Merge 0f432854c6 into edf9e25001

feat: support client verify for derp (add integration tests) (#2046 )
* feat: support client verify for derp * docs: fix doc for integration test * tests: add integration test for DERP verify endpoint * tests: use `tailcfg.DERPMap` instead of `[]byte` * refactor: introduce func `ContainsNodeKey` * tests(dsic): use string builder for cmd args * ci: fix tests order * tests: fix derper failure * chore: cleanup * tests(verify-client): perfer to use `CreateHeadscaleEnv` * refactor(verify-client): simplify error handling * tests: fix `TestDERPVerifyEndpoint` * refactor: make `doVerify` a seperated func --------- Co-authored-by: 117503445 <t117503445@gmail.com>
2024-11-26 08:53:05 +00:00 · 2024-11-22 13:49:57 +01:00 · 2024-11-22 13:23:05 +01:00 · 2024-11-22 13:21:44 +01:00 · 2024-11-22 12:22:28 +01:00 · 2024-11-22 12:22:27 +01:00
41 changed files with 1891 additions and 365 deletions
--- a/.github/workflows/test-integration.yaml
+++ b/.github/workflows/test-integration.yaml
@ -21,6 +21,7 @@ jobs:
          - TestPolicyUpdateWhileRunningWithCLIInDatabase
          - TestOIDCAuthenticationPingAll
          - TestOIDCExpireNodesBasedOnTokenExpiry
+          - TestOIDC024UserCreation
          - TestAuthWebFlowAuthenticationPingAll
          - TestAuthWebFlowLogoutAndRelogin
          - TestUserCommand
@ -38,6 +39,7 @@ jobs:
          - TestNodeMoveCommand
          - TestPolicyCommand
          - TestPolicyBrokenConfigCommand
+          - TestDERPVerifyEndpoint
          - TestResolveMagicDNS
          - TestValidateResolvConf
          - TestDERPServerScenario
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@ -2,16 +2,82 @@

 ## Next

+### Security fix: OIDC changes in Headscale 0.24.0
+
+_Headscale v0.23.0 and earlier_ identified OIDC users by the "username" part of their email address (when `strip_email_domain: true`, the default) or whole email address (when `strip_email_domain: false`).
+
+Depending on how Headscale and your Identity Provider (IdP) were configured, only using the `email` claim could allow a malicious user with an IdP account to take over another Headscale user's account, even when `strip_email_domain: false`.
+
+This would also cause a user to lose access to their Headscale account if they changed their email address.
+
+_Headscale v0.24.0_ now identifies OIDC users by the `iss` and `sub` claims. [These are guaranteed by the OIDC specification to be stable and unique](https://openid.net/specs/openid-connect-core-1_0.html#ClaimStability), even if a user changes email address. A well-designed IdP will typically set `sub` to an opaque identifier like a UUID or numeric ID, which has no relation to the user's name or email address.
+
+This issue _only_ affects Headscale installations which authenticate with OIDC.
+
+Headscale v0.24.0 and later will also automatically update profile fields with OIDC data on login. This means that users can change those details in your IdP, and have it populate to Headscale automatically the next time they log in. However, this may affect the way you reference users in policies.
+
+#### Migrating existing installations
+
+Headscale v0.23.0 and earlier never recorded the `iss` and `sub` fields, so all legacy (existing) OIDC accounts from _need to be migrated_ to be properly secured.
+
+Headscale v0.24.0 has an automatic migration feature, which is enabled by default (`map_legacy_users: true`). **This will be disabled by default in a future version of Headscale – any unmigrated users will get new accounts.**
+
+Headscale v0.24.0 will ignore any `email` claim if the IdP does not provide an `email_verified` claim set to `true`. [What "verified" actually means is contextually dependent](https://openid.net/specs/openid-connect-core-1_0.html#StandardClaims) – Headscale uses it as a signal that the contents of the `email` claim is reasonably trustworthy.
+
+Headscale v0.23.0 and earlier never checked the `email_verified` claim. This means even if an IdP explicitly indicated to Headscale that its `email` claim was untrustworthy, Headscale would have still accepted it.
+
+##### What does automatic migration do?
+
+When automatic migration is enabled (`map_legacy_users: true`), Headscale will first match an OIDC account to a Headscale account by `iss` and `sub`, and then fall back to matching OIDC users similarly to how Headscale v0.23.0 did:
+
+- If `strip_email_domain: true` (the default): the Headscale username matches the "username" part of their email address.
+- If `strip_email_domain: false`: the Headscale username matches the _whole_ email address.
+
+On migration, Headscale will change the account's username to their `preferred_username`. **This could break any ACLs or policies which are configured to match by username.**
+
+Like with Headscale v0.23.0 and earlier, this migration only works for users who haven't changed their email address since their last Headscale login.
+
+A _successful_ automated migration should otherwise be transparent to users.
+
+Once a Headscale account has been migrated, it will be _unavailable_ to be matched by the legacy process. An OIDC login with a matching username, but _non-matching_ `iss` and `sub` will instead get a _new_ Headscale account.
+
+Because of the way OIDC works, Headscale's automated migration process can _only_ work when a user tries to log in after the update. Mass updates would require Headscale implement a protocol like SCIM, which is **extremely** complicated and not available in all identity providers.
+
+Administrators could also attempt to migrate users manually by editing the database, using their own mapping rules with known-good data sources.
+
+Legacy account migration should have no effect on new installations where all users have a recorded `sub` and `iss`.
+
+##### What happens when automatic migration is disabled?
+
+When automatic migration is disabled (`map_legacy_users: false`), Headscale will only try to match an OIDC account to a Headscale account by `iss` and `sub`.
+
+If there is no match, it will get a _new_ Headscale account – even if there was a legacy account which _could_ have matched and migrated.
+
+We recommend new Headscale users explicitly disable automatic migration – but it should otherwise have no effect if every account has a recorded `iss` and `sub`.
+
+When automatic migration is disabled, the `strip_email_domain` setting will have no effect.
+
+Special thanks to @micolous for reviewing, proposing and working with us on these changes.
+
+#### Other OIDC changes
+
+Headscale now uses [the standard OIDC claims](https://openid.net/specs/openid-connect-core-1_0.html#StandardClaims) to populate and update user information every time they log in:
+
+| Headscale profile field | OIDC claim           | Notes / examples                                                                                          |
+| ----------------------- | -------------------- | --------------------------------------------------------------------------------------------------------- |
+| email address           | `email`              | Only used when `"email_verified": true`                                                                   |
+| display name            | `name`               | eg: `Sam Smith`                                                                                           |
+| username                | `preferred_username` | Varies depending on IdP and configuration, eg: `ssmith`, `ssmith@idp.example.com`, `\\example.com\ssmith` |
+| profile picture         | `picture`            | URL to a profile picture or avatar                                                                        |
+
+These should show up nicely in the Tailscale client.
+
+This will also affect the way you [reference users in policies](https://github.com/juanfont/headscale/pull/2205).
+
 ### BREAKING

 - 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.
-  - Users are now identified by `sub` claim in the ID token instead of username, allowing the username, name and email to be updated.
-  - 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.
 - Remove versions older than 1.56 [#2149](https://github.com/juanfont/headscale/pull/2149)
  - Clean up old code required by old versions

@ -23,6 +89,7 @@
 - Added conversion of 'Hostname' to 'givenName' in a node with FQDN rules applied [#2198](https://github.com/juanfont/headscale/pull/2198)
 - Fixed updating of hostname and givenName when it is updated in HostInfo [#2199](https://github.com/juanfont/headscale/pull/2199)
 - Fixed missing `stable-debug` container tag [#2232](https://github.com/juanfont/headscale/pr/2232)
+- Loosened up `server_url` and `base_domain` check. It was overly strict in some cases.

 ## 0.23.0 (2024-09-18)

--- a/Dockerfile.derper
+++ b/Dockerfile.derper
@ -0,0 +1,19 @@
+# For testing purposes only
+
+FROM golang:alpine AS build-env
+
+WORKDIR /go/src
+
+RUN apk add --no-cache git
+ARG VERSION_BRANCH=main
+RUN git clone https://github.com/tailscale/tailscale.git --branch=$VERSION_BRANCH --depth=1
+WORKDIR /go/src/tailscale
+
+ARG TARGETARCH
+RUN GOARCH=$TARGETARCH go install -v ./cmd/derper
+
+FROM alpine:3.18
+RUN apk add --no-cache ca-certificates iptables iproute2 ip6tables curl
+
+COPY --from=build-env /go/bin/* /usr/local/bin/
+ENTRYPOINT [ "/usr/local/bin/derper" ]
--- a/Dockerfile.tailscale-HEAD
+++ b/Dockerfile.tailscale-HEAD
@ -28,7 +28,9 @@ ARG VERSION_GIT_HASH=""
 ENV VERSION_GIT_HASH=$VERSION_GIT_HASH
 ARG TARGETARCH

-RUN GOARCH=$TARGETARCH go install -ldflags="\
+ARG BUILD_TAGS=""
+
+RUN GOARCH=$TARGETARCH go install -tags="${BUILD_TAGS}" -ldflags="\
      -X tailscale.com/version.longStamp=$VERSION_LONG \
      -X tailscale.com/version.shortStamp=$VERSION_SHORT \
      -X tailscale.com/version.gitCommitStamp=$VERSION_GIT_HASH" \
--- a/cmd/headscale/cli/mockoidc.go
+++ b/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
 }
--- a/config-example.yaml
+++ b/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.
-#   # 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
-#   user: `first-name.last-name.example.com`
-#
-#   strip_email_domain: true
+#   # 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
+#   # to force them using the unique identifier from the OIDC and to give them a
+#   # proper display name and picture if available.
+#   # 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
--- a/flake.nix
+++ b/flake.nix
@ -32,7 +32,7 @@

          # 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.
-          vendorHash = "sha256-CMkYTRjmhvTTrB7JbLj0cj9VEyzpG0iUWXkaOagwYTk=";
+          vendorHash = "sha256-Qoqu2k4vvnbRFLmT/v8lI+HCEWqJsHFs8uZRfNmwQpo=";

          subPackages = ["cmd/headscale"];

--- a/hscontrol/app.go
+++ b/hscontrol/app.go
@ -457,6 +457,8 @@ func (h *Headscale) createRouter(grpcMux *grpcRuntime.ServeMux) *mux.Router {
 	router.HandleFunc("/swagger/v1/openapiv2.json", headscale.SwaggerAPIv1).
 		Methods(http.MethodGet)

+	router.HandleFunc("/verify", h.VerifyHandler).Methods(http.MethodPost)
+
 	if h.cfg.DERP.ServerEnabled {
 		router.HandleFunc("/derp", h.DERPServer.DERPHandler)
 		router.HandleFunc("/derp/probe", derpServer.DERPProbeHandler)
--- a/hscontrol/db/db.go
+++ b/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 },
+			},
 		},
 	)

--- a/hscontrol/db/db_test.go
+++ b/hscontrol/db/db_test.go
@ -1,6 +1,7 @@
 package db

 import (
+	"database/sql"
 	"fmt"
 	"io"
 	"net/netip"
@ -16,6 +17,7 @@ import (
 	"github.com/juanfont/headscale/hscontrol/types"
 	"github.com/juanfont/headscale/hscontrol/util"
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 	"gorm.io/gorm"
 	"zgo.at/zcache/v2"
 )
@ -120,12 +122,12 @@ func TestMigrations(t *testing.T) {
 			dbPath: "testdata/0-23-0-to-0-24-0-preauthkey-tags-table.sqlite",
 			wantFunc: func(t *testing.T, h *HSDatabase) {
 				keys, err := Read(h.DB, func(rx *gorm.DB) ([]types.PreAuthKey, error) {
-					kratest, err := ListPreAuthKeys(rx, "kratest")
+					kratest, err := ListPreAuthKeysByUser(rx, 1) // kratest
 					if err != nil {
 						return nil, err
 					}

