Merge fbf6f24f6c into e2d5ee0927

.github/workflows/test-integration.yaml

@@ -21,6 +21,7 @@ jobs:
           - TestPolicyUpdateWhileRunningWithCLIInDatabase
           - TestOIDCAuthenticationPingAll
           - TestOIDCExpireNodesBasedOnTokenExpiry
+          - TestOIDC024UserCreation
           - TestAuthWebFlowAuthenticationPingAll
           - TestAuthWebFlowLogoutAndRelogin
           - TestUserCommand

CHANGELOG.md

@@ -7,8 +7,11 @@
 - Remove `dns.use_username_in_magic_dns` configuration option [#2020](https://github.com/juanfont/headscale/pull/2020)
   - Having usernames in magic DNS is no longer possible.
 - Redo OpenID Connect configuration [#2020](https://github.com/juanfont/headscale/pull/2020)
-  - `strip_email_domain` has been removed, domain is _always_ part of the username for OIDC.
+  - `strip_email_domain` is deprecated, domain is _always_ part of the username for OIDC.
+    - The option is available until the migration strategy is removed.
   - Users are now identified by `sub` claim in the ID token instead of username, allowing the username, name and email to be updated.
+    - By default, users are automatically migrated based on their username when logged in.
+      - This migration can be disabled, and should be on new installations or fully migrated installations [#2170](https://github.com/juanfont/headscale/pull/2170)
   - User has been extended to store username, display name, profile picture url and email.
     - These fields are forwarded to the client, and shows up nicely in the user switcher.
     - These fields can be made available via the API/CLI for non-OIDC users in the future.

cmd/headscale/cli/mockoidc.go

@@ -1,8 +1,10 @@
 package cli
 
 import (
+	"encoding/json"
 	"fmt"
 	"net"
+	"net/http"
 	"os"
 	"strconv"
 	"time"
@@ -64,6 +66,19 @@ func mockOIDC() error {
 		accessTTL = newTTL
 	}
 
+	userStr := os.Getenv("MOCKOIDC_USERS")
+	if userStr == "" {
+		return fmt.Errorf("MOCKOIDC_USERS not defined")
+	}
+
+	var users []mockoidc.MockUser
+	err := json.Unmarshal([]byte(userStr), &users)
+	if err != nil {
+		return fmt.Errorf("unmarshalling users: %w", err)
+	}
+
+	log.Info().Interface("users", users).Msg("loading users from JSON")
+
 	log.Info().Msgf("Access token TTL: %s", accessTTL)
 
 	port, err := strconv.Atoi(portStr)
@@ -71,7 +86,7 @@ func mockOIDC() error {
 		return err
 	}
 
-	mock, err := getMockOIDC(clientID, clientSecret)
+	mock, err := getMockOIDC(clientID, clientSecret, users)
 	if err != nil {
 		return err
 	}
@@ -93,12 +108,18 @@ func mockOIDC() error {
 	return nil
 }
 
-func getMockOIDC(clientID string, clientSecret string) (*mockoidc.MockOIDC, error) {
+func getMockOIDC(clientID string, clientSecret string, users []mockoidc.MockUser) (*mockoidc.MockOIDC, error) {
 	keypair, err := mockoidc.NewKeypair(nil)
 	if err != nil {
 		return nil, err
 	}
 
+	userQueue := mockoidc.UserQueue{}
+
+	for _, user := range users {
+		userQueue.Push(&user)
+	}
+
 	mock := mockoidc.MockOIDC{
 		ClientID:                      clientID,
 		ClientSecret:                  clientSecret,
@@ -107,9 +128,19 @@ func getMockOIDC(clientID string, clientSecret string) (*mockoidc.MockOIDC, erro
 		CodeChallengeMethodsSupported: []string{"plain", "S256"},
 		Keypair:                       keypair,
 		SessionStore:                  mockoidc.NewSessionStore(),
-		UserQueue:                     &mockoidc.UserQueue{},
+		UserQueue:                     &userQueue,
 		ErrorQueue:                    &mockoidc.ErrorQueue{},
 	}
 
+	mock.AddMiddleware(func(h http.Handler) http.Handler {
+		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			log.Info().Msgf("Request: %+v", r)
+			h.ServeHTTP(w, r)
+			if r.Response != nil {
+				log.Info().Msgf("Response: %+v", r.Response)
+			}
+		})
+	})
+
 	return &mock, nil
 }

