Port DNS64, VPN routing and DNS recovery ownership to master

Retain master's context-aware VPN and resolver APIs, per-program logger,
shutdown fencing, native CLAT service identity and firewall behavior.
Keep saved-DNS paths owned by the root ctrld package; isolate the added
ownership/sweep tests with a shared path seam and temporary backups.

Preserve the source DNS64 DNSSEC/cache gates, longest-suffix VPN routing,
DNS-journal convergence, scoped IPv6 handling, target ownership checks,
custom-listener regressions and documented native QA limits.

cmd/cli/cli.go

@@ -1558,12 +1558,20 @@ func uninstall(p *prog, s service.Service) {
 	}
 }
 
+var restoreSavedStaticDNSInterfacesFn = withEachPhysicalInterfaces
+var restoreSavedStaticDNSRestoreFn = restoreDNS
+var savedStaticDNSPathFn = ctrld.SavedStaticDnsSettingsFilePath
+
 // restoreSavedStaticDNS restores DNS from saved static config files on physical interfaces.
 func restoreSavedStaticDNS(excludeIfaceName string, removeSaved bool) {
-	withEachPhysicalInterfaces(excludeIfaceName, "restore static DNS", func(i *net.Interface) error {
-		file := ctrld.SavedStaticDnsSettingsFilePath(i)
+	restoreSavedStaticDNSInterfacesFn(excludeIfaceName, "restore static DNS", func(i *net.Interface) error {
+		if !interceptTargetAllowsStaticRestore(i.Name) {
+			mainLog.Load().Debug().Msgf("Saved static DNS restore skipped on interface %s: intercept target cleanup is pending or ownership is unreadable", i.Name)
+			return nil
+		}
+		file := savedStaticDNSPathFn(i)
 		if _, err := os.Stat(file); err == nil {
-			if err := restoreDNS(i); err != nil {
+			if err := restoreSavedStaticDNSRestoreFn(i); err != nil {
 				mainLog.Load().Error().Err(err).Msgf("Could not restore static DNS on interface %s", i.Name)
 			} else {
 				mainLog.Load().Debug().Msgf("Restored static DNS on interface %s successfully", i.Name)

cmd/cli/dns64.go

@@ -175,6 +175,9 @@ func synthesizeAAAAFromA(req *dns.Msg, aAnswer *dns.Msg, prefix netip.Prefix) *d
 	out.SetReply(req)
 	out.Rcode = aAnswer.Rcode
 	out.Compress = true
+	// An authenticated A RRset alone cannot authenticate synthesized AAAA.
+	// maybeDNS64 also checks the original AAAA denial before setting AD.
+	out.AuthenticatedData = false
 	answers := make([]dns.RR, 0, len(aAnswer.Answer))
 	pb := prefix.Addr().As16()
 	for _, rr := range aAnswer.Answer {
@@ -228,10 +231,7 @@ func answerHasAAAA(answer *dns.Msg) bool {
 // rcodes are never synthesized (RFC 6147 §5.1.2: the name genuinely does
 // not exist or the query failed).
 func dns64Eligible(req, answer *dns.Msg) bool {
-	if req == nil || answer == nil || len(req.Question) == 0 || req.CheckingDisabled {
-		return false
-	}
-	if req.Question[0].Qtype != dns.TypeAAAA {
+	if !dns64RequestAllowed(req) || answer == nil {
 		return false
 	}
 	if answer.Rcode != dns.RcodeSuccess {
@@ -240,6 +240,13 @@ func dns64Eligible(req, answer *dns.Msg) bool {
 	return !answerHasAAAA(answer)
 }
 
+// Apply the same client gate to cold synthesis and fresh/stale variants.
+// In particular, RFC 6147 section 5.5 forbids synthesis for CD+DO clients.
+// Retain the existing conservative bypass for all CD requests.
+func dns64RequestAllowed(req *dns.Msg) bool {
+	return req != nil && len(req.Question) > 0 && req.Question[0].Qtype == dns.TypeAAAA && !req.CheckingDisabled
+}
+
 // dns64Active reports whether synthesis should currently run, re-evaluating
 // network class and (if needed) kicking off background prefix discovery at
 // most every dns64RecheckInterval.
@@ -307,7 +314,13 @@ func dns64CacheVariant(prefix netip.Prefix) string {
 }
 
 func dns64CacheKey(msg *dns.Msg, upstream string, prefix netip.Prefix) dnscache.Key {
-	return dnscache.NewVariantKey(msg, upstream, dns64CacheVariant(prefix))
+	variant := dns64CacheVariant(prefix)
+	// DO changes the authentication and DNSSEC data in a synthesized reply.
+	// Do not reuse a non-DO result for a DO client (or the reverse).
+	if opt := msg.IsEdns0(); opt != nil && opt.Do() {
+		variant += ":do"
+	}
+	return dnscache.NewVariantKey(msg, upstream, variant)
 }
 
 func (p *prog) resetDNS64State() {
@@ -477,6 +490,12 @@ func (p *prog) maybeDNS64(ctx context.Context, req *dns.Msg, answer *dns.Msg, re
 		// DNS64 variant to avoid repeating both upstream lookups.
 		return answer, prefix
 	}
+	// RFC 6147 section 5.5: AD may describe synthesis only when both the
+	// AAAA denial and the A response were authenticated by our upstream.
+	// Without DO, synthesized responses must not assert AD.
+	if opt := req.IsEdns0(); opt != nil && opt.Do() {
+		synth.AuthenticatedData = answer.AuthenticatedData && aAnswer.AuthenticatedData
+	}
 	ctrld.Log(ctx, mainLog.Load().Debug(), "dns64: synthesized AAAA from A records via NAT64 prefix %s", prefix)
 	return synth, prefix
 }