-					testkra, err := ListPreAuthKeys(rx, "testkra")
+					testkra, err := ListPreAuthKeysByUser(rx, 2) // testkra
 					if err != nil {
 						return nil, err
 					}
@ -256,3 +258,110 @@ func testCopyOfDatabase(src string) (string, error) {
 func emptyCache() *zcache.Cache[string, types.Node] {
 	return zcache.New[string, types.Node](time.Minute, time.Hour)
 }
+
+func TestConstraints(t *testing.T) {
+	tests := []struct {
+		name string
+		run  func(*testing.T, *gorm.DB)
+	}{
+		{
+			name: "no-duplicate-username-if-no-oidc",
+			run: func(t *testing.T, db *gorm.DB) {
+				_, err := CreateUser(db, "user1")
+				require.NoError(t, err)
+				_, err = CreateUser(db, "user1")
+				require.Error(t, err)
+				// assert.Contains(t, err.Error(), "UNIQUE constraint failed: users.username")
+				require.Contains(t, err.Error(), "user already exists")
+			},
+		},
+		{
+			name: "no-oidc-duplicate-username-and-id",
+			run: func(t *testing.T, db *gorm.DB) {
+				user := types.User{
+					Model: gorm.Model{ID: 1},
+					Name:  "user1",
+				}
+				user.ProviderIdentifier = sql.NullString{String: "http://test.com/user1", Valid: true}
+
+				err := db.Save(&user).Error
+				require.NoError(t, err)
+
+				user = types.User{
+					Model: gorm.Model{ID: 2},
+					Name:  "user1",
+				}
+				user.ProviderIdentifier = sql.NullString{String: "http://test.com/user1", Valid: true}
+
+				err = db.Save(&user).Error
+				require.Error(t, err)
+				require.Contains(t, err.Error(), "UNIQUE constraint failed: users.provider_identifier")
+			},
+		},
+		{
+			name: "no-oidc-duplicate-id",
+			run: func(t *testing.T, db *gorm.DB) {
+				user := types.User{
+					Model: gorm.Model{ID: 1},
+					Name:  "user1",
+				}
+				user.ProviderIdentifier = sql.NullString{String: "http://test.com/user1", Valid: true}
+
+				err := db.Save(&user).Error
+				require.NoError(t, err)
+
+				user = types.User{
+					Model: gorm.Model{ID: 2},
+					Name:  "user1.1",
+				}
+				user.ProviderIdentifier = sql.NullString{String: "http://test.com/user1", Valid: true}
+
+				err = db.Save(&user).Error
+				require.Error(t, err)
+				require.Contains(t, err.Error(), "UNIQUE constraint failed: users.provider_identifier")
+			},
+		},
+		{
+			name: "allow-duplicate-username-cli-then-oidc",
+			run: func(t *testing.T, db *gorm.DB) {
+				_, err := CreateUser(db, "user1") // Create CLI username
+				require.NoError(t, err)
+
+				user := types.User{
+					Name: "user1",
+				}
+				user.ProviderIdentifier.String = "http://test.com/user1"
+
+				err = db.Save(&user).Error
+				require.NoError(t, err)
+			},
+		},
+		{
+			name: "allow-duplicate-username-oidc-then-cli",
+			run: func(t *testing.T, db *gorm.DB) {
+				user := types.User{
+					Name: "user1",
+				}
+				user.ProviderIdentifier.String = "http://test.com/user1"
+
+				err := db.Save(&user).Error
+				require.NoError(t, err)
+
+				_, err = CreateUser(db, "user1") // Create CLI username
+				require.NoError(t, err)
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			db, err := newTestDB()
+			if err != nil {
+				t.Fatalf("creating database: %s", err)
+			}
+
+			tt.run(t, db.DB)
+		})
+
+	}
+}
--- a/hscontrol/db/node.go
+++ b/hscontrol/db/node.go
@ -91,15 +91,15 @@ func (hsdb *HSDatabase) ListEphemeralNodes() (types.Nodes, error) {
 	})
 }

-func (hsdb *HSDatabase) getNode(user string, name string) (*types.Node, error) {
+func (hsdb *HSDatabase) getNode(uid types.UserID, name string) (*types.Node, error) {
 	return Read(hsdb.DB, func(rx *gorm.DB) (*types.Node, error) {
-		return getNode(rx, user, name)
+		return getNode(rx, uid, name)
 	})
 }

 // getNode finds a Node by name and user and returns the Node struct.
-func getNode(tx *gorm.DB, user string, name string) (*types.Node, error) {
-	nodes, err := ListNodesByUser(tx, user)
+func getNode(tx *gorm.DB, uid types.UserID, name string) (*types.Node, error) {
+	nodes, err := ListNodesByUser(tx, uid)
 	if err != nil {
 		return nil, err
 	}
--- a/hscontrol/db/node_test.go
+++ b/hscontrol/db/node_test.go
@ -29,10 +29,10 @@ func (s *Suite) TestGetNode(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "testnode")
+	_, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.NotNil)

 	nodeKey := key.NewNode()
@ -50,7 +50,7 @@ func (s *Suite) TestGetNode(c *check.C) {
 	trx := db.DB.Save(node)
 	c.Assert(trx.Error, check.IsNil)

-	_, err = db.getNode("test", "testnode")
+	_, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.IsNil)
 }

@ -58,7 +58,7 @@ func (s *Suite) TestGetNodeByID(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	_, err = db.GetNodeByID(0)
@ -87,7 +87,7 @@ func (s *Suite) TestGetNodeByAnyNodeKey(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	_, err = db.GetNodeByID(0)
@ -135,7 +135,7 @@ func (s *Suite) TestHardDeleteNode(c *check.C) {
 	_, err = db.DeleteNode(&node, xsync.NewMapOf[types.NodeID, bool]())
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode(user.Name, "testnode3")
+	_, err = db.getNode(types.UserID(user.ID), "testnode3")
 	c.Assert(err, check.NotNil)
 }

@ -143,7 +143,7 @@ func (s *Suite) TestListPeers(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	_, err = db.GetNodeByID(0)
@ -189,7 +189,7 @@ func (s *Suite) TestGetACLFilteredPeers(c *check.C) {
 	for _, name := range []string{"test", "admin"} {
 		user, err := db.CreateUser(name)
 		c.Assert(err, check.IsNil)
-		pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+		pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 		c.Assert(err, check.IsNil)
 		stor = append(stor, base{user, pak})
 	}
@ -281,10 +281,10 @@ func (s *Suite) TestExpireNode(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "testnode")
+	_, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.NotNil)

 	nodeKey := key.NewNode()
@ -302,7 +302,7 @@ func (s *Suite) TestExpireNode(c *check.C) {
 	}
 	db.DB.Save(node)

-	nodeFromDB, err := db.getNode("test", "testnode")
+	nodeFromDB, err := db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.IsNil)
 	c.Assert(nodeFromDB, check.NotNil)

@ -312,7 +312,7 @@ func (s *Suite) TestExpireNode(c *check.C) {
 	err = db.NodeSetExpiry(nodeFromDB.ID, now)
 	c.Assert(err, check.IsNil)

-	nodeFromDB, err = db.getNode("test", "testnode")
+	nodeFromDB, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.IsNil)

 	c.Assert(nodeFromDB.IsExpired(), check.Equals, true)
@ -322,10 +322,10 @@ func (s *Suite) TestSetTags(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "testnode")
+	_, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.NotNil)

 	nodeKey := key.NewNode()
@ -348,7 +348,7 @@ func (s *Suite) TestSetTags(c *check.C) {
 	sTags := []string{"tag:test", "tag:foo"}
 	err = db.SetTags(node.ID, sTags)
 	c.Assert(err, check.IsNil)
-	node, err = db.getNode("test", "testnode")
+	node, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.IsNil)
 	c.Assert(node.ForcedTags, check.DeepEquals, sTags)

@ -356,7 +356,7 @@ func (s *Suite) TestSetTags(c *check.C) {
 	eTags := []string{"tag:bar", "tag:test", "tag:unknown", "tag:test"}
 	err = db.SetTags(node.ID, eTags)
 	c.Assert(err, check.IsNil)
-	node, err = db.getNode("test", "testnode")
+	node, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.IsNil)
 	c.Assert(
 		node.ForcedTags,
@ -367,7 +367,7 @@ func (s *Suite) TestSetTags(c *check.C) {
 	// test removing tags
 	err = db.SetTags(node.ID, []string{})
 	c.Assert(err, check.IsNil)
-	node, err = db.getNode("test", "testnode")
+	node, err = db.getNode(types.UserID(user.ID), "testnode")
 	c.Assert(err, check.IsNil)
 	c.Assert(node.ForcedTags, check.DeepEquals, []string{})
 }
@ -567,7 +567,7 @@ func TestAutoApproveRoutes(t *testing.T) {
 			user, err := adb.CreateUser("test")
 			assert.NoError(t, err)

-			pak, err := adb.CreatePreAuthKey(user.Name, false, false, nil, nil)
+			pak, err := adb.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 			assert.NoError(t, err)

 			nodeKey := key.NewNode()
@ -699,10 +699,10 @@ func TestListEphemeralNodes(t *testing.T) {
 	user, err := db.CreateUser("test")
 	assert.NoError(t, err)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	assert.NoError(t, err)

-	pakEph, err := db.CreatePreAuthKey(user.Name, false, true, nil, nil)
+	pakEph, err := db.CreatePreAuthKey(types.UserID(user.ID), false, true, nil, nil)
 	assert.NoError(t, err)

 	node := types.Node{
--- a/hscontrol/db/preauth_keys.go
+++ b/hscontrol/db/preauth_keys.go
@ -23,29 +23,27 @@ var (
 )

 func (hsdb *HSDatabase) CreatePreAuthKey(
-	// TODO(kradalby): Should be ID, not name
-	userName string,
+	uid types.UserID,
 	reusable bool,
 	ephemeral bool,
 	expiration *time.Time,
 	aclTags []string,
 ) (*types.PreAuthKey, error) {
 	return Write(hsdb.DB, func(tx *gorm.DB) (*types.PreAuthKey, error) {
-		return CreatePreAuthKey(tx, userName, reusable, ephemeral, expiration, aclTags)
+		return CreatePreAuthKey(tx, uid, reusable, ephemeral, expiration, aclTags)
 	})
 }

 // CreatePreAuthKey creates a new PreAuthKey in a user, and returns it.
 func CreatePreAuthKey(
 	tx *gorm.DB,
-	// TODO(kradalby): Should be ID, not name
-	userName string,
+	uid types.UserID,
 	reusable bool,
 	ephemeral bool,
 	expiration *time.Time,
 	aclTags []string,
 ) (*types.PreAuthKey, error) {
-	user, err := GetUserByUsername(tx, userName)
+	user, err := GetUserByID(tx, uid)
 	if err != nil {
 		return nil, err
 	}
@ -89,15 +87,15 @@ func CreatePreAuthKey(
 	return &key, nil
 }

-func (hsdb *HSDatabase) ListPreAuthKeys(userName string) ([]types.PreAuthKey, error) {
+func (hsdb *HSDatabase) ListPreAuthKeys(uid types.UserID) ([]types.PreAuthKey, error) {
 	return Read(hsdb.DB, func(rx *gorm.DB) ([]types.PreAuthKey, error) {
-		return ListPreAuthKeys(rx, userName)
+		return ListPreAuthKeysByUser(rx, uid)
 	})
 }

-// ListPreAuthKeys returns the list of PreAuthKeys for a user.
-func ListPreAuthKeys(tx *gorm.DB, userName string) ([]types.PreAuthKey, error) {
-	user, err := GetUserByUsername(tx, userName)
+// ListPreAuthKeysByUser returns the list of PreAuthKeys for a user.
+func ListPreAuthKeysByUser(tx *gorm.DB, uid types.UserID) ([]types.PreAuthKey, error) {
+	user, err := GetUserByID(tx, uid)
 	if err != nil {
 		return nil, err
 	}
--- a/hscontrol/db/preauth_keys_test.go
+++ b/hscontrol/db/preauth_keys_test.go
@ -11,14 +11,14 @@ import (
 )

 func (*Suite) TestCreatePreAuthKey(c *check.C) {
-	_, err := db.CreatePreAuthKey("bogus", true, false, nil, nil)
-
+	// ID does not exist
+	_, err := db.CreatePreAuthKey(12345, true, false, nil, nil)
 	c.Assert(err, check.NotNil)

 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	key, err := db.CreatePreAuthKey(user.Name, true, false, nil, nil)
+	key, err := db.CreatePreAuthKey(types.UserID(user.ID), true, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	// Did we get a valid key?
@ -26,17 +26,18 @@ func (*Suite) TestCreatePreAuthKey(c *check.C) {
 	c.Assert(len(key.Key), check.Equals, 48)

 	// Make sure the User association is populated
-	c.Assert(key.User.Name, check.Equals, user.Name)
+	c.Assert(key.User.ID, check.Equals, user.ID)

-	_, err = db.ListPreAuthKeys("bogus")
+	// ID does not exist
+	_, err = db.ListPreAuthKeys(1000000)
 	c.Assert(err, check.NotNil)

-	keys, err := db.ListPreAuthKeys(user.Name)
+	keys, err := db.ListPreAuthKeys(types.UserID(user.ID))
 	c.Assert(err, check.IsNil)
 	c.Assert(len(keys), check.Equals, 1)

