state: apply a new pre-auth key's tags on re-registration

Re-registering a tagged node with a different key discarded the new key's
tags and left a stale auth-key reference; retag on key change and persist it.

Fixes #3370

.github/workflows/test-integration.yaml

@@ -352,6 +352,8 @@ jobs:
           - TestTagsAuthKeyWithTagCannotAddViaCLI
           - TestTagsAuthKeyWithTagCannotChangeViaCLI
           - TestTagsAuthKeyWithTagAdminOverrideReauthPreserves
+          - TestTagsReauthDifferentKeyRetagsNode
+          - TestTagsReauthDifferentKeyRemovesTag
           - TestTagsAuthKeyWithTagCLICannotModifyAdminTags
           - TestTagsAuthKeyWithoutTagCannotRequestTags
           - TestTagsAuthKeyWithoutTagRegisterNoTags

CHANGELOG.md

@@ -52,6 +52,7 @@ keys remain all-access.
 ### Changes
 
 - Fix tagged node stuck expired after `tailscale logout`, unable to re-authenticate [#3394](https://github.com/juanfont/headscale/pull/3394)
+- Re-registering a tagged node with a different pre-auth key now applies the new key's tags instead of silently keeping the old ones [#3394](https://github.com/juanfont/headscale/pull/3394)
 
 ## 0.29.2 (2026-07-01)
 

hscontrol/state/auth_tagged_expiry_test.go

@@ -553,6 +553,558 @@ func TestIssue3371_TaggedNodePastExpirySelfHealsOnReregister(t *testing.T) {
 	require.Equal(t, nodeID, healed.ID(), "must be the same node")
 }
 
