set date for 0.24.1 release

Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>

.github/workflows/test-integration.yaml

@@ -25,6 +25,7 @@ jobs:
           - TestOIDCAuthenticationPingAll
           - TestOIDCExpireNodesBasedOnTokenExpiry
           - TestOIDC024UserCreation
+          - TestOIDCAuthenticationWithPKCE
           - TestAuthWebFlowAuthenticationPingAll
           - TestAuthWebFlowLogoutAndRelogin
           - TestUserCommand

.github/workflows/test.yml

@@ -34,4 +34,10 @@ jobs:
 
       - name: Run tests
         if: steps.changed-files.outputs.files == 'true'
+        env:
+          # As of 2025-01-06, these env vars was not automatically
+          # set anymore which breaks the initdb for postgres on
+          # some of the database migration tests.
+          LC_ALL: "en_US.UTF-8"
+          LC_CTYPE: "en_US.UTF-8"
         run: nix develop --command -- gotestsum

CHANGELOG.md

@@ -1,8 +1,19 @@
 # CHANGELOG
 
-## Next
+## 0.24.1 (2025-01-23)
 
-## 0.24.0 (2024-xx-xx)
+### Changes
+
+- Fix migration issue with user table for PostgreSQL
+  [#2367](https://github.com/juanfont/headscale/pull/2367)
+- Relax username validation to allow emails
+  [#2364](https://github.com/juanfont/headscale/pull/2364)
+- Remove invalid routes and add stronger constraints for routes to avoid API panic
+  [#2371](https://github.com/juanfont/headscale/pull/2371)
+- Fix panic when `derp.update_frequency` is 0
+  [#2368](https://github.com/juanfont/headscale/pull/2368)
+
+## 0.24.0 (2025-01-17)
 
 ### Security fix: OIDC changes in Headscale 0.24.0
 
@@ -153,7 +164,7 @@ This will also affect the way you
 
 ### Changes
 
-- Improved compatibilty of built-in DERP server with clients connecting over
+- Improved compatibility of built-in DERP server with clients connecting over
   WebSocket [#2132](https://github.com/juanfont/headscale/pull/2132)
 - Allow nodes to use SSH agent forwarding
   [#2145](https://github.com/juanfont/headscale/pull/2145)
@@ -172,6 +183,7 @@ This will also affect the way you
   [#2261](https://github.com/juanfont/headscale/pull/2261)
 - Add `dns.extra_records_path` configuration option [#2262](https://github.com/juanfont/headscale/issues/2262)
 - Support client verify for DERP [#2046](https://github.com/juanfont/headscale/pull/2046)
+- Add PKCE Verifier for OIDC [#2314](https://github.com/juanfont/headscale/pull/2314)
 
 ## 0.23.0 (2024-09-18)
 
@@ -261,7 +273,7 @@ part of adopting [#1460](https://github.com/juanfont/headscale/pull/1460).
   - `prefixes.allocation` can be set to assign IPs at `sequential` or `random`.
     [#1869](https://github.com/juanfont/headscale/pull/1869)
 - MagicDNS domains no longer contain usernames []()
-  - This is in preperation to fix Headscales implementation of tags which
+  - This is in preparation to fix Headscales implementation of tags which
     currently does not correctly remove the link between a tagged device and a
     user. As tagged devices will not have a user, this will require a change to
     the DNS generation, removing the username, see

cmd/headscale/cli/routes.go

@@ -251,10 +251,15 @@ func routesToPtables(routes []*v1.Route) pterm.TableData {
 			isPrimaryStr = strconv.FormatBool(route.GetIsPrimary())
 		}
 
+		var nodeName string
+		if route.GetNode() != nil {
+			nodeName = route.GetNode().GetGivenName()
+		}
+
 		tableData = append(tableData,
 			[]string{
 				strconv.FormatUint(route.GetId(), Base10),
-				route.GetNode().GetGivenName(),
+				nodeName,
 				route.GetPrefix(),
 				strconv.FormatBool(route.GetAdvertised()),
 				strconv.FormatBool(route.GetEnabled()),

config-example.yaml

@@ -364,6 +364,18 @@ unix_socket_permission: "0770"
 #   allowed_users:
 #     - alice@example.com
 #
+#   # Optional: PKCE (Proof Key for Code Exchange) configuration
+#   # PKCE adds an additional layer of security to the OAuth 2.0 authorization code flow
+#   # by preventing authorization code interception attacks
+#   # See https://datatracker.ietf.org/doc/html/rfc7636
+#   pkce:
+#     # Enable or disable PKCE support (default: false)
+#     enabled: false
+#     # PKCE method to use:
+#     # - plain: Use plain code verifier
+#     # - S256: Use SHA256 hashed code verifier (default, recommended)
+#     method: S256
+#
 #   # Map legacy users from pre-0.24.0 versions of headscale to the new OIDC users
 #   # by taking the username from the legacy user and matching it with the username
 #   # provided by the OIDC. This is useful when migrating from legacy users to OIDC

docs/ref/dns.md

@@ -1,13 +1,13 @@
 # DNS
 
-Headscale supports [most DNS features](../about/features.md) from Tailscale. DNS releated settings can be configured
+Headscale supports [most DNS features](../about/features.md) from Tailscale. DNS related settings can be configured
 within `dns` section of the [configuration file](./configuration.md).
 
 ## Setting extra DNS records
 
 Headscale allows to set extra DNS records which are made available via
 [MagicDNS](https://tailscale.com/kb/1081/magicdns). Extra DNS records can be configured either via static entries in the
-[configuration file](./configuration.md) or from a JSON file that Headscale continously watches for changes:
+[configuration file](./configuration.md) or from a JSON file that Headscale continuously watches for changes:
 
 * Use the `dns.extra_records` option in the [configuration file](./configuration.md) for entries that are static and
   don't change while Headscale is running. Those entries are processed when Headscale is starting up and changes to the

docs/ref/integration/web-ui.md

@@ -11,7 +11,7 @@ Headscale doesn't provide a built-in web interface but users may pick one from t
 | --------------- | ------------------------------------------------------- | ----------------------------------------------------------------------------------- |
 | headscale-webui | [Github](https://github.com/ifargle/headscale-webui)    | A simple headscale web UI for small-scale deployments.                              |
 | headscale-ui    | [Github](https://github.com/gurucomputing/headscale-ui) | A web frontend for the headscale Tailscale-compatible coordination server           |
-| HeadscaleUi     | [GitHub](https://github.com/simcu/headscale-ui)         | A static headscale admin ui, no backend enviroment required                         |
+| HeadscaleUi     | [GitHub](https://github.com/simcu/headscale-ui)         | A static headscale admin ui, no backend environment required                         |
 | Headplane       | [GitHub](https://github.com/tale/headplane)             | An advanced Tailscale inspired frontend for headscale                               |
 | headscale-admin | [Github](https://github.com/GoodiesHQ/headscale-admin)  | Headscale-Admin is meant to be a simple, modern web interface for headscale         |
 | ouroboros       | [Github](https://github.com/yellowsink/ouroboros)       | Ouroboros is designed for users to manage their own devices, rather than for admins |

docs/ref/oidc.md

@@ -45,6 +45,18 @@ oidc:
   allowed_users:
     - alice@example.com
 
+  # Optional: PKCE (Proof Key for Code Exchange) configuration
+  # PKCE adds an additional layer of security to the OAuth 2.0 authorization code flow
+  # by preventing authorization code interception attacks
+  # See https://datatracker.ietf.org/doc/html/rfc7636
+  pkce:
+    # Enable or disable PKCE support (default: false)
+    enabled: false
+    # PKCE method to use:
+    # - plain: Use plain code verifier
+    # - S256: Use SHA256 hashed code verifier (default, recommended)
+    method: S256
+
   # If `strip_email_domain` is set to `true`, the domain part of the username email address will be removed.
   # This will transform `first-name.last-name@example.com` to the user `first-name.last-name`
   # If `strip_email_domain` is set to `false` the domain part will NOT be removed resulting to the following

docs/setup/install/source.md

@@ -16,7 +16,7 @@ README](https://github.com/juanfont/headscale#contributing) for more information
 ### Install from source
 
 ```shell
-# Install prerequistes
+# Install prerequisites
 pkg_add go
 
 git clone https://github.com/juanfont/headscale.git
@@ -42,7 +42,7 @@ cp headscale /usr/local/sbin
 ### Install from source via cross compile
 