 	// Make sure the User association is populated
-	c.Assert((keys)[0].User.Name, check.Equals, user.Name)
+	c.Assert((keys)[0].User.ID, check.Equals, user.ID)
 }

 func (*Suite) TestExpiredPreAuthKey(c *check.C) {
@ -44,7 +45,7 @@ func (*Suite) TestExpiredPreAuthKey(c *check.C) {
 	c.Assert(err, check.IsNil)

 	now := time.Now().Add(-5 * time.Second)
-	pak, err := db.CreatePreAuthKey(user.Name, true, false, &now, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), true, false, &now, nil)
 	c.Assert(err, check.IsNil)

 	key, err := db.ValidatePreAuthKey(pak.Key)
@ -62,7 +63,7 @@ func (*Suite) TestValidateKeyOk(c *check.C) {
 	user, err := db.CreateUser("test3")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, true, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), true, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	key, err := db.ValidatePreAuthKey(pak.Key)
@ -74,7 +75,7 @@ func (*Suite) TestAlreadyUsedKey(c *check.C) {
 	user, err := db.CreateUser("test4")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	node := types.Node{
@ -96,7 +97,7 @@ func (*Suite) TestReusableBeingUsedKey(c *check.C) {
 	user, err := db.CreateUser("test5")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, true, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), true, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	node := types.Node{
@ -118,7 +119,7 @@ func (*Suite) TestNotReusableNotBeingUsedKey(c *check.C) {
 	user, err := db.CreateUser("test6")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	key, err := db.ValidatePreAuthKey(pak.Key)
@ -130,7 +131,7 @@ func (*Suite) TestExpirePreauthKey(c *check.C) {
 	user, err := db.CreateUser("test3")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, true, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), true, false, nil, nil)
 	c.Assert(err, check.IsNil)
 	c.Assert(pak.Expiration, check.IsNil)

@ -147,7 +148,7 @@ func (*Suite) TestNotReusableMarkedAsUsed(c *check.C) {
 	user, err := db.CreateUser("test6")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)
 	pak.Used = true
 	db.DB.Save(&pak)
@ -160,15 +161,15 @@ func (*Suite) TestPreAuthKeyACLTags(c *check.C) {
 	user, err := db.CreateUser("test8")
 	c.Assert(err, check.IsNil)

-	_, err = db.CreatePreAuthKey(user.Name, false, false, nil, []string{"badtag"})
+	_, err = db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, []string{"badtag"})
 	c.Assert(err, check.NotNil) // Confirm that malformed tags are rejected

 	tags := []string{"tag:test1", "tag:test2"}
 	tagsWithDuplicate := []string{"tag:test1", "tag:test2", "tag:test2"}
-	_, err = db.CreatePreAuthKey(user.Name, false, false, nil, tagsWithDuplicate)
+	_, err = db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, tagsWithDuplicate)
 	c.Assert(err, check.IsNil)

-	listedPaks, err := db.ListPreAuthKeys("test8")
+	listedPaks, err := db.ListPreAuthKeys(types.UserID(user.ID))
 	c.Assert(err, check.IsNil)
 	gotTags := listedPaks[0].Proto().GetAclTags()
 	sort.Sort(sort.StringSlice(gotTags))
--- a/hscontrol/db/routes.go
+++ b/hscontrol/db/routes.go
@ -639,7 +639,7 @@ func EnableAutoApprovedRoutes(

 		log.Trace().
 			Str("node", node.Hostname).
-			Str("user", node.User.Name).
+			Uint("user.id", node.User.ID).
 			Strs("routeApprovers", routeApprovers).
 			Str("prefix", netip.Prefix(advertisedRoute.Prefix).String()).
 			Msg("looking up route for autoapproving")
--- a/hscontrol/db/routes_test.go
+++ b/hscontrol/db/routes_test.go
@ -35,10 +35,10 @@ func (s *Suite) TestGetRoutes(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "test_get_route_node")
+	_, err = db.getNode(types.UserID(user.ID), "test_get_route_node")
 	c.Assert(err, check.NotNil)

 	route, err := netip.ParsePrefix("10.0.0.0/24")
@ -79,10 +79,10 @@ func (s *Suite) TestGetEnableRoutes(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "test_enable_route_node")
+	_, err = db.getNode(types.UserID(user.ID), "test_enable_route_node")
 	c.Assert(err, check.NotNil)

 	route, err := netip.ParsePrefix(
@ -153,10 +153,10 @@ func (s *Suite) TestIsUniquePrefix(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "test_enable_route_node")
+	_, err = db.getNode(types.UserID(user.ID), "test_enable_route_node")
 	c.Assert(err, check.NotNil)

 	route, err := netip.ParsePrefix(
@ -234,10 +234,10 @@ func (s *Suite) TestDeleteRoutes(c *check.C) {
 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	_, err = db.getNode("test", "test_enable_route_node")
+	_, err = db.getNode(types.UserID(user.ID), "test_enable_route_node")
 	c.Assert(err, check.NotNil)

 	prefix, err := netip.ParsePrefix(
--- a/hscontrol/db/users.go
+++ b/hscontrol/db/users.go
@ -28,11 +28,9 @@ func CreateUser(tx *gorm.DB, name string) (*types.User, error) {
 	if err != nil {
 		return nil, err
 	}
-	user := types.User{}
-	if err := tx.Where("name = ?", name).First(&user).Error; err == nil {
-		return nil, ErrUserExists
+	user := types.User{
+		Name: name,
 	}
-	user.Name = name
 	if err := tx.Create(&user).Error; err != nil {
 		return nil, fmt.Errorf("creating user: %w", err)
 	}
@ -40,21 +38,21 @@ func CreateUser(tx *gorm.DB, name string) (*types.User, error) {
 	return &user, nil
 }

-func (hsdb *HSDatabase) DestroyUser(name string) error {
+func (hsdb *HSDatabase) DestroyUser(uid types.UserID) error {
 	return hsdb.Write(func(tx *gorm.DB) error {
-		return DestroyUser(tx, name)
+		return DestroyUser(tx, uid)
 	})
 }

 // DestroyUser destroys a User. Returns error if the User does
 // not exist or if there are nodes associated with it.
-func DestroyUser(tx *gorm.DB, name string) error {
-	user, err := GetUserByUsername(tx, name)
+func DestroyUser(tx *gorm.DB, uid types.UserID) error {
+	user, err := GetUserByID(tx, uid)
 	if err != nil {
-		return ErrUserNotFound
+		return err
 	}

-	nodes, err := ListNodesByUser(tx, name)
+	nodes, err := ListNodesByUser(tx, uid)
 	if err != nil {
 		return err
 	}
@ -62,7 +60,7 @@ func DestroyUser(tx *gorm.DB, name string) error {
 		return ErrUserStillHasNodes
 	}

-	keys, err := ListPreAuthKeys(tx, name)
+	keys, err := ListPreAuthKeysByUser(tx, uid)
 	if err != nil {
 		return err
 	}
@ -80,17 +78,17 @@ func DestroyUser(tx *gorm.DB, name string) error {
 	return nil
 }

-func (hsdb *HSDatabase) RenameUser(oldName, newName string) error {
+func (hsdb *HSDatabase) RenameUser(uid types.UserID, newName string) error {
 	return hsdb.Write(func(tx *gorm.DB) error {
-		return RenameUser(tx, oldName, newName)
+		return RenameUser(tx, uid, newName)
 	})
 }

 // RenameUser renames a User. Returns error if the User does
 // not exist or if another User exists with the new name.
-func RenameUser(tx *gorm.DB, oldName, newName string) error {
+func RenameUser(tx *gorm.DB, uid types.UserID, newName string) error {
 	var err error
-	oldUser, err := GetUserByUsername(tx, oldName)
+	oldUser, err := GetUserByID(tx, uid)
 	if err != nil {
 		return err
 	}
@ -98,50 +96,25 @@ func RenameUser(tx *gorm.DB, oldName, newName string) error {
 	if err != nil {
 		return err
 	}
-	_, err = GetUserByUsername(tx, newName)
-	if err == nil {
-		return ErrUserExists
-	}
-	if !errors.Is(err, ErrUserNotFound) {
-		return err
-	}

 	oldUser.Name = newName

-	if result := tx.Save(&oldUser); result.Error != nil {
-		return result.Error
+	if err := tx.Save(&oldUser).Error; err != nil {
+		return err
 	}

 	return nil
 }

-func (hsdb *HSDatabase) GetUserByName(name string) (*types.User, error) {
+func (hsdb *HSDatabase) GetUserByID(uid types.UserID) (*types.User, error) {
 	return Read(hsdb.DB, func(rx *gorm.DB) (*types.User, error) {
-		return GetUserByUsername(rx, name)
+		return GetUserByID(rx, uid)
 	})
 }

-func GetUserByUsername(tx *gorm.DB, name string) (*types.User, error) {
+func GetUserByID(tx *gorm.DB, uid types.UserID) (*types.User, error) {
 	user := types.User{}
-	if result := tx.First(&user, "name = ?", name); errors.Is(
-		result.Error,
-		gorm.ErrRecordNotFound,
-	) {
-		return nil, ErrUserNotFound
-	}
-
-	return &user, nil
-}
-
-func (hsdb *HSDatabase) GetUserByID(id types.UserID) (*types.User, error) {
-	return Read(hsdb.DB, func(rx *gorm.DB) (*types.User, error) {
-		return GetUserByID(rx, id)
-	})
-}
-
-func GetUserByID(tx *gorm.DB, id types.UserID) (*types.User, error) {
-	user := types.User{}
-	if result := tx.First(&user, "id = ?", id); errors.Is(
+	if result := tx.First(&user, "id = ?", uid); errors.Is(
 		result.Error,
 		gorm.ErrRecordNotFound,
 	) {
@ -169,54 +142,69 @@ func GetUserByOIDCIdentifier(tx *gorm.DB, id string) (*types.User, error) {
 	return &user, nil
 }

-func (hsdb *HSDatabase) ListUsers() ([]types.User, error) {
+func (hsdb *HSDatabase) ListUsers(where ...*types.User) ([]types.User, error) {
 	return Read(hsdb.DB, func(rx *gorm.DB) ([]types.User, error) {
-		return ListUsers(rx)
+		return ListUsers(rx, where...)
 	})
 }

 // ListUsers gets all the existing users.
-func ListUsers(tx *gorm.DB) ([]types.User, error) {
+func ListUsers(tx *gorm.DB, where ...*types.User) ([]types.User, error) {
+	if len(where) > 1 {
+		return nil, fmt.Errorf("expect 0 or 1 where User structs, got %d", len(where))
+	}
+
+	var user *types.User
+	if len(where) == 1 {
+		user = where[0]
+	}
+
 	users := []types.User{}
-	if err := tx.Find(&users).Error; err != nil {
+	if err := tx.Where(user).Find(&users).Error; err != nil {
 		return nil, err
 	}

 	return users, nil
 }

-// ListNodesByUser gets all the nodes in a given user.
-func ListNodesByUser(tx *gorm.DB, name string) (types.Nodes, error) {
-	err := util.CheckForFQDNRules(name)
-	if err != nil {
-		return nil, err
-	}
-	user, err := GetUserByUsername(tx, name)
+// GetUserByName returns a user if the provided username is
+// unique, and otherwise an error.
+func (hsdb *HSDatabase) GetUserByName(name string) (*types.User, error) {
+	users, err := hsdb.ListUsers(&types.User{Name: name})
 	if err != nil {
 		return nil, err
 	}

+	if len(users) == 0 {
+		return nil, ErrUserNotFound
+	}
+
+	if len(users) != 1 {
+		return nil, fmt.Errorf("expected exactly one user, found %d", len(users))
+	}
+
+	return &users[0], nil
+}
+
+// ListNodesByUser gets all the nodes in a given user.
+func ListNodesByUser(tx *gorm.DB, uid types.UserID) (types.Nodes, error) {
 	nodes := types.Nodes{}
-	if err := tx.Preload("AuthKey").Preload("AuthKey.User").Preload("User").Where(&types.Node{UserID: user.ID}).Find(&nodes).Error; err != nil {
+	if err := tx.Preload("AuthKey").Preload("AuthKey.User").Preload("User").Where(&types.Node{UserID: uint(uid)}).Find(&nodes).Error; err != nil {
 		return nil, err
 	}

 	return nodes, nil
 }

-func (hsdb *HSDatabase) AssignNodeToUser(node *types.Node, username string) error {
+func (hsdb *HSDatabase) AssignNodeToUser(node *types.Node, uid types.UserID) error {
 	return hsdb.Write(func(tx *gorm.DB) error {
-		return AssignNodeToUser(tx, node, username)
+		return AssignNodeToUser(tx, node, uid)
 	})
 }

 // AssignNodeToUser assigns a Node to a user.
-func AssignNodeToUser(tx *gorm.DB, node *types.Node, username string) error {
-	err := util.CheckForFQDNRules(username)
-	if err != nil {
-		return err
-	}
-	user, err := GetUserByUsername(tx, username)
+func AssignNodeToUser(tx *gorm.DB, node *types.Node, uid types.UserID) error {
+	user, err := GetUserByID(tx, uid)
 	if err != nil {
 		return err
 	}
--- a/hscontrol/db/users_test.go
+++ b/hscontrol/db/users_test.go
@ -1,6 +1,8 @@
 package db

 import (
+	"strings"
+
 	"github.com/juanfont/headscale/hscontrol/types"
 	"github.com/juanfont/headscale/hscontrol/util"
 	"gopkg.in/check.v1"
@ -17,24 +19,24 @@ func (s *Suite) TestCreateAndDestroyUser(c *check.C) {
 	c.Assert(err, check.IsNil)
 	c.Assert(len(users), check.Equals, 1)

-	err = db.DestroyUser("test")
+	err = db.DestroyUser(types.UserID(user.ID))
 	c.Assert(err, check.IsNil)

