Update CHANGELOG.md

Co-authored-by: Kristoffer Dalby <kristoffer@dalby.cc>

.github/FUNDING.yml

@@ -0,0 +1,3 @@
+# These are supported funding model platforms
+
+ko_fi: headscale

CHANGELOG.md

@@ -9,6 +9,9 @@
 - Set `db_ssl` to false by default [#1052](https://github.com/juanfont/headscale/pull/1052)
 - Fix duplicate nodes due to incorrect implementation of the protocol [#1058](https://github.com/juanfont/headscale/pull/1058)
 - Report if a machine is online in CLI more accurately [#1062](https://github.com/juanfont/headscale/pull/1062)
+- Added config option for custom DNS records [#1035](https://github.com/juanfont/headscale/pull/1035)
+- Expire nodes based on OIDC token expiry [#1067](https://github.com/juanfont/headscale/pull/1067)
+- Remove ephemeral nodes on logout [#1098](https://github.com/juanfont/headscale/pull/1098)
 
 ## 0.17.1 (2022-12-05)
 

app.go

@@ -217,6 +217,15 @@ func (h *Headscale) expireEphemeralNodes(milliSeconds int64) {
 	}
 }
 
+// expireExpiredMachines expires machines that have an explicit expiry set
+// after that expiry time has passed.
+func (h *Headscale) expireExpiredMachines(milliSeconds int64) {
+	ticker := time.NewTicker(time.Duration(milliSeconds) * time.Millisecond)
+	for range ticker.C {
+		h.expireExpiredMachinesWorker()
+	}
+}
+
 func (h *Headscale) failoverSubnetRoutes(milliSeconds int64) {
 	ticker := time.NewTicker(time.Duration(milliSeconds) * time.Millisecond)
 	for range ticker.C {
@@ -248,8 +257,7 @@ func (h *Headscale) expireEphemeralNodesWorker() {
 
 		expiredFound := false
 		for _, machine := range machines {
-			if machine.AuthKey != nil && machine.LastSeen != nil &&
-				machine.AuthKey.Ephemeral &&
+			if machine.isEphemeral() && machine.LastSeen != nil &&
 				time.Now().
 					After(machine.LastSeen.Add(h.cfg.EphemeralNodeInactivityTimeout)) {
 				expiredFound = true
@@ -273,6 +281,53 @@ func (h *Headscale) expireEphemeralNodesWorker() {
 	}
 }
 
+func (h *Headscale) expireExpiredMachinesWorker() {
+	namespaces, err := h.ListNamespaces()
+	if err != nil {
+		log.Error().Err(err).Msg("Error listing namespaces")
+
+		return
+	}
+
+	for _, namespace := range namespaces {
+		machines, err := h.ListMachinesInNamespace(namespace.Name)
+		if err != nil {
+			log.Error().
+				Err(err).
+				Str("namespace", namespace.Name).
+				Msg("Error listing machines in namespace")
+
+			return
+		}
+
+		expiredFound := false
+		for index, machine := range machines {
+			if machine.isExpired() &&
+				machine.Expiry.After(h.getLastStateChange(namespace)) {
+				expiredFound = true
+
+				err := h.ExpireMachine(&machines[index])
+				if err != nil {
+					log.Error().
+						Err(err).
+						Str("machine", machine.Hostname).
+						Str("name", machine.GivenName).
+						Msg("🤮 Cannot expire machine")
+				} else {
+					log.Info().
+						Str("machine", machine.Hostname).
+						Str("name", machine.GivenName).
+						Msg("Machine successfully expired")
+				}
+			}
+		}
+
+		if expiredFound {
+			h.setLastStateChangeToNow()
+		}
+	}
+}
+
 func (h *Headscale) grpcAuthenticationInterceptor(ctx context.Context,
 	req interface{},
 	info *grpc.UnaryServerInfo,
@@ -494,6 +549,7 @@ func (h *Headscale) Serve() error {
 	}
 
 	go h.expireEphemeralNodes(updateInterval)
+	go h.expireExpiredMachines(updateInterval)
 
 	go h.failoverSubnetRoutes(updateInterval)
 

cmd/headscale/cli/mockoidc.go

@@ -16,10 +16,11 @@ const (
 	errMockOidcClientIDNotDefined     = Error("MOCKOIDC_CLIENT_ID not defined")
 	errMockOidcClientSecretNotDefined = Error("MOCKOIDC_CLIENT_SECRET not defined")
 	errMockOidcPortNotDefined         = Error("MOCKOIDC_PORT not defined")
-	accessTTL                         = 10 * time.Minute
 	refreshTTL                        = 60 * time.Minute
 )
 