 ```shell
-# Install prerequistes
+# Install prerequisites
 # 1. go v1.20+: headscale newer than 0.21 needs go 1.20+ to compile
 # 2. gmake: Makefile in the headscale repo is written in GNU make syntax
 

docs/usage/connect/apple.md

@@ -15,14 +15,10 @@ Install the official Tailscale iOS client from the [App Store](https://apps.appl
 
 ### Configuring the headscale URL
 
-- Open Tailscale and make sure you are _not_ logged in to any account
-- Open Settings on the iOS device
-- Scroll down to the `third party apps` section, under `Game Center` or `TV Provider`
-- Find Tailscale and select it
-  - If the iOS device was previously logged into Tailscale, switch the `Reset Keychain` toggle to `on`
-- Enter the URL of your headscale instance (e.g `https://headscale.example.com`) under `Alternate Coordination Server URL`
-- Restart the app by closing it from the iOS app switcher, open the app and select the regular sign in option
-  _(non-SSO)_. It should open up to the headscale authentication page.
+- Open the Tailscale app
+- Click the account icon in the top-right corner and select `Log in…`.
+- Tap the top-right options menu button and select `Use custom coordination server`.
+- Enter your instance url (e.g `https://headscale.example.com`)
 - Enter your credentials and log in. Headscale should now be working on your iOS device.
 
 ## macOS

flake.lock

@@ -20,11 +20,11 @@
     },
     "nixpkgs": {
       "locked": {
-        "lastModified": 1734126203,
-        "narHash": "sha256-0XovF7BYP50rTD2v4r55tR5MuBLet7q4xIz6Rgh3BBU=",
+        "lastModified": 1736420959,
+        "narHash": "sha256-dMGNa5UwdtowEqQac+Dr0d2tFO/60ckVgdhZU9q2E2o=",
         "owner": "NixOS",
         "repo": "nixpkgs",
-        "rev": "71a6392e367b08525ee710a93af2e80083b5b3e2",
+        "rev": "32af3611f6f05655ca166a0b1f47b57c762b5192",
         "type": "github"
       },
       "original": {

flake.nix

@@ -31,7 +31,7 @@
           checkFlags = ["-short"];
 
           # When updating go.mod or go.sum, a new sha will need to be calculated,
-          # update this if you have a mismatch after doing a change to thos files.
+          # update this if you have a mismatch after doing a change to those files.
           vendorHash = "sha256-SBfeixT8DQOrK2SWmHHSOBtzRdSZs+pwomHpw6Jd+qc=";
 
           subPackages = ["cmd/headscale"];

hscontrol/app.go

@@ -245,11 +245,11 @@ func (h *Headscale) scheduledTasks(ctx context.Context) {
 
 	lastExpiryCheck := time.Unix(0, 0)
 
-	derpTicker := time.NewTicker(h.cfg.DERP.UpdateFrequency)
-	defer derpTicker.Stop()
-	// If we dont want auto update, just stop the ticker
-	if !h.cfg.DERP.AutoUpdate {
-		derpTicker.Stop()
+	derpTickerChan := make(<-chan time.Time)
+	if h.cfg.DERP.AutoUpdate && h.cfg.DERP.UpdateFrequency != 0 {
+		derpTicker := time.NewTicker(h.cfg.DERP.UpdateFrequency)
+		defer derpTicker.Stop()
+		derpTickerChan = derpTicker.C
 	}
 
 	var extraRecordsUpdate <-chan []tailcfg.DNSRecord
@@ -285,7 +285,7 @@ func (h *Headscale) scheduledTasks(ctx context.Context) {
 				h.nodeNotifier.NotifyAll(ctx, update)
 			}
 
-		case <-derpTicker.C:
+		case <-derpTickerChan:
 			log.Info().Msg("Fetching DERPMap updates")
 			h.DERPMap = derp.GetDERPMap(h.cfg.DERP)
 			if h.cfg.DERP.ServerEnabled && h.cfg.DERP.AutomaticallyAddEmbeddedDerpRegion {

hscontrol/db/db.go

@@ -478,6 +478,38 @@ func NewHeadscaleDatabase(
 				// populate the user with more interesting information.
 				ID: "202407191627",
 				Migrate: func(tx *gorm.DB) error {
+					// Fix an issue where the automigration in GORM expected a constraint to
+					// exists that didnt, and add the one it wanted.
+					// Fixes https://github.com/juanfont/headscale/issues/2351
+					if cfg.Type == types.DatabasePostgres {
+						err := tx.Exec(`
+BEGIN;
+DO $$
+BEGIN
+    IF NOT EXISTS (
+        SELECT 1 FROM pg_constraint
+        WHERE conname = 'uni_users_name'
+    ) THEN
+        ALTER TABLE users ADD CONSTRAINT uni_users_name UNIQUE (name);
+    END IF;
+END $$;
+
+DO $$
+BEGIN
+    IF EXISTS (
+        SELECT 1 FROM pg_constraint
+        WHERE conname = 'users_name_key'
+    ) THEN
+        ALTER TABLE users DROP CONSTRAINT users_name_key;
+    END IF;
+END $$;
+COMMIT;
+`).Error
+						if err != nil {
+							return fmt.Errorf("failed to rename constraint: %w", err)
+						}
+					}
+
 					err := tx.AutoMigrate(&types.User{})
 					if err != nil {
 						return err
@@ -521,6 +553,27 @@ func NewHeadscaleDatabase(
 				},
 				Rollback: func(db *gorm.DB) error { return nil },
 			},
+			{
+				// Add a constraint to routes ensuring they cannot exist without a node.
+				ID: "202501221827",
+				Migrate: func(tx *gorm.DB) error {
+					// Remove any invalid routes associated with a node that does not exist.
+					if tx.Migrator().HasTable(&types.Route{}) && tx.Migrator().HasTable(&types.Node{}) {
+						err := tx.Exec("delete from routes where node_id not in (select id from nodes)").Error
+						if err != nil {
+							return err
+						}
+					}
+
+					err := tx.AutoMigrate(&types.Route{})
+					if err != nil {
+						return err
+					}
+
+					return nil
+				},
+				Rollback: func(db *gorm.DB) error { return nil },
+			},
 		},
 	)
 

hscontrol/db/db_test.go

@@ -6,6 +6,7 @@ import (
 	"io"
 	"net/netip"
 	"os"
+	"os/exec"
 	"path/filepath"
 	"slices"
 	"sort"
@@ -23,7 +24,10 @@ import (
 	"zgo.at/zcache/v2"
 )
 