-	_, err = db.GetUserByName("test")
+	_, err = db.GetUserByID(types.UserID(user.ID))
 	c.Assert(err, check.NotNil)
 }

 func (s *Suite) TestDestroyUserErrors(c *check.C) {
-	err := db.DestroyUser("test")
+	err := db.DestroyUser(9998)
 	c.Assert(err, check.Equals, ErrUserNotFound)

 	user, err := db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

-	err = db.DestroyUser("test")
+	err = db.DestroyUser(types.UserID(user.ID))
 	c.Assert(err, check.IsNil)

 	result := db.DB.Preload("User").First(&pak, "key = ?", pak.Key)
@ -44,7 +46,7 @@ func (s *Suite) TestDestroyUserErrors(c *check.C) {
 	user, err = db.CreateUser("test")
 	c.Assert(err, check.IsNil)

-	pak, err = db.CreatePreAuthKey(user.Name, false, false, nil, nil)
+	pak, err = db.CreatePreAuthKey(types.UserID(user.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	node := types.Node{
@ -57,7 +59,7 @@ func (s *Suite) TestDestroyUserErrors(c *check.C) {
 	trx := db.DB.Save(&node)
 	c.Assert(trx.Error, check.IsNil)

-	err = db.DestroyUser("test")
+	err = db.DestroyUser(types.UserID(user.ID))
 	c.Assert(err, check.Equals, ErrUserStillHasNodes)
 }

@ -70,24 +72,28 @@ func (s *Suite) TestRenameUser(c *check.C) {
 	c.Assert(err, check.IsNil)
 	c.Assert(len(users), check.Equals, 1)

-	err = db.RenameUser("test", "test-renamed")
+	err = db.RenameUser(types.UserID(userTest.ID), "test-renamed")
 	c.Assert(err, check.IsNil)

-	_, err = db.GetUserByName("test")
-	c.Assert(err, check.Equals, ErrUserNotFound)
+	users, err = db.ListUsers(&types.User{Name: "test"})
+	c.Assert(err, check.Equals, nil)
+	c.Assert(len(users), check.Equals, 0)

-	_, err = db.GetUserByName("test-renamed")
+	users, err = db.ListUsers(&types.User{Name: "test-renamed"})
 	c.Assert(err, check.IsNil)
+	c.Assert(len(users), check.Equals, 1)

-	err = db.RenameUser("test-does-not-exit", "test")
+	err = db.RenameUser(99988, "test")
 	c.Assert(err, check.Equals, ErrUserNotFound)

 	userTest2, err := db.CreateUser("test2")
 	c.Assert(err, check.IsNil)
 	c.Assert(userTest2.Name, check.Equals, "test2")

-	err = db.RenameUser("test2", "test-renamed")
-	c.Assert(err, check.Equals, ErrUserExists)
+	err = db.RenameUser(types.UserID(userTest2.ID), "test-renamed")
+	if !strings.Contains(err.Error(), "UNIQUE constraint failed") {
+		c.Fatalf("expected failure with unique constraint, got: %s", err.Error())
+	}
 }

 func (s *Suite) TestSetMachineUser(c *check.C) {
@ -97,7 +103,7 @@ func (s *Suite) TestSetMachineUser(c *check.C) {
 	newUser, err := db.CreateUser("new")
 	c.Assert(err, check.IsNil)

-	pak, err := db.CreatePreAuthKey(oldUser.Name, false, false, nil, nil)
+	pak, err := db.CreatePreAuthKey(types.UserID(oldUser.ID), false, false, nil, nil)
 	c.Assert(err, check.IsNil)

 	node := types.Node{
@ -111,15 +117,15 @@ func (s *Suite) TestSetMachineUser(c *check.C) {
 	c.Assert(trx.Error, check.IsNil)
 	c.Assert(node.UserID, check.Equals, oldUser.ID)

-	err = db.AssignNodeToUser(&node, newUser.Name)
+	err = db.AssignNodeToUser(&node, types.UserID(newUser.ID))
 	c.Assert(err, check.IsNil)
 	c.Assert(node.UserID, check.Equals, newUser.ID)
 	c.Assert(node.User.Name, check.Equals, newUser.Name)

-	err = db.AssignNodeToUser(&node, "non-existing-user")
+	err = db.AssignNodeToUser(&node, 9584849)
 	c.Assert(err, check.Equals, ErrUserNotFound)

-	err = db.AssignNodeToUser(&node, newUser.Name)
+	err = db.AssignNodeToUser(&node, types.UserID(newUser.ID))
 	c.Assert(err, check.IsNil)
 	c.Assert(node.UserID, check.Equals, newUser.ID)
 	c.Assert(node.User.Name, check.Equals, newUser.Name)
--- a/hscontrol/grpcv1.go
+++ b/hscontrol/grpcv1.go
@ -65,24 +65,34 @@ func (api headscaleV1APIServer) RenameUser(
 	ctx context.Context,
 	request *v1.RenameUserRequest,
 ) (*v1.RenameUserResponse, error) {
-	err := api.h.db.RenameUser(request.GetOldName(), request.GetNewName())
+	oldUser, err := api.h.db.GetUserByName(request.GetOldName())
 	if err != nil {
 		return nil, err
 	}

-	user, err := api.h.db.GetUserByName(request.GetNewName())
+	err = api.h.db.RenameUser(types.UserID(oldUser.ID), request.GetNewName())
 	if err != nil {
 		return nil, err
 	}

-	return &v1.RenameUserResponse{User: user.Proto()}, nil
+	newUser, err := api.h.db.GetUserByName(request.GetNewName())
+	if err != nil {
+		return nil, err
+	}
+
+	return &v1.RenameUserResponse{User: newUser.Proto()}, nil
 }

 func (api headscaleV1APIServer) DeleteUser(
 	ctx context.Context,
 	request *v1.DeleteUserRequest,
 ) (*v1.DeleteUserResponse, error) {
-	err := api.h.db.DestroyUser(request.GetName())
+	user, err := api.h.db.GetUserByName(request.GetName())
+	if err != nil {
+		return nil, err
+	}
+
+	err = api.h.db.DestroyUser(types.UserID(user.ID))
 	if err != nil {
 		return nil, err
 	}
@ -131,8 +141,13 @@ func (api headscaleV1APIServer) CreatePreAuthKey(
 		}
 	}

+	user, err := api.h.db.GetUserByName(request.GetUser())
+	if err != nil {
+		return nil, err
+	}
+
 	preAuthKey, err := api.h.db.CreatePreAuthKey(
-		request.GetUser(),
+		types.UserID(user.ID),
 		request.GetReusable(),
 		request.GetEphemeral(),
 		&expiration,
@ -168,7 +183,12 @@ func (api headscaleV1APIServer) ListPreAuthKeys(
 	ctx context.Context,
 	request *v1.ListPreAuthKeysRequest,
 ) (*v1.ListPreAuthKeysResponse, error) {
-	preAuthKeys, err := api.h.db.ListPreAuthKeys(request.GetUser())
+	user, err := api.h.db.GetUserByName(request.GetUser())
+	if err != nil {
+		return nil, err
+	}
+
+	preAuthKeys, err := api.h.db.ListPreAuthKeys(types.UserID(user.ID))
 	if err != nil {
 		return nil, err
 	}
@ -406,10 +426,20 @@ func (api headscaleV1APIServer) ListNodes(
 	ctx context.Context,
 	request *v1.ListNodesRequest,
 ) (*v1.ListNodesResponse, error) {
+	// TODO(kradalby): it looks like this can be simplified a lot,
+	// the filtering of nodes by user, vs nodes as a whole can
+	// probably be done once.
+	// TODO(kradalby): This should be done in one tx.
+
 	isLikelyConnected := api.h.nodeNotifier.LikelyConnectedMap()
 	if request.GetUser() != "" {
+		user, err := api.h.db.GetUserByName(request.GetUser())
+		if err != nil {
+			return nil, err
+		}
+
 		nodes, err := db.Read(api.h.db.DB, func(rx *gorm.DB) (types.Nodes, error) {
-			return db.ListNodesByUser(rx, request.GetUser())
+			return db.ListNodesByUser(rx, types.UserID(user.ID))
 		})
 		if err != nil {
 			return nil, err
@ -465,12 +495,18 @@ func (api headscaleV1APIServer) MoveNode(
 	ctx context.Context,
 	request *v1.MoveNodeRequest,
 ) (*v1.MoveNodeResponse, error) {
+	// TODO(kradalby): This should be done in one tx.
 	node, err := api.h.db.GetNodeByID(types.NodeID(request.GetNodeId()))
 	if err != nil {
 		return nil, err
 	}

-	err = api.h.db.AssignNodeToUser(node, request.GetUser())
+	user, err := api.h.db.GetUserByName(request.GetUser())
+	if err != nil {
+		return nil, err
+	}
+
+	err = api.h.db.AssignNodeToUser(node, types.UserID(user.ID))
 	if err != nil {
 		return nil, err
 	}
--- a/hscontrol/handlers.go
+++ b/hscontrol/handlers.go
@ -4,6 +4,7 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
+	"io"
 	"net/http"
 	"strconv"
 	"strings"
@ -56,6 +57,65 @@ func parseCabailityVersion(req *http.Request) (tailcfg.CapabilityVersion, error)
 	return tailcfg.CapabilityVersion(clientCapabilityVersion), nil
 }

+func (h *Headscale) handleVerifyRequest(
+	req *http.Request,
+) (bool, error) {
+	body, err := io.ReadAll(req.Body)
+	if err != nil {
+		return false, fmt.Errorf("cannot read request body: %w", err)
+	}
+
+	var derpAdmitClientRequest tailcfg.DERPAdmitClientRequest
+	if err := json.Unmarshal(body, &derpAdmitClientRequest); err != nil {
+		return false, fmt.Errorf("cannot parse derpAdmitClientRequest: %w", err)
+	}
+
+	nodes, err := h.db.ListNodes()
+	if err != nil {
+		return false, fmt.Errorf("cannot list nodes: %w", err)
+	}
+
+	return nodes.ContainsNodeKey(derpAdmitClientRequest.NodePublic), nil
+}
+
+// see https://github.com/tailscale/tailscale/blob/964282d34f06ecc06ce644769c66b0b31d118340/derp/derp_server.go#L1159, Derp use verifyClientsURL to verify whether a client is allowed to connect to the DERP server.
+func (h *Headscale) VerifyHandler(
+	writer http.ResponseWriter,
+	req *http.Request,
+) {
+	if req.Method != http.MethodPost {
+		http.Error(writer, "Wrong method", http.StatusMethodNotAllowed)
+
+		return
+	}
+	log.Debug().
+		Str("handler", "/verify").
+		Msg("verify client")
+
+	allow, err := h.handleVerifyRequest(req)
+	if err != nil {
+		log.Error().
+			Caller().
+			Err(err).
+			Msg("Failed to verify client")
+		http.Error(writer, "Internal error", http.StatusInternalServerError)
+	}
+
+	resp := tailcfg.DERPAdmitClientResponse{
+		Allow: allow,
+	}
+
+	writer.Header().Set("Content-Type", "application/json")
+	writer.WriteHeader(http.StatusOK)
+	err = json.NewEncoder(writer).Encode(resp)
+	if err != nil {
+		log.Error().
+			Caller().
+			Err(err).
+			Msg("Failed to write response")
+	}
+}
+
 // KeyHandler provides the Headscale pub key
 // Listens in /key.
 func (h *Headscale) KeyHandler(
--- a/hscontrol/oidc.go
+++ b/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 {
-		user, err = a.db.GetUserByName(claims.Username)
-		if err != nil && !errors.Is(err, db.ErrUserNotFound) {
-			return nil, fmt.Errorf("creating or updating user: %w", err)
-		}
+	// This branch will presist for a number of versions after the OIDC migration and
+	// then be removed following a deprecation.
+	// TODO(kradalby): Remove when strip_email_domain and migration is removed
+	// 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 user == nil {
-			user = &types.User{}
+			// If the user exists, but it already has a provider identifier (OIDC sub), create a new user.
+			// This is to prevent users that have already been migrated to the new OIDC format
+			// to be updated with the new OIDC identifier inexplicitly which might be the cause of an
+			// account takeover.
+			if user != nil && user.ProviderIdentifier.Valid {
+				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
+}
--- a/hscontrol/policy/acls.go
+++ b/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)
 		}
 	}
--- a/hscontrol/types/config.go
+++ b/hscontrol/types/config.go
@ -28,8 +28,9 @@ const (
 	maxDuration           time.Duration = 1<<63 - 1
 )