cmd/cli/dns64_dnssec_test.go

@@ -0,0 +1,143 @@
+package cli
+
+import (
+	"context"
+	"fmt"
+	"net"
+	"testing"
+	"time"
+
+	"github.com/miekg/dns"
+	ctrld "github.com/Control-D-Inc/ctrld"
+	"github.com/Control-D-Inc/ctrld/internal/dnscache"
+)
+
+func TestDNS64DNSSECCacheAndSynthesis(t *testing.T) {
+	captureDebugMainLog(t)
+	for _, do := range []bool{false, true} {
+		for _, denialAD := range []bool{false, true} {
+			for _, aAD := range []bool{false, true} {
+				t.Run(fmt.Sprintf("DO=%v/denialAD=%v/A_AD=%v", do, denialAD, aAD), func(t *testing.T) {
+					req := mkAAAAReq("dnssec.example.")
+					req.SetEdns0(1232, do)
+					denial := new(dns.Msg)
+					denial.SetReply(req)
+					denial.AuthenticatedData = denialAD
+					cache, err := dnscache.NewLRUCache(10)
+					if err != nil {
+						t.Fatal(err)
+					}
+					p := &prog{cache: cache}
+					p.logger.Store(mainLog.Load())
+					p.dns64.active = true
+					p.dns64.prefix = dns64WellKnownPrefix
+					p.dns64.checkedAt = time.Now()
+					calls := 0
+					resolveA := func(q *dns.Msg) *dns.Msg {
+						calls++
+						if q.Question[0].Qtype != dns.TypeA {
+							t.Fatal("not an A lookup")
+						}
+						a := new(dns.Msg)
+						a.SetReply(q)
+						a.AuthenticatedData = aAD
+						a.Answer = []dns.RR{&dns.A{Hdr: dns.RR_Header{Name: q.Question[0].Name, Rrtype: dns.TypeA, Class: dns.ClassINET, Ttl: 60}, A: net.ParseIP("198.51.100.7")}}
+						return a
+					}
+					out, prefix := p.maybeDNS64(context.Background(), req, denial, resolveA)
+					wantAD := do && denialAD && aAD
+					if calls != 1 || !answerHasAAAA(out) || !prefix.IsValid() || out.AuthenticatedData != wantAD {
+						t.Fatalf("cold: calls=%d AAAA=%v prefix=%v AD=%v wantAD=%v", calls, answerHasAAAA(out), prefix, out.AuthenticatedData, wantAD)
+					}
+					now := time.Now()
+					for _, stale := range []bool{false, true} {
+						expiry := now.Add(time.Minute)
+						if stale {
+							expiry = now.Add(-time.Minute)
+						}
+						cache.Add(dns64CacheKey(req, "upstream.0", prefix), dnscache.NewValue(out, expiry))
+						answer, old, hit, variant, _ := p.cachedResponse(req, "upstream.0", prefix, true, now)
+						got := answer
+						if stale {
+							got = old
+						}
+						if got == nil || !answerHasAAAA(got) || got.AuthenticatedData != wantAD || hit == stale || variant == stale {
+							t.Fatalf("normal cache stale=%v: answer=%v old=%v hit=%v variant=%v", stale, answer, old, hit, variant)
+						}
+						cd := req.Copy()
+						cd.CheckingDisabled = true
+						answer, old, hit, variant, _ = p.cachedResponse(cd, "upstream.0", prefix, true, now)
+						if answerHasAAAA(answer) || answerHasAAAA(old) || hit || variant {
+							t.Errorf("CD cache stale=%v leaked synthesis: answer=%v old=%v hit=%v variant=%v", stale, answer, old, hit, variant)
+						}
+						cold, coldPrefix := p.maybeDNS64(context.Background(), cd, denial, resolveA)
+						if cold != denial || coldPrefix.IsValid() || calls != 1 {
+							t.Fatal("CD cold path performed synthesis")
+						}
+					}
+					if denial.AuthenticatedData != denialAD {
+						t.Fatal("mutated denial")
+					}
+				})
+			}
+		}
+	}
+}
+
+func TestDNS64DNSSECOrdinaryCacheFallback(t *testing.T) {
+	req := mkAAAAReq("dnssec.example.")
+	req.CheckingDisabled = true
+	req.SetEdns0(1232, true)
+	ordinary := new(dns.Msg)
+	ordinary.SetReply(req)
+	cache, err := dnscache.NewLRUCache(10)
+	if err != nil {
+		t.Fatal(err)
+	}
+	p := &prog{cache: cache}
+	p.logger.Store(mainLog.Load())
+	now := time.Now()
+	cache.Add(dnscache.NewKey(req, "upstream.0"), dnscache.NewValue(ordinary, now.Add(time.Minute)))
+	answer, _, hit, variant, bypass := p.cachedResponse(req, "upstream.0", dns64WellKnownPrefix, true, now)
+	if !hit || variant || bypass || answerHasAAAA(answer) {
+		t.Fatalf("ordinary cache: hit=%v variant=%v bypass=%v answer=%v", hit, variant, bypass, answer)
+	}
+}
+
+func TestRecoveryOSOnlyCandidatePool(t *testing.T) {
+	for _, reason := range []RecoveryReason{RecoveryReasonNetworkChange, RecoveryReasonRegularFailure} {
+		p := &prog{cfg: &ctrld.Config{Upstream: map[string]*ctrld.UpstreamConfig{"0": {Type: ctrld.ResolverTypeOS}, "nil": nil}}}
+		p.logger.Store(mainLog.Load())
+		pool := p.buildRecoveryUpstreams(reason)
+		if len(pool) != 1 || pool[upstreamOS] != osUpstreamConfig {
+			t.Errorf("reason=%v: OS-only recovery candidates=%v", reason, pool)
+		}
+	}
+}
+
+func TestDNS64DNSSECCacheDOIsolation(t *testing.T) {
+	for _, do := range []bool{false, true} {
+		req := mkAAAAReq("dnssec.example.")
+		req.SetEdns0(1232, do)
+		response := new(dns.Msg)
+		response.SetReply(req)
+		response.AuthenticatedData = do
+		response.Answer = []dns.RR{&dns.AAAA{Hdr: dns.RR_Header{Name: req.Question[0].Name, Rrtype: dns.TypeAAAA, Class: dns.ClassINET, Ttl: 60}, AAAA: net.ParseIP("64:ff9b::c633:6407")}}
+		cache, err := dnscache.NewLRUCache(10)
+		if err != nil {
+			t.Fatal(err)
+		}
+		p := &prog{cache: cache}
+		p.logger.Store(mainLog.Load())
+		now := time.Now()
+		other := req.Copy()
+		other.IsEdns0().SetDo(!do)
+		for _, expiry := range []time.Time{now.Add(time.Minute), now.Add(-time.Minute)} {
+			cache.Add(dns64CacheKey(req, "upstream.0", dns64WellKnownPrefix), dnscache.NewValue(response, expiry))
+			answer, stale, hit, variant, _ := p.cachedResponse(other, "upstream.0", dns64WellKnownPrefix, true, now)
+			if answer != nil || stale != nil || hit || variant {
+				t.Fatalf("DO=%v result reused for DO=%v: answer=%v stale=%v", do, !do, answer, stale)
+			}
+		}
+	}
+}

cmd/cli/dns_intercept_darwin.go

@@ -735,6 +735,21 @@ func flushPFStates() {
 	}
 }
 
+// pfNameserverAddress keeps socket zones out of group-scoped PF addresses.
+// ctrld already has a blanket group exemption in the same anchor.
+func pfNameserverAddress(server string) (string, string, bool) {
+	host, _, err := net.SplitHostPort(server)
+	if err != nil {
+		host = server
+	}
+	addr, err := netip.ParseAddr(host)
+	if err != nil {
+		return "", "", false
+	}
+	host = addr.WithZone("").Unmap().String()
+	return host, pfAddressFamily(host), true
+}
+
 func pfAddressFamily(ip string) string {
 	if addr := net.ParseIP(ip); addr != nil && addr.To4() == nil {
 		return "inet6"
@@ -937,11 +952,10 @@ func (p *prog) buildPFAnchorRulesForState(vpnExemptions []vpnDNSExemption, tunne
 		rules.WriteString("# Scoped to group " + pfGroupName + " so only ctrld's own queries are exempted,\n")
 		rules.WriteString("# preventing other processes from bypassing the redirect by querying these IPs.\n")
 		for _, ns := range osNS {
-			host, _, _ := net.SplitHostPort(ns)
-			if host == "" {
-				host = ns
+			host, af, ok := pfNameserverAddress(ns)
+			if !ok {
+				continue
 			}
-			af := pfAddressFamily(host)
 			rules.WriteString(fmt.Sprintf("pass out quick on ! lo0 %s proto { udp, tcp } from any to %s port 53 group %s\n", af, host, pfGroupName))
 		}
 		rules.WriteString("\n")
@@ -973,10 +987,10 @@ func (p *prog) buildPFAnchorRulesForState(vpnExemptions []vpnDNSExemption, tunne
 		rules.WriteString("# Exempt VPN DNS servers: ctrld's own queries (group-scoped).\n")
 		seen := make(map[string]bool)
 		for _, ex := range vpnExemptions {
-			if !seen[ex.Server] {
-				seen[ex.Server] = true
-				af := pfAddressFamily(ex.Server)
-				rules.WriteString(fmt.Sprintf("pass out quick on ! lo0 %s proto { udp, tcp } from any to %s port 53 group %s\n", af, ex.Server, pfGroupName))
+			host, af, ok := pfNameserverAddress(ex.Server)
+			if ok && !seen[host] {
+				seen[host] = true
+				rules.WriteString(fmt.Sprintf("pass out quick on ! lo0 %s proto { udp, tcp } from any to %s port 53 group %s\n", af, host, pfGroupName))
 			}
 		}
 		rules.WriteString("\n")