-func TestMigrations(t *testing.T) {
+// TestMigrationsSQLite is the main function for testing migrations,
+// we focus on SQLite correctness as it is the main database used in headscale.
+// All migrations that are worth testing should be added here.
+func TestMigrationsSQLite(t *testing.T) {
 	ipp := func(p string) netip.Prefix {
 		return netip.MustParsePrefix(p)
 	}
@@ -375,3 +379,58 @@ func TestConstraints(t *testing.T) {
 		})
 	}
 }
+
+func TestMigrationsPostgres(t *testing.T) {
+	tests := []struct {
+		name     string
+		dbPath   string
+		wantFunc func(*testing.T, *HSDatabase)
+	}{
+		{
+			name:   "user-idx-breaking",
+			dbPath: "testdata/pre-24-postgresdb.pssql.dump",
+			wantFunc: func(t *testing.T, h *HSDatabase) {
+				users, err := Read(h.DB, func(rx *gorm.DB) ([]types.User, error) {
+					return ListUsers(rx)
+				})
+				require.NoError(t, err)
+
+				for _, user := range users {
+					assert.NotEmpty(t, user.Name)
+					assert.Empty(t, user.ProfilePicURL)
+					assert.Empty(t, user.Email)
+				}
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			u := newPostgresDBForTest(t)
+
+			pgRestorePath, err := exec.LookPath("pg_restore")
+			if err != nil {
+				t.Fatal("pg_restore not found in PATH. Please install it and ensure it is accessible.")
+			}
+
+			// Construct the pg_restore command
+			cmd := exec.Command(pgRestorePath, "--verbose", "--if-exists", "--clean", "--no-owner", "--dbname", u.String(), tt.dbPath)
+
+			// Set the output streams
+			cmd.Stdout = os.Stdout
+			cmd.Stderr = os.Stderr
+
+			// Execute the command
+			err = cmd.Run()
+			if err != nil {
+				t.Fatalf("failed to restore postgres database: %s", err)
+			}
+
+			db = newHeadscaleDBFromPostgresURL(t, u)
+
+			if tt.wantFunc != nil {
+				tt.wantFunc(t, db)
+			}
+		})
+	}
+}

hscontrol/db/node.go

@@ -245,7 +245,7 @@ func RenameNode(tx *gorm.DB,
 		return fmt.Errorf("renaming node: %w", err)
 	}
 
-	uniq, err := isUnqiueName(tx, newName)
+	uniq, err := isUniqueName(tx, newName)
 	if err != nil {
 		return fmt.Errorf("checking if name is unique: %w", err)
 	}
@@ -630,7 +630,7 @@ func generateGivenName(suppliedName string, randomSuffix bool) (string, error) {
 	return suppliedName, nil
 }
 
-func isUnqiueName(tx *gorm.DB, name string) (bool, error) {
+func isUniqueName(tx *gorm.DB, name string) (bool, error) {
 	nodes := types.Nodes{}
 	if err := tx.
 		Where("given_name = ?", name).Find(&nodes).Error; err != nil {
@@ -649,7 +649,7 @@ func ensureUniqueGivenName(
 		return "", err
 	}
 
-	unique, err := isUnqiueName(tx, givenName)
+	unique, err := isUniqueName(tx, givenName)
 	if err != nil {
 		return "", err
 	}

hscontrol/db/routes.go

@@ -417,10 +417,10 @@ func SaveNodeRoutes(tx *gorm.DB, node *types.Node) (bool, error) {
 	return sendUpdate, nil
 }
 
-// FailoverNodeRoutesIfNeccessary takes a node and checks if the node's route
+// FailoverNodeRoutesIfNecessary takes a node and checks if the node's route
 // need to be failed over to another host.
 // If needed, the failover will be attempted.
-func FailoverNodeRoutesIfNeccessary(
+func FailoverNodeRoutesIfNecessary(
 	tx *gorm.DB,
 	isLikelyConnected *xsync.MapOf[types.NodeID, bool],
 	node *types.Node,
@@ -473,7 +473,7 @@ nodeRouteLoop:
 		return &types.StateUpdate{
 			Type:        types.StatePeerChanged,
 			ChangeNodes: chng,
-			Message:     "called from db.FailoverNodeRoutesIfNeccessary",
+			Message:     "called from db.FailoverNodeRoutesIfNecessary",
 		}, nil
 	}
 

hscontrol/db/routes_test.go

@@ -342,7 +342,7 @@ func dbForTest(t *testing.T, testName string) *HSDatabase {
 	return db
 }
 
-func TestFailoverNodeRoutesIfNeccessary(t *testing.T) {
+func TestFailoverNodeRoutesIfNecessary(t *testing.T) {
 	su := func(nids ...types.NodeID) *types.StateUpdate {
 		return &types.StateUpdate{
 			ChangeNodes: nids,
@@ -648,7 +648,7 @@ func TestFailoverNodeRoutesIfNeccessary(t *testing.T) {
 				want := tt.want[step]
 
 				got, err := Write(db.DB, func(tx *gorm.DB) (*types.StateUpdate, error) {
-					return FailoverNodeRoutesIfNeccessary(tx, smap(isConnected), node)
+					return FailoverNodeRoutesIfNecessary(tx, smap(isConnected), node)
 				})
 
 				if (err != nil) != tt.wantErr {

hscontrol/db/suite_test.go

@@ -78,13 +78,11 @@ func newSQLiteTestDB() (*HSDatabase, error) {
 func newPostgresTestDB(t *testing.T) *HSDatabase {
 	t.Helper()
 
-	var err error
-	tmpDir, err = os.MkdirTemp("", "headscale-db-test-*")
-	if err != nil {
-		t.Fatal(err)
-	}
+	return newHeadscaleDBFromPostgresURL(t, newPostgresDBForTest(t))
+}
 
-	log.Printf("database path: %s", tmpDir+"/headscale_test.db")
+func newPostgresDBForTest(t *testing.T) *url.URL {
+	t.Helper()
 
 	ctx := context.Background()
 	srv, err := postgrestest.Start(ctx)
@@ -100,10 +98,16 @@ func newPostgresTestDB(t *testing.T) *HSDatabase {
 	t.Logf("created local postgres: %s", u)
 	pu, _ := url.Parse(u)
 
+	return pu
+}
+
+func newHeadscaleDBFromPostgresURL(t *testing.T, pu *url.URL) *HSDatabase {
+	t.Helper()
+
 	pass, _ := pu.User.Password()
 	port, _ := strconv.Atoi(pu.Port())
 
-	db, err = NewHeadscaleDatabase(
+	db, err := NewHeadscaleDatabase(
 		types.DatabaseConfig{
 			Type: types.DatabasePostgres,
 			Postgres: types.PostgresConfig{

hscontrol/mapper/mapper.go

@@ -105,8 +105,7 @@ func generateUserProfiles(
 
 	var profiles []tailcfg.UserProfile
 	for _, user := range userMap {
-		profiles = append(profiles,
-			user.TailscaleUserProfile())
+		profiles = append(profiles, user.TailscaleUserProfile())
 	}
 
 	return profiles
@@ -455,7 +454,7 @@ func (m *Mapper) baseWithConfigMapResponse(
 
 	resp.DERPMap = m.derpMap
 
-	resp.Domain = m.cfg.BaseDomain
+	resp.Domain = m.cfg.Domain()
 