config-example.yaml

@@ -364,12 +364,18 @@ unix_socket_permission: "0770"
 #   allowed_users:
 #     - alice@example.com
 #
-#   # If `strip_email_domain` is set to `true`, the domain part of the username email address will be removed.
+#   # Map legacy users from pre-0.24.0 versions of headscale to the new OIDC users
-#   # This will transform `first-name.last-name@example.com` to the user `first-name.last-name`
+#   # by taking the username from the legacy user and matching it with the username
-#   # If `strip_email_domain` is set to `false` the domain part will NOT be removed resulting to the following
+#   # provided by the OIDC. This is useful when migrating from legacy users to OIDC
-#   user: `first-name.last-name.example.com`
+#   # to force them using the unique identifier from the OIDC and to give them a
-#
+#   # proper display name and picture if available.
-#   strip_email_domain: true
+#   # Note that this will only work if the username from the legacy user is the same
+#   # and ther is a posibility for account takeover should a username have changed
+#   # with the provider.
+#   # Disabling this feature will cause all new logins to be created as new users.
+#   # Note this option will be removed in the future and should be set to false
+#   # on all new installations, or when all users have logged in with OIDC once.
+#   map_legacy_users: true
 
 # Logtail configuration
 # Logtail is Tailscales logging and auditing infrastructure, it allows the control panel

hscontrol/db/db.go

@@ -474,6 +474,8 @@ func NewHeadscaleDatabase(
 				Rollback: func(db *gorm.DB) error { return nil },
 			},
 			{
+				// Pick up new user fields used for OIDC and to
+				// populate the user with more interesting information.
 				ID: "202407191627",
 				Migrate: func(tx *gorm.DB) error {
 					err := tx.AutoMigrate(&types.User{})
@@ -485,6 +487,21 @@ func NewHeadscaleDatabase(
 				},
 				Rollback: func(db *gorm.DB) error { return nil },
 			},
+			{
+				// The unique constraint of Name has been dropped
+				// in favour of a unique together of name and
+				// provider identity.
+				ID: "202408181235",
+				Migrate: func(tx *gorm.DB) error {
+					err := tx.AutoMigrate(&types.User{})
+					if err != nil {
+						return err
+					}
+
+					return nil
+				},
+				Rollback: func(db *gorm.DB) error { return nil },
+			},
 		},
 	)
 

hscontrol/oidc.go

@@ -436,25 +436,42 @@ func (a *AuthProviderOIDC) createOrUpdateUserFromClaim(
 ) (*types.User, error) {
 	var user *types.User
 	var err error
-	user, err = a.db.GetUserByOIDCIdentifier(claims.Sub)
+	user, err = a.db.GetUserByOIDCIdentifier(claims.Identifier())
 	if err != nil && !errors.Is(err, db.ErrUserNotFound) {
 		return nil, fmt.Errorf("creating or updating user: %w", err)
 	}
 
 	// This check is for legacy, if the user cannot be found by the OIDC identifier
 	// look it up by username. This should only be needed once.
-	if user == nil {
+	// This branch will presist for a number of versions after the OIDC migration and
-		user, err = a.db.GetUserByName(claims.Username)
+	// then be removed following a deprecation.
-		if err != nil && !errors.Is(err, db.ErrUserNotFound) {
+	// TODO(kradalby): Remove when strip_email_domain and migration is removed
-			return nil, fmt.Errorf("creating or updating user: %w", err)
+	// after #2170 is cleaned up.
-		}
+	if a.cfg.MapLegacyUsers && user == nil {
+		log.Trace().Str("username", claims.Username).Str("sub", claims.Sub).Msg("user not found by OIDC identifier, looking up by username")
+		if oldUsername, err := getUserName(claims, a.cfg.StripEmaildomain); err == nil {
+			log.Trace().Str("old_username", oldUsername).Str("sub", claims.Sub).Msg("found username")
+			user, err = a.db.GetUserByName(oldUsername)
+			if err != nil && !errors.Is(err, db.ErrUserNotFound) {
+				return nil, fmt.Errorf("getting user: %w", err)
+			}
 
-		// if the user is still not found, create a new empty user.
+			// If the user exists, but it already has a provider identifier (OIDC sub), create a new user.
-		if user == nil {
+			// This is to prevent users that have already been migrated to the new OIDC format
-			user = &types.User{}
+			// to be updated with the new OIDC identifier inexplicitly which might be the cause of an
+			// account takeover.
+			if user != nil && user.ProviderIdentifier != "" {
+				log.Info().Str("username", claims.Username).Str("sub", claims.Sub).Msg("user found by username, but has provider identifier, creating new user.")
+				user = &types.User{}
+			}
 		}
 	}
 