-var errOidcMutuallyExclusive = errors.New(
-	"oidc_client_secret and oidc_client_secret_path are mutually exclusive",
+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")
 )

 type IPAllocationStrategy string
@ -162,8 +163,10 @@ type OIDCConfig struct {
 	AllowedDomains             []string
 	AllowedUsers               []string
 	AllowedGroups              []string
+	StripEmaildomain           bool
 	Expiry                     time.Duration
 	UseExpiryFromToken         bool
+	MapLegacyUsers             bool
 }

 type DERPConfig struct {
@ -272,9 +275,11 @@ 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 +323,18 @@ 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) {
@ -827,11 +836,10 @@ func LoadServerConfig() (*Config, error) {
 	// - DERP run on their own domains
 	// - Control plane runs on login.tailscale.com/controlplane.tailscale.com
 	// - MagicDNS (BaseDomain) for users is on a *.ts.net domain per tailnet (e.g. tail-scale.ts.net)
-	if dnsConfig.BaseDomain != "" &&
-		strings.Contains(serverURL, dnsConfig.BaseDomain) {
-		return nil, errors.New(
-			"server_url cannot contain the base_domain, this will cause the headscale server and embedded DERP to become unreachable from the Tailscale node.",
-		)
+	if dnsConfig.BaseDomain != "" {
+		if err := isSafeServerURL(serverURL, dnsConfig.BaseDomain); err != nil {
+			return nil, err
+		}
 	}

 	return &Config{
@ -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,
@ -924,6 +936,37 @@ func LoadServerConfig() (*Config, error) {
 	}, nil
 }

+// BaseDomain cannot be a suffix of the server URL.
+// This is because Tailscale takes over the domain in BaseDomain,
+// causing the headscale server and DERP to be unreachable.
+// For Tailscale upstream, the following is true:
+// - DERP run on their own domains.
+// - Control plane runs on login.tailscale.com/controlplane.tailscale.com.
+// - MagicDNS (BaseDomain) for users is on a *.ts.net domain per tailnet (e.g. tail-scale.ts.net).
+func isSafeServerURL(serverURL, baseDomain string) error {
+	server, err := url.Parse(serverURL)
+	if err != nil {
+		return err
+	}
+
+	serverDomainParts := strings.Split(server.Host, ".")
+	baseDomainParts := strings.Split(baseDomain, ".")
+
+	if len(serverDomainParts) <= len(baseDomainParts) {
+		return nil
+	}
+
+	s := len(serverDomainParts)
+	b := len(baseDomainParts)
+	for i := range len(baseDomainParts) {
+		if serverDomainParts[s-i-1] != baseDomainParts[b-i-1] {
+			return nil
+		}
+	}
+
+	return errServerURLSuffix
+}
+
 type deprecator struct {
 	warns  set.Set[string]
 	fatals set.Set[string]
--- a/hscontrol/types/config_test.go
+++ b/hscontrol/types/config_test.go
@ -1,6 +1,7 @@
 package types

 import (
+	"fmt"
 	"os"
 	"path/filepath"
 	"testing"
@ -139,7 +140,7 @@ func TestReadConfig(t *testing.T) {
 				return LoadServerConfig()
 			},
 			want:    nil,
-			wantErr: "server_url cannot contain the base_domain, this will cause the headscale server and embedded DERP to become unreachable from the Tailscale node.",
+			wantErr: errServerURLSuffix.Error(),
 		},
 		{
 			name:       "base-domain-not-in-server-url",
@ -333,3 +334,64 @@ tls_letsencrypt_challenge_type: TLS-ALPN-01
 	err = LoadConfig(tmpDir, false)
 	assert.NoError(t, err)
 }
+
+// OK
+// server_url: headscale.com, base: clients.headscale.com
+// server_url: headscale.com, base: headscale.net
+//
+// NOT OK
+// server_url: server.headscale.com, base: headscale.com.
+func TestSafeServerURL(t *testing.T) {
+	tests := []struct {
+		serverURL, baseDomain,
+		wantErr string
+	}{
+		{
+			serverURL:  "https://example.com",
+			baseDomain: "example.org",
+		},
+		{
+			serverURL:  "https://headscale.com",
+			baseDomain: "headscale.com",
+		},
+		{
+			serverURL:  "https://headscale.com",
+			baseDomain: "clients.headscale.com",
+		},
+		{
+			serverURL:  "https://headscale.com",
+			baseDomain: "clients.subdomain.headscale.com",
+		},
+		{
+			serverURL:  "https://headscale.kristoffer.com",
+			baseDomain: "mybase",
+		},
+		{
+			serverURL:  "https://server.headscale.com",
+			baseDomain: "headscale.com",
+			wantErr:    errServerURLSuffix.Error(),
+		},
+		{
+			serverURL:  "https://server.subdomain.headscale.com",
+			baseDomain: "headscale.com",
+			wantErr:    errServerURLSuffix.Error(),
+		},
+		{
+			serverURL: "http://foo\x00",
+			wantErr:   `parse "http://foo\x00": net/url: invalid control character in URL`,
+		},
+	}
+
+	for _, tt := range tests {
+		testName := fmt.Sprintf("server=%s domain=%s", tt.serverURL, tt.baseDomain)
+		t.Run(testName, func(t *testing.T) {
+			err := isSafeServerURL(tt.serverURL, tt.baseDomain)
+			if tt.wantErr != "" {
+				assert.EqualError(t, err, tt.wantErr)
+
+				return
+			}
+			assert.NoError(t, err)
+		})
+	}
+}
--- a/hscontrol/types/node.go
+++ b/hscontrol/types/node.go
@ -223,6 +223,16 @@ func (nodes Nodes) FilterByIP(ip netip.Addr) Nodes {
 	return found
 }

+func (nodes Nodes) ContainsNodeKey(nodeKey key.NodePublic) bool {
+	for _, node := range nodes {
+		if node.NodeKey == nodeKey {
+			return true
+		}
+	}
+
+	return false
+}
+
 func (node *Node) Proto() *v1.Node {
 	nodeProto := &v1.Node{
 		Id:         uint64(node.ID),
--- a/hscontrol/types/preauth_key.go
+++ b/hscontrol/types/preauth_key.go
@ -26,7 +26,7 @@ type PreAuthKey struct {

 func (key *PreAuthKey) Proto() *v1.PreAuthKey {
 	protoKey := v1.PreAuthKey{
-		User:      key.User.Name,
+		User:      key.User.Username(),
 		Id:        strconv.FormatUint(key.ID, util.Base10),
 		Key:       key.Key,
 		Ephemeral: key.Ephemeral,
--- a/hscontrol/types/testdata/base-domain-in-server-url.yaml
+++ b/hscontrol/types/testdata/base-domain-in-server-url.yaml
@ -8,7 +8,7 @@ prefixes:
 database:
  type: sqlite3

-server_url: "https://derp.no"
+server_url: "https://server.derp.no"

 dns:
  magic_dns: true
--- a/hscontrol/types/users.go
+++ b/hscontrol/types/users.go
@ -2,6 +2,7 @@ package types

 import (
 	"cmp"
+	"database/sql"
 	"strconv"

 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
@ -19,10 +20,14 @@ 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 users with 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:"uniqueIndex:idx_name_provider_identifier;index"`

 	// Typically the full name of the user
 	DisplayName string
@ -34,7 +39,7 @@ 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 sql.NullString `gorm:"uniqueIndex:idx_name_provider_identifier;uniqueIndex:idx_provider_identifier"`

 	// Provider is the origin of the user account,
 	// same as RegistrationMethod, without authkey.
@ -51,7 +56,14 @@ type User struct {
 // should be used throughout headscale, in information returned to the
 // user and the Policy engine.
 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.String, 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
@ -107,7 +119,7 @@ func (u *User) Proto() *v1.User {
 		CreatedAt:     timestamppb.New(u.CreatedAt),
 		DisplayName:   u.DisplayName,
 		Email:         u.Email,
-		ProviderId:    u.ProviderIdentifier,
+		ProviderId:    u.ProviderIdentifier.String,
 		Provider:      u.Provider,
 		ProfilePicUrl: u.ProfilePicURL,
 	}
@ -116,6 +128,7 @@ 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 +139,18 @@ 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 = sql.NullString{String: claims.Identifier(), Valid: true}
 	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
--- a/hscontrol/util/dns.go
+++ b/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
+}
--- a/integration/README.md
+++ b/integration/README.md
@ -11,10 +11,10 @@ Tests are located in files ending with `_test.go` and the framework are located

 ## Running integration tests locally

-The easiest way to run tests locally is to use `[act](INSERT LINK)`, a local GitHub Actions runner:
+The easiest way to run tests locally is to use [act](https://github.com/nektos/act), a local GitHub Actions runner:

 ```
-act pull_request -W .github/workflows/test-integration-v2-TestPingAllByIP.yaml
+act pull_request -W .github/workflows/test-integration.yaml
 ```

 Alternatively, the `docker run` command in each GitHub workflow file can be used.
--- a/integration/auth_oidc_test.go
+++ b/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"
@ -48,20 +54,34 @@ func TestOIDCAuthenticationPingAll(t *testing.T) {
 	scenario := AuthOIDCScenario{
 		Scenario: baseScenario,
 	}
-	defer scenario.ShutdownAssertNoPanics(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())
-					httpClient := &http.Client{Transport: insecureTransport}
-					ctx := context.Background()
-					req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
-					resp, err := httpClient.Do(req)
-					if err != nil {
-						log.Printf(
-							"%s failed to login using url %s: %s",
-							c.Hostname(),
-							loginURL,
-							err,
-						)
+				log.Printf("%s logging in with url", c.Hostname())
+				httpClient := &http.Client{Transport: insecureTransport}
+				ctx := context.Background()
+				req, _ := http.NewRequestWithContext(ctx, http.MethodGet, loginURL.String(), nil)
+				resp, err := httpClient.Do(req)
+				if err != nil {
+					log.Printf(
+						"%s failed to login using url %s: %s",
+						c.Hostname(),
+						loginURL,
+						err,
+					)