 	// Do not instruct clients to collect services we do not
 	// support or do anything with them

hscontrol/notifier/notifier.go

@@ -243,7 +243,7 @@ func (n *Notifier) sendAll(update types.StateUpdate) {
 		// has shut down the channel and is waiting for the lock held here in RemoveNode.
 		// This means that there is potential for a deadlock which would stop all updates
 		// going out to clients. This timeout prevents that from happening by moving on to the
-		// next node if the context is cancelled. Afther sendAll releases the lock, the add/remove
+		// next node if the context is cancelled. After sendAll releases the lock, the add/remove
 		// call will succeed and the update will go to the correct nodes on the next call.
 		ctx, cancel := context.WithTimeout(context.Background(), n.cfg.Tuning.NotifierSendTimeout)
 		defer cancel()

hscontrol/oidc.go

@@ -3,9 +3,7 @@ package hscontrol
 import (
 	"bytes"
 	"context"
-	"crypto/rand"
 	_ "embed"
-	"encoding/hex"
 	"errors"
 	"fmt"
 	"html/template"
@@ -28,12 +26,14 @@ import (
 )
 
 const (
-	randomByteSize = 16
+	randomByteSize           = 16
+	defaultOAuthOptionsCount = 3
 )
 
 var (
 	errEmptyOIDCCallbackParams = errors.New("empty OIDC callback params")
 	errNoOIDCIDToken           = errors.New("could not extract ID Token for OIDC callback")
+	errNoOIDCRegistrationInfo  = errors.New("could not get registration info from cache")
 	errOIDCAllowedDomains      = errors.New(
 		"authenticated principal does not match any allowed domain",
 	)
@@ -47,11 +47,17 @@ var (
 	errOIDCNodeKeyMissing = errors.New("could not get node key from cache")
 )
 
+// RegistrationInfo contains both machine key and verifier information for OIDC validation.
+type RegistrationInfo struct {
+	MachineKey key.MachinePublic
+	Verifier   *string
+}
+
 type AuthProviderOIDC struct {
 	serverURL         string
 	cfg               *types.OIDCConfig
 	db                *db.HSDatabase
-	registrationCache *zcache.Cache[string, key.MachinePublic]
+	registrationCache *zcache.Cache[string, RegistrationInfo]
 	notifier          *notifier.Notifier
 	ipAlloc           *db.IPAllocator
 	polMan            policy.PolicyManager
@@ -87,7 +93,7 @@ func NewAuthProviderOIDC(
 		Scopes: cfg.Scope,
 	}
 
-	registrationCache := zcache.New[string, key.MachinePublic](
+	registrationCache := zcache.New[string, RegistrationInfo](
 		registerCacheExpiration,
 		registerCacheCleanup,
 	)
@@ -149,28 +155,52 @@ func (a *AuthProviderOIDC) RegisterHandler(
 		return
 	}
 
-	randomBlob := make([]byte, randomByteSize)
-	if _, err := rand.Read(randomBlob); err != nil {
+	// Set the state and nonce cookies to protect against CSRF attacks
+	state, err := setCSRFCookie(writer, req, "state")
+	if err != nil {
 		http.Error(writer, "Internal server error", http.StatusInternalServerError)
 		return
 	}
 
-	stateStr := hex.EncodeToString(randomBlob)[:32]
+	// Set the state and nonce cookies to protect against CSRF attacks
+	nonce, err := setCSRFCookie(writer, req, "nonce")
+	if err != nil {
+		http.Error(writer, "Internal server error", http.StatusInternalServerError)
+		return
+	}
 
-	// place the node key into the state cache, so it can be retrieved later
-	a.registrationCache.Set(
-		stateStr,
-		machineKey,
-	)
+	// Initialize registration info with machine key
+	registrationInfo := RegistrationInfo{
+		MachineKey: machineKey,
+	}
 
-	// Add any extra parameter provided in the configuration to the Authorize Endpoint request
-	extras := make([]oauth2.AuthCodeOption, 0, len(a.cfg.ExtraParams))
+	extras := make([]oauth2.AuthCodeOption, 0, len(a.cfg.ExtraParams)+defaultOAuthOptionsCount)
+	// Add PKCE verification if enabled
+	if a.cfg.PKCE.Enabled {
+		verifier := oauth2.GenerateVerifier()
+		registrationInfo.Verifier = &verifier
 
+		extras = append(extras, oauth2.AccessTypeOffline)
+
+		switch a.cfg.PKCE.Method {
+		case types.PKCEMethodS256:
+			extras = append(extras, oauth2.S256ChallengeOption(verifier))
+		case types.PKCEMethodPlain:
+			// oauth2 does not have a plain challenge option, so we add it manually
+			extras = append(extras, oauth2.SetAuthURLParam("code_challenge_method", "plain"), oauth2.SetAuthURLParam("code_challenge", verifier))
+		}
+	}
+
+	// Add any extra parameters from configuration
 	for k, v := range a.cfg.ExtraParams {
 		extras = append(extras, oauth2.SetAuthURLParam(k, v))
 	}
+	extras = append(extras, oidc.Nonce(nonce))
 
-	authURL := a.oauth2Config.AuthCodeURL(stateStr, extras...)
+	// Cache the registration info
+	a.registrationCache.Set(state, registrationInfo)
+
+	authURL := a.oauth2Config.AuthCodeURL(state, extras...)
 	log.Debug().Msgf("Redirecting to %s for authentication", authURL)
 
 	http.Redirect(writer, req, authURL, http.StatusFound)
@@ -203,11 +233,34 @@ func (a *AuthProviderOIDC) OIDCCallbackHandler(
 		return
 	}
 
-	idToken, err := a.extractIDToken(req.Context(), code)
+	log.Debug().Interface("cookies", req.Cookies()).Msg("Received oidc callback")
+	cookieState, err := req.Cookie("state")
+	if err != nil {
+		http.Error(writer, "state not found", http.StatusBadRequest)
+		return
+	}
+
+	if state != cookieState.Value {
+		http.Error(writer, "state did not match", http.StatusBadRequest)
+		return
+	}
+
+	idToken, err := a.extractIDToken(req.Context(), code, state)
 	if err != nil {
 		http.Error(writer, err.Error(), http.StatusBadRequest)
 		return
 	}
+
+	nonce, err := req.Cookie("nonce")
+	if err != nil {
+		http.Error(writer, "nonce not found", http.StatusBadRequest)
+		return
+	}
+	if idToken.Nonce != nonce.Value {
+		http.Error(writer, "nonce did not match", http.StatusBadRequest)
+		return
+	}
+
 	nodeExpiry := a.determineNodeExpiry(idToken.Expiry)
 
 	var claims types.OIDCClaims
@@ -296,7 +349,7 @@ func (a *AuthProviderOIDC) OIDCCallbackHandler(
 
 	// Neither node nor machine key was found in the state cache meaning
 	// that we could not reauth nor register the node.
-	http.Error(writer, err.Error(), http.StatusInternalServerError)
+	http.Error(writer, "login session expired, try again", http.StatusInternalServerError)
 	return
 }
 
