key]
+		if !ok {
+			t.Fatalf("unexpected pf anchor check command: pfctl %s", key)
+		}
+		return []byte(output), nil
+	}
+	t.Cleanup(func() {
+		runPFAnchorCheckCommand = original
+	})
+}
+
+func TestEnsurePFAnchorActiveRecentRestoreWithIntactRulesDoesNotStabilize(t *testing.T) {
+	stubPFAnchorCheckCommand(t, map[string]string{
+		"-sn":                       `rdr-anchor "com.controld.ctrld"`,
+		"-sr":                       `anchor "com.controld.ctrld"`,
+		"-a com.controld.ctrld -sr": "pass in quick on lo0",
+		"-a com.controld.ctrld -sn": "rdr on lo0",
+	})
+
+	p := &prog{
+		dnsInterceptState: &pfState{},
+		stopCh:            make(chan struct{}),
+	}
+	restoredAt := time.Now().Add(-time.Second).UnixMilli()
+	p.pfLastRestoreTime.Store(restoredAt)
+
+	if result := p.ensurePFAnchorActive(); result != pfAnchorCheckIntact {
+		t.Fatalf("intact rules result = %v, want intact", result)
+	}
+	if p.pfBackoffMultiplier.Load() != 0 {
+		t.Fatalf("intact rules incremented backoff to %d", p.pfBackoffMultiplier.Load())
+	}
+	if p.pfStabilizing.Load() {
+		t.Fatal("intact rules must not enter stabilization")
+	}
+	if got := p.pfLastRestoreTime.Load(); got != restoredAt {
+		t.Fatalf("intact check changed restore timestamp: got %d, want %d", got, restoredAt)
+	}
+}
+
+func TestEnsurePFAnchorActiveCheckFailureIsNotIntact(t *testing.T) {
+	original := runPFAnchorCheckCommand
+	runPFAnchorCheckCommand = func(...string) ([]byte, error) {
+		return nil, errors.New("pfctl unavailable")
+	}
+	t.Cleanup(func() { runPFAnchorCheckCommand = original })
+
+	p := &prog{dnsInterceptState: &pfState{}}
+	if result := p.ensurePFAnchorActive(); result != pfAnchorCheckFailed {
+		t.Fatalf("failed PF inspection result = %v, want failed", result)
+	}
+}
+
+func TestEnsurePFAnchorActiveRecentActualWipeStartsStabilization(t *testing.T) {
+	stubPFAnchorCheckCommand(t, map[string]string{
+		"-sn": "",
+	})
+
+	stopCh := make(chan struct{})
+	close(stopCh)
+	p := &prog{
+		dnsInterceptState: &pfState{},
+		stopCh:            stopCh,
+	}
+	restoredAt := time.Now().Add(-time.Second).UnixMilli()
+	p.pfLastRestoreTime.Store(restoredAt)
+
+	if result := p.ensurePFAnchorActive(); result != pfAnchorCheckDeferred {
+		t.Fatalf("recent repeated wipe result = %v, want deferred", result)
+	}
+	if got := p.pfBackoffMultiplier.Load(); got != 1 {
+		t.Fatalf("recent repeated wipe backoff = %d, want 1", got)
+	}
+	if got := p.pfLastRestoreTime.Load(); got != restoredAt {
+		t.Fatalf("deferred restore changed restore timestamp: got %d, want %d", got, restoredAt)
+	}
+	deadline := time.Now().Add(time.Second)
+	for p.pfStabilizing.Load() && time.Now().Before(deadline) {
+		time.Sleep(time.Millisecond)
+	}
+	if p.pfStabilizing.Load() {
+		t.Fatal("stabilization goroutine did not observe closed stop channel")
+	}
+}
+
+func TestDNSInterceptIgnoredChangeReconcileDue(t *testing.T) {
+	p := &prog{}
+	start := time.Unix(1_000_000, 0)
+
+	if !p.dnsInterceptIgnoredChangeReconcileDue(start) {
+		t.Fatal("first ignored change must reconcile immediately")
+	}
+	if p.dnsInterceptIgnoredChangeReconcileDue(start.Add(pfIgnoredChangeReconcileInterval - time.Millisecond)) {
+		t.Fatal("ignored changes inside the interval must be coalesced")
+	}
+	if !p.dnsInterceptIgnoredChangeReconcileDue(start.Add(pfIgnoredChangeReconcileInterval)) {
+		t.Fatal("continuous ignored changes must reconcile again at the interval boundary")
+	}
+}
+
+func TestIgnoredNetworkChangeCallbackBoundsWorkWithoutBurningStabilizedSlot(t *testing.T) {
+	outputs := map[string]string{
+		"-sn":                       `rdr-anchor "com.controld.ctrld"`,
+		"-sr":                       `anchor "com.controld.ctrld"`,
+		"-a com.controld.ctrld -sr": "pass in quick on lo0",
+		"-a com.controld.ctrld -sn": "rdr on lo0",
+	}
+	originalCheck := runPFAnchorCheckCommand
+	pfChecks := 0
+	runPFAnchorCheckCommand = func(args ...string) ([]byte, error) {
+		key := strings.Join(args, " ")
+		output, ok := outputs[key]
+		if !ok {
+			t.Fatalf("unexpected pf anchor check command: pfctl %s", key)
+		}
+		if key == "-sn" {
+			pfChecks++
+		}
+		return []byte(output), nil
+	}
+	originalDiscover := discoverTunnelInterfacesForReconcile
+	discoverTunnelInterfacesForReconcile = func() []string { return nil }
+	t.Cleanup(func() {
+		runPFAnchorCheckCommand = originalCheck
+		discoverTunnelInterfacesForReconcile = originalDiscover
+	})
+
+	refreshes := 0
+	vpnDNS := newVPNDNSManager(&mainLog, nil)
+	vpnDNS.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
+		refreshes++
+		return nil
+	}
+	p := &prog{dnsInterceptState: &pfState{}, vpnDNS: vpnDNS}
+	t.Cleanup(func() {
+		p.pfDelayedRecheckMu.Lock()
+		defer p.pfDelayedRecheckMu.Unlock()
+		for _, timer := range p.pfDelayedRecheckTimers {
+			if timer != nil {
+				timer.Stop()
+			}
+		}
+	})
+
+	delta := &netmon.ChangeDelta{
+		Old: &netmon.State{Interface: map[string]netmon.Interface{}},
+		New: &netmon.State{Interface: map[string]netmon.Interface{}},
+	}
+	start := time.Unix(1_000_000, 0)
+	p.handleDNSInterceptIgnoredNetworkChange(delta, start)
+	if pfChecks != 1 || refreshes != 1 {
+		t.Fatalf("first ignored delta work: pf checks=%d refreshes=%d, want 1 each", pfChecks, refreshes)
+	}
+
+	p.pfStabilizing.Store(true)
+	p.handleDNSInterceptIgnoredNetworkChange(delta, start.Add(pfIgnoredChangeReconcileInterval))
+	if pfChecks != 1 || refreshes != 1 {
+		t.Fatalf("stabilized delta ran leading reconciliation: pf checks=%d refreshes=%d", pfChecks, refreshes)
+	}
+
+	p.pfStabilizing.Store(false)
+	resumeAt := start.Add(pfIgnoredChangeReconcileInterval + time.Millisecond)
+	p.handleDNSInterceptIgnoredNetworkChange(delta, resumeAt)
+	if pfChecks != 2 || refreshes != 2 {
+		t.Fatalf("first post-stabilization delta did not reconcile immediately: pf checks=%d refreshes=%d", pfChecks, refreshes)
+	}
+
+	for i := 1; i <= 8; i++ {
+		p.handleDNSInterceptIgnoredNetworkChange(delta, resumeAt.Add(time.Duration(i)*100*time.Millisecond))
+	}
+	if pfChecks != 2 || refreshes != 2 {
+		t.Fatalf("ignored delta burst was not coalesced: pf checks=%d refreshes=%d", pfChecks, refreshes)
+	}
+
+	p.handleDNSInterceptIgnoredNetworkChange(delta, resumeAt.Add(pfIgnoredChangeReconcileInterval))
+	if pfChecks != 3 || refreshes != 3 {
+		t.Fatalf("interval boundary did not reconcile: pf checks=%d refreshes=%d, want 3 each", pfChecks, refreshes)
+	}
+}
+
+func TestRestorePFAnchorFailureIsNotReportedOrTimestamped(t *testing.T) {
+	originalReference := ensurePFAnchorReferenceForRestore
+	originalRebuild := rebuildPFAnchorRulesForReconcile
+	ensurePFAnchorReferenceForRestore = func(*prog) error { return nil }
+	rebuildPFAnchorRulesForReconcile = func(*prog, []vpnDNSExemption) ([]string, error) {
+		return nil, errors.New("pf load failed")
+	}
+	t.Cleanup(func() {
+		ensurePFAnchorReferenceForRestore = originalReference
+		rebuildPFAnchorRulesForReconcile = originalRebuild
+	})
+
+	p := &prog{dnsInterceptState: &pfState{}}
+	if result := p.restorePFAnchor("test"); result != pfAnchorCheckFailed {
+		t.Fatalf("failed restore result = %v, want failed", result)
+	}
+	if got := p.pfLastRestoreTime.Load(); got != 0 {
+		t.Fatalf("failed restore changed timestamp to %d", got)
+	}
+	if len(p.lastTunnelIfaces) != 0 {
+		t.Fatalf("failed restore committed tunnel state: %v", p.lastTunnelIfaces)
+	}
+}
+
+func TestPFStabilizationTimeoutReturnsOwnershipToDelayedRecovery(t *testing.T) {
+	p := &prog{dnsInterceptState: &pfState{}}
+	p.pfStabilizing.Store(true)
+	p.pfStabilizationLoopWithMaxWait(t.Context(), time.Hour, 25*time.Millisecond)
+
+	if p.pfStabilizing.Load() {
+		t.Fatal("stabilization retained ownership after the maximum wait")
+	}
+	p.pfDelayedRecheckMu.Lock()
+	timers := append([]*time.Timer(nil), p.pfDelayedRecheckTimers...)
+	p.pfDelayedRecheckTimers = nil
+	p.pfDelayedRecheckMu.Unlock()
+	if len(timers) != 2 {
+		t.Fatalf("expected bounded timeout to schedule delayed recovery, got %d timers", len(timers))
+	}
+	for _, timer := range timers {
+		timer.Stop()
+	}
+}
+
+func TestStopDNSInterceptWaitsForInFlightPFMutation(t *testing.T) {
+	binDir := t.TempDir()
+	pfctlPath := filepath.Join(binDir, "pfctl")
+	if err := os.WriteFile(pfctlPath, []byte("#!/bin/sh\nexit 0\n"), 0755); err != nil {
+		t.Fatal(err)
+	}
+	t.Setenv("PATH", binDir+":"+os.Getenv("PATH"))
+
+	anchorFile := filepath.Join(t.TempDir(), "anchor")
+	if err := os.WriteFile(anchorFile, []byte("rules"), 0600); err != nil {
+		t.Fatal(err)
+	}
+	p := &prog{dnsInterceptState: &pfState{anchorName: pfAnchorName, anchorFile: anchorFile}}
+	p.pfEnsureRunning.Store(true)
+
+	revoked := make(chan struct{})
+	originalRevokedHook := pfShutdownStateRevokedForTest
+	pfShutdownStateRevokedForTest = func() { close(revoked) }
+	t.Cleanup(func() { pfShutdownStateRevokedForTest = originalRevokedHook })
+
+	done := make(chan error, 1)
+	go func() { done <- p.stopDNSIntercept() }()
+
+	select {
+	case <-revoked:
+	case <-time.After(time.Second):
+		t.Fatal("shutdown did not revoke PF lifecycle state before waiting")
+	}
+	select {
+	case err := <-done:
+		t.Fatalf("shutdown completed before in-flight PF owner released: %v", err)
+	case <-time.After(25 * time.Millisecond):
+	}
+
+	p.pfEnsureRunning.Store(false)
+	if err := <-done; err != nil {
+		t.Fatalf("stopDNSIntercept() error: %v", err)
+	}
+	if _, err := os.Stat(anchorFile); !os.IsNotExist(err) {
+		t.Fatalf("anchor file remained after serialized shutdown: %v", err)
+	}
+}
+
+func TestPostStabilizationReconcileRetainsOwnershipAndForcesRebuild(t *testing.T) {
+	stubPFAnchorCheckCommand(t, map[string]string{
+		"-sn":                       `rdr-anchor "com.controld.ctrld"`,
+		"-sr":                       `anchor "com.controld.ctrld"`,
+		"-a com.controld.ctrld -sr": "pass in quick on lo0",
+		"-a com.controld.ctrld -sn": "rdr on lo0",
+	})
+	originalRestore := restorePFAnchorForReconcile
+	calls := 0
+	restorePFAnchorForReconcile = func(*prog, string) pfAnchorCheckResult {
+		calls++
+		return pfAnchorCheckRestored
+	}
+	t.Cleanup(func() { restorePFAnchorForReconcile = originalRestore })
+
+	p := &prog{
+		dnsInterceptState:      &pfState{},
+		pendingTunnelIfaces:    []string{"utun9"},
+		hasPendingTunnelIfaces: true,
+	}
+	p.pfStabilizing.Store(true)
+	if result := p.reconcilePFAnchorAfterStabilization(); result != pfAnchorCheckRestored {
+		t.Fatalf("post-stabilization result = %v, want restored", result)
+	}
+	if calls != 1 {
+		t.Fatalf("post-stabilization restore calls = %d, want 1", calls)
+	}
+	if !p.pfStabilizing.Load() {
+		t.Fatal("post-stabilization reconcile released loop ownership")
+	}
+	if p.pfBackoffMultiplier.Load() != 0 {
+		t.Fatalf("post-stabilization reconcile changed backoff to %d", p.pfBackoffMultiplier.Load())
+	}
+}
+
+func TestPostStabilizationIntactWithoutPendingAvoidsRebuild(t *testing.T) {
+	stubPFAnchorCheckCommand(t, map[string]string{
+		"-sn":                       `rdr-anchor "com.controld.ctrld"`,
+		"-sr":                       `anchor "com.controld.ctrld"`,
+		"-a com.controld.ctrld -sr": "pass in quick on lo0",
+		"-a com.controld.ctrld -sn": "rdr on lo0",