+// TestIssue3371_ExpiredTaggedNodeSameSpentKeyNotRevalidated is the gating test
+// for the isExpired-gate exclusion (state.go: `&& !existingNodeSameUser.IsTagged()`).
+// A tagged node carrying a stale PAST expiry, re-registering with the SAME
+// single-use key and the SAME node key (no rotation), must take the
+// skip-validation fast path — otherwise the spent key is re-validated and
+// rejected with "authkey already used", the exact lockout #3371 fixes. Without
+// the tagged exclusion this fails; with it the node self-heals. The neighbours
+// all rotate the node key or use a reusable key, so validation runs regardless
+// and none probes this fast-path exclusion.
+func TestIssue3371_ExpiredTaggedNodeSameSpentKeyNotRevalidated(t *testing.T) {
+	s := newRetagTestState(t)
+
+	// Single-use tagged key.
+	pak, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:foo"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: pak.Key},
+		NodeKey:  nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "spent-tagged"},
+	}
+	node, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+	require.True(t, node.IsTagged())
+
+	// Stale past (logout) expiry, and the single-use key is now spent.
+	past := time.Now().Add(-1 * time.Hour)
+	_, ok := s.nodeStore.UpdateNode(node.ID(), func(n *types.Node) {
+		n.Expiry = &past
+	})
+	require.True(t, ok)
+
+	// Re-register with the SAME key and the SAME node key (no rotation). The
+	// tagged exclusion from the isExpired gate must let this skip validation, so
+	// the spent single-use key is not rejected.
+	healed, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err,
+		"a tagged node with a stale past expiry must skip re-validation of its spent key")
+	require.False(t, healed.IsExpired(), "stale expiry cleared")
+	require.Nil(t, healed.AsStruct().Expiry, "tagged node key-expiry disabled")
+	require.Equal(t, node.ID(), healed.ID())
+}
+
+// TestTaggedPAKReauthRetagsExistingTaggedNode reproduces issue #3370: an
+// already-tagged node re-authenticating with a *fresh, valid* tagged pre-auth
+// key carrying *different* tags has that key validated and consumed, but its
+// tags are silently discarded — the node keeps its old tags.
+//
+// Root cause: the in-place re-registration path in HandleNodeFromPreAuthKey
+// only applies a key's tags when a tagged key converts a user-owned node
+// (`pak.IsTagged() && !node.IsTagged()`). An already-tagged node fails
+// `!node.IsTagged()`, so a differently-tagged key leaves the tags unchanged —
+// while the single-use key is still marked used below (hsdb.UsePreAuthKey).
+//
+// Tagged-PAK tags are authorised by possession of the key (only syntactic
+// `tag:` validation at creation; no tagOwners policy is required — the bug
+// reproduces with an empty policy). Re-keying is Tailscale's documented method
+// for changing an auth-key device's tags, so a fresh key's tags must be
+// applied on re-registration.
+//
+// https://github.com/juanfont/headscale/issues/3370
+func TestTaggedPAKReauthRetagsExistingTaggedNode(t *testing.T) {
+	dbPath := t.TempDir() + "/headscale.db"
+	cfg := persistTestConfig(dbPath)
+
+	s, err := NewState(cfg)
+	require.NoError(t, err)
+	t.Cleanup(func() { _ = s.Close() })
+
+	// Empty policy: tagged-PAK tags need no tagOwners entry (issue reproduces
+	// with a completely empty policy).
+
+	// KEY1: single-use tags-only key carrying tag:tag1.
+	key1, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag1"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: key1.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "retag-node"},
+	}
+
+	// Initial registration: node comes up tagged tag:tag1.
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+	require.True(t, first.IsTagged(), "precondition: node registered tagged")
+	require.Equal(t, []string{"tag:tag1"}, first.Tags().AsSlice())
+	nodeID := first.ID()
+	firstIPv4 := first.IPv4()
+	firstIPv6 := first.IPv6()
+
+	// KEY2: fresh single-use tags-only key carrying tag:tag2.
+	key2, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag2"})
+	require.NoError(t, err)
+
+	// `tailscale up --force-reauth --auth-key KEY2`: same machine, rotated node
+	// key, fresh valid key. This validates and consumes KEY2.
+	reReg := regReq
+	reReg.Auth = &tailcfg.RegisterResponseAuth{AuthKey: key2.Key}
+	reReg.NodeKey = key.NewNode().Public()
+
+	second, _, err := s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, nodeID, second.ID(), "must update in place, not duplicate")
+	require.Equal(t, 1, s.ListNodes().Len(), "machine must map to exactly one node")
+	require.True(t, second.IsTagged(), "node must remain tagged")
+
+	// KEY2 was validated and consumed regardless of the outcome.
+	consumed, err := s.GetPreAuthKeyByID(key2.ID)
+	require.NoError(t, err)
+	require.True(t, consumed.Used, "single-use key was consumed by the re-auth")
+
+	// The consumed key's tags must be applied: re-keying retags the device
+	// (Tailscale's documented behaviour). This is the assertion that fails
+	// before the fix — the node keeps ["tag:tag1"].
+	require.Equal(t, []string{"tag:tag2"}, second.Tags().AsSlice(),
+		"re-authenticating with a differently-tagged key must retag the node, "+
+			"not silently discard the tags of the consumed key")
+
+	// Identity continuity: the reporter stresses "same node, same IP". The
+	// re-auth updates in place, so the machine key and both Tailscale IPs are
+	// preserved while the node key rotates. A retag must not re-allocate IPs or
+	// duplicate the node.
+	require.Equal(t, machineKey.Public(), second.MachineKey(),
+		"machine key is the stable identity across re-auth")
+	require.Equal(t, firstIPv4, second.IPv4(), "IPv4 preserved across retag")