cmd/cli/dns_proxy.go

@@ -136,7 +136,7 @@ func (p *prog) addCachedResponse(key dnscache.Key, answer *dns.Msg) {
 }
 
 func (p *prog) cachedResponse(req *dns.Msg, upstream string, dns64Prefix netip.Prefix, dns64Active bool, now time.Time) (answer, stale *dns.Msg, hit, dns64Hit, dns64Bypass bool) {
-	if dns64Active {
+	if dns64Active && dns64RequestAllowed(req) {
 		if cachedValue := p.cache.Get(dns64CacheKey(req, upstream, dns64Prefix)); cachedValue != nil {
 			answer = cachedValue.Msg.Copy()
 			ctrld.SetCacheReply(answer, req, answer.Rcode)
@@ -2942,6 +2942,11 @@ func (p *prog) buildRecoveryUpstreams(reason RecoveryReason) map[string]*ctrld.U
 				upstreams[upstreamPrefix+k] = uc
 			}
 		}
+		// An OS-only configuration still needs a recovery worker. Do not add
+		// OS to mixed pools: their existing recovery boundaries stay intact.
+		if len(upstreams) == 0 {
+			upstreams[upstreamOS] = osUpstreamConfig
+		}
 	}
 	return upstreams
 }

cmd/cli/dns_target_darwin.go

@@ -33,7 +33,14 @@ var (
 	interceptSaveStaticDNSSnapshotFn    = func(iface *net.Interface, dns []string, owned string) error {
 		return saveTargetStaticDNSSnapshot(ctrld.SavedStaticDnsSettingsFilePath(iface), dns, owned)
 	}
-	interceptSaveCurrentStaticDNSFn        = saveCurrentStaticDNS
+	interceptSaveCurrentStaticDNSFn = saveCurrentStaticDNS
+	interceptRemoveSavedDNSFn       = func(iface *net.Interface) error {
+		err := os.Remove(savedStaticDNSPathFn(iface))
+		if errors.Is(err, os.ErrNotExist) {
+			return nil
+		}
+		return err
+	}
 	interceptSetDNSFn                      = setDNS
 	interceptSavedStaticNameserversFn      = ctrld.SavedStaticNameservers
 	interceptResetDNSIgnoreUnusableIfaceFn = resetDnsIgnoreUnusableInterface
@@ -48,6 +55,24 @@ func interceptDNSTargetStatePath() string {
 	return filepath.Join(dir, interceptDNSTargetStateFile)
 }
 
+// A retained target record means cleanup was not completed. The broad saved
+// static sweep must not bypass the target's ownership check or retry failures
+// through an unguarded restore. Unknown state is conservatively left alone.
+func interceptTargetAllowsStaticRestore(service string) bool {
+	data, err := os.ReadFile(interceptDNSTargetStatePathFn())
+	if errors.Is(err, os.ErrNotExist) {
+		return true
+	}
+	if err != nil {
+		return false
+	}
+	var st interceptDNSTargetState
+	if json.Unmarshal(data, &st) != nil || st.Service == "" {
+		return false
+	}
+	return st.Service != service
+}
+
 type interceptDNSTargetState struct {
 	Service string `json:"service"`
 	Value   string `json:"value"`
@@ -75,23 +100,34 @@ func (p *prog) loadInterceptDNSTargetStateLocked() {
 
 // persistInterceptDNSTargetStateLocked writes (or clears) the state file to
 // match in-memory tracking. Callers must hold interceptDNSTargetMu.
-func (p *prog) persistInterceptDNSTargetStateLocked() {
+func (p *prog) persistInterceptDNSTargetStateLocked() error {
 	file := interceptDNSTargetStatePathFn()
 	if p.interceptDNSTargetService == "" {
-		_ = os.Remove(file)
-		return
+		if err := os.Remove(file); err != nil && !errors.Is(err, os.ErrNotExist) {
+			return err
+		}
+		return nil
 	}
 	data, err := json.Marshal(interceptDNSTargetState{Service: p.interceptDNSTargetService, Value: p.interceptDNSTargetSetValue})
 	if err != nil {
-		return
+		return err
 	}
-	if err := os.WriteFile(file, data, 0600); err != nil {
-		mainLog.Load().Debug().Err(err).Msg("intercept DNS target: could not persist state file")
+	// Replace atomically; a failed write must not truncate prior ownership.
+	tmp, err := os.CreateTemp(filepath.Dir(file), ".intercept-target-*")
+	if err != nil {
+		return err
 	}
+	defer os.Remove(tmp.Name())
+	_, writeErr := tmp.Write(data)
+	err = errors.Join(writeErr, tmp.Close())
+	if err != nil {
+		return err
+	}
+	return os.Rename(tmp.Name(), file)
 }
 