+	})
+	originalRestore := restorePFAnchorForReconcile
+	calls := 0
+	restorePFAnchorForReconcile = func(*prog, string) pfAnchorCheckResult {
+		calls++
+		return pfAnchorCheckRestored
+	}
+	t.Cleanup(func() { restorePFAnchorForReconcile = originalRestore })
+
+	p := &prog{dnsInterceptState: &pfState{}}
+	p.pfStabilizing.Store(true)
+	if result := p.reconcilePFAnchorAfterStabilization(); result != pfAnchorCheckIntact {
+		t.Fatalf("post-stabilization result = %v, want intact", result)
+	}
+	if calls != 0 {
+		t.Fatalf("intact post-stabilization anchor rebuilt %d times", calls)
+	}
+	if !p.pfStabilizing.Load() {
+		t.Fatal("intact post-stabilization reconcile released loop ownership")
+	}
+}
+
+func TestTunnelRemovalFailureRetriesBeforeCommittingBaseline(t *testing.T) {
+	originalDiscover := discoverTunnelInterfacesForReconcile
+	originalRestore := restorePFAnchorForReconcile
+	current := []string{}
+	discoverTunnelInterfacesForReconcile = func() []string {
+		return append([]string(nil), current...)
+	}
+	calls := 0
+	restorePFAnchorForReconcile = func(p *prog, _ string) pfAnchorCheckResult {
+		calls++
+		if calls == 1 {
+			return pfAnchorCheckFailed
+		}
+		p.commitPFReconcileState(current)
+		return pfAnchorCheckRestored
+	}
+	t.Cleanup(func() {
+		discoverTunnelInterfacesForReconcile = originalDiscover
+		restorePFAnchorForReconcile = originalRestore
+	})
+
+	p := &prog{
+		dnsInterceptState: &pfState{},
+		lastTunnelIfaces:  []string{"utun7"},
+	}
+	if !p.checkTunnelInterfaceChanges() {
+		t.Fatal("first tunnel removal was not detected")
+	}
+	if !stringSlicesEqual(p.lastTunnelIfaces, []string{"utun7"}) {
+		t.Fatalf("failed removal committed baseline: %v", p.lastTunnelIfaces)
+	}
+	if !p.hasPendingTunnelReconcile() {
+		t.Fatal("failed removal did not retain desired tunnel state for retry")
+	}
+	if !p.checkTunnelInterfaceChanges() {
+		t.Fatal("failed tunnel removal was not retried")
+	}
+	if len(p.lastTunnelIfaces) != 0 {
+		t.Fatalf("successful retry did not commit empty tunnel baseline: %v", p.lastTunnelIfaces)
+	}
+	if calls != 2 {
+		t.Fatalf("restore calls = %d, want 2", calls)
+	}
+}
+
+func TestPendingTunnelStateRetriesAfterStabilization(t *testing.T) {
+	originalDiscover := discoverTunnelInterfacesForReconcile
+	originalRestore := restorePFAnchorForReconcile
+	current := []string{}
+	discoverTunnelInterfacesForReconcile = func() []string { return nil }
+	calls := 0
+	restorePFAnchorForReconcile = func(p *prog, _ string) pfAnchorCheckResult {
+		calls++
+		p.commitPFReconcileState(current)
+		return pfAnchorCheckRestored
+	}
+	t.Cleanup(func() {
+		discoverTunnelInterfacesForReconcile = originalDiscover
+		restorePFAnchorForReconcile = originalRestore
+	})
+
+	p := &prog{
+		dnsInterceptState:      &pfState{},
+		lastTunnelIfaces:       []string{"utun7"},
+		pendingTunnelIfaces:    current,
+		hasPendingTunnelIfaces: true,
+	}
+	if !p.checkTunnelInterfaceChanges() {
+		t.Fatal("pending tunnel removal was not retried after stabilization")
+	}
+	if calls != 1 || len(p.lastTunnelIfaces) != 0 || p.hasPendingTunnelReconcile() {
+		t.Fatalf("pending retry result: calls=%d baseline=%v pending=%v", calls, p.lastTunnelIfaces, p.hasPendingTunnelReconcile())
+	}
+}
+
+func TestTunnelReconcileHonorsPFExecBackoff(t *testing.T) {
+	originalDiscover := discoverTunnelInterfacesForReconcile
+	originalRestore := restorePFAnchorForReconcile
+	current := []string{}
+	discoverTunnelInterfacesForReconcile = func() []string { return nil }
+	calls := 0
+	restorePFAnchorForReconcile = func(p *prog, _ string) pfAnchorCheckResult {
+		calls++
+		p.commitPFReconcileState(current)
+		return pfAnchorCheckRestored
+	}
+	t.Cleanup(func() {
+		discoverTunnelInterfacesForReconcile = originalDiscover
+		restorePFAnchorForReconcile = originalRestore
+	})
+
+	p := &prog{dnsInterceptState: &pfState{}, lastTunnelIfaces: []string{"utun7"}}
+	p.pfExecBackoffUntil.Store(time.Now().Add(time.Minute).UnixMilli())
+	if !p.checkTunnelInterfaceChanges() {
+		t.Fatal("tunnel removal was not detected during PF exec backoff")
+	}
+	if calls != 0 || !stringSlicesEqual(p.lastTunnelIfaces, []string{"utun7"}) {
+		t.Fatalf("PF restore ran during exec backoff: calls=%d baseline=%v", calls, p.lastTunnelIfaces)
+	}
+	if p.checkTunnelInterfaceChanges() {
+		t.Fatal("identical deferred tunnel retry bypassed the ignored-event limiter")
+	}
+	p.pfExecBackoffUntil.Store(0)
+	if !p.checkTunnelInterfaceChanges() || calls != 1 || len(p.lastTunnelIfaces) != 0 {
+		t.Fatalf("tunnel removal did not retry after backoff: calls=%d baseline=%v", calls, p.lastTunnelIfaces)
+	}
+}
+
+func TestTunnelRapidReversalClearsUnappliedPendingState(t *testing.T) {
+	originalDiscover := discoverTunnelInterfacesForReconcile
+	discoverTunnelInterfacesForReconcile = func() []string { return nil }
+	t.Cleanup(func() { discoverTunnelInterfacesForReconcile = originalDiscover })
+
+	p := &prog{
+		dnsInterceptState:      &pfState{},
+		pendingTunnelIfaces:    []string{"utun9"},
+		hasPendingTunnelIfaces: true,
+	}
+	p.pfStabilizing.Store(true)
+	if !p.checkTunnelInterfaceChanges() {
+		t.Fatal("rapid tunnel reversal was not observed")
+	}
+	if p.hasPendingTunnelReconcile() || len(p.lastTunnelIfaces) != 0 {
+		t.Fatalf("rapid reversal left unapplied tunnel state: baseline=%v pending=%v", p.lastTunnelIfaces, p.hasPendingTunnelReconcile())
+	}
+}
+
+func TestTunnelAdditionIsCoalescedUntilSuccessfulRebuild(t *testing.T) {
+	originalDiscover := discoverTunnelInterfacesForReconcile
+	current := []string{"utun9"}
+	discoverTunnelInterfacesForReconcile = func() []string {
+		return append([]string(nil), current...)
+	}
+	t.Cleanup(func() { discoverTunnelInterfacesForReconcile = originalDiscover })
+
+	p := &prog{dnsInterceptState: &pfState{}}
+	p.pfStabilizing.Store(true)
+	if !p.checkTunnelInterfaceChanges() {
+		t.Fatal("new tunnel was not detected")
+	}
+	if p.checkTunnelInterfaceChanges() {
+		t.Fatal("identical pending tunnel state was not coalesced")
+	}
+	if len(p.lastTunnelIfaces) != 0 {
+		t.Fatalf("pending tunnel was committed before PF rebuild: %v", p.lastTunnelIfaces)
+	}
+	if !p.hasPendingTunnelReconcile() {
+		t.Fatal("new tunnel was not retained as pending")
+	}
+
+	p.commitPFReconcileState(current)
+	if !stringSlicesEqual(p.lastTunnelIfaces, current) {
+		t.Fatalf("successful rebuild baseline = %v, want %v", p.lastTunnelIfaces, current)
+	}
+	if p.hasPendingTunnelReconcile() {
+		t.Fatal("successful rebuild did not clear pending tunnel state")
+	}
+}
+
+// TestVPNDNSRefreshDeferredWhileStabilizing covers the ignored network-change path,
+// which can trigger a VPN DNS refresh from outside stabilization.
+//
+// A refresh rebuilds and reloads the pf anchor. Stabilization owns pf while a VPN's
+// ruleset is still settling, so refreshing then is the mutual-overwrite collision
+// stabilization exists to prevent - and these deltas arrive exactly when a VPN is
+// coming up. Deferring is safe: checkTunnelInterfaceChanges keeps the observation
+// pending, so the transition is retried afterwards.
+//
+// The watchdog tick carries the same guard for the same reason; it is not driven here
+// because that would mean running its 30s loop.
+func TestVPNDNSRefreshDeferredWhileStabilizing(t *testing.T) {
+	newProg := func(t *testing.T, refreshes *int, tunnels []string) *prog {
+		t.Helper()
+		outputs := map[string]string{
+			"-sn":                       `rdr-anchor "com.controld.ctrld"`,
+			"-sr":                       `anchor "com.controld.ctrld"`,
+			"-a com.controld.ctrld -sr": "pass in quick on lo0",
+			"-a com.controld.ctrld -sn": "rdr on lo0",
+		}
+		originalCheck := runPFAnchorCheckCommand
+		runPFAnchorCheckCommand = func(args ...string) ([]byte, error) {
+			output, ok := outputs[strings.Join(args, " ")]
+			if !ok {
+				return nil, fmt.Errorf("unexpected pf anchor check command")
+			}
+			return []byte(output), nil
+		}
+		// Discovery reports no tunnels. With a seeded baseline that is a removal, which
+		// checkTunnelInterfaceChanges reports as a change without touching pf while
+		// stabilizing - so this fixture never reaches a real pfctl write.
+		originalDiscover := discoverTunnelInterfacesForReconcile
+		discoverTunnelInterfacesForReconcile = func() []string { return nil }
+		t.Cleanup(func() {
+			runPFAnchorCheckCommand = originalCheck
+			discoverTunnelInterfacesForReconcile = originalDiscover
+		})
+
+		vpnDNS := newVPNDNSManager(&mainLog, nil)
+		vpnDNS.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
+			*refreshes++
+			return nil
+		}
+		p := &prog{dnsInterceptState: &pfState{}, vpnDNS: vpnDNS, lastTunnelIfaces: tunnels}
+		t.Cleanup(func() {
+			p.pfDelayedRecheckMu.Lock()
+			defer p.pfDelayedRecheckMu.Unlock()
+			for _, timer := range p.pfDelayedRecheckTimers {
+				if timer != nil {
+					timer.Stop()
+				}
+			}
+		})
+		return p
+	}
+	delta := func() *netmon.ChangeDelta {
+		return &netmon.ChangeDelta{
+			Old: &netmon.State{Interface: map[string]netmon.Interface{}},
+			New: &netmon.State{Interface: map[string]netmon.Interface{}},
+		}
+	}
+
+	t.Run("tunnel change during stabilization does not refresh", func(t *testing.T) {
+		refreshes := 0
+		// Seeded baseline plus empty discovery = a tunnel transition to report, so the
+		// refresh is eligible on everything except the stabilization guard.
+		p := newProg(t, &refreshes, []string{"utun9"})
+		p.pfStabilizing.Store(true)
+
+		p.handleDNSInterceptIgnoredNetworkChange(delta(), time.Unix(1_000_000, 0))
+
+		if refreshes != 0 {
+			t.Errorf("refreshed %d time(s) while stabilizing — that rebuilds the anchor under a settling VPN ruleset", refreshes)
+		}
+	})
+
+	t.Run("refresh still happens outside stabilization", func(t *testing.T) {
+		refreshes := 0
+		p := newProg(t, &refreshes, nil)
+
+		p.handleDNSInterceptIgnoredNetworkChange(delta(), time.Unix(1_000_000, 0))
+
+		if refreshes == 0 {
+			t.Error("no refresh outside stabilization — the guard must defer, not disable")
+		}
+	})
+}
+
+// TestExemptVPNDNSServersDeferredWhileStabilizing checks the mutation point itself,
+// not just the call sites: any future caller reaching it during stabilization is
+// refused before the anchor is rewritten.
+//
+// It returns before pfEnsureRunning is taken and before any pfctl work, so this drives
+// the real function without touching the host's pf state.
+func TestExemptVPNDNSServersDeferredWhileStabilizing(t *testing.T) {
+	p := &prog{dnsInterceptState: &pfState{}}
+	p.pfStabilizing.Store(true)
+
+	err := p.exemptVPNDNSServers([]vpnDNSExemption{{Server: "192.168.1.1"}})
+	if err == nil {
+		t.Fatal("exemption applied while stabilizing — that rewrites the anchor under a settling VPN ruleset")
+	}
+	if !strings.Contains(err.Error(), "stabilization") {
+		t.Errorf("error does not name the reason: %v", err)
+	}
+	// The refusal must happen before the reconcile latch is claimed, or a deferral
+	// would lock out the reconcile that runs once stabilization ends.
+	if p.pfEnsureRunning.Load() {
+		t.Error("pfEnsureRunning was left held by a deferred exemption")
+	}
+}