+	require.Equal(t, firstIPv6, second.IPv6(), "IPv6 preserved across retag")
+	require.NotEqual(t, first.NodeKey(), second.NodeKey(),
+		"--force-reauth rotates the node key")
+
+	// A retagged node stays a tagged node: user-less and key-expiry disabled.
+	require.Nil(t, second.AsStruct().Expiry, "tagged node keeps nil key expiry")
+}
+
+// TestTaggedPAKReauthSameKeyPreservesTags is the counterpart constraint to
+// #3370: re-authenticating with the *same* tagged key must NOT clobber the
+// node's current tags, even after an admin retagged it via
+// `headscale nodes tag`. This is the unit-level guard for the integration
+// test TestTagsAuthKeyWithTagAdminOverrideReauthPreserves (admin decisions are
+// authoritative), and it is why the retag discriminator must key on the
+// pre-auth key's *identity* (a different key) rather than on "validation ran"
+// (a --force-reauth with the same key also runs validation). This test passes
+// today and must keep passing after the #3370 fix.
+func TestTaggedPAKReauthSameKeyPreservesTags(t *testing.T) {
+	dbPath := t.TempDir() + "/headscale.db"
+	cfg := persistTestConfig(dbPath)
+
+	s, err := NewState(cfg)
+	require.NoError(t, err)
+	t.Cleanup(func() { _ = s.Close() })
+
+	// tag:admin must be permitted for the admin SetNodeTags call.
+	_, err = s.SetPolicy([]byte(`{"tagOwners":{"tag:admin":["admin@"]}}`))
+	require.NoError(t, err)
+
+	// Reusable tagged key (the shape used by the admin-override integration
+	// test) so the same key can be presented twice.
+	pak, err := s.CreatePreAuthKey(nil, true, false, nil, []string{"tag:orig"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: pak.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "sticky-node"},
+	}
+
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, []string{"tag:orig"}, first.Tags().AsSlice())
+	nodeID := first.ID()
+
+	// Admin retags the node out-of-band.
+	tagged, _, err := s.SetNodeTags(nodeID, []string{"tag:admin"})
+	require.NoError(t, err)
+	require.Equal(t, []string{"tag:admin"}, tagged.Tags().AsSlice())
+
+	// `--force-reauth` with the SAME key: rotate the node key so validation
+	// runs, exactly like the client does.
+	reReg := regReq
+	reReg.NodeKey = key.NewNode().Public()
+
+	second, _, err := s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, nodeID, second.ID())
+	require.Equal(t, []string{"tag:admin"}, second.Tags().AsSlice(),
+		"re-authenticating with the same key must preserve the admin-assigned tags")
+}
+
+// TestTaggedPAKReauthSpentKeySameNodeKeyRejected pins the authorization boundary
+// the retag must respect: presenting a *spent* single-use tagged key to retag an
+// already-tagged node must be rejected, even when the client reuses its node key
+// (the skip-validation fast path). Without forcing validation on a retag, a
+// used/revoked/expired tagged credential could still apply its tags — replaying
+// a dead key to escalate a machine onto a tag, and defeating key revocation. The
+// existing isExpired comment already declares the boundary "must not depend on
+// the client rotating its key"; retag must honour the same rule.
+func TestTaggedPAKReauthSpentKeySameNodeKeyRejected(t *testing.T) {
+	s := newRetagTestState(t)
+
+	// KEY1: single-use tag:tag1, used to register.
+	key1, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag1"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: key1.Key},
+		NodeKey:  nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "retag-node"},
+	}
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, []string{"tag:tag1"}, first.Tags().AsSlice())
+
+	// KEY2: single-use tag:tag2, spent elsewhere so it is already Used.
+	key2, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag2"})
+	require.NoError(t, err)
+	_, _, err = s.HandleNodeFromPreAuthKey(tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: key2.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "other-node"},
+	}, key.NewMachine().Public())
+	require.NoError(t, err)
+
+	// Re-register the FIRST node with the now-spent KEY2, REUSING its node key
+	// (no rotation) so it targets the skip-validation fast path. A spent key must
+	// be rejected, and the node's tags must be unchanged.
+	reReg := regReq
+	reReg.Auth = &tailcfg.RegisterResponseAuth{AuthKey: key2.Key}
+	// reReg.NodeKey stays nodeKey (same) -> fast path.
+
+	_, _, err = s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.Error(t, err, "a spent tagged key must not be able to retag on the fast path")
+	require.Contains(t, err.Error(), "authkey already used")
+
+	after, ok := s.GetNodeByID(first.ID())
+	require.True(t, ok)
+	require.Equal(t, []string{"tag:tag1"}, after.Tags().AsSlice(),
+		"a rejected spent key must not have applied its tags")
+}
+
+// retagReauthCase drives the #3370 retag scenario with configurable key shapes
+// so the sibling cases below stay a few lines each. It registers a node with
+// key1, then re-registers the same machine with key2, and returns the
+// re-registered node. rotateNodeKey mirrors --force-reauth (the client rotates
+// its node key); when false the client reuses its node key.
+func retagReauthCase(
+	t *testing.T,
+	s *State,
+	key1Tags, key2Tags []string,
+	key1User, key2User *types.UserID,
+	reusable, rotateNodeKey bool,
+) (types.NodeView, types.NodeView) {
+	t.Helper()
+
+	key1, err := s.CreatePreAuthKey(key1User, reusable, false, nil, key1Tags)
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	nodeKey := key.NewNode()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: key1.Key},
+		NodeKey:  nodeKey.Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "retag-node"},
+	}
+
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+
+	key2, err := s.CreatePreAuthKey(key2User, reusable, false, nil, key2Tags)