+	// if the user is still not found, create a new empty user.
+	if user == nil {
+		user = &types.User{}
+	}
+
 	user.FromClaim(claims)
 	err = a.db.DB.Save(user).Error
 	if err != nil {
@@ -502,3 +519,24 @@ func renderOIDCCallbackTemplate(
 
 	return &content, nil
 }
+
+// TODO(kradalby): Reintroduce when strip_email_domain is removed
+// after #2170 is cleaned up
+// DEPRECATED: DO NOT USE
+func getUserName(
+	claims *types.OIDCClaims,
+	stripEmaildomain bool,
+) (string, error) {
+	if !claims.EmailVerified {
+		return "", fmt.Errorf("email not verified")
+	}
+	userName, err := util.NormalizeToFQDNRules(
+		claims.Email,
+		stripEmaildomain,
+	)
+	if err != nil {
+		return "", err
+	}
+
+	return userName, nil
+}

hscontrol/policy/acls.go

@@ -178,7 +178,12 @@ func (pol *ACLPolicy) CompileFilterRules(
 		for srcIndex, src := range acl.Sources {
 			srcs, err := pol.expandSource(src, nodes)
 			if err != nil {
-				return nil, fmt.Errorf("parsing policy, acl index: %d->%d: %w", index, srcIndex, err)
+				return nil, fmt.Errorf(
+					"parsing policy, acl index: %d->%d: %w",
+					index,
+					srcIndex,
+					err,
+				)
 			}
 			srcIPs = append(srcIPs, srcs...)
 		}
@@ -335,12 +340,21 @@ func (pol *ACLPolicy) CompileSSHPolicy(
 		case "check":
 			checkAction, err := sshCheckAction(sshACL.CheckPeriod)
 			if err != nil {
-				return nil, fmt.Errorf("parsing SSH policy, parsing check duration, index: %d: %w", index, err)
+				return nil, fmt.Errorf(
+					"parsing SSH policy, parsing check duration, index: %d: %w",
+					index,
+					err,
+				)
 			} else {
 				action = *checkAction
 			}
 		default:
-			return nil, fmt.Errorf("parsing SSH policy, unknown action %q, index: %d: %w", sshACL.Action, index, err)
+			return nil, fmt.Errorf(
+				"parsing SSH policy, unknown action %q, index: %d: %w",
+				sshACL.Action,
+				index,
+				err,
+			)
 		}
 
 		principals := make([]*tailcfg.SSHPrincipal, 0, len(sshACL.Sources))
@@ -977,10 +991,7 @@ func FilterNodesByACL(
 			continue
 		}
 
-		log.Printf("Checking if %s can access %s", node.Hostname, peer.Hostname)
-
 		if node.CanAccess(filter, nodes[index]) || peer.CanAccess(filter, node) {
-			log.Printf("CAN ACCESS %s can access %s", node.Hostname, peer.Hostname)
 			result = append(result, peer)
 		}
 	}

hscontrol/types/config.go

@@ -162,8 +162,10 @@ type OIDCConfig struct {
 	AllowedDomains             []string
 	AllowedUsers               []string
 	AllowedGroups              []string
+	StripEmaildomain           bool
 	Expiry                     time.Duration
 	UseExpiryFromToken         bool
+	MapLegacyUsers             bool
 }
 
 type DERPConfig struct {
@@ -272,9 +274,11 @@ func LoadConfig(path string, isFile bool) error {
 	viper.SetDefault("database.sqlite.write_ahead_log", true)
 
 	viper.SetDefault("oidc.scope", []string{oidc.ScopeOpenID, "profile", "email"})
+	viper.SetDefault("oidc.strip_email_domain", true)
 	viper.SetDefault("oidc.only_start_if_oidc_is_available", true)
 	viper.SetDefault("oidc.expiry", "180d")
 	viper.SetDefault("oidc.use_expiry_from_token", false)
+	viper.SetDefault("oidc.map_legacy_users", true)
 
 	viper.SetDefault("logtail.enabled", false)
 	viper.SetDefault("randomize_client_port", false)
@@ -318,14 +322,18 @@ func validateServerConfig() error {
 	depr.warn("dns_config.use_username_in_magic_dns")
 	depr.warn("dns.use_username_in_magic_dns")
 
-	depr.fatal("oidc.strip_email_domain")
+	// TODO(kradalby): Reintroduce when strip_email_domain is removed
+	// after #2170 is cleaned up
+	// depr.fatal("oidc.strip_email_domain")
 	depr.fatal("dns.use_username_in_musername_in_magic_dns")
 	depr.fatal("dns_config.use_username_in_musername_in_magic_dns")
 
 	depr.Log()
 
 	for _, removed := range []string{
-		"oidc.strip_email_domain",
+		// TODO(kradalby): Reintroduce when strip_email_domain is removed
+		// after #2170 is cleaned up
+		// "oidc.strip_email_domain",
 		"dns_config.use_username_in_musername_in_magic_dns",
 	} {
 		if viper.IsSet(removed) {
@@ -897,6 +905,10 @@ func LoadServerConfig() (*Config, error) {
 				}
 			}(),
 			UseExpiryFromToken: viper.GetBool("oidc.use_expiry_from_token"),
+			// TODO(kradalby): Remove when strip_email_domain is removed
+			// after #2170 is cleaned up
+			StripEmaildomain: viper.GetBool("oidc.strip_email_domain"),
+			MapLegacyUsers:   viper.GetBool("oidc.map_legacy_users"),
 		},
 
 		LogTail:             logTailConfig,

hscontrol/types/users.go

@@ -19,10 +19,14 @@ type UserID uint64
 // that contain our machines.
 type User struct {
 	gorm.Model
+	// The index `idx_name_provider_identifier` is to enforce uniqueness
+	// between Name and ProviderIdentifier. This ensures that
+	// you can have multiple usersnames of the same name in OIDC,
+	// but not if you only run with CLI users.
 