+var accessTTL = 2 * time.Minute
+
 func init() {
 	rootCmd.AddCommand(mockOidcCmd)
 }
@@ -54,6 +55,16 @@ func mockOIDC() error {
 	if portStr == "" {
 		return errMockOidcPortNotDefined
 	}
+	accessTTLOverride := os.Getenv("MOCKOIDC_ACCESS_TTL")
+	if accessTTLOverride != "" {
+		newTTL, err := time.ParseDuration(accessTTLOverride)
+		if err != nil {
+			return err
+		}
+		accessTTL = newTTL
+	}
+
+	log.Info().Msgf("Access token TTL: %s", accessTTL)
 
 	port, err := strconv.Atoi(portStr)
 	if err != nil {

config-example.yaml

@@ -235,6 +235,17 @@ dns_config:
   # Search domains to inject.
   domains: []
 
+  # Extra DNS records
+  # so far only A-records are supported (on the tailscale side)
+  # See https://github.com/juanfont/headscale/blob/main/docs/dns-records.md#Limitations
+  # extra_records:
+  #   - name: "grafana.myvpn.example.com"
+  #     type: "A"
+  #     value: "100.64.0.3"
+  #
+  #   # you can also put it in one line
+  #   - { name: "prometheus.myvpn.example.com", type: "A", value: "100.64.0.3" }
+
   # Whether to use [MagicDNS](https://tailscale.com/kb/1081/magicdns/).
   # Only works if there is at least a nameserver defined.
   magic_dns: true

config.go

@@ -408,7 +408,7 @@ func GetDNSConfig() (*tailcfg.DNSConfig, string) {
 		}
 
 		if viper.IsSet("dns_config.restricted_nameservers") {
-			if len(dnsConfig.Nameservers) > 0 {
+			if len(dnsConfig.Resolvers) > 0 {
 				dnsConfig.Routes = make(map[string][]*dnstype.Resolver)
 				restrictedDNS := viper.GetStringMapStringSlice(
 					"dns_config.restricted_nameservers",
@@ -440,7 +440,7 @@ func GetDNSConfig() (*tailcfg.DNSConfig, string) {
 
 		if viper.IsSet("dns_config.domains") {
 			domains := viper.GetStringSlice("dns_config.domains")
-			if len(dnsConfig.Nameservers) > 0 {
+			if len(dnsConfig.Resolvers) > 0 {
 				dnsConfig.Domains = domains
 			} else if domains != nil {
 				log.Warn().
@@ -448,6 +448,20 @@ func GetDNSConfig() (*tailcfg.DNSConfig, string) {
 			}
 		}
 
+		if viper.IsSet("dns_config.extra_records") {
+			var extraRecords []tailcfg.DNSRecord
+
+			err := viper.UnmarshalKey("dns_config.extra_records", &extraRecords)
+			if err != nil {
+				log.Error().
+					Str("func", "getDNSConfig").
+					Err(err).
+					Msgf("Could not parse dns_config.extra_records")
+			}
+
+			dnsConfig.ExtraRecords = extraRecords
+		}
+
 		if viper.IsSet("dns_config.magic_dns") {
 			dnsConfig.Proxied = viper.GetBool("dns_config.magic_dns")
 		}

docs/README.md

@@ -12,6 +12,7 @@ please ask on [Discord](https://discord.gg/c84AZQhmpx) instead of opening an Iss
 - [Running headscale on Linux](running-headscale-linux.md)
 - [Control headscale remotely](remote-cli.md)
 - [Using a Windows client with headscale](windows-client.md)
+- [Configuring OIDC](oidc.md)
 
 ### References
 
@@ -29,6 +30,7 @@ written by community members. It is _not_ verified by `headscale` developers.
 - [Running headscale in a container](running-headscale-container.md)
 - [Running headscale on OpenBSD](running-headscale-openbsd.md)
 - [Running headscale behind a reverse proxy](reverse-proxy.md)
+- [Set Custom DNS records](dns-records.md)
 