+	require.NoError(t, err)
+
+	reReg := regReq
+
+	reReg.Auth = &tailcfg.RegisterResponseAuth{AuthKey: key2.Key}
+	if rotateNodeKey {
+		reReg.NodeKey = key.NewNode().Public()
+	}
+
+	second, _, err := s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, first.ID(), second.ID(), "must update in place, not duplicate")
+
+	return first, second
+}
+
+// TestTaggedPAKReauthReusableKeyRetags: a *reusable* differently-tagged key
+// must retag too. The retag must key on key identity, not on the single-use
+// `Used` flag, so it cannot be coupled to single-use semantics.
+func TestTaggedPAKReauthReusableKeyRetags(t *testing.T) {
+	s := newRetagTestState(t)
+	_, second := retagReauthCase(t, s,
+		[]string{"tag:tag1"}, []string{"tag:tag2"}, nil, nil, true /*reusable*/, true)
+	require.Equal(t, []string{"tag:tag2"}, second.Tags().AsSlice())
+}
+
+// TestTaggedPAKReauthDifferentKeySameNodeKey: retag must fire even when the
+// client reuses its node key (no rotation). The trigger is key identity,
+// decoupled from NodeKey rotation.
+func TestTaggedPAKReauthDifferentKeySameNodeKey(t *testing.T) {
+	s := newRetagTestState(t)
+	_, second := retagReauthCase(t, s,
+		[]string{"tag:tag1"}, []string{"tag:tag2"}, nil, nil, false, false /*same node key*/)
+	require.Equal(t, []string{"tag:tag2"}, second.Tags().AsSlice())
+}
+
+// TestTaggedPAKReauthSameSingleUseKeySameNodeKeyPreservesTags guards the #2830
+// container-restart permutation for a tags-only single-use key: presenting the
+// SAME (already-used) single-use key with the SAME node key must take the
+// skip-validation fast path, succeed, and keep the node's tags — not reject
+// with "authkey already used" and not spuriously retag. This confirms the
+// keyChanged/isRetag additions never fire for a same-key restart, the exact
+// property #2830/#3312 depend on. (The existing #3312 test uses a user-owned
+// one-shot key; this covers the tags-only single-use key.)
+func TestTaggedPAKReauthSameSingleUseKeySameNodeKeyPreservesTags(t *testing.T) {
+	s := newRetagTestState(t)
+
+	pak, err := s.CreatePreAuthKey(nil, false /*single-use*/, false, nil, []string{"tag:tag1"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: pak.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "restart-node"},
+	}
+
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, []string{"tag:tag1"}, first.Tags().AsSlice())
+
+	// Container restart: same key, same node key, same machine. The single-use
+	// key is already consumed, so re-validation would reject it.
+	second, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err,
+		"same-key restart of a tagged node must skip validation, not reject a spent single-use key")
+	require.Equal(t, first.ID(), second.ID(), "must update in place")
+	require.Equal(t, []string{"tag:tag1"}, second.Tags().AsSlice(),
+		"same-key restart must preserve tags (no spurious retag)")
+	require.Equal(t, 1, s.ListNodes().Len(), "no duplicate node")
+}
+
+// TestTaggedPAKReauthUserScopedKeyRetags: a user-scoped tagged key
+// (User != nil, the `headscale preauthkeys create -u <user> --tags` shape)
+// exercises the pak.User != nil branch of findExistingNodeForPAK, a different
+// lookup path from tags-only keys. It must still retag.
+func TestTaggedPAKReauthUserScopedKeyRetags(t *testing.T) {
+	s := newRetagTestState(t)
+	user := s.CreateUserForTest("owner")
+	uid := user.TypedID()
+	_, second := retagReauthCase(t, s,
+		[]string{"tag:tag1"}, []string{"tag:tag2"}, uid, uid, false, true)
+	require.Equal(t, []string{"tag:tag2"}, second.Tags().AsSlice())
+	require.True(t, second.IsTagged())
+}
+
+// TestTaggedPAKReauthReplacesNotMerges pins the Tailscale KB 1068 rule that
+// re-keying *replaces* the tag set (it does not union). Re-keying a
+// {tag1,tag2} node with a {tag1} key must drop tag2.
+func TestTaggedPAKReauthReplacesNotMerges(t *testing.T) {
+	s := newRetagTestState(t)
+	_, second := retagReauthCase(t, s,
+		[]string{"tag:tag1", "tag:tag2"}, []string{"tag:tag1"}, nil, nil, false, true)
+	require.Equal(t, []string{"tag:tag1"}, second.Tags().AsSlice(),
+		"re-keying replaces the tag set; tag:tag2 must be removed, not merged")
+}
+
+// TestExpiredTaggedNodeReauthRetags: a tagged node that looks expired (a stale
+// logout stamp — see #3371) re-authenticating with a fresh differently-tagged
+// key must still retag. Combines the isExpired validation path with the retag.
+func TestExpiredTaggedNodeReauthRetags(t *testing.T) {
+	s := newRetagTestState(t)
+
+	key1, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag1"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: key1.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "retag-node"},
+	}
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+
+	// Force a stale past expiry onto the tagged node.
+	past := time.Now().Add(-1 * time.Hour)
+	_, ok := s.nodeStore.UpdateNode(first.ID(), func(n *types.Node) {
+		n.Expiry = &past
+	})
+	require.True(t, ok)
+
+	key2, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag2"})
+	require.NoError(t, err)
+
+	reReg := regReq
+	reReg.Auth = &tailcfg.RegisterResponseAuth{AuthKey: key2.Key}
+	reReg.NodeKey = key.NewNode().Public()
+
+	second, _, err := s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, []string{"tag:tag2"}, second.Tags().AsSlice(),
+		"an expired (stale logout stamp) tagged node must retag on fresh-key re-auth")
+	require.Nil(t, second.AsStruct().Expiry,
+		"retag must clear a stale expiry: the node is tagged and tagged nodes never expire")
+	require.False(t, second.IsExpired(),
+		"a retagged node must not remain expired")
+}
+
+// TestTaggedPAKReauthRetagPreservesFutureAdminExpiry pins the composition
+// decision between #3370 (retag) and #3371 (never wrongly expire a tagged