cmd/cli/dns_intercept_ignored_change_windows_test.go

@@ -0,0 +1,20 @@
+//go:build windows
+
+package cli
+
+import (
+	"testing"
+	"time"
+)
+
+func TestDNSInterceptIgnoredChangeReconcileDueWindowsPreservesImmediateBehavior(t *testing.T) {
+	p := &prog{}
+	now := time.Now()
+
+	if !p.dnsInterceptIgnoredChangeReconcileDue(now) {
+		t.Fatal("first ignored Windows change must reconcile immediately")
+	}
+	if !p.dnsInterceptIgnoredChangeReconcileDue(now) {
+		t.Fatal("Windows ignored changes must not inherit the macOS pf rate limit")
+	}
+}

cmd/cli/dns_intercept_others.go

@@ -4,6 +4,7 @@ package cli
 
 import (
 	"fmt"
+	"time"
 )
 
 // startDNSIntercept is not supported on this platform.
@@ -23,8 +24,8 @@ func (p *prog) exemptVPNDNSServers(exemptions []vpnDNSExemption) error {
 }
 
 // ensurePFAnchorActive is a no-op on unsupported platforms.
-func (p *prog) ensurePFAnchorActive() bool {
-	return false
+func (p *prog) ensurePFAnchorActive() pfAnchorCheckResult {
+	return pfAnchorCheckSkipped
 }
 
 // checkTunnelInterfaceChanges is a no-op on unsupported platforms.
@@ -32,6 +33,10 @@ func (p *prog) checkTunnelInterfaceChanges() bool {
 	return false
 }
 
+func (p *prog) dnsInterceptIgnoredChangeReconcileDue(time.Time) bool {
+	return false
+}
+
 // scheduleDelayedRechecks is a no-op on unsupported platforms.
 func (p *prog) scheduleDelayedRechecks() {}
 

cmd/cli/dns_intercept_settle.go

@@ -19,21 +19,9 @@ func (p *prog) refreshDNSAfterVPNSettle(reason string) (routes, domainlessServer
 		return 0, 0, 0
 	}
 
-	beforeExemptions := p.vpnDNS.CurrentExemptions()
 	routes, domainlessServers, exemptions = p.vpnDNS.RefreshRoutesOnly()
-	afterExemptions := p.vpnDNS.CurrentExemptions()
-
-	if vpnDNSExemptionsEqual(beforeExemptions, afterExemptions) {
-		mainLog.Load().Info().Msgf("DNS intercept: post-settle VPN DNS route refresh completed — %d routes, %d domainless servers, %d exemptions (pf unchanged)",
-			routes, domainlessServers, exemptions)
-		return routes, domainlessServers, exemptions
-	}
-
-	if err := p.exemptVPNDNSServers(afterExemptions); err != nil {
-		mainLog.Load().Warn().Err(err).Msg("DNS intercept: post-settle VPN DNS exemption update failed")
-	} else {
-		mainLog.Load().Info().Msgf("DNS intercept: post-settle VPN DNS exemptions changed — updated pf/WFP with %d exemptions", len(afterExemptions))
-	}
+	mainLog.Load().Info().Msgf("DNS intercept: post-settle VPN DNS route refresh completed — %d routes, %d domainless servers, %d exemptions",
+		routes, domainlessServers, exemptions)
 	return routes, domainlessServers, exemptions
 }
 

cmd/cli/dns_intercept_settle_test.go

@@ -43,7 +43,12 @@ func TestRefreshDNSAfterVPNSettleRefreshesOSResolverAndVPNRoutes(t *testing.T) {
 	if got := p.vpnDNS.UpstreamForDomain("jira.cc.bmwgroup.net."); len(got) != 1 || got[0] != "10.102.26.10" {
 		t.Fatalf("expected refreshed VPN DNS route, got %v", got)
 	}
-	if len(exemptionUpdates) != 0 {
-		t.Fatalf("expected route-only refresh to avoid pf exemption updates, got %+v", exemptionUpdates)
+	if len(exemptionUpdates) != 1 || len(exemptionUpdates[0]) != 1 || exemptionUpdates[0][0].Server != "10.102.26.10" {
+		t.Fatalf("expected one serialized pf exemption update for the late VPN DNS server, got %+v", exemptionUpdates)
+	}
+
+	p.refreshDNSAfterVPNSettle("test-repeat")
+	if len(exemptionUpdates) != 1 {
+		t.Fatalf("unchanged post-settle VPN DNS state rewrote pf: %+v", exemptionUpdates)
 	}
 }

cmd/cli/dns_intercept_windows.go

@@ -1616,8 +1616,8 @@ func parseIPv4AsUint32(ipStr string) uint32 {
 }
 
 // ensurePFAnchorActive is a no-op on Windows (WFP handles intercept differently).
-func (p *prog) ensurePFAnchorActive() bool {
-	return false
+func (p *prog) ensurePFAnchorActive() pfAnchorCheckResult {
+	return pfAnchorCheckSkipped
 }
 