@@ -318,8 +371,21 @@ func extractCodeAndStateParamFromRequest(
 func (a *AuthProviderOIDC) extractIDToken(
 	ctx context.Context,
 	code string,
+	state string,
 ) (*oidc.IDToken, error) {
-	oauth2Token, err := a.oauth2Config.Exchange(ctx, code)
+	var exchangeOpts []oauth2.AuthCodeOption
+
+	if a.cfg.PKCE.Enabled {
+		regInfo, ok := a.registrationCache.Get(state)
+		if !ok {
+			return nil, errNoOIDCRegistrationInfo
+		}
+		if regInfo.Verifier != nil {
+			exchangeOpts = []oauth2.AuthCodeOption{oauth2.VerifierOption(*regInfo.Verifier)}
+		}
+	}
+
+	oauth2Token, err := a.oauth2Config.Exchange(ctx, code, exchangeOpts...)
 	if err != nil {
 		return nil, fmt.Errorf("could not exchange code for token: %w", err)
 	}
@@ -394,7 +460,7 @@ func validateOIDCAllowedUsers(
 // cache. If the machine key is found, it will try retrieve the
 // node information from the database.
 func (a *AuthProviderOIDC) getMachineKeyFromState(state string) (*types.Node, *key.MachinePublic) {
-	machineKey, ok := a.registrationCache.Get(state)
+	regInfo, ok := a.registrationCache.Get(state)
 	if !ok {
 		return nil, nil
 	}
@@ -403,9 +469,9 @@ func (a *AuthProviderOIDC) getMachineKeyFromState(state string) (*types.Node, *k
 	// The error is not important, because if it does not
 	// exist, then this is a new node and we will move
 	// on to registration.
-	node, _ := a.db.GetNodeByMachineKey(machineKey)
+	node, _ := a.db.GetNodeByMachineKey(regInfo.MachineKey)
 
-	return node, &machineKey
+	return node, &regInfo.MachineKey
 }
 
 // reauthenticateNode updates the node expiry in the database
@@ -554,3 +620,22 @@ func getUserName(
 
 	return userName, nil
 }
+
+func setCSRFCookie(w http.ResponseWriter, r *http.Request, name string) (string, error) {
+	val, err := util.GenerateRandomStringURLSafe(64)
+	if err != nil {
+		return val, err
+	}
+
+	c := &http.Cookie{
+		Path:     "/oidc/callback",
+		Name:     name,
+		Value:    val,
+		MaxAge:   int(time.Hour.Seconds()),
+		Secure:   r.TLS != nil,
+		HttpOnly: true,
+	}
+	http.SetCookie(w, c)
+
+	return val, nil
+}

hscontrol/policy/acls.go

@@ -62,7 +62,7 @@ func theInternet() *netipx.IPSet {
 	internetBuilder.RemovePrefix(tsaddr.CGNATRange())
 
 	// Delete "cant find DHCP networks"
-	internetBuilder.RemovePrefix(netip.MustParsePrefix("fe80::/10")) // link-loca
+	internetBuilder.RemovePrefix(netip.MustParsePrefix("fe80::/10")) // link-local
 	internetBuilder.RemovePrefix(netip.MustParsePrefix("169.254.0.0/16"))
 
 	theInternetSet, _ := internetBuilder.IPSet()

hscontrol/poll.go

@@ -387,7 +387,7 @@ func (m *mapSession) serveLongPoll() {
 
 func (m *mapSession) pollFailoverRoutes(where string, node *types.Node) {
 	update, err := db.Write(m.h.db.DB, func(tx *gorm.DB) (*types.StateUpdate, error) {
-		return db.FailoverNodeRoutesIfNeccessary(tx, m.h.nodeNotifier.LikelyConnectedMap(), node)
+		return db.FailoverNodeRoutesIfNecessary(tx, m.h.nodeNotifier.LikelyConnectedMap(), node)
 	})
 	if err != nil {
 		m.errf(err, fmt.Sprintf("failed to ensure failover routes, %s", where))
@@ -453,7 +453,7 @@ func (m *mapSession) handleEndpointUpdate() {
 	// If there is no NetInfo, keep the previous one.
 	// From 1.66 the client only sends it if changed:
 	// https://github.com/tailscale/tailscale/commit/e1011f138737286ecf5123ff887a7a5800d129a2
-	// TODO(kradalby): evaulate if we need better comparing of hostinfo
+	// TODO(kradalby): evaluate if we need better comparing of hostinfo
 	// before we take the changes.
 	if m.req.Hostinfo.NetInfo == nil && m.node.Hostinfo != nil {
 		m.req.Hostinfo.NetInfo = m.node.Hostinfo.NetInfo

hscontrol/templates/apple.go

@@ -27,50 +27,27 @@ func Apple(url string) *elem.Element {
 						elem.Text("App store"),
 					),
 				),
-				elem.Li(nil,
-					elem.Text("Open Tailscale and make sure you are "),
-					elem.I(nil, elem.Text("not ")),
-					elem.Text("logged in to any account"),
-				),
-				elem.Li(nil,
-					elem.Text("Open Settings on the iOS device"),
+				elem.Li(
+					nil,
+					elem.Text("Open the Tailscale app"),
 				),
 				elem.Li(
 					nil,
-					elem.Text(
-						`Scroll down to the "third party apps" section, under "Game Center" or "TV Provider"`,
-					),
+					elem.Text(`Click the account icon in the top-right corner and select "Log in…".`),
 				),
-				elem.Li(nil,
-					elem.Text("Find Tailscale and select it"),
-					elem.Ul(nil,
-						elem.Li(
-							nil,
-							elem.Text(
-								`If the iOS device was previously logged into Tailscale, switch the "Reset Keychain" toggle to "on"`,
-							),
-						),
-					),
+				elem.Li(
+					nil,
+					elem.Text(`Tap the top-right options menu button and select "Use custom coordination server".`),
 				),
 				elem.Li(
 					nil,
 					elem.Text(
 						fmt.Sprintf(
-							`Enter "%s" under "Alternate Coordination Server URL"`,
+							`Enter your instance URL: "%s"`,
 							url,
 						),
 					),
 				),
-				elem.Li(
-					nil,
-					elem.Text(
-						"Restart the app by closing it from the iOS app switcher, open the app and select the regular sign in option ",
-					),
-					elem.I(nil, elem.Text("(non-SSO)")),
-					elem.Text(
-						". It should open up to the headscale authentication page.",
-					),
-				),
 				elem.Li(
 					nil,
 					elem.Text(

hscontrol/types/config.go

@@ -26,11 +26,14 @@ import (
 const (
 	defaultOIDCExpiryTime               = 180 * 24 * time.Hour // 180 Days
 	maxDuration           time.Duration = 1<<63 - 1
+	PKCEMethodPlain       string        = "plain"
+	PKCEMethodS256        string        = "S256"
 )
 
 var (
 	errOidcMutuallyExclusive = errors.New("oidc_client_secret and oidc_client_secret_path are mutually exclusive")
 	errServerURLSuffix       = errors.New("server_url cannot be part of base_domain in a way that could make the DERP and headscale server unreachable")
+	errInvalidPKCEMethod     = errors.New("pkce.method must be either 'plain' or 'S256'")
 )
 
 type IPAllocationStrategy string
@@ -162,6 +165,11 @@ type LetsEncryptConfig struct {
 	ChallengeType string
 }
 