+// node): a deliberate FUTURE expiry set by an admin via `headscale nodes expire`
+// is a node property, not tied to the auth key, so re-keying an already-tagged
+// node with a different key must retag it WITHOUT wiping that future expiry.
+// Only a stale PAST expiry is cleared (see TestExpiredTaggedNodeReauthRetags).
+// Symmetric with the same-key relogin path.
+func TestTaggedPAKReauthRetagPreservesFutureAdminExpiry(t *testing.T) {
+	s := newRetagTestState(t)
+
+	key1, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag1"})
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: key1.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "retag-node"},
+	}
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+
+	// Admin sets a deliberate future expiry on the tagged node
+	// (`headscale nodes expire`), which SetNodeExpiry permits.
+	future := time.Now().Add(30 * 24 * time.Hour)
+	_, _, err = s.SetNodeExpiry(first.ID(), &future)
+	require.NoError(t, err)
+
+	// Re-key with a different tagged key.
+	key2, err := s.CreatePreAuthKey(nil, false, false, nil, []string{"tag:tag2"})
+	require.NoError(t, err)
+
+	reReg := regReq
+	reReg.Auth = &tailcfg.RegisterResponseAuth{AuthKey: key2.Key}
+	reReg.NodeKey = key.NewNode().Public()
+
+	second, _, err := s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, []string{"tag:tag2"}, second.Tags().AsSlice(), "node retags")
+	require.NotNil(t, second.AsStruct().Expiry,
+		"a deliberate future admin expiry must survive a different-key retag")
+	require.Equal(t, future.Unix(), second.AsStruct().Expiry.Unix(),
+		"the admin expiry value must be unchanged")
+}
+
+// newRetagTestState builds a State with an empty policy (tagged-PAK tags need
+// no tagOwners entry).
+func newRetagTestState(t *testing.T) *State {
+	t.Helper()
+
+	cfg := persistTestConfig(t.TempDir() + "/headscale.db")
+	s, err := NewState(cfg)
+	require.NoError(t, err)
+	t.Cleanup(func() { _ = s.Close() })
+
+	return s
+}
+
+// TestPreAuthKeyReauthPersistsAuthKeyID pins the root cause behind the
+// ephemeral-flag revert bug found while auditing #3370: on re-registration
+// with a *different* key, HandleNodeFromPreAuthKey updates node.AuthKeyID in
+// the NodeStore (state.go, in the in-place closure) but AuthKeyID is excluded
+// from nodeUpdateColumns (added for #2862 to avoid persisting a *deleted* key's
+// stale reference on MapRequest). The exclusion is correct for MapRequest, but
+// on the re-registration path the presented key is freshly loaded and valid, so
+// the new auth_key_id must be persisted. Otherwise a control-plane restart
+// reloads the OLD key, and any key-scoped property (notably Ephemeral) silently
+// reverts — an ephemeral->non-ephemeral re-auth leaves a node that looks
+// persistent in memory but is ephemeral again after restart and can be GC'd.
+//
+// Drives the real handler twice, then reopens the DB to prove the association
+// survives the reload.
+func TestPreAuthKeyReauthPersistsAuthKeyID(t *testing.T) {
+	dbPath := t.TempDir() + "/headscale.db"
+	cfg := persistTestConfig(dbPath)
+
+	s, err := NewState(cfg)
+	require.NoError(t, err)
+
+	user := s.CreateUserForTest("rekey-user")
+
+	// KEY A: ephemeral, single-use.
+	keyA, err := s.CreatePreAuthKey(user.TypedID(), false, true /*ephemeral*/, nil, nil)
+	require.NoError(t, err)
+
+	machineKey := key.NewMachine()
+	regReq := tailcfg.RegisterRequest{
+		Auth:     &tailcfg.RegisterResponseAuth{AuthKey: keyA.Key},
+		NodeKey:  key.NewNode().Public(),
+		Hostinfo: &tailcfg.Hostinfo{Hostname: "rekey-node"},
+		Expiry:   time.Now().Add(24 * time.Hour),
+	}
+
+	first, _, err := s.HandleNodeFromPreAuthKey(regReq, machineKey.Public())
+	require.NoError(t, err)
+
+	nodeID := first.ID()
+	require.True(t, first.IsEphemeral(), "precondition: registered with an ephemeral key")
+
+	// KEY B: non-ephemeral, single-use, same user. `--force-reauth` rotates the
+	// node key so this is a genuine re-registration that consumes KEY B.
+	keyB, err := s.CreatePreAuthKey(user.TypedID(), false, false /*non-ephemeral*/, nil, nil)
+	require.NoError(t, err)
+
+	reReg := regReq
+	reReg.Auth = &tailcfg.RegisterResponseAuth{AuthKey: keyB.Key}
+	reReg.NodeKey = key.NewNode().Public()
+
+	second, _, err := s.HandleNodeFromPreAuthKey(reReg, machineKey.Public())
+	require.NoError(t, err)
+	require.Equal(t, nodeID, second.ID(), "must update in place")
+
+	// In-memory, the node now tracks KEY B (non-ephemeral).
+	require.NotNil(t, second.AuthKeyID().Get())
+	require.Equal(t, keyB.ID, second.AuthKeyID().Get(),
+		"NodeStore must reference the key just used to re-authenticate")
+	require.False(t, second.IsEphemeral(),
+		"re-auth with a non-ephemeral key must make the node non-ephemeral")
+
+	// Restart the control plane: reload state from the database only.
+	require.NoError(t, s.Close())
+
+	s2, err := NewState(cfg)
+	require.NoError(t, err)
+	t.Cleanup(func() { _ = s2.Close() })
+
+	reloaded, ok := s2.GetNodeByID(nodeID)
+	require.True(t, ok, "node must reload from DB after restart")
+
+	// This is the assertion that fails today: auth_key_id was never persisted on
+	// re-registration, so the reload resurrects KEY A and the node is ephemeral
+	// again — at risk of GC on the next disconnect.
+	require.NotNil(t, reloaded.AuthKeyID().Get())
+	require.Equal(t, keyB.ID, reloaded.AuthKeyID().Get(),
+		"auth_key_id must persist across restart, not revert to the old key")
+	require.False(t, reloaded.IsEphemeral(),
+		"ephemerality must not silently revert after a control-plane restart")
+}
+
 // TestTaggedNodeCanHaveKeyExpiry matches Tailscale: a tagged node has key
 // expiry disabled by default, but it can still be set explicitly (e.g. via
 // `headscale nodes expire`).