 	// Username for the user, is used if email is empty
 	// Should not be used, please use Username().
-	Name string `gorm:"unique"`
+	Name string `gorm:"index,uniqueIndex:idx_name_provider_identifier"`
 
 	// Typically the full name of the user
 	DisplayName string
@@ -34,7 +38,7 @@ type User struct {
 	// Unique identifier of the user from OIDC,
 	// comes from `sub` claim in the OIDC token
 	// and is used to lookup the user.
-	ProviderIdentifier string `gorm:"index"`
+	ProviderIdentifier string `gorm:"unique,index,uniqueIndex:idx_name_provider_identifier"`
 
 	// Provider is the origin of the user account,
 	// same as RegistrationMethod, without authkey.
@@ -50,8 +54,15 @@ type User struct {
 // enabled with OIDC, which means that there is a domain involved which
 // should be used throughout headscale, in information returned to the
 // user and the Policy engine.
+// If the username does not contain an '@' it will be added to the end.
 func (u *User) Username() string {
-	return cmp.Or(u.Email, u.Name, u.ProviderIdentifier, strconv.FormatUint(uint64(u.ID), 10))
+	username := cmp.Or(u.Email, u.Name, u.ProviderIdentifier, strconv.FormatUint(uint64(u.ID), 10))
+	// TODO(kradalby): Wire up all of this for the future
+	// if !strings.Contains(username, "@") {
+	// 	username = username + "@"
+	// }
+
+	return username
 }
 
 // DisplayNameOrUsername returns the DisplayName if it exists, otherwise
@@ -116,6 +127,7 @@ func (u *User) Proto() *v1.User {
 type OIDCClaims struct {
 	// Sub is the user's unique identifier at the provider.
 	Sub string `json:"sub"`
+	Iss string `json:"iss"`
 
 	// Name is the user's full name.
 	Name              string   `json:"name,omitempty"`
@@ -126,12 +138,18 @@ type OIDCClaims struct {
 	Username          string   `json:"preferred_username,omitempty"`
 }
 
+func (c *OIDCClaims) Identifier() string {
+	return c.Iss + "/" + c.Sub
+}
+
 // FromClaim overrides a User from OIDC claims.
 // All fields will be updated, except for the ID.
 func (u *User) FromClaim(claims *OIDCClaims) {
-	u.ProviderIdentifier = claims.Sub
+	u.ProviderIdentifier = claims.Identifier()
 	u.DisplayName = claims.Name
-	u.Email = claims.Email
+	if claims.EmailVerified {
+		u.Email = claims.Email
+	}
 	u.Name = claims.Username
 	u.ProfilePicURL = claims.ProfilePictureURL
 	u.Provider = util.RegisterMethodOIDC

hscontrol/util/dns.go

@@ -182,3 +182,33 @@ func GenerateIPv6DNSRootDomain(ipPrefix netip.Prefix) []dnsname.FQDN {
 
 	return fqdns
 }
+
+// TODO(kradalby): Reintroduce when strip_email_domain is removed
+// after #2170 is cleaned up
+// DEPRECATED: DO NOT USE
+// NormalizeToFQDNRules will replace forbidden chars in user
+// it can also return an error if the user doesn't respect RFC 952 and 1123.
+func NormalizeToFQDNRules(name string, stripEmailDomain bool) (string, error) {
+
+	name = strings.ToLower(name)
+	name = strings.ReplaceAll(name, "'", "")
+	atIdx := strings.Index(name, "@")
+	if stripEmailDomain && atIdx > 0 {
+		name = name[:atIdx]
+	} else {
+		name = strings.ReplaceAll(name, "@", ".")
+	}
+	name = invalidCharsInUserRegex.ReplaceAllString(name, "-")
+
+	for _, elt := range strings.Split(name, ".") {
+		if len(elt) > LabelHostnameLength {
+			return "", fmt.Errorf(
+				"label %v is more than 63 chars: %w",
+				elt,
+				ErrInvalidUserName,
+			)
+		}
+	}
+
+	return name, nil
+}

integration/auth_oidc_test.go

@@ -3,6 +3,7 @@ package integration
 import (
 	"context"
 	"crypto/tls"
+	"encoding/json"
 	"errors"
 	"fmt"
 	"io"
@@ -10,14 +11,19 @@ import (
 	"net"
 	"net/http"
 	"net/netip"
+	"sort"
 	"strconv"
 	"testing"
 	"time"
 