-						return err
-					}
+					return err
+				}

-					if resp.StatusCode != http.StatusOK {
-						log.Printf("%s response code of oidc login request was %s", c.Hostname(), resp.Status)
+				if resp.StatusCode != http.StatusOK {
+					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)
-					if err != nil {
-						log.Printf("%s failed to read response body: %s", c.Hostname(), err)
+				_, err = io.ReadAll(resp.Body)
+				if err != nil {
+					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,
+	}
+}
--- a/integration/cli_test.go
+++ b/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
--- a/integration/derp_verify_endpoint_test.go
+++ b/integration/derp_verify_endpoint_test.go
@ -0,0 +1,96 @@
+package integration
+
+import (
+	"encoding/json"
+	"fmt"
+	"net"
+	"strconv"
+	"strings"
+	"testing"
+
+	"github.com/juanfont/headscale/hscontrol/util"
+	"github.com/juanfont/headscale/integration/dsic"
+	"github.com/juanfont/headscale/integration/hsic"
+	"github.com/juanfont/headscale/integration/integrationutil"
+	"github.com/juanfont/headscale/integration/tsic"
+	"tailscale.com/tailcfg"
+)
+
+func TestDERPVerifyEndpoint(t *testing.T) {
+	IntegrationSkip(t)
+
+	// Generate random hostname for the headscale instance
+	hash, err := util.GenerateRandomStringDNSSafe(6)
+	assertNoErr(t, err)
+	testName := "derpverify"
+	hostname := fmt.Sprintf("hs-%s-%s", testName, hash)
+
+	headscalePort := 8080
+
+	// Create cert for headscale
+	certHeadscale, keyHeadscale, err := integrationutil.CreateCertificate(hostname)
+	assertNoErr(t, err)
+
+	scenario, err := NewScenario(dockertestMaxWait())
+	assertNoErr(t, err)
+	defer scenario.ShutdownAssertNoPanics(t)
+
+	spec := map[string]int{
+		"user1": len(MustTestVersions),
+	}
+
+	derper, err := scenario.CreateDERPServer("head",
+		dsic.WithCACert(certHeadscale),
+		dsic.WithVerifyClientURL(fmt.Sprintf("https://%s/verify", net.JoinHostPort(hostname, strconv.Itoa(headscalePort)))),
+	)
+	assertNoErr(t, err)
+
+	derpMap := tailcfg.DERPMap{
+		Regions: map[int]*tailcfg.DERPRegion{
+			900: {
+				RegionID:   900,
+				RegionCode: "test-derpverify",
+				RegionName: "TestDerpVerify",
+				Nodes: []*tailcfg.DERPNode{
+					{
+						Name:     "TestDerpVerify",
+						RegionID: 900,
+						HostName: derper.GetHostname(),
+						STUNPort: derper.GetSTUNPort(),
+						STUNOnly: false,
+						DERPPort: derper.GetDERPPort(),
+					},
+				},
+			},
+		},
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{tsic.WithCACert(derper.GetCert())},
+		hsic.WithHostname(hostname),
+		hsic.WithPort(headscalePort),
+		hsic.WithCustomTLS(certHeadscale, keyHeadscale),
+		hsic.WithHostnameAsServerURL(),
+		hsic.WithDERPConfig(derpMap))
+	assertNoErrHeadscaleEnv(t, err)
+
+	allClients, err := scenario.ListTailscaleClients()
+	assertNoErrListClients(t, err)
+
+	for _, client := range allClients {
+		report, err := client.DebugDERPRegion("test-derpverify")
+		assertNoErr(t, err)
+		successful := false
+		for _, line := range report.Info {
+			if strings.Contains(line, "Successfully established a DERP connection with node") {
+				successful = true
+
+				break
+			}
+		}
+		if !successful {
+			stJSON, err := json.Marshal(report)
+			assertNoErr(t, err)
+			t.Errorf("Client %s could not establish a DERP connection: %s", client.Hostname(), string(stJSON))
+		}
+	}
+}
--- a/integration/dockertestutil/execute.go
+++ b/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)
 	}
 }
--- a/integration/dsic/dsic.go
+++ b/integration/dsic/dsic.go
@ -0,0 +1,321 @@
+package dsic
+
+import (
+	"crypto/tls"
+	"errors"
+	"fmt"
+	"log"
+	"net"
+	"net/http"
+	"strconv"
+	"strings"
+	"time"
+
+	"github.com/juanfont/headscale/hscontrol/util"
+	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/juanfont/headscale/integration/integrationutil"
+	"github.com/ory/dockertest/v3"
+	"github.com/ory/dockertest/v3/docker"
+)
+
+const (
+	dsicHashLength       = 6
+	dockerContextPath    = "../."
+	caCertRoot           = "/usr/local/share/ca-certificates"
+	DERPerCertRoot       = "/usr/local/share/derper-certs"
+	dockerExecuteTimeout = 60 * time.Second
+)
+
+var errDERPerStatusCodeNotOk = errors.New("DERPer status code not OK")
+
+// DERPServerInContainer represents DERP Server in Container (DSIC).
+type DERPServerInContainer struct {
+	version  string
+	hostname string
+
+	pool      *dockertest.Pool
+	container *dockertest.Resource
+	network   *dockertest.Network
+
+	stunPort            int
+	derpPort            int
+	caCerts             [][]byte
+	tlsCert             []byte
+	tlsKey              []byte
+	withExtraHosts      []string
+	withVerifyClientURL string
+	workdir             string
+}
+
+// Option represent optional settings that can be given to a
+// DERPer instance.
+type Option = func(c *DERPServerInContainer)
+
+// WithCACert adds it to the trusted surtificate of the Tailscale container.
+func WithCACert(cert []byte) Option {
+	return func(dsic *DERPServerInContainer) {
+		dsic.caCerts = append(dsic.caCerts, cert)
+	}
+}
+
+// WithOrCreateNetwork sets the Docker container network to use with
+// the DERPer instance, if the parameter is nil, a new network,
+// isolating the DERPer, will be created. If a network is
+// passed, the DERPer instance will join the given network.
+func WithOrCreateNetwork(network *dockertest.Network) Option {
+	return func(tsic *DERPServerInContainer) {
+		if network != nil {
+			tsic.network = network
+
+			return
+		}
+
+		network, err := dockertestutil.GetFirstOrCreateNetwork(
+			tsic.pool,
+			tsic.hostname+"-network",
+		)
+		if err != nil {
+			log.Fatalf("failed to create network: %s", err)
+		}
+
+		tsic.network = network
+	}
+}
+
+// WithDockerWorkdir allows the docker working directory to be set.
+func WithDockerWorkdir(dir string) Option {
+	return func(tsic *DERPServerInContainer) {
+		tsic.workdir = dir
+	}
+}
+
+// WithVerifyClientURL sets the URL to verify the client.
+func WithVerifyClientURL(url string) Option {
+	return func(tsic *DERPServerInContainer) {
+		tsic.withVerifyClientURL = url
+	}
+}
+
+// WithExtraHosts adds extra hosts to the container.
+func WithExtraHosts(hosts []string) Option {
+	return func(tsic *DERPServerInContainer) {
+		tsic.withExtraHosts = hosts
+	}
+}
+
+// New returns a new TailscaleInContainer instance.
+func New(
+	pool *dockertest.Pool,
+	version string,
+	network *dockertest.Network,
+	opts ...Option,
+) (*DERPServerInContainer, error) {
+	hash, err := util.GenerateRandomStringDNSSafe(dsicHashLength)
+	if err != nil {
+		return nil, err
+	}
+
+	hostname := fmt.Sprintf("derp-%s-%s", strings.ReplaceAll(version, ".", "-"), hash)
+	tlsCert, tlsKey, err := integrationutil.CreateCertificate(hostname)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create certificates for headscale test: %w", err)
+	}
+	dsic := &DERPServerInContainer{
+		version:  version,
+		hostname: hostname,
+		pool:     pool,
+		network:  network,
+		tlsCert:  tlsCert,
+		tlsKey:   tlsKey,
+		stunPort: 3478, //nolint
+		derpPort: 443,  //nolint
+	}
+
+	for _, opt := range opts {
+		opt(dsic)
+	}
+
+	var cmdArgs strings.Builder
+	fmt.Fprintf(&cmdArgs, "--hostname=%s", hostname)
+	fmt.Fprintf(&cmdArgs, " --certmode=manual")
+	fmt.Fprintf(&cmdArgs, " --certdir=%s", DERPerCertRoot)
+	fmt.Fprintf(&cmdArgs, " --a=:%d", dsic.derpPort)
+	fmt.Fprintf(&cmdArgs, " --stun=true")
+	fmt.Fprintf(&cmdArgs, " --stun-port=%d", dsic.stunPort)
+	if dsic.withVerifyClientURL != "" {
+		fmt.Fprintf(&cmdArgs, " --verify-client-url=%s", dsic.withVerifyClientURL)
+	}
+
+	runOptions := &dockertest.RunOptions{
+		Name:       hostname,
+		Networks:   []*dockertest.Network{dsic.network},
+		ExtraHosts: dsic.withExtraHosts,
+		// we currently need to give us some time to inject the certificate further down.
+		Entrypoint: []string{"/bin/sh", "-c", "/bin/sleep 3 ; update-ca-certificates ; derper " + cmdArgs.String()},
+		ExposedPorts: []string{
+			"80/tcp",
+			fmt.Sprintf("%d/tcp", dsic.derpPort),
+			fmt.Sprintf("%d/udp", dsic.stunPort),
+		},
+	}
+
+	if dsic.workdir != "" {
+		runOptions.WorkingDir = dsic.workdir
+	}
+
+	// dockertest isnt very good at handling containers that has already
+	// been created, this is an attempt to make sure this container isnt
+	// present.
+	err = pool.RemoveContainerByName(hostname)
+	if err != nil {
+		return nil, err
+	}
+
+	var container *dockertest.Resource
+	buildOptions := &dockertest.BuildOptions{
+		Dockerfile: "Dockerfile.derper",
+		ContextDir: dockerContextPath,
+		BuildArgs:  []docker.BuildArg{},
+	}
+	switch version {
+	case "head":
+		buildOptions.BuildArgs = append(buildOptions.BuildArgs, docker.BuildArg{
+			Name:  "VERSION_BRANCH",
+			Value: "main",
+		})
+	default:
+		buildOptions.BuildArgs = append(buildOptions.BuildArgs, docker.BuildArg{
+			Name:  "VERSION_BRANCH",
+			Value: "v" + version,
+		})
+	}
+	container, err = pool.BuildAndRunWithBuildOptions(
+		buildOptions,
+		runOptions,
+		dockertestutil.DockerRestartPolicy,
+		dockertestutil.DockerAllowLocalIPv6,
+		dockertestutil.DockerAllowNetworkAdministration,
+	)
+	if err != nil {
+		return nil, fmt.Errorf(
+			"%s could not start tailscale DERPer container (version: %s): %w",
+			hostname,
+			version,
+			err,
+		)
+	}
+	log.Printf("Created %s container\n", hostname)
+
+	dsic.container = container
+
+	for i, cert := range dsic.caCerts {
+		err = dsic.WriteFile(fmt.Sprintf("%s/user-%d.crt", caCertRoot, i), cert)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS certificate to container: %w", err)
+		}
+	}
+	if len(dsic.tlsCert) != 0 {
+		err = dsic.WriteFile(fmt.Sprintf("%s/%s.crt", DERPerCertRoot, dsic.hostname), dsic.tlsCert)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS certificate to container: %w", err)
+		}
+	}
+	if len(dsic.tlsKey) != 0 {
+		err = dsic.WriteFile(fmt.Sprintf("%s/%s.key", DERPerCertRoot, dsic.hostname), dsic.tlsKey)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS key to container: %w", err)
+		}
+	}
+
+	return dsic, nil
+}
+
+// Shutdown stops and cleans up the DERPer container.
+func (t *DERPServerInContainer) Shutdown() error {
+	err := t.SaveLog("/tmp/control")
+	if err != nil {
+		log.Printf(
+			"Failed to save log from %s: %s",
+			t.hostname,
+			fmt.Errorf("failed to save log: %w", err),
+		)
+	}
+
+	return t.pool.Purge(t.container)
+}
+
+// GetCert returns the TLS certificate of the DERPer instance.
+func (t *DERPServerInContainer) GetCert() []byte {
+	return t.tlsCert
+}
+
+// Hostname returns the hostname of the DERPer instance.
+func (t *DERPServerInContainer) Hostname() string {
+	return t.hostname
+}
+
+// Version returns the running DERPer version of the instance.
+func (t *DERPServerInContainer) Version() string {
+	return t.version
+}
+
+// ID returns the Docker container ID of the DERPServerInContainer
+// instance.
+func (t *DERPServerInContainer) ID() string {
+	return t.container.Container.ID
+}
+
+func (t *DERPServerInContainer) GetHostname() string {
+	return t.hostname
+}
+
+// GetSTUNPort returns the STUN port of the DERPer instance.
+func (t *DERPServerInContainer) GetSTUNPort() int {
+	return t.stunPort
+}
+
+// GetDERPPort returns the DERP port of the DERPer instance.
+func (t *DERPServerInContainer) GetDERPPort() int {
+	return t.derpPort
+}
+
+// WaitForRunning blocks until the DERPer instance is ready to be used.
+func (t *DERPServerInContainer) WaitForRunning() error {
+	url := "https://" + net.JoinHostPort(t.GetHostname(), strconv.Itoa(t.GetDERPPort())) + "/"
+	log.Printf("waiting for DERPer to be ready at %s", url)
+
+	insecureTransport := http.DefaultTransport.(*http.Transport).Clone()      //nolint
+	insecureTransport.TLSClientConfig = &tls.Config{InsecureSkipVerify: true} //nolint
+	client := &http.Client{Transport: insecureTransport}
+
+	return t.pool.Retry(func() error {
+		resp, err := client.Get(url) //nolint
+		if err != nil {
+			return fmt.Errorf("headscale is not ready: %w", err)
+		}
+
+		if resp.StatusCode != http.StatusOK {
+			return errDERPerStatusCodeNotOk
+		}
+
+		return nil
+	})
+}
+
+// ConnectToNetwork connects the DERPer instance to a network.
+func (t *DERPServerInContainer) ConnectToNetwork(network *dockertest.Network) error {
+	return t.container.ConnectToNetwork(network)
+}
+
+// WriteFile save file inside the container.
+func (t *DERPServerInContainer) WriteFile(path string, data []byte) error {
+	return integrationutil.WriteFileToContainer(t.pool, t.container, path, data)
+}
+
+// SaveLog saves the current stdout log of the container to a path
+// on the host system.
+func (t *DERPServerInContainer) SaveLog(path string) error {
+	_, _, err := dockertestutil.SaveLog(t.pool, t.container, path)
+
+	return err
+}
--- a/integration/embedded_derp_test.go
+++ b/integration/embedded_derp_test.go
@ -55,7 +55,7 @@ func TestDERPServerWebsocketScenario(t *testing.T) {
 	spec := map[string]ClientsSpec{
 		"user1": {
 			Plain:         0,
-			WebsocketDERP: len(MustTestVersions),
+			WebsocketDERP: 2,
 		},
 	}

@ -239,10 +239,13 @@ func (s *EmbeddedDERPServerScenario) CreateHeadscaleEnv(

 		if clientCount.WebsocketDERP > 0 {
 			// Containers that use DERP-over-WebSocket
+			// Note that these clients *must* be built
+			// from source, which is currently
+			// only done for HEAD.
 			err = s.CreateTailscaleIsolatedNodesInUser(
 				hash,
 				userName,
-				"all",
+				tsic.VersionHead,
 				clientCount.WebsocketDERP,
 				tsic.WithWebsocketDERP(true),
 			)
@ -307,7 +310,7 @@ func (s *EmbeddedDERPServerScenario) CreateTailscaleIsolatedNodesInUser(
 			cert := hsServer.GetCert()

 			opts = append(opts,
-				tsic.WithHeadscaleTLS(cert),
+				tsic.WithCACert(cert),
 			)

 			user.createWaitGroup.Go(func() error {
--- a/integration/hsic/hsic.go
+++ b/integration/hsic/hsic.go
@ -1,19 +1,12 @@
 package hsic

 import (
-	"bytes"
-	"crypto/rand"
-	"crypto/rsa"
 	"crypto/tls"
-	"crypto/x509"
-	"crypto/x509/pkix"
 	"encoding/json"
-	"encoding/pem"
 	"errors"
 	"fmt"
 	"io"
 	"log"
-	"math/big"
 	"net"
 	"net/http"
 	"net/url"
@ -32,11 +25,14 @@ import (
 	"github.com/juanfont/headscale/integration/integrationutil"
 	"github.com/ory/dockertest/v3"
 	"github.com/ory/dockertest/v3/docker"
+	"gopkg.in/yaml.v3"
+	"tailscale.com/tailcfg"
 )

 const (
 	hsicHashLength       = 6
 	dockerContextPath    = "../."
+	caCertRoot           = "/usr/local/share/ca-certificates"
 	aclPolicyPath        = "/etc/headscale/acl.hujson"
 	tlsCertPath          = "/etc/headscale/tls.cert"
 	tlsKeyPath           = "/etc/headscale/tls.key"
@ -64,6 +60,7 @@ type HeadscaleInContainer struct {
 	// optional config
 	port             int
 	extraPorts       []string
+	caCerts          [][]byte
 	hostPortBindings map[string][]string
 	aclPolicy        *policy.ACLPolicy
 	env              map[string]string
@ -88,18 +85,29 @@ func WithACLPolicy(acl *policy.ACLPolicy) Option {
 	}
 }