hscontrol/state/state.go

@@ -2443,7 +2443,17 @@ func (s *State) HandleNodeFromPreAuthKey(
 	isOwnershipConversion := existsSameUser && existingNodeSameUser.Valid() &&
 		pak.IsTagged() && !existingNodeSameUser.IsTagged()
 
-	if isExistingNodeReregistering && !isNodeKeyRotation && !isExpired && !isOwnershipConversion {
+	// A tagged key that differs from the one the node last authed with retags
+	// the node (see the in-place update below). Applying a key's tags is an
+	// authorisation decision, so the key must be validated rather than ride the
+	// skip-validation fast-path; otherwise a spent, revoked or expired tagged
+	// key could still retag a node that reuses its node key. Like isExpired,
+	// this boundary must not depend on the client rotating its key.
+	isRetag := existsSameUser && existingNodeSameUser.Valid() &&
+		pak.IsTagged() && existingNodeSameUser.IsTagged() &&
+		(!existingNodeSameUser.AuthKeyID().Valid() || existingNodeSameUser.AuthKeyID().Get() != pak.ID)
+
+	if isExistingNodeReregistering && !isNodeKeyRotation && !isExpired && !isOwnershipConversion && !isRetag {
 		// Existing, still-valid node re-registering with same NodeKey: skip
 		// validation. Pre-auth keys are only needed for initial authentication.
 		// Critical for containers that run "tailscale up --authkey=KEY" on every
@@ -2491,8 +2501,10 @@ func (s *State) HandleNodeFromPreAuthKey(
 
 	var finalNode types.NodeView
 
-	// If this node exists for this user, update the node in place.
-	// Note: For tags-only keys (pak.User == nil), existsSameUser is always false.
+	// If this node exists for this user, update the node in place. For a
+	// tags-only key (pak.User == nil) this is true when the machine already has
+	// a tagged node (findExistingNodeForPAK matches it under UserID 0); for a
+	// user-owned key it is true when the same user already has the node.
 	if existsSameUser && existingNodeSameUser.Valid() {
 		log.Trace().
 			Caller().
@@ -2534,17 +2546,37 @@ func (s *State) HandleNodeFromPreAuthKey(
 
 			node.RegisterMethod = util.RegisterMethodAuthKey
 
-			// Tags from PreAuthKey are only applied during initial registration.
-			// On re-registration the node keeps its existing tags and ownership,
-			// except when a tagged key converts a user-owned node: that adopts
-			// the key's tags and drops user ownership (tagged nodes are
-			// user-less and never expire). Only update AuthKey reference
-			// otherwise.
-			if pak.IsTagged() && !node.IsTagged() {
+			// Tags from a PreAuthKey are applied on initial registration and
+			// re-applied whenever a *different* key is presented on
+			// re-registration: re-keying is Tailscale's documented way to change
+			// an auth-key device's tags (KB 1068 - "generate a new auth key with
+			// the new set of tags ... doing so replaces the device's existing
+			// tags"). Presenting the SAME key again (container restart,
+			// #2830/#3312) preserves the node's current tags and any admin
+			// override. A tagged key presented for a user-owned node also converts
+			// it, dropping user ownership.
+			//
+			// node.AuthKeyID still holds the prior key's ID here (it is reassigned
+			// below), and SetNodeTags leaves AuthKeyID intact, so an admin retag
+			// cannot masquerade as a new key.
+			keyChanged := node.AuthKeyID == nil || *node.AuthKeyID != pak.ID
+			if pak.IsTagged() && (!node.IsTagged() || keyChanged) {
+				wasUserOwned := !node.IsTagged()
+
 				node.Tags = pak.Tags
 				node.UserID = nil
 				node.User = nil
-				node.Expiry = nil
+
+				// Converting a user-owned node to tagged drops the user's key
+				// expiry (tagged nodes never expire). But retagging an
+				// already-tagged node must preserve a deliberate FUTURE expiry
+				// set via `headscale nodes expire` - that is a node property, not
+				// tied to the auth key - and only clear a stale PAST expiry. This
+				// keeps the retag path symmetric with the same-key relogin path
+				// (#3371) rather than silently overriding an admin decision.
+				if wasUserOwned || node.IsExpired() {
+					node.Expiry = nil
+				}
 			}
 
 			node.AuthKey = pak
@@ -2586,8 +2618,14 @@ func (s *State) HandleNodeFromPreAuthKey(
 