 // checkTunnelInterfaceChanges is a no-op on Windows (WFP handles intercept differently).
@@ -1625,6 +1625,12 @@ func (p *prog) checkTunnelInterfaceChanges() bool {
 	return false
 }
 
+// Windows preserves the existing immediate reconciliation behavior. NRPT/WFP
+// and adapter DNS settling have different lifecycle requirements from macOS pf.
+func (p *prog) dnsInterceptIgnoredChangeReconcileDue(time.Time) bool {
+	return true
+}
+
 // pfAnchorRecheckDelay is the delay for deferred pf anchor re-checks.
 // Defined here as a stub for Windows (referenced from dns_proxy.go).
 const pfAnchorRecheckDelay = 2 * time.Second

cmd/cli/dns_proxy.go

@@ -1754,65 +1754,13 @@ func (p *prog) monitorNetworkChanges(ctx context.Context) error {
 			p.Debug().Msg("Ignoring interface change - no valid interfaces affected")
 			// check if the default IPs are still on an interface that is up
 			ValidateDefaultLocalIPsFromDelta(delta.New)
-			// Even minor interface changes can trigger macOS pf reloads — verify anchor.
-			// We check immediately AND schedule delayed re-checks (2s + 4s) to catch
-			// programs like Windscribe that modify pf rules and DNS settings
-			// asynchronously after the network change event fires.
+			// Minor interface changes can still accompany pf/WFP or VPN DNS changes.
+			// On macOS, bound the immediate full reconciliation so link-local-only
+			// notification storms do not run pfctl/scutil work for every event.
+			// Windows keeps the existing immediate behavior. Tunnel changes always
+			// bypass the macOS limit, and delayed checks provide a trailing refresh.
 			if dnsIntercept && p.dnsInterceptState != nil {
-				if !p.pfStabilizing.Load() {
-					p.ensurePFAnchorActive()
-				}
-				// Check tunnel interfaces unconditionally — it decides internally
-				// whether to enter stabilization or rebuild immediately.
-				p.checkTunnelInterfaceChanges()
-				// Schedule delayed re-checks to catch async VPN teardown changes.
-				// These also refresh the OS resolver and VPN DNS routes.
-				p.scheduleDelayedRechecks()
-
-				// Detect interface appearance/disappearance — hypervisors (Parallels,
-				// VMware, VirtualBox) reload pf when creating/destroying virtual network
-				// interfaces, which can corrupt pf's internal translation state.
-				if delta.Old != nil {
-					interfaceChanged := false
-					var changedIface string
-					for ifaceName := range delta.Old.Interface {
-						if ifaceName == "lo0" {
-							continue
-						}
-						if _, exists := delta.New.Interface[ifaceName]; !exists {
-							interfaceChanged = true
-							changedIface = ifaceName
-							break
-						}
-					}
-					if !interfaceChanged {
-						for ifaceName := range delta.New.Interface {
-							if ifaceName == "lo0" {
-								continue
-							}
-							if _, exists := delta.Old.Interface[ifaceName]; !exists {
-								interfaceChanged = true
-								changedIface = ifaceName
-								break
-							}
-						}
-					}
-					if interfaceChanged {
-						p.Info().Str("interface", changedIface).
-							Msg("DNS intercept: interface appeared/disappeared — starting interception probe monitor")
-						go p.pfInterceptMonitor()
-						// A VM/container bridge appearing/disappearing changes the
-						// effective forwarded-source set; rebuild the anchor if so, since
-						// the probe monitor alone won't (an intact anchor passes its probe).
-						p.reconcileForwardedSources()
-					}
-				}
-			}
-			// Refresh VPN DNS on tunnel interface changes (e.g., Tailscale connect/disconnect)
-			// even though the physical interface didn't change. Runs after tunnel checks
-			// so the pf anchor rebuild includes current VPN DNS exemptions.
-			if dnsIntercept && p.vpnDNS != nil {
-				p.vpnDNS.Refresh(ctx, true)
+				p.handleDNSInterceptIgnoredNetworkChange(delta, time.Now())
 			}
 			return
 		}
@@ -1919,6 +1867,79 @@ func (p *prog) monitorNetworkChanges(ctx context.Context) error {
 	return nil
 }
 
+// handleDNSInterceptIgnoredNetworkChange runs the DNS-intercept work for a
+// network delta that did not affect a usable interface. Keeping this path in a
+// method lets tests exercise the callback wiring with synthetic deltas.
+func (p *prog) handleDNSInterceptIgnoredNetworkChange(delta *netmon.ChangeDelta, now time.Time) {
+	reconcileNow := false
+	// Stabilization owns PF repair. Do not consume the next leading-edge slot
+	// until an ignored delta can actually perform the corresponding PF check.
+	if !p.pfStabilizing.Load() {
+		reconcileNow = p.dnsInterceptIgnoredChangeReconcileDue(now)
+		if reconcileNow {
+			p.ensurePFAnchorActive()
+		}
+	}
+
+	// Check tunnel interfaces unconditionally — it decides internally whether
+	// to enter stabilization or rebuild immediately.
+	tunnelChanged := p.checkTunnelInterfaceChanges()
+	// Schedule delayed re-checks to catch async VPN teardown changes. These also
+	// refresh the OS resolver and VPN DNS routes.
+	p.scheduleDelayedRechecks()
+
+	// Detect interface appearance/disappearance — hypervisors (Parallels,
+	// VMware, VirtualBox) reload pf when creating/destroying virtual network
+	// interfaces, which can corrupt pf's internal translation state. The rdr
+	// rules survive in text form (watchdog says "intact") but stop evaluating.
+	// Spawn an async monitor that probes pf interception with backoff and forces
+	// a full pf reload if broken.
+	if delta.Old != nil {
+		interfaceChanged := false
+		var changedIface string
+		for ifaceName := range delta.Old.Interface {
+			if ifaceName == "lo0" {
+				continue
+			}
+			if _, exists := delta.New.Interface[ifaceName]; !exists {
+				interfaceChanged = true
+				changedIface = ifaceName
+				break
+			}
+		}
+		if !interfaceChanged {
+			for ifaceName := range delta.New.Interface {
+				if ifaceName == "lo0" {
+					continue
+				}
+				if _, exists := delta.Old.Interface[ifaceName]; !exists {
+					interfaceChanged = true
+					changedIface = ifaceName
+					break
+				}
+			}
+		}
+		if interfaceChanged {
+			mainLog.Load().Info().Str("interface", changedIface).
+				Msg("DNS intercept: interface appeared/disappeared — starting interception probe monitor")
+			go p.pfInterceptMonitor()
+			// A VM/container bridge appearing/disappearing changes the effective
+			// forwarded-source set; an intact anchor/probe does not detect that.
+			p.reconcileForwardedSources()
+		}
+	}
+
+	// Refresh VPN DNS immediately for real tunnel changes even when the periodic
+	// ignored-change reconciliation is currently rate-limited - but not while
+	// stabilization owns pf. A refresh rebuilds the anchor, and these deltas arrive
+	// exactly when a VPN is bringing its own ruleset up, which is the collision
+	// stabilization is there to prevent. checkTunnelInterfaceChanges keeps the
+	// observation pending, so the transition is retried rather than dropped.
+	if p.vpnDNS != nil && (reconcileNow || tunnelChanged) && !p.pfStabilizing.Load() {
+		p.vpnDNS.Refresh(ctrld.LoggerCtx(context.Background(), p.logger.Load()), true)
+	}
+}
+
 // interfaceStatesEqual compares two interface states
 func interfaceStatesEqual(a, b *netmon.Interface) bool {
 	if a == nil || b == nil {

cmd/cli/pf_ruleset.go

@@ -0,0 +1,79 @@
+package cli
+
+import (
+	"fmt"
+	"strings"
+)
+
+// pfNoRulesMarker is what pfctl prints for a ruleset that contains nothing.
+const pfNoRulesMarker = "(no rules)"
+
+// pfFilterRuleLines reduces pfctl output to the lines that are actually pf rules.
+//
+// It exists because every pfctl reader here uses CombinedOutput, and pfctl on macOS
+// writes "No ALTQ support in kernel" and "ALTQ related functions disabled" to stderr on
+// essentially every show command, so raw output is never a clean rule list. An empty
+// ruleset can also report "(no rules)", which is a status line rather than a rule.
+//
+// Two consequences follow from getting this wrong, and both have bitten this file:
+// callers that test the output for emptiness can never see empty, and callers that feed
+// the lines back into "pfctl -f -" would splice non-rule text into a ruleset and have
+// the reload rejected.
+//
+// Registry access and platform specifics stay elsewhere; this is pure string handling
+// so it can be tested on any host.
+func pfFilterRuleLines(output string) []string {
+	var rules []string
+	for _, line := range strings.Split(output, "\n") {
+		line = strings.TrimSpace(line)
+		if line == "" {
+			continue
+		}
+		// pfctl stderr warnings, merged in by CombinedOutput.
+		if strings.Contains(line, "ALTQ") {
+			continue
+		}
+		// Status line for an empty ruleset, not a rule.
+		if line == pfNoRulesMarker {
+			continue
+		}
+		rules = append(rules, line)
+	}
+	return rules
+}
+
+// pfRulesetEmpty reports whether pfctl output describes a ruleset with no rules.
+//
+// Use this rather than testing the raw output for emptiness: the merged stderr warnings
+// described above mean a raw test is always false, so the condition it guards - an
+// anchor whose contents were flushed - would never be detected.
+func pfRulesetEmpty(output string) bool {
+	return len(pfFilterRuleLines(output)) == 0
+}
+
+// pfContainsRule checks if any line in the slice contains the given rule string.
+// Uses substring matching because pfctl may append extra tokens like " all" to rules
+// (e.g., `rdr-anchor "com.controld.ctrld" all`), which would fail exact matching.
+func pfContainsRule(lines []string, rule string) bool {
+	for _, line := range lines {
+		if strings.Contains(line, rule) {
+			return true
+		}
+	}
+	return false
+}
+
+// pfAnchorReferencesPresent reports whether ctrld's anchor references appear in the
+// running ruleset, given the output of "pfctl -sn" and "pfctl -sr".
+//
+// Removing the references means reloading the entire main ruleset, and that reload
+// carries no options section - so it resets system-wide pf options, including any
+// third-party "set skip" directives. Doing that when there is nothing of ours to
+// remove is pure collateral damage, which is what a startup rollback would otherwise
+// cause after failing before the references were ever added.
+func pfAnchorReferencesPresent(natOutput, filterOutput, anchorName string) bool {
+	rdrAnchorRef := fmt.Sprintf("rdr-anchor %q", anchorName)
+	anchorRef := fmt.Sprintf("anchor %q", anchorName)
+	return pfContainsRule(pfFilterRuleLines(natOutput), rdrAnchorRef) ||
+		pfContainsRule(pfFilterRuleLines(filterOutput), anchorRef)
+}