 ## Misc
 

docs/dns-records.md

@@ -0,0 +1,83 @@
+# Setting custom DNS records
+
+## Goal
+
+This documentation has the goal of showing how a user can set custom DNS records with `headscale`s magic dns.
+An example use case is to serve apps on the same host via a reverse proxy like NGINX, in this case a Prometheus monitoring stack. This allows to nicely access the service with "http://grafana.myvpn.example.com" instead of the hostname and portnum combination "http://hostname-in-magic-dns.myvpn.example.com:3000".
+
+## Setup
+
+### 1. Change the configuration
+
+1. Change the `config.yaml` to contain the desired records like so:
+
+```yaml
+dns_config:
+  ...
+  extra_records:
+    - name: "prometheus.myvpn.example.com"
+      type: "A"
+      value: "100.64.0.3"
+
+    - name: "grafana.myvpn.example.com"
+      type: "A"
+      value: "100.64.0.3"
+  ...
+```
+
+2. Restart your headscale instance.
+
+Beware of the limitations listed later on!
+
+### 2. Verify that the records are set
+
+You can use a DNS querying tool of your choice on one of your hosts to verify that your newly set records are actually available in MagicDNS, here we used [`dig`](https://man.archlinux.org/man/dig.1.en):
+
+```
+$ dig grafana.myvpn.example.com
+
+; <<>> DiG 9.18.10 <<>> grafana.myvpn.example.com
+;; global options: +cmd
+;; Got answer:
+;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 44054
+;; flags: qr rd ra; QUERY: 1, ANSWER: 1, AUTHORITY: 0, ADDITIONAL: 1
+
+;; OPT PSEUDOSECTION:
+; EDNS: version: 0, flags:; udp: 65494
+;; QUESTION SECTION:
+;grafana.myvpn.example.com.         IN      A
+
+;; ANSWER SECTION:
+grafana.myvpn.example.com.  593     IN      A       100.64.0.3
+
+;; Query time: 0 msec
+;; SERVER: 127.0.0.53#53(127.0.0.53) (UDP)
+;; WHEN: Sat Dec 31 11:46:55 CET 2022
+;; MSG SIZE  rcvd: 66
+```
+
+### 3. Optional: Setup the reverse proxy
+
+The motivating example here was to be able to access internal monitoring services on the same host without specifying a port:
+
+```
+server {
+    listen 80;
+    listen [::]:80;
+
+    server_name grafana.myvpn.example.com;
+
+    location / {
+        proxy_pass http://localhost:3000;
+        proxy_set_header Host $http_host;
+        proxy_set_header X-Real-IP $remote_addr;
+        proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
+        proxy_set_header X-Forwarded-Proto $scheme;
+    }
+
+}
+```
+
+## Limitations
+
+[Not all types of records are supported](https://github.com/tailscale/tailscale/blob/main/ipn/ipnlocal/local.go#L2891-L2909), especially no CNAME records.