-// ensureInterceptDNSTarget guarantees macOS always has an emittable DNS
-// target while DNS intercept mode is active.
+// ensureInterceptDNSTarget provides an emittable DNS target when ownership
+// and discovery permit it; externally changed DNS is not permission to reinstall.
 //
 // Intercept mode deliberately never manages interface DNS: pf redirects DNS
 // packets in flight. But pf can only redirect packets macOS actually sends,
@@ -203,6 +239,14 @@ func (p *prog) ensureInterceptDNSTarget(systemDiscovery []string) {
 			return
 		}
 	}
+	// Tracking is not proof that the target is still installed. An external
+	// edit (including clearing DNS) is not permission to reinstall it. Retain
+	// the cleanup record until shutdown, preventing periodic reconciliation
+	// from reinterpreting the same edit as a new DNS-less admission.
+	if p.interceptDNSTargetService == iface.Name && !isInterceptDNSTargetOnly(snapshot, p.interceptDNSTargetSetValue) && !hasIPv4DNS(filterOwnTarget(snapshot, p.interceptDNSTargetSetValue)) {
+		diagnostic.failed(decision, "owned_target_changed", nil)
+		return
+	}
 	// Never count ctrld's own previously-set entry as network-provided DNS,
 	// or the next recovery on the same DNS-less network would remove it and
 	// the one after re-add it.
@@ -267,12 +311,21 @@ func (p *prog) ensureInterceptDNSTarget(systemDiscovery []string) {
 			mainLog.Load().Debug().Err(err).Msgf("intercept DNS target: could not save static DNS for %q", iface.Name)
 		}
 	}
+	p.setInterceptDNSTargetLocked(iface.Name, target)
+	if err := p.persistInterceptDNSTargetStateLocked(); err != nil {
+		p.setInterceptDNSTargetLocked("", "")
+		resolvedReason = ""
+		diagnostic.failed(decision, "ownership_persistence", err)
+		mainLog.Load().Warn().Err(err).Msg("intercept DNS target: not changing DNS without persisted ownership")
+		return
+	}
 	if err := interceptSetDNSFn(iface, []string{target}); err != nil {
+		// A command error can follow a partial OS mutation. Keep the durable
+		// cleanup record; the next observation decides what still belongs to us.
+		resolvedReason = ""
 		mainLog.Load().Warn().Err(err).Msgf("intercept DNS target: could not set %s on %q", target, iface.Name)
 		return
 	}
-	p.setInterceptDNSTargetLocked(iface.Name, target)
-	p.persistInterceptDNSTargetStateLocked()
 	journal(mainLog.Load().Warn()).Str("service", iface.Name).Str("target", target).
 		Bool("native_clat_fallback", nativeFallback).
 		Str("reason", "dns_less_network").
@@ -306,7 +359,15 @@ func (p *prog) removeInterceptDNSTargetLocked(reason string) {
 		return
 	}
 	if !isInterceptDNSTargetOnly(cur, val) {
-		p.clearInterceptDNSTargetStateLocked()
+		// The generic stop/uninstall sweep must not replay a stale snapshot
+		// over the external edit. On failure keep ownership so its guard skips.
+		if err := interceptRemoveSavedDNSFn(iface); err != nil {
+			mainLog.Load().Warn().Err(err).Msg("intercept DNS target: could not discard stale backup; retaining cleanup state")
+			return
+		}
+		if !p.clearInterceptDNSTargetStateLocked() {
+			return
+		}
 		// ctrld owns the DNS of the service no longer, and a later outage
 		// report needs the moment that ownership ended.
 		journal(mainLog.Load().Info()).Str("service", svc).Str("target", val).
@@ -323,7 +384,9 @@ func (p *prog) removeInterceptDNSTargetLocked(reason string) {
 		mainLog.Load().Warn().Err(err).Msgf("intercept DNS target: could not reset DNS on %q; retaining cleanup state", svc)
 		return
 	}
-	p.clearInterceptDNSTargetStateLocked()
+	if !p.clearInterceptDNSTargetStateLocked() {
+		return
+	}
 	journal(mainLog.Load().Info()).Str("service", svc).Str("target", val).Str("reason", reason).
 		Msgf("intercept DNS target: removed %s from %q (%s)", val, svc, reason)
 }
@@ -332,9 +395,15 @@ func (p *prog) interceptDNSTargetOwnershipLocked() dnsTargetOwnership {
 	return dnsTargetOwnership{p.interceptDNSTargetService, p.interceptDNSTargetSetValue}
 }
 
-func (p *prog) clearInterceptDNSTargetStateLocked() {
+func (p *prog) clearInterceptDNSTargetStateLocked() bool {
+	service, value := p.interceptDNSTargetService, p.interceptDNSTargetSetValue
 	p.setInterceptDNSTargetLocked("", "")
-	p.persistInterceptDNSTargetStateLocked()
+	if err := p.persistInterceptDNSTargetStateLocked(); err != nil {
+		p.setInterceptDNSTargetLocked(service, value)
+		mainLog.Load().Warn().Err(err).Msg("intercept DNS target: could not clear ownership; retaining cleanup state")
+		return false
+	}
+	return true
 }
 
 // setInterceptDNSTargetLocked stores the service that ctrld owns and the value

cmd/cli/dns_target_darwin_test.go

@@ -41,6 +41,14 @@ func newInterceptTargetHarness(t *testing.T) *interceptTargetHarness {
 		statePath:    filepath.Join(t.TempDir(), interceptDNSTargetStateFile),
 	}
 
+	// Master's saved DNS path belongs to ctrld, not the CLI homedir.
+	// Isolate the production remove/sweep paths without touching host backups.
+	savedDir := t.TempDir()
+	origSavedPath := savedStaticDNSPathFn
+	savedStaticDNSPathFn = func(iface *net.Interface) string {
+		return filepath.Join(savedDir, ".dns_"+iface.Name)
+	}
+	t.Cleanup(func() { savedStaticDNSPathFn = origSavedPath })
 	origPath := interceptDNSTargetStatePathFn
 	origRoute := interceptDefaultRouteInterfaceFn
 	origIface := interceptInterfaceByNameFn
@@ -144,12 +152,14 @@ func newInterceptTargetHarness(t *testing.T) *interceptTargetHarness {
 }
 
 func newInterceptTargetProg() *prog {
-	return &prog{
+	p := &prog{
 		cfg: &ctrld.Config{Listener: map[string]*ctrld.ListenerConfig{
 			"0": {IP: "127.0.0.1", Port: 5354},
 		}},
 		dnsInterceptState: &pfState{},
 	}
+	p.logger.Store(mainLog.Load())
+	return p
 }
 
 func persistInterceptTargetForTest(t *testing.T, p *prog, service, value string) {
@@ -158,7 +168,9 @@ func persistInterceptTargetForTest(t *testing.T, p *prog, service, value string)
 	defer p.interceptDNSTargetMu.Unlock()
 	p.interceptDNSTargetLoaded = true
 	p.setInterceptDNSTargetLocked(service, value)
-	p.persistInterceptDNSTargetStateLocked()
+	if err := p.persistInterceptDNSTargetStateLocked(); err != nil {
+		t.Fatal(err)
+	}
 }
 
 func TestEnsureInterceptDNSTargetRequiresCompletedDiscovery(t *testing.T) {

cmd/cli/dns_target_diagnostic_darwin_test.go

@@ -240,14 +240,11 @@ func TestEnsureInterceptDNSTargetResolutionDoesNotClaimWriteSuccess(t *testing.T
 	h.dhcpErr = nil
 	h.setErr = errors.New("synthetic set failure")
 	p.ensureInterceptDNSTarget([]string{})
-	event := oneRecoveryEvent(t, logs, dnsTargetResolvedMessage)
-	wantField(t, event, "outcome", "decision_available")
-	wantField(t, event, "reason", "dns_less_network")
-	wantField(t, event, "action", "unchanged")
-	wantField(t, event, "ownership_before", false)
-	wantField(t, event, "ownership_after", false)
-	if len(h.setCalls) != 1 || p.interceptDNSTargetService != "" {
-		t.Fatal("failed target write was not exercised or acquired ownership")
+	if events := jsonLogEvents(t, logs, dnsTargetResolvedMessage); len(events) != 0 {
+		t.Fatal("failed target write reported a resolved decision")
+	}
+	if len(h.setCalls) != 1 || p.interceptDNSTargetService != "Wi-Fi" {
+		t.Fatal("failed target write did not retain cleanup state for possible partial mutation")
 	}
 }
 