cmd/cli/pf_ruleset_test.go

@@ -0,0 +1,157 @@
+package cli
+
+import "testing"
+
+// altqNoise is what macOS pfctl writes to stderr on show commands. Because every
+// pfctl reader here uses CombinedOutput, it lands in the middle of the data being
+// parsed — which is why these helpers exist.
+const altqNoise = "No ALTQ support in kernel\nALTQ related functions disabled\n"
+
+// TestPFRulesetEmpty is the regression guard for a flushed anchor being undetectable.
+//
+// The anchor-content checks in verifyPFState and ensurePFAnchorActive decide whether pf
+// still has ctrld's rules. Testing the raw pfctl output for emptiness can never be true
+// on macOS, because the merged ALTQ warnings are always present — so a genuinely flushed
+// anchor reads as healthy and neither the startup gate nor the watchdog restore fires.
+func TestPFRulesetEmpty(t *testing.T) {
+	tests := []struct {
+		name   string
+		output string
+		want   bool
+	}{
+		{
+			// The case that was broken: nothing but merged stderr.
+			name:   "only ALTQ warnings",
+			output: altqNoise,
+			want:   true,
+		},
+		{
+			// As captured on macOS 26.6 from "pfctl -sn -a com.controld.ctrld".
+			name:   "ALTQ warnings plus the empty-ruleset marker",
+			output: altqNoise + "(no rules)\n",
+			want:   true,
+		},
+		{
+			name:   "empty output",
+			output: "",
+			want:   true,
+		},
+		{
+			name:   "whitespace only",
+			output: "\n  \n\t\n",
+			want:   true,
+		},
+		{
+			name:   "a real rdr rule behind the warnings",
+			output: altqNoise + "rdr on lo0 inet proto udp from any to ! 127.0.0.1 port = 53 -> 127.0.0.1 port 5354\n",
+			want:   false,
+		},
+		{
+			name:   "a real filter rule behind the warnings",
+			output: altqNoise + "pass in quick on lo0 reply-to lo0 inet proto udp from any to 127.0.0.1 port = 5354\n",
+			want:   false,
+		},
+		{
+			name:   "rule with no warnings at all",
+			output: "anchor \"com.controld.ctrld\" all\n",
+			want:   false,
+		},
+	}
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := pfRulesetEmpty(tc.output); got != tc.want {
+				t.Errorf("pfRulesetEmpty() = %v, want %v\noutput:\n%s", got, tc.want, tc.output)
+			}
+		})
+	}
+}
+
+// TestPFFilterRuleLines checks what survives filtering, since these lines are fed back
+// into "pfctl -f -" by the ruleset-rebuild paths. Splicing a warning or the
+// empty-ruleset marker into a ruleset would have the reload rejected outright.
+func TestPFFilterRuleLines(t *testing.T) {
+	got := pfFilterRuleLines(altqNoise + "(no rules)\nrdr-anchor \"com.controld.ctrld\" all\n\nanchor \"com.controld.ctrld\" all\n")
+	want := []string{
+		`rdr-anchor "com.controld.ctrld" all`,
+		`anchor "com.controld.ctrld" all`,
+	}
+	if len(got) != len(want) {
+		t.Fatalf("got %d lines %q, want %d %q", len(got), got, len(want), want)
+	}
+	for i := range want {
+		if got[i] != want[i] {
+			t.Errorf("line %d = %q, want %q", i, got[i], want[i])
+		}
+	}
+
+	if lines := pfFilterRuleLines(altqNoise); lines != nil {
+		t.Errorf("warnings alone must yield no rule lines, got %q", lines)
+	}
+}
+
+// TestPFAnchorReferencesPresent guards when the main ruleset may be rewritten.
+//
+// Removing our anchor references means reloading the whole main ruleset, and that
+// reload carries no options section — so it resets system-wide pf options, including
+// third-party "set skip" directives. Startup rollback runs after failures that happen
+// before the references were ever added, so without this check it would reset another
+// application's pf options while removing nothing of ours.
+func TestPFAnchorReferencesPresent(t *testing.T) {
+	const anchor = "com.controld.ctrld"
+	const otherAppRules = "scrub-anchor \"com.apple/*\" all fragment reassemble\nanchor \"com.vendor.vpn\" all\n"
+
+	tests := []struct {
+		name   string
+		nat    string
+		filter string
+		want   bool
+	}{
+		{
+			name:   "both references present",
+			nat:    altqNoise + "rdr-anchor \"com.controld.ctrld\" all\n",
+			filter: altqNoise + "anchor \"com.controld.ctrld\" all\n",
+			want:   true,
+		},
+		{
+			// pfctl appends tokens like " all", so matching is substring-based.
+			name:   "rdr reference only",
+			nat:    altqNoise + "rdr-anchor \"com.controld.ctrld\" all\n",
+			filter: altqNoise + otherAppRules,
+			want:   true,
+		},
+		{
+			name:   "filter reference only",
+			nat:    altqNoise,
+			filter: altqNoise + "anchor \"com.controld.ctrld\"\n",
+			want:   true,
+		},
+		{
+			// The rollback case: we failed before adding anything, and another
+			// application owns the ruleset. Rewriting it would be pure collateral.
+			name:   "someone else's ruleset, none of ours",
+			nat:    altqNoise,
+			filter: altqNoise + otherAppRules,
+			want:   false,
+		},
+		{
+			name:   "empty ruleset",
+			nat:    altqNoise + "(no rules)\n",
+			filter: altqNoise + "(no rules)\n",
+			want:   false,
+		},
+		{
+			// A different anchor whose name merely contains ours must not count.
+			name:   "another anchor with a similar name",
+			nat:    altqNoise,
+			filter: altqNoise + "anchor \"com.vendor.controld-shim\" all\n",
+			want:   false,
+		},
+	}
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := pfAnchorReferencesPresent(tc.nat, tc.filter, anchor); got != tc.want {
+				t.Errorf("pfAnchorReferencesPresent() = %v, want %v", got, tc.want)
+			}
+		})
+	}
+}

cmd/cli/prog.go

@@ -84,6 +84,16 @@ var noopLogf = func(format string, args ...any) {}
 
 var useSystemdResolved = false
 
+type pfAnchorCheckResult uint8
+
+const (
+	pfAnchorCheckSkipped pfAnchorCheckResult = iota
+	pfAnchorCheckIntact
+	pfAnchorCheckRestored
+	pfAnchorCheckDeferred
+	pfAnchorCheckFailed
+)
+
 type prog struct {
 	mu                   sync.Mutex
 	waitCh               chan struct{}
@@ -151,11 +161,12 @@ type prog struct {
 	// On Windows: *wfpState, on macOS: *pfState, nil on other platforms.
 	dnsInterceptState any
 
-	// lastTunnelIfaces tracks the set of active VPN/tunnel interfaces (utun*, ipsec*, etc.)
-	// discovered during the last pf anchor rule build. When the set changes (e.g., a VPN
-	// connects and creates utun420), we rebuild the pf anchor to add interface-specific
-	// intercept rules for the new interface. Protected by mu.
-	lastTunnelIfaces []string //lint:ignore U1000 used on darwin
+	// lastTunnelIfaces tracks the tunnel set included in the last successfully loaded
+	// pf anchor. Pending tunnel state is kept separately so failed PF work is retried
+	// instead of being mistaken for an applied update. Protected by mu.
+	lastTunnelIfaces       []string //lint:ignore U1000 used on darwin
+	pendingTunnelIfaces    []string //lint:ignore U1000 used on darwin
+	hasPendingTunnelIfaces bool     //lint:ignore U1000 used on darwin
 
 	// pfStabilizing is true while we're waiting for a VPN's pf ruleset to settle.
 	// While true, the watchdog and network change callbacks do NOT restore our rules.
@@ -178,10 +189,10 @@ type prog struct {
 	// interception with exponential backoff and auto-heals if broken.
 	pfMonitorRunning atomic.Bool //lint:ignore U1000 used on darwin
 
-	// pfEnsureRunning ensures only one pf anchor validation/restoration runs at a time.
-	// Network-change callbacks, delayed rechecks, and the periodic watchdog can all
-	// converge during macOS interface churn; concurrent pfctl/scutil exec storms can
-	// exhaust process/file limits and make the outage worse.
+	// pfEnsureRunning ensures only one pf validation or mutation runs at a time.
+	// Network callbacks, VPN exemption updates, delayed rechecks, probes, and the
+	// watchdog can converge during macOS churn; concurrent pfctl/scutil work can
+	// exhaust process/file limits or interleave anchor snapshots.
 	pfEnsureRunning atomic.Bool //lint:ignore U1000 used on darwin
 
 	// pfExecBackoffUntil suppresses pf anchor validation after pfctl/scutil execs
@@ -193,6 +204,11 @@ type prog struct {
 	pfDelayedRecheckMu     sync.Mutex    //lint:ignore U1000 used on darwin
 	pfDelayedRecheckTimers []*time.Timer //lint:ignore U1000 used on darwin
 
+	// pfIgnoredChangeLastReconcile bounds immediate pf/VPN-DNS work for noisy
+	// ignored macOS network deltas. Tunnel changes bypass this limit, and the
+	// existing delayed checks provide a trailing reconciliation after churn.
+	pfIgnoredChangeLastReconcile atomic.Int64 //lint:ignore U1000 used on darwin
+
 	// pfProbeExpected holds the domain name of a pending pf interception probe.
 	pfProbeExpected atomic.Value // string
 