+// WithCACert adds it to the trusted surtificate of the container.
+func WithCACert(cert []byte) Option {
+	return func(hsic *HeadscaleInContainer) {
+		hsic.caCerts = append(hsic.caCerts, cert)
+	}
+}
+
 // WithTLS creates certificates and enables HTTPS.
 func WithTLS() Option {
 	return func(hsic *HeadscaleInContainer) {
-		cert, key, err := createCertificate(hsic.hostname)
+		cert, key, err := integrationutil.CreateCertificate(hsic.hostname)
 		if err != nil {
 			log.Fatalf("failed to create certificates for headscale test: %s", err)
 		}

-		// TODO(kradalby): Move somewhere appropriate
-		hsic.env["HEADSCALE_TLS_CERT_PATH"] = tlsCertPath
-		hsic.env["HEADSCALE_TLS_KEY_PATH"] = tlsKeyPath
+		hsic.tlsCert = cert
+		hsic.tlsKey = key
+	}
+}

+// WithCustomTLS uses the given certificates for the Headscale instance.
+func WithCustomTLS(cert, key []byte) Option {
+	return func(hsic *HeadscaleInContainer) {
 		hsic.tlsCert = cert
 		hsic.tlsKey = key
 	}
@ -146,6 +154,13 @@ func WithTestName(testName string) Option {
 	}
 }

+// WithHostname sets the hostname of the Headscale instance.
+func WithHostname(hostname string) Option {
+	return func(hsic *HeadscaleInContainer) {
+		hsic.hostname = hostname
+	}
+}
+
 // WithHostnameAsServerURL sets the Headscale ServerURL based on
 // the Hostname.
 func WithHostnameAsServerURL() Option {
@ -203,6 +218,34 @@ func WithEmbeddedDERPServerOnly() Option {
 	}
 }

+// WithDERPConfig configures Headscale use a custom
+// DERP server only.
+func WithDERPConfig(derpMap tailcfg.DERPMap) Option {
+	return func(hsic *HeadscaleInContainer) {
+		contents, err := yaml.Marshal(derpMap)
+		if err != nil {
+			log.Fatalf("failed to marshal DERP map: %s", err)
+
+			return
+		}
+
+		hsic.env["HEADSCALE_DERP_PATHS"] = "/etc/headscale/derp.yml"
+		hsic.filesInContainer = append(hsic.filesInContainer,
+			fileInContainer{
+				path:     "/etc/headscale/derp.yml",
+				contents: contents,
+			})
+
+		// Disable global DERP server and embedded DERP server
+		hsic.env["HEADSCALE_DERP_URLS"] = ""
+		hsic.env["HEADSCALE_DERP_SERVER_ENABLED"] = "false"
+
+		// Envknob for enabling DERP debug logs
+		hsic.env["DERP_DEBUG_LOGS"] = "true"
+		hsic.env["DERP_PROBER_DEBUG_LOGS"] = "true"
+	}
+}
+
 // WithTuning allows changing the tuning settings easily.
 func WithTuning(batchTimeout time.Duration, mapSessionChanSize int) Option {
 	return func(hsic *HeadscaleInContainer) {
@ -300,6 +343,10 @@ func New(
 		"HEADSCALE_DEBUG_HIGH_CARDINALITY_METRICS=1",
 		"HEADSCALE_DEBUG_DUMP_CONFIG=1",
 	}
+	if hsic.hasTLS() {
+		hsic.env["HEADSCALE_TLS_CERT_PATH"] = tlsCertPath
+		hsic.env["HEADSCALE_TLS_KEY_PATH"] = tlsKeyPath
+	}
 	for key, value := range hsic.env {
 		env = append(env, fmt.Sprintf("%s=%s", key, value))
 	}
@ -313,7 +360,7 @@ func New(
 		// Cmd:          []string{"headscale", "serve"},
 		// TODO(kradalby): Get rid of this hack, we currently need to give us some
 		// to inject the headscale configuration further down.
-		Entrypoint: []string{"/bin/bash", "-c", "/bin/sleep 3 ; headscale serve ; /bin/sleep 30"},
+		Entrypoint: []string{"/bin/bash", "-c", "/bin/sleep 3 ; update-ca-certificates ; headscale serve ; /bin/sleep 30"},
 		Env:        env,
 	}

@ -351,6 +398,14 @@ func New(

 	hsic.container = container

+	// Write the CA certificates to the container
+	for i, cert := range hsic.caCerts {
+		err = hsic.WriteFile(fmt.Sprintf("%s/user-%d.crt", caCertRoot, i), cert)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS certificate to container: %w", err)
+		}
+	}
+
 	err = hsic.WriteFile("/etc/headscale/config.yaml", []byte(MinimumConfigYAML()))
 	if err != nil {
 		return nil, fmt.Errorf("failed to write headscale config to container: %w", err)
@ -749,86 +804,3 @@ func (t *HeadscaleInContainer) SendInterrupt() error {

 	return nil
 }
-
-// nolint
-func createCertificate(hostname string) ([]byte, []byte, error) {
-	// From:
-	// https://shaneutt.com/blog/golang-ca-and-signed-cert-go/
-
-	ca := &x509.Certificate{
-		SerialNumber: big.NewInt(2019),
-		Subject: pkix.Name{
-			Organization: []string{"Headscale testing INC"},
-			Country:      []string{"NL"},
-			Locality:     []string{"Leiden"},
-		},
-		NotBefore: time.Now(),
-		NotAfter:  time.Now().Add(60 * time.Hour),
-		IsCA:      true,
-		ExtKeyUsage: []x509.ExtKeyUsage{
-			x509.ExtKeyUsageClientAuth,
-			x509.ExtKeyUsageServerAuth,
-		},
-		KeyUsage:              x509.KeyUsageDigitalSignature | x509.KeyUsageCertSign,
-		BasicConstraintsValid: true,
-	}
-
-	caPrivKey, err := rsa.GenerateKey(rand.Reader, 4096)
-	if err != nil {
-		return nil, nil, err
-	}
-
-	cert := &x509.Certificate{
-		SerialNumber: big.NewInt(1658),
-		Subject: pkix.Name{
-			CommonName:   hostname,
-			Organization: []string{"Headscale testing INC"},
-			Country:      []string{"NL"},
-			Locality:     []string{"Leiden"},
-		},
-		NotBefore:    time.Now(),
-		NotAfter:     time.Now().Add(60 * time.Minute),
-		SubjectKeyId: []byte{1, 2, 3, 4, 6},
-		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageClientAuth, x509.ExtKeyUsageServerAuth},
-		KeyUsage:     x509.KeyUsageDigitalSignature,
-		DNSNames:     []string{hostname},
-	}
-
-	certPrivKey, err := rsa.GenerateKey(rand.Reader, 4096)
-	if err != nil {
-		return nil, nil, err
-	}
-
-	certBytes, err := x509.CreateCertificate(
-		rand.Reader,
-		cert,
-		ca,
-		&certPrivKey.PublicKey,
-		caPrivKey,
-	)
-	if err != nil {
-		return nil, nil, err
-	}
-
-	certPEM := new(bytes.Buffer)
-
-	err = pem.Encode(certPEM, &pem.Block{
-		Type:  "CERTIFICATE",
-		Bytes: certBytes,
-	})
-	if err != nil {
-		return nil, nil, err
-	}
-
-	certPrivKeyPEM := new(bytes.Buffer)
-
-	err = pem.Encode(certPrivKeyPEM, &pem.Block{
-		Type:  "RSA PRIVATE KEY",
-		Bytes: x509.MarshalPKCS1PrivateKey(certPrivKey),
-	})
-	if err != nil {
-		return nil, nil, err
-	}
-
-	return certPEM.Bytes(), certPrivKeyPEM.Bytes(), nil
-}
--- a/integration/integrationutil/util.go
+++ b/integration/integrationutil/util.go
@ -3,9 +3,16 @@ package integrationutil
 import (
 	"archive/tar"
 	"bytes"
+	"crypto/rand"
+	"crypto/rsa"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/pem"
 	"fmt"
 	"io"
+	"math/big"
 	"path/filepath"
+	"time"

 	"github.com/juanfont/headscale/integration/dockertestutil"
 	"github.com/ory/dockertest/v3"
@ -93,3 +100,86 @@ func FetchPathFromContainer(

 	return buf.Bytes(), nil
 }
+
+// nolint
+func CreateCertificate(hostname string) ([]byte, []byte, error) {
+	// From:
+	// https://shaneutt.com/blog/golang-ca-and-signed-cert-go/
+
+	ca := &x509.Certificate{
+		SerialNumber: big.NewInt(2019),
+		Subject: pkix.Name{
+			Organization: []string{"Headscale testing INC"},
+			Country:      []string{"NL"},
+			Locality:     []string{"Leiden"},
+		},
+		NotBefore: time.Now(),
+		NotAfter:  time.Now().Add(60 * time.Hour),
+		IsCA:      true,
+		ExtKeyUsage: []x509.ExtKeyUsage{
+			x509.ExtKeyUsageClientAuth,
+			x509.ExtKeyUsageServerAuth,
+		},
+		KeyUsage:              x509.KeyUsageDigitalSignature | x509.KeyUsageCertSign,
+		BasicConstraintsValid: true,
+	}
+
+	caPrivKey, err := rsa.GenerateKey(rand.Reader, 4096)
+	if err != nil {
+		return nil, nil, err
+	}
+
+	cert := &x509.Certificate{
+		SerialNumber: big.NewInt(1658),
+		Subject: pkix.Name{
+			CommonName:   hostname,
+			Organization: []string{"Headscale testing INC"},
+			Country:      []string{"NL"},
+			Locality:     []string{"Leiden"},
+		},
+		NotBefore:    time.Now(),
+		NotAfter:     time.Now().Add(60 * time.Minute),
+		SubjectKeyId: []byte{1, 2, 3, 4, 6},
+		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageClientAuth, x509.ExtKeyUsageServerAuth},
+		KeyUsage:     x509.KeyUsageDigitalSignature,
+		DNSNames:     []string{hostname},
+	}
+
+	certPrivKey, err := rsa.GenerateKey(rand.Reader, 4096)
+	if err != nil {
+		return nil, nil, err
+	}
+
+	certBytes, err := x509.CreateCertificate(
+		rand.Reader,
+		cert,
+		ca,
+		&certPrivKey.PublicKey,
+		caPrivKey,
+	)
+	if err != nil {
+		return nil, nil, err
+	}
+
+	certPEM := new(bytes.Buffer)
+
+	err = pem.Encode(certPEM, &pem.Block{
+		Type:  "CERTIFICATE",
+		Bytes: certBytes,
+	})
+	if err != nil {
+		return nil, nil, err
+	}
+
+	certPrivKeyPEM := new(bytes.Buffer)
+
+	err = pem.Encode(certPrivKeyPEM, &pem.Block{
+		Type:  "RSA PRIVATE KEY",
+		Bytes: x509.MarshalPKCS1PrivateKey(certPrivKey),
+	})
+	if err != nil {
+		return nil, nil, err
+	}
+
+	return certPEM.Bytes(), certPrivKeyPEM.Bytes(), nil
+}
--- a/integration/scenario.go
+++ b/integration/scenario.go
@ -14,6 +14,7 @@ import (
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/juanfont/headscale/hscontrol/util"
 	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/juanfont/headscale/integration/dsic"
 	"github.com/juanfont/headscale/integration/hsic"
 	"github.com/juanfont/headscale/integration/tsic"
 	"github.com/ory/dockertest/v3"
@ -140,6 +141,7 @@ type Scenario struct {
 	// TODO(kradalby): support multiple headcales for later, currently only
 	// use one.
 	controlServers *xsync.MapOf[string, ControlServer]
+	derpServers    []*dsic.DERPServerInContainer

 	users map[string]*User

@ -224,6 +226,13 @@ func (s *Scenario) ShutdownAssertNoPanics(t *testing.T) {
 		}
 	}