+	"github.com/google/go-cmp/cmp"
+	"github.com/google/go-cmp/cmp/cmpopts"
+	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/juanfont/headscale/hscontrol/types"
 	"github.com/juanfont/headscale/hscontrol/util"
 	"github.com/juanfont/headscale/integration/dockertestutil"
 	"github.com/juanfont/headscale/integration/hsic"
+	"github.com/oauth2-proxy/mockoidc"
 	"github.com/ory/dockertest/v3"
 	"github.com/ory/dockertest/v3/docker"
 	"github.com/samber/lo"
@@ -50,18 +56,32 @@ func TestOIDCAuthenticationPingAll(t *testing.T) {
 	}
 	defer scenario.ShutdownAssertNoPanics(t)
 
+	// Logins to MockOIDC is served by a queue with a strict order,
+	// if we use more than one node per user, the order of the logins
+	// will not be deterministic and the test will fail.
 	spec := map[string]int{
-		"user1": len(MustTestVersions),
+		"user1": 1,
+		"user2": 1,
 	}
 
-	oidcConfig, err := scenario.runMockOIDC(defaultAccessTTL)
+	mockusers := []mockoidc.MockUser{
+		oidcMockUser("user1", true),
+		oidcMockUser("user2", false),
+	}
+
+	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,
 		"CREDENTIALS_DIRECTORY_TEST":        "/tmp",
 		"HEADSCALE_OIDC_CLIENT_SECRET_PATH": "${CREDENTIALS_DIRECTORY_TEST}/hs_client_oidc_secret",
+		// TODO(kradalby): Remove when strip_email_domain is removed
+		// after #2170 is cleaned up
+		"HEADSCALE_OIDC_MAP_LEGACY_USERS":   "0",
+		"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": "0",
 	}
 
 	err = scenario.CreateHeadscaleEnv(
@@ -91,6 +111,55 @@ func TestOIDCAuthenticationPingAll(t *testing.T) {
 
 	success := pingAllHelper(t, allClients, allAddrs)
 	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
+
+	headscale, err := scenario.Headscale()
+	assertNoErr(t, err)
+
+	var listUsers []v1.User
+	err = executeAndUnmarshal(headscale,
+		[]string{
+			"headscale",
+			"users",
+			"list",
+			"--output",
+			"json",
+		},
+		&listUsers,
+	)
+	assertNoErr(t, err)
+
+	want := []v1.User{
+		{
+			Id:   "1",
+			Name: "user1",
+		},
+		{
+			Id:         "2",
+			Name:       "user1",
+			Email:      "user1@headscale.net",
+			Provider:   "oidc",
+			ProviderId: oidcConfig.Issuer + "/user1",
+		},
+		{
+			Id:   "3",
+			Name: "user2",
+		},
+		{
+			Id:         "4",
+			Name:       "user2",
+			Email:      "", // Unverified
+			Provider:   "oidc",
+			ProviderId: oidcConfig.Issuer + "/user2",
+		},
+	}
+
+	sort.Slice(listUsers, func(i, j int) bool {
+		return listUsers[i].Id < listUsers[j].Id
+	})
+
+	if diff := cmp.Diff(want, listUsers, cmpopts.IgnoreUnexported(v1.User{}), cmpopts.IgnoreFields(v1.User{}, "CreatedAt")); diff != "" {
+		t.Fatalf("unexpected users: %s", diff)
+	}
 }
 
 // This test is really flaky.
@@ -111,11 +180,16 @@ func TestOIDCExpireNodesBasedOnTokenExpiry(t *testing.T) {
 	defer scenario.ShutdownAssertNoPanics(t)
 
 	spec := map[string]int{
-		"user1": 3,
+		"user1": 1,
+		"user2": 1,
 	}
 
-	oidcConfig, err := scenario.runMockOIDC(shortAccessTTL)
+	oidcConfig, err := scenario.runMockOIDC(shortAccessTTL, []mockoidc.MockUser{
+		oidcMockUser("user1", true),
+		oidcMockUser("user2", false),
+	})
 	assertNoErrf(t, "failed to run mock OIDC server: %s", err)
+	defer scenario.mockOIDC.Close()
 
 	oidcMap := map[string]string{
 		"HEADSCALE_OIDC_ISSUER":                oidcConfig.Issuer,
@@ -159,6 +233,297 @@ func TestOIDCExpireNodesBasedOnTokenExpiry(t *testing.T) {
 	assertTailscaleNodesLogout(t, allClients)
 }
 