@@ -829,6 +845,39 @@ func (p *prog) deAllocateIP() error {
 	return nil
 }
 
+// Seams for the intercept-start failure lifecycle. Choosing between the interface-DNS
+// fallback and refusing it has side effects - restoring the host's DNS, then
+// terminating - which a test has to observe without reconfiguring the host or exiting
+// the test binary. The intercept start itself is indirected for the same reason: it is
+// the real platform interceptor, which on macOS mutates pf and on Windows installs an
+// NRPT rule, so a test of what happens *after* it fails must not be the thing that
+// runs it.
+var (
+	startDNSInterceptFn     = (*prog).startDNSIntercept
+	setDnsForRunningIfaceFn = (*prog).setDnsForRunningIface
+	resetDNSFn              = (*prog).resetDNS
+	refuseFallbackFatal     = func(format string, v ...any) {
+		mainLog.Load().Fatal().Msgf(format, v...)
+	}
+)
+
+// interfaceDNSFallbackViable reports whether the interface-DNS fallback can actually
+// direct queries to ctrld's listener.
+//
+// Interface DNS names a resolver by IP and has no port field - true of macOS interface
+// settings and of Windows NRPT rules - so pointing the system straight at a listener
+// that did not bind :53 sends queries to whatever owns :53 instead, and that resolver's
+// upstream is ctrld's address: a loop, not a fallback.
+//
+// A nil or portless listener is treated as viable: the port is resolved elsewhere and
+// defaults to 53, so there is nothing to refuse yet.
+//
+// master no longer supports the router-local forwarding-resolver path, so there is
+// no intermediary that can make a non-53 listener reachable from interface DNS.
+func interfaceDNSFallbackViable(lc *ctrld.ListenerConfig) bool {
+	return lc == nil || lc.Port == 0 || lc.Port == 53
+}
+
 func (p *prog) setDNS() {
 	setDnsOK := false
 	defer func() {
@@ -861,7 +910,30 @@ func (p *prog) setDNS() {
 	// modifying interface DNS settings. This eliminates race conditions with VPN
 	// software that also manages DNS. See issue #489.
 	if dnsIntercept {
-		if err := p.startDNSIntercept(); err != nil {
+		if err := startDNSInterceptFn(p); err != nil {
+			// Interface DNS cannot express a port: macOS interface settings and Windows
+			// NRPT rules both name a resolver by IP alone. So it is only a usable
+			// fallback when the listener actually bound :53. When something else owns
+			// :53 - mDNSResponder on macOS, which is the whole reason the :5354 fallback
+			// exists - pointing the system at 127.0.0.1 hands queries to that other
+			// resolver, whose own upstream is now ctrld's address. That is a resolution
+			// loop, not degraded operation: a healthy ctrld listener nothing on the host
+			// can reach, no working DNS, and no recovery short of stopping the service.
+			//
+			// Refuse instead, after putting the host's own DNS back. A visible startup
+			// failure beats DNS that is broken by design, and it stops a fallback that
+			// cannot work from quietly undoing the fail-closed verification above.
+			if lc := cfg.FirstListener(); !interfaceDNSFallbackViable(lc) {
+				mainLog.Load().Error().Err(err).Msgf("DNS intercept mode failed with the listener on port %d", lc.Port)
+				// Leave the host resolvable: restore static settings or DHCP rather than
+				// exiting with an interface still pointed at a ctrld that is not serving.
+				resetDNSFn(p, false, true)
+				refuseFallbackFatal("Refusing to fall back to interface DNS: it cannot direct queries to %s:%d, which would leave this host with no working resolver. Free port 53 for ctrld, or resolve the intercept failure, then start again.", lc.IP, lc.Port)
+				// Unreachable in production - the line above exits - but returning
+				// explicitly keeps the refusal from depending on that, so nothing can
+				// fall through to installing the fallback this just rejected.
+				return
+			}
 			p.Error().Err(err).Msg("DNS intercept mode failed — falling back to interface DNS settings")
 			// Fall through to traditional setDNS behavior.
 		} else {
@@ -913,7 +985,7 @@ func (p *prog) setDNS() {
 	slices.Sort(nameservers)
 
 	netIfaceName := ""
-	netIface := p.setDnsForRunningIface(nameservers)
+	netIface := setDnsForRunningIfaceFn(p, nameservers)
 	if netIface != nil {
 		netIfaceName = netIface.Name
 	}

cmd/cli/prog_intercept_fallback_test.go

@@ -0,0 +1,180 @@
+package cli
+
+import (
+	"errors"
+	"fmt"
+	"net"
+	"strings"
+	"testing"
+
+	"github.com/Control-D-Inc/ctrld"
+)
+
+// TestInterfaceDNSFallbackViable covers when the interface-DNS fallback may be used
+// after DNS intercept fails to start.
+//
+// The fallback names a resolver by IP with no port, so it can only reach a listener on
+// :53. Taking it with the listener on a redirect-dependent port produced a total DNS
+// outage on macOS: the interface points at 127.0.0.1, mDNSResponder answers there, and
+// its upstream is ctrld's own address - a resolution loop with a healthy ctrld listener
+// nothing can reach. Intercept startup refuses the fallback in that case rather than
+// creating it.
+func TestInterfaceDNSFallbackViable(t *testing.T) {
+	tests := []struct {
+		name string
+		lc   *ctrld.ListenerConfig
+		want bool
+	}{
+		{
+			name: "listener on 53 can be reached by interface DNS",
+			lc:   &ctrld.ListenerConfig{IP: "127.0.0.1", Port: 53},
+			want: true,
+		},
+		{
+			// The reported outage: no local resolver, so the :5354 fallback port
+			// cannot be expressed by interface DNS.
+			name: "listener on the fallback port cannot",
+			lc:   &ctrld.ListenerConfig{IP: "127.0.0.1", Port: 5354},
+			want: false,
+		},
+		{
+			name: "any other non-53 port cannot",
+			lc:   &ctrld.ListenerConfig{IP: "127.0.0.1", Port: 5300},
+			want: false,
+		},
+
+		{
+			// Port is resolved elsewhere and defaults to 53; nothing to refuse yet.
+			name: "unset port is not refused",
+			lc:   &ctrld.ListenerConfig{IP: "127.0.0.1"},
+			want: true,
+		},
+		{
+			name: "no listener is not refused",
+			lc:   nil,
+			want: true,
+		},
+		{
+			// A non-loopback listener on 53 is still reachable by IP.
+			name: "non-loopback listener on 53",
+			lc:   &ctrld.ListenerConfig{IP: "192.168.1.10", Port: 53},
+			want: true,
+		},
+	}
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := interfaceDNSFallbackViable(tc.lc); got != tc.want {
+				t.Errorf("interfaceDNSFallbackViable() = %v, want %v", got, tc.want)
+			}
+		})
+	}
+}
+
+// interceptFallbackHarness drives setDNS() through the intercept-start failure path and
+// records the side effects that decide whether the host ends up with a working
+// resolver.
+//
+// Every host-touching step is stubbed, including the intercept start itself: this test
+// runs untagged on Linux, macOS and Windows runners, where the real startDNSIntercept
+// would set up pf or install an NRPT rule on the machine running the tests. Stubbing it
+// also makes the precondition deterministic - the failure under test is injected rather
+// than depending on the runner denying a privileged operation.
+type interceptFallbackHarness struct {
+	interceptCalls       int
+	installedNameservers []string
+	installCalls         int
+	resetCalls           int
+	refusals             []string
+}
+
+func newInterceptFallbackHarness(t *testing.T, lc *ctrld.ListenerConfig) *interceptFallbackHarness {
+	t.Helper()
+	h := &interceptFallbackHarness{}
+
+	origStart, origInstall := startDNSInterceptFn, setDnsForRunningIfaceFn
+	origReset, origFatal := resetDNSFn, refuseFallbackFatal
+	origCfg, origMode, origIntercept, origHard := cfg, interceptMode, dnsIntercept, hardIntercept
+	t.Cleanup(func() {
+		startDNSInterceptFn, setDnsForRunningIfaceFn = origStart, origInstall
+		resetDNSFn, refuseFallbackFatal = origReset, origFatal
+		cfg, interceptMode, dnsIntercept, hardIntercept = origCfg, origMode, origIntercept, origHard
+	})
+
+	// Never reach the real interceptor: it would configure pf on macOS and NRPT on
+	// Windows, on the machine running the tests.
+	startDNSInterceptFn = func(_ *prog) error {
+		h.interceptCalls++
+		return errors.New("dns intercept: injected start failure")
+	}
+	setDnsForRunningIfaceFn = func(_ *prog, nameservers []string) *net.Interface {
+		h.installCalls++
+		h.installedNameservers = nameservers
+		return nil
+	}
+	resetDNSFn = func(_ *prog, _ bool, _ bool) { h.resetCalls++ }
+	refuseFallbackFatal = func(format string, v ...any) {
+		h.refusals = append(h.refusals, fmt.Sprintf(format, v...))
+	}
+
+	cfg = ctrld.Config{}
+	cfg.Service.InterceptMode = "dns"
+	cfg.Listener = map[string]*ctrld.ListenerConfig{"0": lc}
+	watchdogOff := false
+	cfg.Service.DnsWatchdogEnabled = &watchdogOff
+	interceptMode, dnsIntercept, hardIntercept = "dns", false, false
+	return h
+}
+
+func (h *interceptFallbackHarness) run(t *testing.T) {
+	t.Helper()
+	p := &prog{cfg: &cfg}
+	p.logger.Store(mainLog.Load())
+	p.setDNS()
+}
+
+// TestSetDNSRefusesUnreachableFallback is the behaviour test for the reported outage: it
+// drives the real setDNS() lifecycle rather than the classification helper alone.
+//
+// Deleting or bypassing the guard in setDNS makes the first case fail, because interface
+// DNS then gets installed pointing at a listener that cannot answer on :53 - which is
+// the resolution loop this refuses to create.
+func TestSetDNSRefusesUnreachableFallback(t *testing.T) {
+	t.Run("non-53 listener refuses the fallback and restores DNS", func(t *testing.T) {
+		h := newInterceptFallbackHarness(t, &ctrld.ListenerConfig{IP: "127.0.0.1", Port: 5354})
+		h.run(t)
+
+		if h.interceptCalls != 1 {
+			t.Fatalf("intercept start called %d time(s) through the seam, want 1 — the real platform interceptor must never run here", h.interceptCalls)
+		}
+		if h.installCalls != 0 {
+			t.Errorf("interface DNS was installed %d time(s) for a listener on :5354 — that is the resolver loop", h.installCalls)
+		}
+		if h.resetCalls == 0 {
+			t.Error("host DNS was not restored before refusing, leaving the interface pointed at a ctrld that is not serving")
+		}
+		if len(h.refusals) == 0 {
+			t.Fatal("refusal was not surfaced: startup must fail loudly rather than silently skip the fallback")
+		}
+		if !strings.Contains(h.refusals[0], "5354") {
+			t.Errorf("refusal does not name the unreachable port: %q", h.refusals[0])
+		}
+	})
+
+	t.Run("listener on 53 still reaches the interface-DNS fallback", func(t *testing.T) {
+		h := newInterceptFallbackHarness(t, &ctrld.ListenerConfig{IP: "127.0.0.1", Port: 53})
+		h.run(t)
+
+		if h.interceptCalls != 1 {
+			t.Fatalf("intercept start called %d time(s) through the seam, want 1", h.interceptCalls)
+		}
+		if h.installCalls != 1 {
+			t.Errorf("interface DNS installed %d time(s), want 1: a listener on :53 is reachable, so the fallback must still apply", h.installCalls)
+		}
+		if len(h.refusals) != 0 {
+			t.Errorf("unexpected refusal for a reachable listener: %v", h.refusals)
+		}
+		if len(h.installedNameservers) == 0 {
+			t.Error("fallback installed no nameservers")
+		}
+	})
+}