 		_, err = hsdb.Write(s.db.DB, func(tx *gorm.DB) (*types.Node, error) {
 			// Explicitly select all node columns so GORM includes nil/zero-value fields
-			// (see nodeUpdateColumns comment).
-			err := tx.Select(nodeUpdateColumns).Updates(updatedNodeView.AsStruct()).Error
+			// (see nodeUpdateColumns comment). AuthKeyID is normally excluded to
+			// avoid persisting a deleted key's stale reference on MapRequest
+			// (#2862), but re-registration presents a freshly-validated key, so
+			// its ID must be persisted here — otherwise a restart reloads the old
+			// key and any key-scoped property (e.g. Ephemeral) silently reverts.
+			reregColumns := append(slices.Clone(nodeUpdateColumns), "AuthKeyID")
+
+			err := tx.Select(reregColumns).Updates(updatedNodeView.AsStruct()).Error
 			if err != nil {
 				return nil, fmt.Errorf("saving node: %w", err)
 			}

integration/tags_test.go

@@ -579,6 +579,213 @@ func TestTagsAuthKeyWithTagAdminOverrideReauthPreserves(t *testing.T) {
 	t.Logf("Test 2.5 PASS: Admin tags preserved through reauth (admin decisions are authoritative)")
 }
 
+// TestTagsReauthDifferentKeyRetagsNode reproduces issue #3370 end-to-end with a
+// real tailscale client: a node registered with a single-use tag:valid-owned
+// key is re-authenticated via `tailscale up --force-reauth` with a *fresh*
+// single-use tag:second key. Tailscale's documented behaviour (KB 1068) is that
+// re-keying replaces the device's tags, verified by the reporter against SaaS on
+// the same node/IP. Before the fix headscale consumes the new key but keeps the
+// old tag; after the fix the node retags in place.
+//
+// Unlike Test 2.5 (same reusable key + admin override -> tags preserved), this
+// presents a *different* key, so it exercises the opposite arm of the retag
+// discriminator. It also asserts what a state-unit test cannot: the new tag
+// propagates to the node's own Self view and netmap, and the node ID and IPs are
+// unchanged.
+//
+// https://github.com/juanfont/headscale/issues/3370
+func TestTagsReauthDifferentKeyRetagsNode(t *testing.T) {
+	IntegrationSkip(t)
+
+	spec := ScenarioSpec{
+		NodesPerUser: 0,
+		Users:        []string{tagTestUser},
+	}
+
+	scenario, err := NewScenario(spec)
+
+	require.NoError(t, err)
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	err = scenario.CreateHeadscaleEnv(
+		[]tsic.Option{},
+		hsic.WithACLPolicy(tagsTestPolicy()),
+		hsic.WithTestName("tags-rekey-retag"),
+	)
+	requireNoErrHeadscaleEnv(t, err)
+
+	headscale, err := scenario.Headscale()
+	requireNoErrGetHeadscale(t, err)
+
+	userMap, err := headscale.MapUsers()
+	require.NoError(t, err)
+
+	userID := mustParseID(userMap[tagTestUser].Id)
+
+	// KEY1: single-use tag:valid-owned.
+	key1, err := scenario.CreatePreAuthKeyWithTags(userID, false, false, []string{"tag:valid-owned"})
+	require.NoError(t, err)
+
+	client, err := scenario.CreateTailscaleNode(
+		"head",
+		tsic.WithNetwork(scenario.networks[scenario.testDefaultNetwork]),
+	)
+	require.NoError(t, err)
+
+	err = client.Login(headscale.GetEndpoint(), key1.Key)
+	require.NoError(t, err)
+
+	var (
+		initialNodeID uint64
+		initialIPs    []string
+	)
+
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		nodes, err := headscale.ListNodes()
+		assert.NoError(c, err)
+		assert.Len(c, nodes, 1)
+
+		if len(nodes) == 1 {
+			initialNodeID = mustParseID(nodes[0].Id)
+			initialIPs = nodes[0].IpAddresses
+			assertNodeHasTagsWithCollect(c, nodes[0], []string{"tag:valid-owned"})
+		}
+	}, integrationutil.StatusReadyTimeout, integrationutil.SlowPoll, "waiting for initial registration")
+
+	t.Logf("Step 1: node %d registered with tag:valid-owned, IPs %v", initialNodeID, initialIPs)
+
+	// KEY2: fresh single-use tag:second. Re-key via --force-reauth.
+	key2, err := scenario.CreatePreAuthKeyWithTags(userID, false, false, []string{"tag:second"})
+	require.NoError(t, err)
+
+	//nolint:errcheck // result is verified via EventuallyWithT below
+	client.Execute([]string{
+		"tailscale", "up",
+		"--login-server=" + headscale.GetEndpoint(),
+		"--hostname=" + client.Hostname(),
+		"--authkey=" + key2.Key,
+		"--force-reauth",
+	})
+
+	// Server-side: node retagged in place, same node ID and IPs, no duplicate.
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		nodes, err := headscale.ListNodes()
+		assert.NoError(c, err)
+		assert.Len(c, nodes, 1, "must not duplicate the node")
+
+		if len(nodes) == 1 {