+// TODO(kradalby):
+// - Test that creates a new user when one exists when migration is turned off
+// - Test that takes over a user when one exists when migration is turned on
+//   - But email is not verified
+//   - stripped email domain on/off
+func TestOIDC024UserCreation(t *testing.T) {
+	IntegrationSkip(t)
+
+	tests := []struct {
+		name          string
+		config        map[string]string
+		emailVerified bool
+		cliUsers      []string
+		oidcUsers     []string
+		want          func(iss string) []v1.User
+	}{
+		{
+			name: "no-migration-verified-email",
+			config: map[string]string{
+				"HEADSCALE_OIDC_MAP_LEGACY_USERS": "0",
+			},
+			emailVerified: true,
+			cliUsers:      []string{"user1", "user2"},
+			oidcUsers:     []string{"user1", "user2"},
+			want: func(iss string) []v1.User {
+				return []v1.User{
+					{
+						Id:   "1",
+						Name: "user1",
+					},
+					{
+						Id:         "2",
+						Name:       "user1",
+						Email:      "user1@headscale.net",
+						Provider:   "oidc",
+						ProviderId: iss + "/user1",
+					},
+					{
+						Id:   "3",
+						Name: "user2",
+					},
+					{
+						Id:         "4",
+						Name:       "user2",
+						Email:      "user2@headscale.net",
+						Provider:   "oidc",
+						ProviderId: iss + "/user2",
+					},
+				}
+			},
+		},
+		{
+			name: "no-migration-not-verified-email",
+			config: map[string]string{
+				"HEADSCALE_OIDC_MAP_LEGACY_USERS": "0",
+			},
+			emailVerified: false,
+			cliUsers:      []string{"user1", "user2"},
+			oidcUsers:     []string{"user1", "user2"},
+			want: func(iss string) []v1.User {
+				return []v1.User{
+					{
+						Id:   "1",
+						Name: "user1",
+					},
+					{
+						Id:         "2",
+						Name:       "user1",
+						Provider:   "oidc",
+						ProviderId: iss + "/user1",
+					},
+					{
+						Id:   "3",
+						Name: "user2",
+					},
+					{
+						Id:         "4",
+						Name:       "user2",
+						Provider:   "oidc",
+						ProviderId: iss + "/user2",
+					},
+				}
+			},
+		},
+		{
+			name: "migration-strip-domains-verified-email",
+			config: map[string]string{
+				"HEADSCALE_OIDC_MAP_LEGACY_USERS":   "1",
+				"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": "1",
+			},
+			emailVerified: true,
+			cliUsers:      []string{"user1", "user2"},
+			oidcUsers:     []string{"user1", "user2"},
+			want: func(iss string) []v1.User {
+				return []v1.User{
+					{
+						Id:         "1",
+						Name:       "user1",
+						Email:      "user1@headscale.net",
+						Provider:   "oidc",
+						ProviderId: iss + "/user1",
+					},
+					{
+						Id:         "2",
+						Name:       "user2",
+						Email:      "user2@headscale.net",
+						Provider:   "oidc",
+						ProviderId: iss + "/user2",
+					},
+				}
+			},
+		},
+		{
+			name: "migration-strip-domains-not-verified-email",
+			config: map[string]string{
+				"HEADSCALE_OIDC_MAP_LEGACY_USERS":   "1",
+				"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": "1",
+			},
+			emailVerified: false,
+			cliUsers:      []string{"user1", "user2"},
+			oidcUsers:     []string{"user1", "user2"},
+			want: func(iss string) []v1.User {
+				return []v1.User{
+					{
+						Id:   "1",
+						Name: "user1",
+					},
+					{
+						Id:         "2",
+						Name:       "user1",
+						Provider:   "oidc",
+						ProviderId: iss + "/user1",
+					},
+					{
+						Id:   "3",
+						Name: "user2",
+					},
+					{
+						Id:         "4",
+						Name:       "user2",
+						Provider:   "oidc",
+						ProviderId: iss + "/user2",
+					},
+				}
+			},
+		},
+		{
+			name: "migration-no-strip-domains-verified-email",
+			config: map[string]string{
+				"HEADSCALE_OIDC_MAP_LEGACY_USERS":   "1",
+				"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": "0",
+			},
+			emailVerified: true,
+			cliUsers:      []string{"user1.headscale.net", "user2.headscale.net"},
+			oidcUsers:     []string{"user1", "user2"},
+			want: func(iss string) []v1.User {
+				return []v1.User{
+					// Hmm I think we will have to overwrite the initial name here
+					// createuser with "user1.headscale.net", but oidc with "user1"
+					{
+						Id:         "1",
+						Name:       "user1",
+						Email:      "user1@headscale.net",
+						Provider:   "oidc",
+						ProviderId: iss + "/user1",
+					},
+					{
+						Id:         "2",
+						Name:       "user2",
+						Email:      "user2@headscale.net",
+						Provider:   "oidc",
+						ProviderId: iss + "/user2",
+					},
+				}
+			},
+		},
+		{
+			name: "migration-no-strip-domains-not-verified-email",
+			config: map[string]string{
+				"HEADSCALE_OIDC_MAP_LEGACY_USERS":   "1",
+				"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": "0",
+			},
+			emailVerified: false,
+			cliUsers:      []string{"user1.headscale.net", "user2.headscale.net"},
+			oidcUsers:     []string{"user1", "user2"},
+			want: func(iss string) []v1.User {
+				return []v1.User{
+					{
+						Id:   "1",
+						Name: "user1.headscale.net",
+					},
+					{
+						Id:         "2",
+						Name:       "user1",
+						Provider:   "oidc",
+						ProviderId: iss + "/user1",
+					},
+					{
+						Id:   "3",
+						Name: "user2.headscale.net",
+					},
+					{
+						Id:         "4",
+						Name:       "user2",
+						Provider:   "oidc",
+						ProviderId: iss + "/user2",
+					},
+				}
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			baseScenario, err := NewScenario(dockertestMaxWait())
+			assertNoErr(t, err)
+
+			scenario := AuthOIDCScenario{
+				Scenario: baseScenario,
+			}
+			defer scenario.ShutdownAssertNoPanics(t)
+
+			spec := map[string]int{}
+			for _, user := range tt.cliUsers {
+				spec[user] = 1
+			}
+
+			var mockusers []mockoidc.MockUser
+			for _, user := range tt.oidcUsers {
+				mockusers = append(mockusers, oidcMockUser(user, tt.emailVerified))
+			}
+
+			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,
+				"CREDENTIALS_DIRECTORY_TEST":        "/tmp",
+				"HEADSCALE_OIDC_CLIENT_SECRET_PATH": "${CREDENTIALS_DIRECTORY_TEST}/hs_client_oidc_secret",
+			}
+
+			for k, v := range tt.config {
+				oidcMap[k] = v
+			}
+
+			err = scenario.CreateHeadscaleEnv(
+				spec,
+				hsic.WithTestName("oidcmigration"),
+				hsic.WithConfigEnv(oidcMap),
+				hsic.WithTLS(),
+				hsic.WithHostnameAsServerURL(),
+				hsic.WithFileInContainer("/tmp/hs_client_oidc_secret", []byte(oidcConfig.ClientSecret)),
+			)
+			assertNoErrHeadscaleEnv(t, err)
+
+			// Ensure that the nodes have logged in, this is what
+			// triggers user creation via OIDC.
+			err = scenario.WaitForTailscaleSync()
+			assertNoErrSync(t, err)
+
+			headscale, err := scenario.Headscale()
+			assertNoErr(t, err)
+
+			want := tt.want(oidcConfig.Issuer)
+
+			var listUsers []v1.User
+			err = executeAndUnmarshal(headscale,
+				[]string{
+					"headscale",
+					"users",
+					"list",
+					"--output",
+					"json",
+				},
+				&listUsers,
+			)
+			assertNoErr(t, err)
+
+			sort.Slice(listUsers, func(i, j int) bool {
+				return listUsers[i].Id < listUsers[j].Id
+			})
+
+			if diff := cmp.Diff(want, listUsers, cmpopts.IgnoreUnexported(v1.User{}), cmpopts.IgnoreFields(v1.User{}, "CreatedAt")); diff != "" {
+				t.Errorf("unexpected users: %s", diff)
+			}
+		})
+	}
+}
+
 func (s *AuthOIDCScenario) CreateHeadscaleEnv(
 	users map[string]int,
 	opts ...hsic.Option,
@@ -174,6 +539,13 @@ func (s *AuthOIDCScenario) CreateHeadscaleEnv(
 	}
 