+	for _, derp := range s.derpServers {
+		err := derp.Shutdown()
+		if err != nil {
+			log.Printf("failed to tear down derp server: %s", err)
+		}
+	}
+
 	if err := s.pool.RemoveNetwork(s.network); err != nil {
 		log.Printf("failed to remove network: %s", err)
 	}
@ -352,7 +361,7 @@ func (s *Scenario) CreateTailscaleNodesInUser(
 			hostname := headscale.GetHostname()

 			opts = append(opts,
-				tsic.WithHeadscaleTLS(cert),
+				tsic.WithCACert(cert),
 				tsic.WithHeadscaleName(hostname),
 			)

@ -651,3 +660,20 @@ func (s *Scenario) WaitForTailscaleLogout() error {

 	return nil
 }
+
+// CreateDERPServer creates a new DERP server in a container.
+func (s *Scenario) CreateDERPServer(version string, opts ...dsic.Option) (*dsic.DERPServerInContainer, error) {
+	derp, err := dsic.New(s.pool, version, s.network, opts...)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create DERP server: %w", err)
+	}
+
+	err = derp.WaitForRunning()
+	if err != nil {
+		return nil, fmt.Errorf("failed to reach DERP server: %w", err)
+	}
+
+	s.derpServers = append(s.derpServers, derp)
+
+	return derp, nil
+}
--- a/integration/tailscale.go
+++ b/integration/tailscale.go
@ -30,6 +30,7 @@ type TailscaleClient interface {
 	FQDN() (string, error)
 	Status(...bool) (*ipnstate.Status, error)
 	Netmap() (*netmap.NetworkMap, error)
+	DebugDERPRegion(region string) (*ipnstate.DebugDERPRegionReport, error)
 	Netcheck() (*netcheck.Report, error)
 	WaitForNeedsLogin() error
 	WaitForRunning() error
--- a/integration/tsic/tsic.go
+++ b/integration/tsic/tsic.go
@ -12,6 +12,7 @@ import (
 	"net/netip"
 	"net/url"
 	"os"
+	"reflect"
 	"strconv"
 	"strings"
 	"time"
@ -32,7 +33,7 @@ const (
 	defaultPingTimeout   = 300 * time.Millisecond
 	defaultPingCount     = 10
 	dockerContextPath    = "../."
-	headscaleCertPath    = "/usr/local/share/ca-certificates/headscale.crt"
+	caCertRoot           = "/usr/local/share/ca-certificates"
 	dockerExecuteTimeout = 60 * time.Second
 )

@ -44,6 +45,11 @@ var (
 	errTailscaleCannotUpWithoutAuthkey = errors.New("cannot up without authkey")
 	errTailscaleNotConnected           = errors.New("tailscale not connected")
 	errTailscaledNotReadyForLogin      = errors.New("tailscaled not ready for login")
+	errInvalidClientConfig             = errors.New("verifiably invalid client config requested")
+)
+
+const (
+	VersionHead = "head"
 )

 func errTailscaleStatus(hostname string, err error) error {
@ -65,7 +71,7 @@ type TailscaleInContainer struct {
 	fqdn string

 	// optional config
-	headscaleCert     []byte
+	caCerts           [][]byte
 	headscaleHostname string
 	withWebsocketDERP bool
 	withSSH           bool
@ -74,17 +80,23 @@ type TailscaleInContainer struct {
 	withExtraHosts    []string
 	workdir           string
 	netfilter         string
+
+	// build options, solely for HEAD
+	buildConfig TailscaleInContainerBuildConfig
+}
+
+type TailscaleInContainerBuildConfig struct {
+	tags []string
 }

 // Option represent optional settings that can be given to a
 // Tailscale instance.
 type Option = func(c *TailscaleInContainer)

-// WithHeadscaleTLS takes the certificate of the Headscale instance
-// and adds it to the trusted surtificate of the Tailscale container.
-func WithHeadscaleTLS(cert []byte) Option {
+// WithCACert adds it to the trusted surtificate of the Tailscale container.
+func WithCACert(cert []byte) Option {
 	return func(tsic *TailscaleInContainer) {
-		tsic.headscaleCert = cert
+		tsic.caCerts = append(tsic.caCerts, cert)
 	}
 }

@ -113,7 +125,7 @@ func WithOrCreateNetwork(network *dockertest.Network) Option {
 }

 // WithHeadscaleName set the name of the headscale instance,
-// mostly useful in combination with TLS and WithHeadscaleTLS.
+// mostly useful in combination with TLS and WithCACert.
 func WithHeadscaleName(hsName string) Option {
 	return func(tsic *TailscaleInContainer) {
 		tsic.headscaleHostname = hsName
@ -175,6 +187,22 @@ func WithNetfilter(state string) Option {
 	}
 }

+// WithBuildTag adds an additional value to the `-tags=` parameter
+// of the Go compiler, allowing callers to customize the Tailscale client build.
+// This option is only meaningful when invoked on **HEAD** versions of the client.
+// Attempts to use it with any other version is a bug in the calling code.
+func WithBuildTag(tag string) Option {
+	return func(tsic *TailscaleInContainer) {
+		if tsic.version != VersionHead {
+			panic(errInvalidClientConfig)
+		}
+
+		tsic.buildConfig.tags = append(
+			tsic.buildConfig.tags, tag,
+		)
+	}
+}
+
 // New returns a new TailscaleInContainer instance.
 func New(
 	pool *dockertest.Pool,
@ -219,18 +247,20 @@ func New(
 	}

 	if tsic.withWebsocketDERP {
+		if version != VersionHead {
+			return tsic, errInvalidClientConfig
+		}
+
+		WithBuildTag("ts_debug_websockets")(tsic)
+
 		tailscaleOptions.Env = append(
 			tailscaleOptions.Env,
 			fmt.Sprintf("TS_DEBUG_DERP_WS_CLIENT=%t", tsic.withWebsocketDERP),
 		)
 	}

-	if tsic.headscaleHostname != "" {
-		tailscaleOptions.ExtraHosts = []string{
-			"host.docker.internal:host-gateway",
-			fmt.Sprintf("%s:host-gateway", tsic.headscaleHostname),
-		}
-	}
+	tailscaleOptions.ExtraHosts = append(tailscaleOptions.ExtraHosts,
+		"host.docker.internal:host-gateway")

 	if tsic.workdir != "" {
 		tailscaleOptions.WorkingDir = tsic.workdir
@ -245,14 +275,36 @@ func New(
 	}

 	var container *dockertest.Resource
+
+	if version != VersionHead {
+		// build options are not meaningful with pre-existing images,
+		// let's not lead anyone astray by pretending otherwise.
+		defaultBuildConfig := TailscaleInContainerBuildConfig{}
+		hasBuildConfig := !reflect.DeepEqual(defaultBuildConfig, tsic.buildConfig)
+		if hasBuildConfig {
+			return tsic, errInvalidClientConfig
+		}
+	}
+
 	switch version {
-	case "head":
+	case VersionHead:
 		buildOptions := &dockertest.BuildOptions{
 			Dockerfile: "Dockerfile.tailscale-HEAD",
 			ContextDir: dockerContextPath,
 			BuildArgs:  []docker.BuildArg{},
 		}

+		buildTags := strings.Join(tsic.buildConfig.tags, ",")
+		if len(buildTags) > 0 {
+			buildOptions.BuildArgs = append(
+				buildOptions.BuildArgs,
+				docker.BuildArg{
+					Name:  "BUILD_TAGS",
+					Value: buildTags,
+				},
+			)
+		}
+
 		container, err = pool.BuildAndRunWithBuildOptions(
 			buildOptions,
 			tailscaleOptions,
@ -294,8 +346,8 @@ func New(

 	tsic.container = container

-	if tsic.hasTLS() {
-		err = tsic.WriteFile(headscaleCertPath, tsic.headscaleCert)
+	for i, cert := range tsic.caCerts {
+		err = tsic.WriteFile(fmt.Sprintf("%s/user-%d.crt", caCertRoot, i), cert)
 		if err != nil {
 			return nil, fmt.Errorf("failed to write TLS certificate to container: %w", err)
 		}
@ -304,10 +356,6 @@ func New(
 	return tsic, nil
 }

-func (t *TailscaleInContainer) hasTLS() bool {
-	return len(t.headscaleCert) != 0
-}
-
 // Shutdown stops and cleans up the Tailscale container.
 func (t *TailscaleInContainer) Shutdown() error {
 	err := t.SaveLog("/tmp/control")
@ -682,6 +730,34 @@ func (t *TailscaleInContainer) watchIPN(ctx context.Context) (*ipn.Notify, error
 	}
 }

+func (t *TailscaleInContainer) DebugDERPRegion(region string) (*ipnstate.DebugDERPRegionReport, error) {
+	if !util.TailscaleVersionNewerOrEqual("1.34", t.version) {
+		panic("tsic.DebugDERPRegion() called with unsupported version: " + t.version)
+	}
+
+	command := []string{
+		"tailscale",
+		"debug",
+		"derp",
+		region,
+	}
+
+	result, stderr, err := t.Execute(command)
+	if err != nil {
+		fmt.Printf("stderr: %s\n", stderr) // nolint
+
+		return nil, fmt.Errorf("failed to execute tailscale debug derp command: %w", err)
+	}
+
+	var report ipnstate.DebugDERPRegionReport
+	err = json.Unmarshal([]byte(result), &report)
+	if err != nil {
+		return nil, fmt.Errorf("failed to unmarshal tailscale derp region report: %w", err)
+	}
+
+	return &report, err
+}
+
 // Netcheck returns the current Netcheck Report (netcheck.Report) of the Tailscale instance.
 func (t *TailscaleInContainer) Netcheck() (*netcheck.Report, error) {
 	command := []string{
Author	SHA1	Message	Date
Kristoffer Dalby	31f6a2de1b	Merge `0f432854c6` into `edf9e25001`	2024-11-22 13:49:57 +01:00
ArcticLampyrid	edf9e25001	feat: support client verify for derp (add integration tests) (#2046 ) Some checks are pending Build / build (push) Waiting to run Details Build documentation / build (push) Waiting to run Details Build documentation / deploy (push) Blocked by required conditions Details Tests / test (push) Waiting to run Details * feat: support client verify for derp * docs: fix doc for integration test * tests: add integration test for DERP verify endpoint * tests: use `tailcfg.DERPMap` instead of `[]byte` * refactor: introduce func `ContainsNodeKey` * tests(dsic): use string builder for cmd args * ci: fix tests order * tests: fix derper failure * chore: cleanup * tests(verify-client): perfer to use `CreateHeadscaleEnv` * refactor(verify-client): simplify error handling * tests: fix `TestDERPVerifyEndpoint` * refactor: make `doVerify` a seperated func --------- Co-authored-by: 117503445 <t117503445@gmail.com>	2024-11-22 13:23:05 +01:00
Motiejus Jakštys	c6336adb01	config: loosen up BaseDomain and ServerURL checks (#2248 ) * config: loosen up BaseDomain and ServerURL checks Requirements [here][1]: > OK: > server_url: headscale.com, base: clients.headscale.com > server_url: headscale.com, base: headscale.net > > Not OK: > server_url: server.headscale.com, base: headscale.com > > Essentially we have to prevent the possibility where the headscale > server has a URL which can also be assigned to a node. > > So for the Not OK scenario: > > if the server is: server.headscale.com, and a node joins with the name > server, it will be assigned server.headscale.com and that will break > the connection for nodes which will now try to connect to that node > instead of the headscale server. Fixes #2210 [1]: https://github.com/juanfont/headscale/issues/2210#issuecomment-2488165187 * server_url and base_domain: re-word error message, fix a one-off bug and add a test case for the bug. * lint * lint again	2024-11-22 13:21:44 +01:00
Kristoffer Dalby	0f432854c6	fix constraints Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:28 +01:00
Kristoffer Dalby	0710e1aa4c	nits Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:27 +01:00
Kristoffer Dalby	1c767dfb0f	use userID instead of username everywhere Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:26 +01:00
Kristoffer Dalby	d149180ff8	make preauthkey tags test stable Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:25 +01:00
Kristoffer Dalby	d3c3b76a0d	fix oidc test, add tests for migration Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:25 +01:00
Kristoffer Dalby	14d678c0de	restore strip_email_domain for migration Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:24 +01:00
Kristoffer Dalby	eae63ec562	add iss to identifier, only set email if verified Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:23 +01:00
Kristoffer Dalby	2581a2d8cf	add @ to end of username if not present Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:22 +01:00
Kristoffer Dalby	22bcbef778	remove log print Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:21 +01:00
Kristoffer Dalby	78374b2d4d	update changelog Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:21 +01:00
Kristoffer Dalby	270e3a7a49	Harden OIDC migration and make optional This commit hardens the migration part of the OIDC from the old username based approach to the new sub based approach and makes it possible for the operator to opt out entirely. Fixes #1990 Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>	2024-11-22 12:22:19 +01:00
enoperm	5fbf3f8327	Websocket derp test fixes (#2247 ) * integration testing: add and validate build-time options for tailscale head * fixup! integration testing: add and validate build-time options for tailscale head integration testing: comply with linter * fixup! fixup! integration testing: add and validate build-time options for tailscale head integration testing: tsic.New must never return nil * fixup! fixup! fixup! integration testing: add and validate build-time options for tailscale head * minor fixes	2024-11-22 11:57:01 +01:00