cmd/cli/vpn_dns.go

@@ -47,6 +47,9 @@ type vpnDNSManager struct {
 	// as additional nameservers for queries that match split-DNS rules
 	// (from ctrld config, AD domain, or VPN suffix config).
 	domainlessServers []string
+	// appliedExemptions advances only after the platform PF/WFP callback succeeds.
+	// Keeping it separate from discovered configs makes failed rule updates retryable.
+	appliedExemptions []vpnDNSExemption
 	// retainedAfterEmptyDiscovery means Windows reported an empty VPN DNS
 	// snapshot once while previous VPN DNS state existed. We keep that last-known
 	// state for one guarded refresh cycle because Windows can briefly report an
@@ -55,9 +58,13 @@ type vpnDNSManager struct {
 	// discoverVPNDNS is injected for tests so Refresh does not depend on the
 	// runner host's real VPN/virtual adapter state.
 	discoverVPNDNS func(context.Context) []ctrld.VPNDNSConfig
-	// refreshRunning keeps noisy network-change storms from running overlapping
-	// scutil/networksetup VPN DNS discovery work.
-	refreshRunning atomic.Bool
+	// refreshStateMu keeps noisy network-change storms from running overlapping
+	// full VPN DNS refreshes and retains one trailing refresh when an event arrives
+	// during discovery so the newest OS state is not lost.
+	refreshStateMu sync.Mutex
+	refreshRunning bool
+	refreshPending bool
+	discoveryMu    sync.Mutex
 	// Called when VPN DNS server list changes, to update intercept exemptions.
 	onServersChanged vpnDNSExemptFunc
 }
@@ -75,15 +82,41 @@ func newVPNDNSManager(logger *atomic.Pointer[ctrld.Logger], exemptFunc vpnDNSExe
 }
 
 // Refresh re-discovers VPN DNS configs from the OS.
-// Called on network change events.
+// Called on network change events. Overlapping calls are coalesced into one
+// trailing refresh so a newer OS snapshot is never silently discarded.
 func (m *vpnDNSManager) Refresh(ctx context.Context, guardAgainstNoNameservers ...bool) {
 	logger := ctrld.LoggerFromCtx(ctx)
 	guardedRefresh := len(guardAgainstNoNameservers) > 0 && guardAgainstNoNameservers[0]
-	if !m.refreshRunning.CompareAndSwap(false, true) {
-		ctrld.Log(ctx, logger.Debug(), "VPN DNS refresh already running, skipping duplicate")
+	m.refreshStateMu.Lock()
+	if m.refreshRunning {
+		m.refreshPending = true
+		m.refreshStateMu.Unlock()
+		ctrld.Log(ctx, logger.Debug(), "VPN DNS refresh already running, coalescing trailing refresh")
 		return
 	}
-	defer m.refreshRunning.Store(false)
+	m.refreshRunning = true
+	m.refreshStateMu.Unlock()
+
+	for {
+		m.refreshOnce(ctx, guardedRefresh)
+
+		m.refreshStateMu.Lock()
+		if m.refreshPending {
+			m.refreshPending = false
+			m.refreshStateMu.Unlock()
+			guardedRefresh = true
+			continue
+		}
+		m.refreshRunning = false
+		m.refreshStateMu.Unlock()
+		return
+	}
+}
+
+func (m *vpnDNSManager) refreshOnce(ctx context.Context, guardAgainstNoNameservers bool) {
+	logger := ctrld.LoggerFromCtx(ctx)
+	m.discoveryMu.Lock()
+	defer m.discoveryMu.Unlock()
 
 	ctrld.Log(ctx, logger.Debug(), "Refreshing VPN DNS configurations")
 	discoverVPNDNS := m.discoverVPNDNS
@@ -110,9 +143,7 @@ func (m *vpnDNSManager) Refresh(ctx context.Context, guardAgainstNoNameservers .
 	m.mu.Lock()
 	defer m.mu.Unlock()
 
-	previousExemptions := m.currentExemptionsLocked()
-
-	if vpnDNSSettlingEnabled && len(configs) == 0 && guardedRefresh && m.hasVPNDNSStateLocked() {
+	if vpnDNSSettlingEnabled && len(configs) == 0 && guardAgainstNoNameservers && m.hasVPNDNSStateLocked() {
 		if !m.retainedAfterEmptyDiscovery {
 			exemptions := m.currentExemptionsLocked()
 			m.retainedAfterEmptyDiscovery = true
@@ -122,6 +153,8 @@ func (m *vpnDNSManager) Refresh(ctx context.Context, guardAgainstNoNameservers .
 			if m.onServersChanged != nil {
 				if err := m.onServersChanged(exemptions); err != nil {
 					ctrld.Log(ctx, logger.Error().Err(err), "Failed to re-apply retained VPN DNS exemptions")
+				} else {
+					m.appliedExemptions = append([]vpnDNSExemption(nil), exemptions...)
 				}
 			}
 			return
@@ -200,41 +233,47 @@ func (m *vpnDNSManager) Refresh(ctx context.Context, guardAgainstNoNameservers .
 	ctrld.Log(ctx, logger.Debug(), "VPN DNS refresh completed: %d configs, %d routes, %d domainless servers, %d unique exemptions",
 		len(m.configs), len(m.routes), len(m.domainlessServers), len(exemptions))
 
-	// Update intercept rules to permit VPN DNS traffic only when the exemption set
-	// actually changes. Network-change events can fire repeatedly while macOS/VPN
-	// state is otherwise identical; rewriting pf for identical exemptions can feed
-	// a self-triggering network-change loop. Empty exemptions are still applied
-	// when they differ from the previous set, so stale VPN exemptions are cleared
-	// on disconnect.
-	m.updateInterceptExemptionsIfChanged(ctx, logger, previousExemptions, exemptions, "VPN DNS")
+	// Update intercept rules only when desired exemptions differ from the last
+	// successfully applied set. Failed PF/WFP callbacks remain retryable on the
+	// next refresh even when discovery returns the same VPN DNS state.
+	m.updateInterceptExemptionsIfChanged(ctx, logger, exemptions, "VPN DNS")
 }
 
-func (m *vpnDNSManager) updateInterceptExemptionsIfChanged(ctx context.Context, logger *ctrld.Logger, before, after []vpnDNSExemption, reason string) {
+func (m *vpnDNSManager) updateInterceptExemptionsIfChanged(ctx context.Context, logger *ctrld.Logger, desired []vpnDNSExemption, reason string) {
 	if m.onServersChanged == nil {
 		return
 	}
-	if vpnDNSExemptionsEqual(before, after) {
+	if vpnDNSExemptionsEqual(m.appliedExemptions, desired) {
 		ctrld.Log(ctx, logger.Debug(), "VPN DNS exemptions unchanged after %s refresh; skipping intercept rule update", reason)
 		return
 	}
-	if err := m.onServersChanged(after); err != nil {
+	if err := m.onServersChanged(desired); err != nil {
 		ctrld.Log(ctx, logger.Error().Err(err), "Failed to update intercept exemptions for VPN DNS servers")
+		return
 	}
+	m.appliedExemptions = append([]vpnDNSExemption(nil), desired...)
 }
 
-// RefreshRoutesOnly re-discovers VPN DNS configs and updates only ctrld's
-// in-memory split-DNS routes. It intentionally does not call onServersChanged,
-// so it does not rewrite/reload pf/WFP rules. Use this for post-settle discovery
-// checks where we only need to learn late-published VPN search domains.
+// RefreshRoutesOnly re-discovers VPN DNS configs and updates ctrld's
+// in-memory split-DNS routes. It applies intercept exemptions only when that set
+// changes, while holding the shared discovery lane so a concurrent full refresh
+// cannot commit a newer snapshot and then be overwritten by this one.
 func (m *vpnDNSManager) RefreshRoutesOnly() (routes, domainlessServers, exemptions int) {
 	logger := mainLog.Load()
+	if m.logger != nil && m.logger.Load() != nil {
+		logger = m.logger.Load()
+	}
+	ctx := ctrld.LoggerCtx(context.Background(), logger)
 
-	logger.Debug().Msg("Refreshing VPN DNS route state only")
+	m.discoveryMu.Lock()
+	defer m.discoveryMu.Unlock()
+
+	ctrld.Log(ctx, logger.Debug(), "Refreshing VPN DNS route state only")
 	discoverVPNDNS := m.discoverVPNDNS
 	if discoverVPNDNS == nil {
 		discoverVPNDNS = ctrld.DiscoverVPNDNS
 	}
-	configs := discoverVPNDNS(context.Background())
+	configs := discoverVPNDNS(ctx)
 
 	if dri, err := netmon.DefaultRouteInterface(); err == nil && dri != "" {
 		for i := range configs {
@@ -275,10 +314,26 @@ func (m *vpnDNSManager) RefreshRoutesOnly() (routes, domainlessServers, exemptio
 		}
 	}
 	m.domainlessServers = domainless
+	currentExemptions := m.currentExemptionsLocked()
 
-	logger.Debug().Msgf("VPN DNS route-only refresh completed: %d configs, %d routes, %d domainless servers, %d exemptions",
-		len(m.configs), len(m.routes), len(m.domainlessServers), len(m.currentExemptionsLocked()))
-	return len(m.routes), len(m.domainlessServers), len(m.currentExemptionsLocked())
+	ctrld.Log(ctx, logger.Debug(), "VPN DNS route-only refresh completed: %d configs, %d routes, %d domainless servers, %d exemptions",
+		len(m.configs), len(m.routes), len(m.domainlessServers), len(currentExemptions))
+	m.updateInterceptExemptionsIfChanged(ctx, logger, currentExemptions, "route-only VPN DNS")
+	return len(m.routes), len(m.domainlessServers), len(currentExemptions)
+}
+
+func (m *vpnDNSManager) markInterceptExemptionsApplied(applied []vpnDNSExemption) {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+	if vpnDNSExemptionsEqual(m.currentExemptionsLocked(), applied) {
+		m.appliedExemptions = append([]vpnDNSExemption(nil), applied...)
+	}
+}
+
+func (m *vpnDNSManager) interceptExemptionsPending() bool {
+	m.mu.RLock()
+	defer m.mu.RUnlock()
+	return !vpnDNSExemptionsEqual(m.appliedExemptions, m.currentExemptionsLocked())
 }
 
 func (m *vpnDNSManager) hasVPNDNSStateLocked() bool {

cmd/cli/vpn_dns_test.go

@@ -2,9 +2,11 @@ package cli
 
 import (
 	"context"
+	"errors"
 	"sync"
 	"sync/atomic"
 	"testing"
+	"time"
 
 	"github.com/Control-D-Inc/ctrld"
 )
@@ -16,7 +18,7 @@ func withVPNDNSSettlingEnabled(t *testing.T) {
 	t.Cleanup(func() { vpnDNSSettlingEnabled = old })
 }
 