+type PKCEConfig struct {
+	Enabled bool
+	Method  string
+}
+
 type OIDCConfig struct {
 	OnlyStartIfOIDCIsAvailable bool
 	Issuer                     string
@@ -176,6 +184,7 @@ type OIDCConfig struct {
 	Expiry                     time.Duration
 	UseExpiryFromToken         bool
 	MapLegacyUsers             bool
+	PKCE                       PKCEConfig
 }
 
 type DERPConfig struct {
@@ -226,6 +235,24 @@ type Tuning struct {
 	NodeMapSessionBufferedChanSize int
 }
 
+func validatePKCEMethod(method string) error {
+	if method != PKCEMethodPlain && method != PKCEMethodS256 {
+		return errInvalidPKCEMethod
+	}
+	return nil
+}
+
+// Domain returns the hostname/domain part of the ServerURL.
+// If the ServerURL is not a valid URL, it returns the BaseDomain.
+func (c *Config) Domain() string {
+	u, err := url.Parse(c.ServerURL)
+	if err != nil {
+		return c.BaseDomain
+	}
+
+	return u.Hostname()
+}
+
 // LoadConfig prepares and loads the Headscale configuration into Viper.
 // This means it sets the default values, reads the configuration file and
 // environment variables, and handles deprecated configuration options.
@@ -293,6 +320,8 @@ func LoadConfig(path string, isFile bool) error {
 	viper.SetDefault("oidc.expiry", "180d")
 	viper.SetDefault("oidc.use_expiry_from_token", false)
 	viper.SetDefault("oidc.map_legacy_users", true)
+	viper.SetDefault("oidc.pkce.enabled", false)
+	viper.SetDefault("oidc.pkce.method", "S256")
 
 	viper.SetDefault("logtail.enabled", false)
 	viper.SetDefault("randomize_client_port", false)
@@ -340,6 +369,12 @@ func validateServerConfig() error {
 	// after #2170 is cleaned up
 	// depr.fatal("oidc.strip_email_domain")
 
+	if viper.GetBool("oidc.enabled") {
+		if err := validatePKCEMethod(viper.GetString("oidc.pkce.method")); err != nil {
+			return err
+		}
+	}
+
 	depr.Log()
 
 	for _, removed := range []string{
@@ -593,7 +628,7 @@ func dns() (DNSConfig, error) {
 	// UnmarshalKey is compatible with Environment Variables.
 	// err := viper.UnmarshalKey("dns", &dns)
 	// if err != nil {
-	// 	return DNSConfig{}, fmt.Errorf("unmarshaling dns config: %w", err)
+	// 	return DNSConfig{}, fmt.Errorf("unmarshalling dns config: %w", err)
 	// }
 
 	dns.MagicDNS = viper.GetBool("dns.magic_dns")
@@ -608,7 +643,7 @@ func dns() (DNSConfig, error) {
 
 		err := viper.UnmarshalKey("dns.extra_records", &extraRecords)
 		if err != nil {
-			return DNSConfig{}, fmt.Errorf("unmarshaling dns extra records: %w", err)
+			return DNSConfig{}, fmt.Errorf("unmarshalling dns extra records: %w", err)
 		}
 		dns.ExtraRecords = extraRecords
 	}
@@ -928,6 +963,10 @@ func LoadServerConfig() (*Config, error) {
 			// after #2170 is cleaned up
 			StripEmaildomain: viper.GetBool("oidc.strip_email_domain"),
 			MapLegacyUsers:   viper.GetBool("oidc.map_legacy_users"),
+			PKCE: PKCEConfig{
+				Enabled: viper.GetBool("oidc.pkce.enabled"),
+				Method:  viper.GetString("oidc.pkce.method"),
+			},
 		},
 
 		LogTail:             logTailConfig,

hscontrol/types/routes.go

@@ -13,7 +13,7 @@ import (
 type Route struct {
 	gorm.Model
 
-	NodeID uint64
+	NodeID uint64 `gorm:"not null"`
 	Node   *Node
 
 	// TODO(kradalby): change this custom type to netip.Prefix
@@ -79,7 +79,6 @@ func (rs Routes) Proto() []*v1.Route {
 	for _, route := range rs {
 		protoRoute := v1.Route{
 			Id:         uint64(route.ID),
-			Node:       route.Node.Proto(),
 			Prefix:     route.Prefix.String(),
 			Advertised: route.Advertised,
 			Enabled:    route.Enabled,
@@ -88,6 +87,10 @@ func (rs Routes) Proto() []*v1.Route {
 			UpdatedAt:  timestamppb.New(route.UpdatedAt),
 		}
 
+		if route.Node != nil {
+			protoRoute.Node = route.Node.Proto()
+		}
+
 		if route.DeletedAt.Valid {
 			protoRoute.DeletedAt = timestamppb.New(route.DeletedAt.Time)
 		}

hscontrol/types/users.go

@@ -10,6 +10,7 @@ import (
 
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/juanfont/headscale/hscontrol/util"
+	"github.com/rs/zerolog/log"
 	"google.golang.org/protobuf/types/known/timestamppb"
 	"gorm.io/gorm"
 	"tailscale.com/tailcfg"
@@ -173,9 +174,11 @@ func (c *OIDCClaims) Identifier() string {
 // FromClaim overrides a User from OIDC claims.
 // All fields will be updated, except for the ID.
 func (u *User) FromClaim(claims *OIDCClaims) {
-	err := util.CheckForFQDNRules(claims.Username)
+	err := util.ValidateUsername(claims.Username)
 	if err == nil {
 		u.Name = claims.Username
+	} else {
+		log.Debug().Err(err).Msgf("Username %s is not valid", claims.Username)
 	}
 
 	if claims.EmailVerified {

hscontrol/types/users_test.go

@@ -1,10 +1,12 @@
 package types
 
 import (
+	"database/sql"
 	"encoding/json"
 	"testing"
 
 	"github.com/google/go-cmp/cmp"
+	"github.com/juanfont/headscale/hscontrol/util"
 )
 