 	for userName, clientCount := range users {
+		if clientCount != 1 {
+			// OIDC scenario only supports one client per user.
+			// This is because the MockOIDC server can only serve login
+			// requests based on a queue it has been given on startup.
+			// We currently only populates it with one login request per user.
+			return fmt.Errorf("client count must be 1 for OIDC scenario.")
+		}
 		log.Printf("creating user %s with %d clients", userName, clientCount)
 		err = s.CreateUser(userName)
 		if err != nil {
@@ -194,7 +566,7 @@ func (s *AuthOIDCScenario) CreateHeadscaleEnv(
 	return nil
 }
 
-func (s *AuthOIDCScenario) runMockOIDC(accessTTL time.Duration) (*types.OIDCConfig, error) {
+func (s *AuthOIDCScenario) runMockOIDC(accessTTL time.Duration, users []mockoidc.MockUser) (*types.OIDCConfig, error) {
 	port, err := dockertestutil.RandomFreeHostPort()
 	if err != nil {
 		log.Fatalf("could not find an open port: %s", err)
@@ -205,6 +577,11 @@ func (s *AuthOIDCScenario) runMockOIDC(accessTTL time.Duration) (*types.OIDCConf
 
 	hostname := fmt.Sprintf("hs-oidcmock-%s", hash)
 