+			assertNodeHasTagsWithCollect(c, nodes[0], []string{"tag:second"})
+			assert.Equal(c, initialNodeID, mustParseID(nodes[0].Id), "node ID must be unchanged")
+			assert.ElementsMatch(c, initialIPs, nodes[0].IpAddresses, "IPs must be preserved")
+		}
+	}, integrationutil.ScaledTimeout(20*time.Second), integrationutil.SlowPoll, "server must reflect the retag")
+
+	// Node self view: the new tag propagates to the client (issue #2978 surface).
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		assertNodeSelfHasTagsWithCollect(c, client, []string{"tag:second"})
+	}, integrationutil.StatusReadyTimeout, integrationutil.SlowPoll, "node self view must reflect the retag")
+
+	// Netmap: independent serialization surface.
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		assertNetmapSelfHasTagsWithCollect(c, client, []string{"tag:second"})
+	}, integrationutil.StatusReadyTimeout, integrationutil.SlowPoll, "netmap self must reflect the retag")
+
+	t.Logf("Test #3370 PASS: re-keying with a different tagged key retagged the node in place")
+}
+
+// TestTagsReauthDifferentKeyRemovesTag is the sharpest proof of the KB 1068
+// "replaces, not merges" rule at the integration level: a node registered with
+// a two-tag key is re-keyed with a single-tag key, and the second tag must be
+// *removed*, not retained. Tag removal is the highest-risk propagation path
+// (peers must stop seeing the removed tag), so it is worth a real-client test.
+//
+// https://github.com/juanfont/headscale/issues/3370
+func TestTagsReauthDifferentKeyRemovesTag(t *testing.T) {
+	IntegrationSkip(t)
+
+	spec := ScenarioSpec{
+		NodesPerUser: 0,
+		Users:        []string{tagTestUser},
+	}
+
+	scenario, err := NewScenario(spec)
+
+	require.NoError(t, err)
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	err = scenario.CreateHeadscaleEnv(
+		[]tsic.Option{},
+		hsic.WithACLPolicy(tagsTestPolicy()),
+		hsic.WithTestName("tags-rekey-remove"),
+	)
+	requireNoErrHeadscaleEnv(t, err)
+
+	headscale, err := scenario.Headscale()
+	requireNoErrGetHeadscale(t, err)
+
+	userMap, err := headscale.MapUsers()
+	require.NoError(t, err)
+
+	userID := mustParseID(userMap[tagTestUser].Id)
+
+	// KEY1: single-use with BOTH tags.
+	key1, err := scenario.CreatePreAuthKeyWithTags(userID, false, false, []string{"tag:valid-owned", "tag:second"})
+	require.NoError(t, err)
+
+	client, err := scenario.CreateTailscaleNode(
+		"head",
+		tsic.WithNetwork(scenario.networks[scenario.testDefaultNetwork]),
+	)
+	require.NoError(t, err)
+
+	err = client.Login(headscale.GetEndpoint(), key1.Key)
+	require.NoError(t, err)
+
+	var initialNodeID uint64
+
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		nodes, err := headscale.ListNodes()
+		assert.NoError(c, err)
+		assert.Len(c, nodes, 1)
+
+		if len(nodes) == 1 {
+			initialNodeID = mustParseID(nodes[0].Id)
+			assertNodeHasTagsWithCollect(c, nodes[0], []string{"tag:second", "tag:valid-owned"})
+		}
+	}, integrationutil.StatusReadyTimeout, integrationutil.SlowPoll, "waiting for initial registration")
+
+	// KEY2: fresh single-use with ONLY tag:valid-owned. Re-key.
+	key2, err := scenario.CreatePreAuthKeyWithTags(userID, false, false, []string{"tag:valid-owned"})
+	require.NoError(t, err)
+
+	//nolint:errcheck // result is verified via EventuallyWithT below
+	client.Execute([]string{
+		"tailscale", "up",
+		"--login-server=" + headscale.GetEndpoint(),
+		"--hostname=" + client.Hostname(),
+		"--authkey=" + key2.Key,
+		"--force-reauth",
+	})
+
+	// tag:second must be gone on every surface.
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		nodes, err := headscale.ListNodes()
+		assert.NoError(c, err)
+		assert.Len(c, nodes, 1)
+
+		if len(nodes) == 1 {
+			assertNodeHasTagsWithCollect(c, nodes[0], []string{"tag:valid-owned"})
+			assert.Equal(c, initialNodeID, mustParseID(nodes[0].Id))
+		}
+	}, integrationutil.ScaledTimeout(20*time.Second), integrationutil.SlowPoll, "re-keying must replace (remove tag:second), not merge")
+
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		assertNodeSelfHasTagsWithCollect(c, client, []string{"tag:valid-owned"})
+	}, integrationutil.StatusReadyTimeout, integrationutil.SlowPoll, "removed tag must clear from node self view")
+
+	t.Logf("Test #3370 PASS: re-keying replaced the tag set (tag:second removed)")
+}
+
 // TestTagsAuthKeyWithTagCLICannotModifyAdminTags tests that the client CLI
 // cannot modify admin-assigned tags.
 //