cmd/cli/dns_target_ownership_darwin_test.go

@@ -0,0 +1,168 @@
+//go:build darwin
+
+package cli
+
+import (
+	"errors"
+	"fmt"
+	"net"
+	"os"
+	"path/filepath"
+	"slices"
+	"testing"
+)
+
+func TestInterceptDNSTargetOwnershipPersistenceBeforeMutation(t *testing.T) {
+	h := newInterceptTargetHarness(t)
+	h.nativeCLAT = true
+	h.dhcpErr = errors.New("no DHCPv4")
+	h.dns["Wi-Fi"] = []string{"2001:db8::53"}
+	h.statePath = filepath.Join(t.TempDir(), "absent", "ownership")
+	p := newInterceptTargetProg()
+	p.cfg.Listener["0"].IP = "127.0.0.9"
+	p.cfg.Listener["0"].Port = 5353
+	p.ensureInterceptDNSTarget([]string{})
+	if len(h.setCalls) != 0 || p.interceptDNSTargetService != "" || !slices.Equal(h.dns["Wi-Fi"], []string{"2001:db8::53"}) {
+		t.Fatalf("persistence failure mutated DNS: calls=%v dns=%v owner=%s", h.setCalls, h.dns["Wi-Fi"], p.interceptDNSTargetService)
+	}
+}
+
+func TestInterceptDNSTargetExternalEditInvalidatesBackup(t *testing.T) {
+	h := newInterceptTargetHarness(t)
+	p := newInterceptTargetProg()
+	p.cfg.Listener["0"].IP = "127.0.0.9"
+	p.cfg.Listener["0"].Port = 5353
+	p.ensureInterceptDNSTarget([]string{})
+	target := p.interceptDNSTargetValue()
+	if !slices.Equal(h.dns["Wi-Fi"], []string{target}) {
+		t.Fatal("listener-aware target not installed")
+	}
+	backup := savedStaticDNSPathFn(&net.Interface{Name: "Wi-Fi"})
+	if err := os.WriteFile(backup, []byte("2001:db8::old"), 0600); err != nil {
+		t.Fatal(err)
+	}
+	external := []string{"2001:db8::54"}
+	h.dns["Wi-Fi"] = slices.Clone(external)
+	for range 2 {
+		p.ensureInterceptDNSTarget([]string{})
+	}
+	if !slices.Equal(h.dns["Wi-Fi"], external) || len(h.setCalls) != 1 {
+		t.Fatal("reconciliation overwrote external DNS")
+	}
+	p.removeInterceptDNSTarget("stop")
+	oldEach, oldRestore := restoreSavedStaticDNSInterfacesFn, restoreSavedStaticDNSRestoreFn
+	t.Cleanup(func() { restoreSavedStaticDNSInterfacesFn, restoreSavedStaticDNSRestoreFn = oldEach, oldRestore })
+	restoreSavedStaticDNSInterfacesFn = func(_, _ string, f func(*net.Interface) error) { _ = f(&net.Interface{Name: "Wi-Fi"}) }
+	restoreSavedStaticDNSRestoreFn = func(*net.Interface) error { t.Fatal("full stop sweep replayed stale DNS"); return nil }
+	restoreSavedStaticDNS("", false)
+	if _, err := os.Stat(backup); !errors.Is(err, os.ErrNotExist) {
+		t.Fatalf("stale backup remains available to stop sweep: %v", err)
+	}
+	if !slices.Equal(h.dns["Wi-Fi"], external) {
+		t.Fatal("stop overwrote external DNS")
+	}
+}
+
+func TestInterceptDNSTargetFailedOwnershipClearRetainsState(t *testing.T) {
+	h := newInterceptTargetHarness(t)
+	p := newInterceptTargetProg()
+	p.ensureInterceptDNSTarget([]string{})
+	if err := os.Remove(h.statePath); err != nil {
+		t.Fatal(err)
+	}
+	if err := os.Mkdir(h.statePath, 0700); err != nil {
+		t.Fatal(err)
+	}
+	if err := os.WriteFile(filepath.Join(h.statePath, "busy"), nil, 0600); err != nil {
+		t.Fatal(err)
+	}
+	p.removeInterceptDNSTarget("stop")
+	if p.interceptDNSTargetService != "Wi-Fi" {
+		t.Fatal("failed ownership clear reported completed cleanup")
+	}
+}
+
+func TestInterceptDNSTargetTrackedValueIsNotActualDNS(t *testing.T) {
+	for _, port := range []int{53, 5353} {
+		t.Run(fmt.Sprint(port), func(t *testing.T) {
+			logs := captureDebugMainLog(t)
+			h := newInterceptTargetHarness(t)
+			p := newInterceptTargetProg()
+			p.cfg.Listener["0"].IP = "127.0.0.9"
+			p.cfg.Listener["0"].Port = port
+			p.ensureInterceptDNSTarget([]string{})
+			h.dns["Wi-Fi"] = nil
+			p.ensureInterceptDNSTarget([]string{})
+			event := oneRecoveryEvent(t, logs, dnsTargetFailedMessage)
+			wantField(t, event, "stage", "owned_target_changed")
+			if len(h.setCalls) != 1 || len(h.dns["Wi-Fi"]) != 0 {
+				t.Fatal("reinstalled after external clear")
+			}
+		})
+	}
+}
+
+func TestInterceptDNSTargetFailedCleanupGuardsFullSweep(t *testing.T) {
+	h := newInterceptTargetHarness(t)
+	p := newInterceptTargetProg()
+	p.ensureInterceptDNSTarget([]string{})
+	backup := savedStaticDNSPathFn(&net.Interface{Name: "Wi-Fi"})
+	if err := os.WriteFile(backup, []byte("2001:db8::53"), 0600); err != nil {
+		t.Fatal(err)
+	}
+	h.resetErr = errors.New("reset failed")
+	p.removeInterceptDNSTarget("stop")
+	oldEach, oldRestore := restoreSavedStaticDNSInterfacesFn, restoreSavedStaticDNSRestoreFn
+	t.Cleanup(func() { restoreSavedStaticDNSInterfacesFn, restoreSavedStaticDNSRestoreFn = oldEach, oldRestore })
+	restoreSavedStaticDNSInterfacesFn = func(_, _ string, f func(*net.Interface) error) { _ = f(&net.Interface{Name: "Wi-Fi"}) }
+	restoreSavedStaticDNSRestoreFn = func(*net.Interface) error { t.Fatal("sweep bypassed failed guarded cleanup"); return nil }
+	restoreSavedStaticDNS("", true)
+	if _, err := os.Stat(backup); err != nil {
+		t.Fatal("failed cleanup lost backup:", err)
+	}
+	if p.interceptDNSTargetService != "Wi-Fi" {
+		t.Fatal("failed cleanup lost state")
+	}
+}
+
+func TestInterceptDNSTargetStaticRestoreSkipIsNotFailure(t *testing.T) {
+	for _, state := range []string{`{"service":"Wi-Fi","value":"127.0.0.53"}`, `invalid ownership`} {
+		t.Run(state, func(t *testing.T) {
+			h := newInterceptTargetHarness(t)
+			logs := captureDebugMainLog(t)
+			if err := os.WriteFile(h.statePath, []byte(state), 0600); err != nil {
+				t.Fatal(err)
+			}
+			backup := savedStaticDNSPathFn(&net.Interface{Name: "Wi-Fi"})
+			const savedDNS = "2001:db8::53"
+			if err := os.WriteFile(backup, []byte(savedDNS), 0600); err != nil {
+				t.Fatal(err)
+			}
+			oldEach, oldRestore := restoreSavedStaticDNSInterfacesFn, restoreSavedStaticDNSRestoreFn
+			t.Cleanup(func() { restoreSavedStaticDNSInterfacesFn, restoreSavedStaticDNSRestoreFn = oldEach, oldRestore })
+			calls := 0
+			restoreSavedStaticDNSInterfacesFn = func(_, _ string, f func(*net.Interface) error) {
+				calls++
+				if err := f(&net.Interface{Name: "Wi-Fi"}); err != nil {
+					t.Fatalf("ownership skip reported as restore failure: %v", err)
+				}
+			}
+			restoreSavedStaticDNSRestoreFn = func(*net.Interface) error {
+				t.Fatal("ownership skip restored DNS")
+				return nil
+			}
+			restoreSavedStaticDNS("", true)
+			if calls != 1 {
+				t.Fatalf("interface sweeps=%d, want 1", calls)
+			}
+			event := oneRecoveryEvent(t, logs, "Saved static DNS restore skipped on interface Wi-Fi: intercept target cleanup is pending or ownership is unreadable")
+			wantField(t, event, "level", "debug")
+			if data, err := os.ReadFile(backup); err != nil || string(data) != savedDNS {
+				t.Fatalf("ownership skip changed backup: %q, %v", data, err)
+			}
+			if data, err := os.ReadFile(h.statePath); err != nil || string(data) != state {
+				t.Fatalf("ownership skip changed state: %q, %v", data, err)
+			}
+		})
+	}
+}