 func TestUnmarshallOIDCClaims(t *testing.T) {
@@ -73,3 +75,149 @@ func TestUnmarshallOIDCClaims(t *testing.T) {
 		})
 	}
 }
+
+func TestOIDCClaimsJSONToUser(t *testing.T) {
+	tests := []struct {
+		name    string
+		jsonstr string
+		want    User
+	}{
+		{
+			name: "normal-bool",
+			jsonstr: `
+{
+  "sub": "test",
+  "email": "test@test.no",
+  "email_verified": true
+}
+			`,
+			want: User{
+				Provider: util.RegisterMethodOIDC,
+				Email:    "test@test.no",
+				ProviderIdentifier: sql.NullString{
+					String: "/test",
+					Valid:  true,
+				},
+			},
+		},
+		{
+			name: "string-bool-true",
+			jsonstr: `
+{
+  "sub": "test2",
+  "email": "test2@test.no",
+  "email_verified": "true"
+}
+			`,
+			want: User{
+				Provider: util.RegisterMethodOIDC,
+				Email:    "test2@test.no",
+				ProviderIdentifier: sql.NullString{
+					String: "/test2",
+					Valid:  true,
+				},
+			},
+		},
+		{
+			name: "string-bool-false",
+			jsonstr: `
+{
+  "sub": "test3",
+  "email": "test3@test.no",
+  "email_verified": "false"
+}
+			`,
+			want: User{
+				Provider: util.RegisterMethodOIDC,
+				ProviderIdentifier: sql.NullString{
+					String: "/test3",
+					Valid:  true,
+				},
+			},
+		},
+		{
+			// From https://github.com/juanfont/headscale/issues/2333
+			name: "okta-oidc-claim-20250121",
+			jsonstr: `
+{
+  "sub": "00u7dr4qp7XXXXXXXXXX",
+  "name": "Tim Horton",
+  "email": "tim.horton@company.com",
+  "ver": 1,
+  "iss": "https://sso.company.com/oauth2/default",
+  "aud": "0oa8neto4tXXXXXXXXXX",
+  "iat": 1737455152,
+  "exp": 1737458752,
+  "jti": "ID.zzJz93koTunMKv5Bq-XXXXXXXXXXXXXXXXXXXXXXXXX",
+  "amr": [
+    "pwd"
+  ],
+  "idp": "00o42r3s2cXXXXXXXX",
+  "nonce": "nonce",
+  "preferred_username": "tim.horton@company.com",
+  "auth_time": 1000,
+  "at_hash": "preview_at_hash"
+}
+			`,
+			want: User{
+				Provider:    util.RegisterMethodOIDC,
+				DisplayName: "Tim Horton",
+				Name:        "tim.horton@company.com",
+				ProviderIdentifier: sql.NullString{
+					String: "https://sso.company.com/oauth2/default/00u7dr4qp7XXXXXXXXXX",
+					Valid:  true,
+				},
+			},
+		},
+		{
+			// From https://github.com/juanfont/headscale/issues/2333
+			name: "okta-oidc-claim-20250121",
+			jsonstr: `
+{
+  "aud": "79xxxxxx-xxxx-xxxx-xxxx-892146xxxxxx",
+  "iss": "https://login.microsoftonline.com//v2.0",
+  "iat": 1737346441,
+  "nbf": 1737346441,
+  "exp": 1737350341,
+  "aio": "AWQAm/8ZAAAABKne9EWr6ygVO2DbcRmoPIpRM819qqlP/mmK41AAWv/C2tVkld4+znbG8DaXFdLQa9jRUzokvsT7rt9nAT6Fg7QC+/ecDWsF5U+QX11f9Ox7ZkK4UAIWFcIXpuZZvRS7",
+  "email": "user@domain.com",
+  "name": "XXXXXX XXXX",
+  "oid": "54c2323d-5052-4130-9588-ad751909003f",
+  "preferred_username": "user@domain.com",
+  "rh": "1.AXUAXdg0Rfc11UifLDJv67ChfSluoXmD9z1EmK-JIUYuSK9cAQl1AA.",
+  "sid": "5250a0a2-0b4e-4e68-8652-b4e97866411d",
+  "sub": "I-70OQnj3TogrNSfkZQqB3f7dGwyBWSm1dolHNKrMzQ",
+  "tid": "<redacted>",
+  "uti": "zAuXeEtMM0GwcTAcOsBZAA",
+  "ver": "2.0"
+}
+			`,
+			want: User{
+				Provider:    util.RegisterMethodOIDC,
+				DisplayName: "XXXXXX XXXX",
+				Name:        "user@domain.com",
+				ProviderIdentifier: sql.NullString{
+					String: "https://login.microsoftonline.com//v2.0/I-70OQnj3TogrNSfkZQqB3f7dGwyBWSm1dolHNKrMzQ",
+					Valid:  true,
+				},
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			var got OIDCClaims
+			if err := json.Unmarshal([]byte(tt.jsonstr), &got); err != nil {
+				t.Errorf("TestOIDCClaimsJSONToUser() error = %v", err)
+				return
+			}
+
+			var user User
+
+			user.FromClaim(&got)
+			if diff := cmp.Diff(user, tt.want); diff != "" {
+				t.Errorf("TestOIDCClaimsJSONToUser() mismatch (-want +got):\n%s", diff)
+			}
+		})
+	}
+}

hscontrol/util/dns.go

@@ -6,6 +6,7 @@ import (
 	"net/netip"
 	"regexp"
 	"strings"
+	"unicode"
 
 	"go4.org/netipx"
 	"tailscale.com/util/dnsname"
@@ -20,10 +21,49 @@ const (
 	LabelHostnameLength = 63
 )
 
+var invalidDNSRegex = regexp.MustCompile("[^a-z0-9-.]+")
 var invalidCharsInUserRegex = regexp.MustCompile("[^a-z0-9-.]+")
 
 var ErrInvalidUserName = errors.New("invalid user name")
 
+// ValidateUsername checks if a username is valid.
+// It must be at least 2 characters long, start with a letter, and contain
+// only letters, numbers, hyphens, dots, and underscores.
+// It cannot contain more than one '@'.
+// It cannot contain invalid characters.
+func ValidateUsername(username string) error {
+	// Ensure the username meets the minimum length requirement
+	if len(username) < 2 {
+		return errors.New("username must be at least 2 characters long")
+	}
+
+	// Ensure the username does not start with a number
+	if unicode.IsDigit(rune(username[0])) {
+		return errors.New("username cannot start with a number")
+	}
+
+	atCount := 0
+	for _, char := range username {
+		switch {
+		case unicode.IsLetter(char),
+			unicode.IsDigit(char),
+			char == '-',
+			char == '.',
+			char == '_':
+			// Valid characters
+		case char == '@':
+			atCount++
+			if atCount > 1 {
+				return errors.New("username cannot contain more than one '@'")
+			}
+		default:
+			return fmt.Errorf("username contains invalid character: '%c'", char)
+		}
+	}
+
+	return nil
+}
+
 func CheckForFQDNRules(name string) error {
 	if len(name) > LabelHostnameLength {
 		return fmt.Errorf(
@@ -39,7 +79,7 @@ func CheckForFQDNRules(name string) error {
 			ErrInvalidUserName,
 		)
 	}
-	if invalidCharsInUserRegex.MatchString(name) {
+	if invalidDNSRegex.MatchString(name) {
 		return fmt.Errorf(
 			"DNS segment should only be composed of lowercase ASCII letters numbers, hyphen and dots. %v doesn't comply with theses rules: %w",
 			name,
@@ -52,7 +92,7 @@ func CheckForFQDNRules(name string) error {
 
 func ConvertWithFQDNRules(name string) string {
 	name = strings.ToLower(name)
-	name = invalidCharsInUserRegex.ReplaceAllString(name, "")
+	name = invalidDNSRegex.ReplaceAllString(name, "")
 
 	return name
 }
@@ -197,7 +237,7 @@ func NormalizeToFQDNRules(name string, stripEmailDomain bool) (string, error) {
 	} else {
 		name = strings.ReplaceAll(name, "@", ".")
 	}
-	name = invalidCharsInUserRegex.ReplaceAllString(name, "-")
+	name = invalidDNSRegex.ReplaceAllString(name, "-")
 
 	for _, elt := range strings.Split(name, ".") {
 		if len(elt) > LabelHostnameLength {

integration/auth_oidc_test.go

@@ -10,6 +10,8 @@ import (
 	"log"
 	"net"
 	"net/http"
+	"net/http/cookiejar"
+	"net/http/httptest"
 	"net/netip"
 	"sort"
 	"strconv"
@@ -534,6 +536,86 @@ func TestOIDC024UserCreation(t *testing.T) {
 	}
 }
 