-func TestVPNDNSRefreshSkipsConcurrentDuplicate(t *testing.T) {
+func TestVPNDNSRefreshCoalescesConcurrentTrailingRefresh(t *testing.T) {
 	m := newVPNDNSManager(&mainLog, nil)
 	started := make(chan struct{})
 	release := make(chan struct{})
@@ -25,9 +27,16 @@ func TestVPNDNSRefreshSkipsConcurrentDuplicate(t *testing.T) {
 	var calls atomic.Int32
 
 	m.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
-		calls.Add(1)
+		call := calls.Add(1)
 		once.Do(func() { close(started) })
 		<-release
+		if call == 2 {
+			return []ctrld.VPNDNSConfig{{
+				InterfaceName: "utun-latest",
+				Servers:       []string{"10.0.0.2"},
+				Domains:       []string{"latest.internal"},
+			}}
+		}
 		return nil
 	}
 
@@ -41,8 +50,11 @@ func TestVPNDNSRefreshSkipsConcurrentDuplicate(t *testing.T) {
 	close(release)
 	<-done
 
-	if calls.Load() != 1 {
-		t.Fatalf("expected overlapping refresh to be skipped, got %d discovery calls", calls.Load())
+	if calls.Load() != 2 {
+		t.Fatalf("expected one active and one trailing discovery call, got %d", calls.Load())
+	}
+	if got := m.Routes()["latest.internal"]; len(got) != 1 || got[0] != "10.0.0.2" {
+		t.Fatalf("trailing refresh did not publish latest OS snapshot: %v", got)
 	}
 }
 
@@ -76,7 +88,9 @@ func TestVPNDNSRefreshRetainsStateForOneGuardedEmptyDiscovery(t *testing.T) {
 func TestVPNDNSRefreshClearsOnSecondGuardedEmptyDiscovery(t *testing.T) {
 	withVPNDNSSettlingEnabled(t)
 	var gotExemptions []vpnDNSExemption
+	updates := 0
 	m := newVPNDNSManager(&mainLog, func(exemptions []vpnDNSExemption) error {
+		updates++
 		gotExemptions = exemptions
 		return nil
 	})
@@ -86,6 +100,7 @@ func TestVPNDNSRefreshClearsOnSecondGuardedEmptyDiscovery(t *testing.T) {
 		Servers:       []string{"10.25.37.21"},
 	}}
 	m.domainlessServers = []string{"10.25.37.21"}
+	m.appliedExemptions = []vpnDNSExemption{{Server: "10.25.37.21", Interface: "Ethernet 6"}}
 	m.retainedAfterEmptyDiscovery = true
 
 	m.Refresh(context.Background(), true)
@@ -93,8 +108,8 @@ func TestVPNDNSRefreshClearsOnSecondGuardedEmptyDiscovery(t *testing.T) {
 	if got := m.DomainlessServers(); len(got) != 0 {
 		t.Fatalf("expected domainless servers to be cleared on second empty discovery, got %v", got)
 	}
-	if len(gotExemptions) != 0 {
-		t.Fatalf("expected empty exemptions after clearing stale state, got %v", gotExemptions)
+	if updates != 1 || len(gotExemptions) != 0 {
+		t.Fatalf("expected one empty exemption update after clearing stale state, calls=%d exemptions=%v", updates, gotExemptions)
 	}
 	if m.retainedAfterEmptyDiscovery {
 		t.Fatal("expected retained empty-discovery marker to be cleared with stale state")
@@ -126,6 +141,56 @@ func TestVPNDNSRefreshSkipsUnchangedInterceptExemptions(t *testing.T) {
 	}
 }
 
+func TestVPNDNSRefreshRetriesFailedInterceptExemptionUpdate(t *testing.T) {
+	attempts := 0
+	m := newVPNDNSManager(&mainLog, func([]vpnDNSExemption) error {
+		attempts++
+		if attempts == 1 {
+			return errors.New("pf update failed")
+		}
+		return nil
+	})
+	m.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
+		return []ctrld.VPNDNSConfig{{
+			InterfaceName: "utun-test",
+			Servers:       []string{"10.102.26.10"},
+			Domains:       []string{"internal.test"},
+		}}
+	}
+
+	m.Refresh(context.Background(), true)
+	if !m.interceptExemptionsPending() {
+		t.Fatal("failed intercept exemption update was not retained for retry")
+	}
+	m.Refresh(context.Background(), true)
+	if m.interceptExemptionsPending() {
+		t.Fatal("successful intercept exemption retry did not advance applied state")
+	}
+	m.Refresh(context.Background(), true)
+
+	if attempts != 2 {
+		t.Fatalf("intercept exemption update attempts = %d, want failed attempt plus one retry", attempts)
+	}
+	if len(m.appliedExemptions) != 1 || m.appliedExemptions[0].Server != "10.102.26.10" {
+		t.Fatalf("applied exemptions = %+v, want successful retry state", m.appliedExemptions)
+	}
+}
+
+func TestVPNDNSMarkAppliedExemptionsRejectsStaleSnapshot(t *testing.T) {
+	m := newVPNDNSManager(&mainLog, nil)
+	m.configs = []ctrld.VPNDNSConfig{{InterfaceName: "utun-new", Servers: []string{"10.0.0.2"}}}
+
+	m.markInterceptExemptionsApplied([]vpnDNSExemption{{Server: "10.0.0.1", Interface: "utun-old"}})
+	if !m.interceptExemptionsPending() {
+		t.Fatal("stale PF snapshot incorrectly advanced applied exemptions")
+	}
+
+	m.markInterceptExemptionsApplied([]vpnDNSExemption{{Server: "10.0.0.2", Interface: "utun-new"}})
+	if m.interceptExemptionsPending() {
+		t.Fatal("current PF snapshot did not advance applied exemptions")
+	}
+}
+
 func TestVPNDNSTransportFailureSuppressesFallbackOnlyWhileRetainingState(t *testing.T) {
 	withVPNDNSSettlingEnabled(t)
 	m := newVPNDNSManager(&mainLog, nil)
@@ -145,3 +210,89 @@ func TestVPNDNSTransportFailureSuppressesFallbackOnlyWhileRetainingState(t *test
 		t.Fatal("expected reachable DNS response to clear retained empty-discovery state")
 	}
 }
+
+func TestVPNDNSFullAndRouteOnlyDiscoveryAreSerialized(t *testing.T) {
+	var updateMu sync.Mutex
+	var exemptionUpdates []string
+	m := newVPNDNSManager(&mainLog, func(exemptions []vpnDNSExemption) error {
+		updateMu.Lock()
+		defer updateMu.Unlock()
+		if len(exemptions) == 0 {
+			exemptionUpdates = append(exemptionUpdates, "")
+		} else {
+			exemptionUpdates = append(exemptionUpdates, exemptions[0].Server)
+		}
+		return nil
+	})
+	firstStarted := make(chan struct{})
+	releaseFirst := make(chan struct{})
+	secondStarted := make(chan struct{})
+	var calls atomic.Int32
+
+	m.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
+		switch calls.Add(1) {
+		case 1:
+			close(firstStarted)
+			<-releaseFirst
+			return []ctrld.VPNDNSConfig{{
+				InterfaceName: "utun-old",
+				Servers:       []string{"10.0.0.1"},
+				Domains:       []string{"old.internal"},
+			}}
+		case 2:
+			close(secondStarted)
+			return []ctrld.VPNDNSConfig{{
+				InterfaceName: "utun-new",
+				Servers:       []string{"10.0.0.2"},
+				Domains:       []string{"new.internal"},
+			}}
+		default:
+			t.Fatalf("unexpected discovery call %d", calls.Load())
+			return nil
+		}
+	}
+
+	routesDone := make(chan struct{})
+	go func() {
+		defer close(routesDone)
+		m.RefreshRoutesOnly()
+	}()
+	<-firstStarted
+
+	fullDone := make(chan struct{})
+	go func() {
+		defer close(fullDone)
+		m.Refresh(context.Background(), false)
+	}()
+
+	select {
+	case <-secondStarted:
+		t.Fatal("full and route-only VPN DNS discovery overlapped")
+	case <-time.After(50 * time.Millisecond):
+	}
+	close(releaseFirst)
+
+	select {
+	case <-routesDone:
+	case <-time.After(time.Second):
+		t.Fatal("route-only refresh did not finish")
+	}
+	select {
+	case <-fullDone:
+	case <-time.After(time.Second):
+		t.Fatal("full refresh did not finish")
+	}
+
+	routes := m.Routes()
+	if _, ok := routes["old.internal"]; ok {
+		t.Fatalf("older route-only snapshot overwrote newer full refresh: %v", routes)
+	}
+	if got := routes["new.internal"]; len(got) != 1 || got[0] != "10.0.0.2" {
+		t.Fatalf("final VPN DNS routes = %v, want new.internal -> 10.0.0.2", routes)
+	}
+	updateMu.Lock()
+	defer updateMu.Unlock()
+	if len(exemptionUpdates) != 2 || exemptionUpdates[0] != "10.0.0.1" || exemptionUpdates[1] != "10.0.0.2" {
+		t.Fatalf("serialized exemption updates = %v, want old then new", exemptionUpdates)
+	}
+}

docs/pf-dns-intercept.md

@@ -258,11 +258,22 @@ The full pf reload is VPN-safe: it reassembles from `pfctl -sr` + `pfctl -sn`
 ### What about `set skip on lo0`?
 Some pf.conf files include `set skip on lo0` which tells pf to skip ALL processing on loopback. **This would break our approach** since both the `rdr on lo0` and `pass in on lo0` rules would be skipped.
 
-**Mitigation:** When injecting anchor references via `ensurePFAnchorReference()`,
-we strip `lo0` from any `set skip on` directives before reloading. The watchdog
-also checks for `set skip on lo0` and triggers a restore if detected. The
-interception probe provides an additional safety net — if `set skip on lo0` gets
-re-applied by another program, the probe will fail and trigger a full reload.
+**Mitigation:** the interception probe. `probePFIntercept()` sends a real query from
+outside the `_ctrld` group and confirms the listener received the redirect, which cannot
+succeed while pf is bypassing loopback — so a skip on `lo0` shows up as a probe failure
+and triggers a full reload.
+
+**Not implemented, contrary to earlier versions of this document:** ctrld does *not*
+strip `lo0` from `set skip on` directives, and the watchdog does *not* inspect skip
+state. Apple's `pfctl` offers no way to read it — `pfctl(8)` accepts `-s` nat, queue,
+rules, Anchors, states, Sources, info, References, labels, timeouts, memory, Tables,
+osfp, Interfaces, all, with no options or skip modifier — so text-based detection is not
+available on macOS.
+
+Adding an explicit check is tracked as follow-up: `pfctl(8)` documents
+`-s Interfaces -v` as additionally listing which interfaces have skip rules activated,
+which is the query to build on once its output shape is confirmed on a host that has a
+skip configured.
 
 ## Cleanup