cmd/cli/dns_target_stub.go

@@ -2,6 +2,8 @@
 
 package cli
 
+func interceptTargetAllowsStaticRestore(_ string) bool { return true }
+
 // ensureInterceptDNSTarget is a no-op on non-Darwin platforms: the DNS-less
 // network problem it solves is specific to macOS pf interception blocking
 // IPv6 port 53 with no IPv4 fallback (issue #533). Windows intercept mode

cmd/cli/listener_5353_darwin_test.go

@@ -0,0 +1,69 @@
+//go:build darwin
+
+package cli
+
+import (
+	"fmt"
+	ctrld "github.com/Control-D-Inc/ctrld"
+	"strings"
+	"testing"
+)
+
+func TestPFScopedNameserverAddress(t *testing.T) {
+	for _, tc := range []struct{ server, host, family string }{
+		{"[fe80::1%en0]:53", "fe80::1", "inet6"},
+		{"2001:db8::53", "2001:db8::53", "inet6"},
+		{"192.0.2.53:53", "192.0.2.53", "inet"},
+	} {
+		host, family, ok := pfNameserverAddress(tc.server)
+		if !ok || host != tc.host || family != tc.family {
+			t.Fatalf("PF nameserver %q: %q %q %v", tc.server, host, family, ok)
+		}
+	}
+	if _, _, ok := pfNameserverAddress("not an address"); ok {
+		t.Fatal("invalid PF address accepted")
+	}
+}
+
+func TestPFRecoveryScopedNameserverRules(t *testing.T) {
+	captureDebugMainLog(t)
+	p := &prog{cfg: &ctrld.Config{Listener: map[string]*ctrld.ListenerConfig{"0": {IP: "127.0.0.2", Port: 5353}}}}
+	p.logger.Store(mainLog.Load())
+	// Recovery converts OS-discovered addresses into this exemption list.
+	rules := p.buildPFAnchorRulesForTunnels([]vpnDNSExemption{
+		{Server: "fe80::1%en0"}, {Server: "fe80::1%en1"}, {Server: "192.0.2.53"},
+	}, nil)
+	want := "pass out quick on ! lo0 inet6 proto { udp, tcp } from any to fe80::1 port 53 group " + pfGroupName
+	if strings.Count(rules, want) != 1 {
+		t.Fatalf("scoped recovery exemption missing or duplicated: %s", rules)
+	}
+	if strings.Contains(rules, "%en0") || strings.Contains(rules, "%en1") || strings.Contains(rules, "inet proto { udp, tcp } from any to fe80:") {
+		t.Fatal("socket zone or IPv4 family leaked into recovery PF rules")
+	}
+	if !strings.Contains(rules, "inet proto { udp, tcp } from any to 192.0.2.53 port 53 group "+pfGroupName) {
+		t.Fatal("IPv4 recovery exemption changed")
+	}
+}
+
+func TestCustomListener5353PFRules(t *testing.T) {
+	captureDebugMainLog(t)
+	for _, ip := range []string{"127.0.0.1", "127.0.0.2", "127.0.0.53", "192.0.2.10"} {
+		t.Run(ip, func(t *testing.T) {
+			p := &prog{cfg: &ctrld.Config{Listener: map[string]*ctrld.ListenerConfig{"0": {IP: ip, Port: 5353}}}}
+			p.logger.Store(mainLog.Load())
+			rules := p.buildPFAnchorRulesForTunnels(nil, []string{"utun9"})
+			for _, proto := range []string{"udp", "tcp"} {
+				want := fmt.Sprintf("rdr on lo0 inet proto %s from any to ! %s port 53 -> %s port 5353", proto, ip, ip)
+				if !strings.Contains(rules, want) {
+					t.Errorf("missing redirect %s", want)
+				}
+			}
+			if strings.Contains(rules, "port 5354") {
+				t.Fatal("explicit port replaced with automatic fallback")
+			}
+			if p.interceptDNSTargetValue() == ip {
+				t.Fatal("target equals rdr exclusion: no port translation")
+			}
+		})
+	}
+}

cmd/cli/listener_5353_linux_test.go

@@ -0,0 +1,32 @@
+//go:build linux
+
+package cli
+
+import (
+	ctrld "github.com/Control-D-Inc/ctrld"
+	"net"
+	"testing"
+)
+
+// Socket-only Linux control. Native macOS PF delivery is a separate QA gate.
+func TestCustomListener5353Binding(t *testing.T) {
+	captureDebugMainLog(t)
+	for _, ip := range []string{"127.0.0.1", "127.0.0.2"} {
+		t.Run(ip, func(t *testing.T) {
+			cfg := &ctrld.Config{Listener: map[string]*ctrld.ListenerConfig{"0": {IP: ip, Port: 5353}}}
+			changed, ok := tryUpdateListenerConfigIntercept(cfg, func() {}, false)
+			if !ok || changed {
+				t.Fatalf("custom listener did not bind unchanged: changed=%v ok=%v", changed, ok)
+			}
+			occupied, err := net.Listen("tcp4", net.JoinHostPort(ip, "5353"))
+			if err != nil {
+				t.Fatal(err)
+			}
+			defer occupied.Close()
+			changed, ok = tryUpdateListenerConfigIntercept(cfg, func() {}, false)
+			if ok || changed || cfg.Listener["0"].IP != ip || cfg.Listener["0"].Port != 5353 {
+				t.Fatal("occupied explicit listener silently fell back")
+			}
+		})
+	}
+}

cmd/cli/listener_5353_target_darwin_test.go

@@ -0,0 +1,41 @@
+//go:build darwin
+
+package cli
+
+import (
+	"errors"
+	"slices"
+	"testing"
+)
+
+func TestNativeCLATCustomListener5353Lifecycle(t *testing.T) {
+	for _, ip := range []string{"127.0.0.1", "127.0.0.2", "127.0.0.53", "192.0.2.10"} {
+		t.Run(ip, func(t *testing.T) {
+			h := newInterceptTargetHarness(t)
+			h.nativeCLAT = true
+			h.dhcpErr = errors.New("DHCPv4 intentionally absent")
+			p := newInterceptTargetProg()
+			p.cfg.Listener["0"].IP = ip
+			p.cfg.Listener["0"].Port = 5353
+			target := p.interceptDNSTargetValue()
+			p.ensureInterceptDNSTarget([]string{})
+			p.ensureInterceptDNSTarget([]string{})
+			if !slices.Equal(h.dns["Wi-Fi"], []string{target}) || len(h.setCalls) != 1 {
+				t.Fatalf("target was not installed idempotently: %v writes %v", h.dns, h.setCalls)
+			}
+			if target == ip {
+				t.Fatal("OS DNS would hit port53 at listener instead of PF port5353 redirect")
+			}
+			h.dhcpErr = nil
+			h.dhcp = []string{"192.0.2.53"}
+			h.nativeCLAT = false
+			p.ensureInterceptDNSTarget([]string{"192.0.2.53"})
+			if len(h.dns["Wi-Fi"]) != 0 || p.interceptDNSTargetService != "" {
+				t.Fatalf("DHCP return failed to remove target: %+v", h.dns)
+			}
+			if p.cfg.Listener["0"].IP != ip || p.cfg.Listener["0"].Port != 5353 {
+				t.Fatal("target lifecycle changed configured listener")
+			}
+		})
+	}
+}