+func TestOIDCAuthenticationWithPKCE(t *testing.T) {
+	IntegrationSkip(t)
+	t.Parallel()
+
+	baseScenario, err := NewScenario(dockertestMaxWait())
+	assertNoErr(t, err)
+
+	scenario := AuthOIDCScenario{
+		Scenario: baseScenario,
+	}
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	// Single user with one node for testing PKCE flow
+	spec := map[string]int{
+		"user1": 1,
+	}
+
+	mockusers := []mockoidc.MockUser{
+		oidcMockUser("user1", true),
+	}
+
+	oidcConfig, err := scenario.runMockOIDC(defaultAccessTTL, mockusers)
+	assertNoErrf(t, "failed to run mock OIDC server: %s", err)
+	defer scenario.mockOIDC.Close()
+
+	oidcMap := map[string]string{
+		"HEADSCALE_OIDC_ISSUER":             oidcConfig.Issuer,
+		"HEADSCALE_OIDC_CLIENT_ID":          oidcConfig.ClientID,
+		"HEADSCALE_OIDC_CLIENT_SECRET_PATH": "${CREDENTIALS_DIRECTORY_TEST}/hs_client_oidc_secret",
+		"CREDENTIALS_DIRECTORY_TEST":        "/tmp",
+		"HEADSCALE_OIDC_PKCE_ENABLED":       "1", // Enable PKCE
+		"HEADSCALE_OIDC_MAP_LEGACY_USERS":   "0",
+		"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": "0",
+	}
+
+	err = scenario.CreateHeadscaleEnv(
+		spec,
+		hsic.WithTestName("oidcauthpkce"),
+		hsic.WithConfigEnv(oidcMap),
+		hsic.WithTLS(),
+		hsic.WithHostnameAsServerURL(),
+		hsic.WithFileInContainer("/tmp/hs_client_oidc_secret", []byte(oidcConfig.ClientSecret)),
+	)
+	assertNoErrHeadscaleEnv(t, err)
+
+	// Get all clients and verify they can connect
+	allClients, err := scenario.ListTailscaleClients()
+	assertNoErrListClients(t, err)
+
+	allIps, err := scenario.ListTailscaleClientsIPs()
+	assertNoErrListClientIPs(t, err)
+
+	err = scenario.WaitForTailscaleSync()
+	assertNoErrSync(t, err)
+
+	// Verify PKCE was used in authentication
+	headscale, err := scenario.Headscale()
+	assertNoErr(t, err)
+
+	var listUsers []v1.User
+	err = executeAndUnmarshal(headscale,
+		[]string{
+			"headscale",
+			"users",
+			"list",
+			"--output",
+			"json",
+		},
+		&listUsers,
+	)
+	assertNoErr(t, err)
+
+	allAddrs := lo.Map(allIps, func(x netip.Addr, index int) string {
+		return x.String()
+	})
+
+	success := pingAllHelper(t, allClients, allAddrs)
+	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
+}
+
 func (s *AuthOIDCScenario) CreateHeadscaleEnv(
 	users map[string]int,
 	opts ...hsic.Option,
@@ -667,6 +749,24 @@ func (s *AuthOIDCScenario) runMockOIDC(accessTTL time.Duration, users []mockoidc
 	}, nil
 }
 
+type LoggingRoundTripper struct{}
+
+func (t LoggingRoundTripper) RoundTrip(req *http.Request) (*http.Response, error) {
+	noTls := &http.Transport{
+		TLSClientConfig: &tls.Config{InsecureSkipVerify: true}, // nolint
+	}
+	resp, err := noTls.RoundTrip(req)
+	if err != nil {
+		return nil, err
+	}
+
+	log.Printf("---")
+	log.Printf("method: %s | url: %s", resp.Request.Method, resp.Request.URL.String())
+	log.Printf("status: %d | cookies: %+v", resp.StatusCode, resp.Cookies())
+
+	return resp, nil
+}
+
 func (s *AuthOIDCScenario) runTailscaleUp(
 	userStr, loginServer string,
 ) error {
@@ -678,35 +778,39 @@ func (s *AuthOIDCScenario) runTailscaleUp(
 	log.Printf("running tailscale up for user %s", userStr)
 	if user, ok := s.users[userStr]; ok {
 		for _, client := range user.Clients {
-			c := client
+			tsc := client
 			user.joinWaitGroup.Go(func() error {
-				loginURL, err := c.LoginWithURL(loginServer)
+				loginURL, err := tsc.LoginWithURL(loginServer)
 				if err != nil {
-					log.Printf("%s failed to run tailscale up: %s", c.Hostname(), err)
+					log.Printf("%s failed to run tailscale up: %s", tsc.Hostname(), err)
 				}
 
-				loginURL.Host = fmt.Sprintf("%s:8080", headscale.GetIP())
+				loginURL.Host = fmt.Sprintf("%s:8080", headscale.GetHostname())
 				loginURL.Scheme = "http"
 
 				if len(headscale.GetCert()) > 0 {
 					loginURL.Scheme = "https"
 				}
 
-				insecureTransport := &http.Transport{
-					TLSClientConfig: &tls.Config{InsecureSkipVerify: true}, // nolint
+				httptest.NewRecorder()
+				hc := &http.Client{
+					Transport: LoggingRoundTripper{},
+				}
+				hc.Jar, err = cookiejar.New(nil)
+				if err != nil {
+					log.Printf("failed to create cookie jar: %s", err)
 				}
 
-				log.Printf("%s login url: %s\n", c.Hostname(), loginURL.String())
+				log.Printf("%s login url: %s\n", tsc.Hostname(), loginURL.String())
 
-				log.Printf("%s logging in with url", c.Hostname())
-				httpClient := &http.Client{Transport: insecureTransport}
+				log.Printf("%s logging in with url", tsc.Hostname())
 				ctx := context.Background()
 				req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
-				resp, err := httpClient.Do(req)
+				resp, err := hc.Do(req)
 				if err != nil {
 					log.Printf(
 						"%s failed to login using url %s: %s",
-						c.Hostname(),
+						tsc.Hostname(),
 						loginURL,
 						err,
 					)
@@ -714,8 +818,10 @@ func (s *AuthOIDCScenario) runTailscaleUp(
 					return err
 				}
 
+				log.Printf("cookies: %+v", hc.Jar.Cookies(loginURL))
+
 				if resp.StatusCode != http.StatusOK {
-					log.Printf("%s response code of oidc login request was %s", c.Hostname(), resp.Status)
+					log.Printf("%s response code of oidc login request was %s", tsc.Hostname(), resp.Status)
 					body, _ := io.ReadAll(resp.Body)
 					log.Printf("body: %s", body)
 
@@ -726,12 +832,12 @@ func (s *AuthOIDCScenario) runTailscaleUp(
 
 				_, err = io.ReadAll(resp.Body)
 				if err != nil {
-					log.Printf("%s failed to read response body: %s", c.Hostname(), err)
+					log.Printf("%s failed to read response body: %s", tsc.Hostname(), err)
 
 					return err
 				}
 
-				log.Printf("Finished request for %s to join tailnet", c.Hostname())
+				log.Printf("Finished request for %s to join tailnet", tsc.Hostname())
 				return nil
 			})