+	usersJSON, err := json.Marshal(users)
+	if err != nil {
+		return nil, err
+	}
+
 	mockOidcOptions := &dockertest.RunOptions{
 		Name:         hostname,
 		Cmd:          []string{"headscale", "mockoidc"},
@@ -219,6 +596,7 @@ func (s *AuthOIDCScenario) runMockOIDC(accessTTL time.Duration) (*types.OIDCConf
 			"MOCKOIDC_CLIENT_ID=superclient",
 			"MOCKOIDC_CLIENT_SECRET=supersecret",
 			fmt.Sprintf("MOCKOIDC_ACCESS_TTL=%s", accessTTL.String()),
+			fmt.Sprintf("MOCKOIDC_USERS=%s", string(usersJSON)),
 		},
 	}
 
@@ -310,45 +688,40 @@ func (s *AuthOIDCScenario) runTailscaleUp(
 
 				log.Printf("%s login url: %s\n", c.Hostname(), loginURL.String())
 
-				if err := s.pool.Retry(func() error {
+				log.Printf("%s logging in with url", c.Hostname())
-					log.Printf("%s logging in with url", c.Hostname())
+				httpClient := &http.Client{Transport: insecureTransport}
-					httpClient := &http.Client{Transport: insecureTransport}
+				ctx := context.Background()
-					ctx := context.Background()
+				req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
-					req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
+				resp, err := httpClient.Do(req)
-					resp, err := httpClient.Do(req)
+				if err != nil {
-					if err != nil {
+					log.Printf(
-						log.Printf(
+						"%s failed to login using url %s: %s",
-							"%s failed to login using url %s: %s",
+						c.Hostname(),
-							c.Hostname(),
+						loginURL,
-							loginURL,
+						err,
-							err,
+					)
-						)
 
-						return err
+					return err
-					}
+				}
 
-					if resp.StatusCode != http.StatusOK {
+				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", c.Hostname(), resp.Status)
+					body, _ := io.ReadAll(resp.Body)
+					log.Printf("body: %s", body)
 
-						return errStatusCodeNotOK
+					return errStatusCodeNotOK
-					}
+				}
 
-					defer resp.Body.Close()
+				defer resp.Body.Close()
 
-					_, err = io.ReadAll(resp.Body)
+				_, err = io.ReadAll(resp.Body)
-					if err != nil {
+				if err != nil {
-						log.Printf("%s failed to read response body: %s", c.Hostname(), err)
+					log.Printf("%s failed to read response body: %s", c.Hostname(), err)
 
-						return err
-					}
-
-					return nil
-				}); err != nil {
 					return err
 				}
 
 				log.Printf("Finished request for %s to join tailnet", c.Hostname())
-
 				return nil
 			})
 
@@ -395,3 +768,12 @@ func assertTailscaleNodesLogout(t *testing.T, clients []TailscaleClient) {
 		assert.Equal(t, "NeedsLogin", status.BackendState)
 	}
 }
+
+func oidcMockUser(username string, emailVerified bool) mockoidc.MockUser {
+	return mockoidc.MockUser{
+		Subject:           username,
+		PreferredUsername: username,
+		Email:             fmt.Sprintf("%s@headscale.net", username),
+		EmailVerified:     emailVerified,
+	}
+}

integration/cli_test.go

@@ -212,7 +212,9 @@ func TestPreAuthKeyCommand(t *testing.T) {
 			continue
 		}
 
-		assert.Equal(t, listedPreAuthKeys[index].GetAclTags(), []string{"tag:test1", "tag:test2"})
+		tags := listedPreAuthKeys[index].GetAclTags()
+		sort.Strings(tags)
+		assert.Equal(t, []string{"tag:test1", "tag:test2"}, tags)
 	}
 
 	// Test key expiry

integration/dockertestutil/execute.go

@@ -74,7 +74,7 @@ func ExecuteCommand(
 	select {
 	case res := <-resultChan:
 		if res.err != nil {
-			return stdout.String(), stderr.String(), res.err
+			return stdout.String(), stderr.String(), fmt.Errorf("command failed, stderr: %s: %w", stderr.String(), res.err)
 		}
 
 		if res.exitCode != 0 {
@@ -83,12 +83,12 @@ func ExecuteCommand(
 			// log.Println("stdout: ", stdout.String())
 			// log.Println("stderr: ", stderr.String())
 
-			return stdout.String(), stderr.String(), ErrDockertestCommandFailed
+			return stdout.String(), stderr.String(), fmt.Errorf("command failed, stderr: %s: %w", stderr.String(), ErrDockertestCommandFailed)
 		}
 
 		return stdout.String(), stderr.String(), nil
 	case <-time.After(execConfig.timeout):
 
-		return stdout.String(), stderr.String(), ErrDockertestCommandTimeout
+		return stdout.String(), stderr.String(), fmt.Errorf("command failed, stderr: %s: %w", stderr.String(), ErrDockertestCommandTimeout)
 	}
 }