cmd/cli/listener_5353_test.go

@@ -0,0 +1,34 @@
+package cli
+
+import (
+	ctrld "github.com/Control-D-Inc/ctrld"
+	"testing"
+)
+
+func TestCustomListener5353Contract(t *testing.T) {
+	for _, tc := range []struct{ ip, target string }{
+		{"127.0.0.1", "127.0.0.53"}, {"127.0.0.2", "127.0.0.53"},
+		{"127.0.0.53", "127.0.0.54"}, {"192.0.2.10", "127.0.0.53"},
+	} {
+		t.Run(tc.ip, func(t *testing.T) {
+			if !isExplicitInterceptListener(tc.ip, 5353) {
+				t.Fatal("5353 was not explicit")
+			}
+			p := &prog{cfg: &ctrld.Config{Listener: map[string]*ctrld.ListenerConfig{"0": {IP: tc.ip, Port: 5353}}}}
+			if got := p.interceptDNSTargetValue(); got != tc.target {
+				t.Fatalf("target=%s want %s", got, tc.target)
+			}
+			current := p.cfg.Listener
+			generated := map[string]*ctrld.ListenerConfig{"0": {IP: "127.0.0.1", Port: 53}}
+			preserveBoundListeners(generated, current)
+			if generated["0"].IP != tc.ip || generated["0"].Port != 5353 {
+				t.Fatalf("generated reload lost bound listener: %+v", generated["0"])
+			}
+			explicit := map[string]*ctrld.ListenerConfig{"0": {IP: tc.ip, Port: 5353}}
+			preserveBoundListeners(explicit, map[string]*ctrld.ListenerConfig{"0": {IP: "127.0.0.1", Port: 5354}})
+			if explicit["0"].IP != tc.ip || explicit["0"].Port != 5353 {
+				t.Fatalf("explicit reload normalized: %+v", explicit["0"])
+			}
+		})
+	}
+}

cmd/cli/prog.go

@@ -320,6 +320,8 @@ type prog struct {
 
 	// VPN DNS manager for split DNS routing when intercept mode is active.
 	vpnDNS *vpnDNSManager
+	// Serializes journal reads with publication after an intercept startup retry.
+	vpnDNSJournalMu sync.Mutex
 
 	// rejectedDestinationsKey is the signature of the organization allowed
 	// destination entries that were last reported as unusable, so re-parsing an
@@ -1224,6 +1226,27 @@ func (p *prog) startNetworkJournal() func() {
 // drop. The search suffixes name the organization of the endpoint, so the
 // journal holds their number only.
 func (p *prog) logDNSConfigChanges(entries []dnsResolverEntry) {
+	// The poller emits one batch per changed snapshot (at most once per poll),
+	// not one discovery per resolver. Late DNS publication on an unchanged
+	// tunnel otherwise has no network event to refresh split routing.
+	// Join the existing shutdown fence before touching the manager or PF/WFP:
+	// closeNetMonitor drains this callback before restoring the host's DNS.
+	if len(entries) > 0 && p.beginNetworkActivity() {
+		defer p.netMonitorWG.Done()
+		// setDNS publishes the manager before signalling completion. The journal
+		// starts earlier; never race initial manager publication or initialize a
+		// manager in traditional/hard intercept mode.
+		select {
+		case <-p.csSetDnsDone:
+			p.vpnDNSJournalMu.Lock()
+			manager := p.vpnDNS
+			p.vpnDNSJournalMu.Unlock()
+			if manager != nil {
+				manager.Refresh(ctrld.LoggerCtx(context.Background(), p.logger.Load()), true)
+			}
+		default:
+		}
+	}
 	for _, entry := range entries {
 		journal(mainLog.Load().Info()).
 			Strs("nameservers", entry.Nameservers).
@@ -1564,8 +1587,10 @@ func (p *prog) setDNS(systemNameservers []string) {
 				// Discovers search domains from virtual/VPN interfaces and forwards
 				// matching queries to the DNS server on that interface.
 				// Skipped in --intercept-mode hard where all DNS goes through ctrld.
+				p.vpnDNSJournalMu.Lock()
 				p.vpnDNS = newVPNDNSManager(&p.logger, p.exemptVPNDNSServers)
 				p.vpnDNS.Refresh(ctrld.LoggerCtx(context.Background(), p.logger.Load()))
+				p.vpnDNSJournalMu.Unlock()
 			}
 
 			setDnsOK = true
@@ -1814,7 +1839,9 @@ func (p *prog) resetDNS(isStart bool, restoreStatic bool) {
 		}
 
 		// Clean up VPN DNS manager
+		p.vpnDNSJournalMu.Lock()
 		p.vpnDNS = nil
+		p.vpnDNSJournalMu.Unlock()
 
 		return
 	}

cmd/cli/vpn_dns.go

@@ -184,11 +184,7 @@ func (m *vpnDNSManager) refreshOnce(ctx context.Context, guardAgainstNoNameserve
 			config.InterfaceName, len(config.Domains), len(config.Servers))
 
 		for _, domain := range config.Domains {
-			// Normalize domain: remove leading dot, Linux routing domain prefix (~),
-			// and convert to lowercase.
-			domain = strings.TrimPrefix(domain, "~") // Linux resolvectl routing domain prefix
-			domain = strings.TrimPrefix(domain, ".")
-			domain = strings.ToLower(domain)
+			domain = normalizeVPNDomain(domain)
 
 			if domain != "" {
 				m.routes[domain] = append([]string{}, config.Servers...)
@@ -302,9 +298,7 @@ func (m *vpnDNSManager) RefreshRoutesOnly() (routes, domainlessServers, exemptio
 
 	for _, config := range configs {
 		for _, domain := range config.Domains {
-			domain = strings.TrimPrefix(domain, "~")
-			domain = strings.TrimPrefix(domain, ".")
-			domain = strings.ToLower(domain)
+			domain = normalizeVPNDomain(domain)
 			if domain != "" {
 				m.routes[domain] = append([]string{}, config.Servers...)
 			}
@@ -409,6 +403,14 @@ func (m *vpnDNSManager) VPNDNSReachable() {
 	m.retainedAfterEmptyDiscovery = false
 }
 
+// normalizeVPNDomain accepts OS suffix and Linux routing-domain spellings.
+// The root alone is not a split-DNS route (including the Linux ~. catch-all).
+func normalizeVPNDomain(domain string) string {
+	domain = strings.TrimPrefix(domain, "~")
+	domain = strings.TrimPrefix(domain, ".")
+	return strings.ToLower(strings.TrimSuffix(domain, "."))
+}
+
 // UpstreamForDomain checks if the domain matches any VPN search domain.
 // Returns VPN DNS servers if matched, nil otherwise.
 // Uses suffix matching: "foo.provisur.local" matches "provisur.local"
@@ -424,16 +426,17 @@ func (m *vpnDNSManager) UpstreamForDomain(domain string) []string {
 	domain = strings.TrimSuffix(domain, ".")
 	domain = strings.ToLower(domain)
 
-	// First try exact match
-	if servers, ok := m.routes[domain]; ok {
-		return append([]string{}, servers...) // Return copy to avoid race conditions
-	}
-
-	// Try suffix matching - check if domain ends with any of our VPN domains
-	for vpnDomain, servers := range m.routes {
-		if strings.HasSuffix(domain, "."+vpnDomain) {
-			return append([]string{}, servers...) // Return copy
+	// Walk label boundaries from most to least specific. Map iteration order
+	// must never choose a parent VPN's resolver over a matching child zone.
+	for domain != "" {
+		if servers, ok := m.routes[domain]; ok {
+			return append([]string{}, servers...)
 		}
+		i := strings.IndexByte(domain, '.')
+		if i < 0 {
+			break
+		}
+		domain = domain[i+1:]
 	}
 
 	return nil

cmd/cli/vpn_dns_convergence_test.go

@@ -0,0 +1,135 @@
+package cli
+
+import (
+	"context"
+	"reflect"
+	"sync"
+	"sync/atomic"
+	"testing"
+	"time"
+
+	"github.com/Control-D-Inc/ctrld"
+)
+
+func TestVPNDNSLongestNormalizedSuffixAcrossRefreshes(t *testing.T) {
+	for _, routeOnly := range []bool{false, true} {
+		t.Run(map[bool]string{false: "full", true: "route-only"}[routeOnly], func(t *testing.T) {
+			m := newVPNDNSManager(&mainLog, nil)
+			m.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
+				return []ctrld.VPNDNSConfig{
+					{Domains: []string{".EXAMPLE.com."}, Servers: []string{"10.0.0.1"}},
+					{Domains: []string{"~Child.Example.COM."}, Servers: []string{"10.0.0.2", "10.0.0.3"}},
+					{Domains: []string{".", "~."}, Servers: []string{"10.0.0.4"}},
+				}
+			}
+			if routeOnly {
+				m.RefreshRoutesOnly()
+			} else {
+				m.Refresh(context.Background(), true)
+			}
+			for query, want := range map[string][]string{
+				"example.com.": {"10.0.0.1"}, "other.example.com": {"10.0.0.1"},
+				"child.example.com.":           {"10.0.0.2", "10.0.0.3"},
+				"HOST.Deep.Child.Example.COM.": {"10.0.0.2", "10.0.0.3"},
+				"notexample.com.":              nil, "example.com.other.": nil, "public.test.": nil,
+			} {
+				for i := 0; i < 1000; i++ {
+					if got := m.UpstreamForDomain(query); !reflect.DeepEqual(got, want) {
+						t.Fatalf("%s: got %v want %v", query, got, want)
+					}
+				}
+			}
+			got := m.UpstreamForDomain("child.example.com")
+			got[0] = "mutated"
+			if m.UpstreamForDomain("child.example.com")[0] != "10.0.0.2" {
+				t.Fatal("lookup leaked mutable slice")
+			}
+		})
+	}
+}
+
+// Drive the real poller diff -> journal callback -> manager discovery path.
+// Both OS boundaries are fixtures, so this test cannot touch host DNS or PF.
+func TestVPNDNSJournalLatePublicationConverges(t *testing.T) {
+	m := newVPNDNSManager(&mainLog, nil)
+	var discoveryCalls, updates int
+	var snapshot []ctrld.VPNDNSConfig
+	m.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig { discoveryCalls++; return snapshot }
+	m.onServersChanged = func([]vpnDNSExemption) error { updates++; return nil }
+	p := &prog{vpnDNS: m, csSetDnsDone: make(chan struct{})}
+	p.logger.Store(mainLog.Load())
+	close(p.csSetDnsDone)
+	var table []dnsResolverEntry
+	poller := newDNSConfigPoller(func() ([]dnsResolverEntry, error) { return table, nil })
+	emit := func() { p.logDNSConfigChanges(poller.pollOnce(time.Now())) }
+	emit() // empty startup baseline
+	for _, server := range []string{"10.0.0.1", "10.0.0.2"} {
+		snapshot = []ctrld.VPNDNSConfig{{InterfaceName: "utun-fixture", Domains: []string{"corp.example."}, Servers: []string{server}}}
+		table = []dnsResolverEntry{{Interface: "utun-fixture", Nameservers: []string{server}}}
+		emit()
+		if got := m.UpstreamForDomain("host.corp.example."); len(got) != 1 || got[0] != server {
+			t.Fatalf("late DNS-only change not published: %v", got)
+		}
+		for i := 0; i < 100; i++ {
+			emit()
+		}
+	}
+	if discoveryCalls != 2 || updates != 2 {
+		t.Fatalf("unchanged tables caused refresh storm: discoveries=%d updates=%d", discoveryCalls, updates)
+	}
+	// Removal is a DNS-only delta too; keep Windows' one-empty-snapshot guard.
+	snapshot = nil
+	table = nil
+	emit()
+	if vpnDNSSettlingEnabled { // Preserve Windows' one-empty-snapshot guard.
+		m.Refresh(context.Background(), true)
+	}
+	if got := m.UpstreamForDomain("host.corp.example"); len(got) != 0 {
+		t.Fatalf("removed DNS retained: %v", got)
+	}
+	p.closeNetMonitor()
+}
+
+func TestVPNDNSJournalShutdownDrainsAndRejectsRefresh(t *testing.T) {
+	m := newVPNDNSManager(&mainLog, nil)
+	entered, release := make(chan struct{}), make(chan struct{})
+	var calls, updates atomic.Int32
+	m.discoverVPNDNS = func(context.Context) []ctrld.VPNDNSConfig {
+		calls.Add(1)
+		close(entered)
+		<-release
+		return []ctrld.VPNDNSConfig{{Domains: []string{"corp.example"}, Servers: []string{"10.0.0.1"}}}
+	}
+	m.onServersChanged = func([]vpnDNSExemption) error { updates.Add(1); return nil }
+	p := &prog{vpnDNS: m, csSetDnsDone: make(chan struct{})}
+	p.logger.Store(mainLog.Load())
+	entries := []dnsResolverEntry{{Action: resolverActionChanged}}
+	p.logDNSConfigChanges(entries)
+	if calls.Load() != 0 {
+		t.Fatal("discovery ran before DNS initialization")
+	}
+	close(p.csSetDnsDone)
+	callbackDone := make(chan struct{})
+	go func() { defer close(callbackDone); p.logDNSConfigChanges(entries) }()
+	<-entered
+	stopDone := make(chan struct{})
+	go func() { p.closeNetMonitor(); close(stopDone) }()
+	<-p.networkActivityDone()
+	select {
+	case <-stopDone:
+		t.Fatal("shutdown did not drain in-flight refresh")
+	default:
+	}
+	close(release)
+	<-callbackDone
+	<-stopDone
+	var wg sync.WaitGroup
+	for i := 0; i < 100; i++ {
+		wg.Add(1)
+		go func() { defer wg.Done(); p.logDNSConfigChanges(entries) }()
+	}
+	wg.Wait()
+	if calls.Load() != 1 || updates.Load() != 1 {
+		t.Fatalf("post-stop mutation: discovery=%d updates=%d", calls.Load(), updates.Load())
+	}
+}