docs/oidc.md

@@ -0,0 +1,137 @@
+# Configuring Headscale to use OIDC authentication
+
+In order to authenticate users through a centralized solution one must enable the OIDC integration.
+
+Known limitations:
+
+- No dynamic ACL support
+- OIDC groups cannot be used in ACLs
+
+## Basic configuration
+
+In your `config.yaml`, customize this to your liking:
+
+```yaml
+oidc:
+  # Block further startup until the OIDC provider is healthy and available
+  only_start_if_oidc_is_available: true
+  # Specified by your OIDC provider
+  issuer: "https://your-oidc.issuer.com/path"
+  # Specified/generated by your OIDC provider
+  client_id: "your-oidc-client-id"
+  client_secret: "your-oidc-client-secret"
+
+  # Customize the scopes used in the OIDC flow, defaults to "openid", "profile" and "email" and add custom query
+  # parameters to the Authorize Endpoint request. Scopes default to "openid", "profile" and "email".
+  scope: ["openid", "profile", "email", "custom"]
+  # Optional: Passed on to the browser login request – used to tweak behaviour for the OIDC provider
+  extra_params:
+    domain_hint: example.com
+
+  # Optional: List allowed principal domains and/or users. If an authenticated user's domain is not in this list,
+  # the authentication request will be rejected.
+  allowed_domains:
+    - example.com
+  # Optional. Note that groups from Keycloak have a leading '/'.
+  allowed_groups:
+    - /headscale
+  # Optional.
+  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 namespace `first-name.last-name`
+  # If `strip_email_domain` is set to `false` the domain part will NOT be removed resulting to the following
+  # namespace: `first-name.last-name.example.com`
+  strip_email_domain: true
+```
+
+## Azure AD example
+
+In order to integrate Headscale with Azure Active Directory, we'll need to provision an App Registration with the correct scopes and redirect URI. Here with Terraform:
+
+```hcl
+resource "azuread_application" "headscale" {
+  display_name = "Headscale"
+
+  sign_in_audience = "AzureADMyOrg"
+  fallback_public_client_enabled = false
+
+  required_resource_access {
+    // Microsoft Graph
+    resource_app_id = "00000003-0000-0000-c000-000000000000"
+
+    resource_access {
+      // scope: profile
+      id   = "14dad69e-099b-42c9-810b-d002981feec1"
+      type = "Scope"
+    }
+    resource_access {
+      // scope: openid
+      id   = "37f7f235-527c-4136-accd-4a02d197296e"
+      type = "Scope"
+    }
+    resource_access {
+      // scope: email
+      id   = "64a6cdd6-aab1-4aaf-94b8-3cc8405e90d0"
+      type = "Scope"
+    }
+  }
+  web {
+    # Points at your running Headscale instance
+    redirect_uris = ["https://headscale.example.com/oidc/callback"]
+
+    implicit_grant {
+      access_token_issuance_enabled = false
+      id_token_issuance_enabled = true
+    }
+  }
+
+  group_membership_claims = ["SecurityGroup"]
+  optional_claims {
+    # Expose group memberships
+    id_token {
+      name = "groups"
+    }
+  }
+}
+
+resource "azuread_application_password" "headscale-application-secret" {
+  display_name          = "Headscale Server"
+  application_object_id = azuread_application.headscale.object_id
+}
+
+resource "azuread_service_principal" "headscale" {
+  application_id = azuread_application.headscale.application_id
+}
+
+resource "azuread_service_principal_password" "headscale" {
+  service_principal_id = azuread_service_principal.headscale.id
+  end_date_relative    = "44640h"
+}
+
+output "headscale_client_id" {
+  value = azuread_application.headscale.application_id
+}
+
+output "headscale_client_secret" {
+  value = azuread_application_password.headscale-application-secret.value
+}
+```
+
+And in your Headscale `config.yaml`:
+
+```yaml
+oidc:
+  issuer: "https://login.microsoftonline.com/<tenant-UUID>/v2.0"
+  client_id: "<client-id-from-terraform>"
+  client_secret: "<client-secret-from-terraform>"
+
+  # Optional: add "groups"
+  scope: ["openid", "profile", "email"]
+  extra_params:
+    # Use your own domain, associated with Azure AD
+    domain_hint: example.com
+    # Optional: Force the Azure AD account picker
+    prompt: select_account
+```

docs/reverse-proxy.md

@@ -98,3 +98,17 @@ spec:
             upgrade_configs:
               - upgrade_type: tailscale-control-protocol
 ```
+
+## Caddy
+
+The following Caddyfile is all that is necessary to use Caddy as a reverse proxy for headscale, in combination with the `config.yaml` specifications above to disable headscale's built in TLS. Replace values as necessary - `<YOUR_SERVER_NAME>` should be the FQDN at which headscale will be served, and `<IP:PORT>` should be the IP address and port where headscale is running. In most cases, this will be `localhost:8080`.
+
+```
+<YOUR_SERVER_NAME> {
+    reverse_proxy <IP:PORT>
+}
+```
+
+Caddy v2 will [automatically](https://caddyserver.com/docs/automatic-https) provision a certficate for your domain/subdomain, force HTTPS, and proxy websockets - no further configuration is necessary.
+
+For a slightly more complex configuration which utilizes Docker containers to manage Caddy, Headscale, and Headscale-UI, [Guru Computing's guide](https://blog.gurucomputing.com.au/smart-vpns-with-headscale/) is an excellent reference.

grpcv1.go

@@ -176,6 +176,7 @@ func (api headscaleV1APIServer) RegisterMachine(
 	machine, err := api.h.RegisterMachineFromAuthCallback(
 		request.GetKey(),
 		request.GetNamespace(),
+		nil,
 		RegisterMethodCLI,
 	)
 	if err != nil {

integration/auth_oidc_test.go

@@ -9,8 +9,10 @@ import (
 	"log"
 	"net"
 	"net/http"
+	"net/netip"
 	"strconv"
 	"testing"
+	"time"
 
 	"github.com/juanfont/headscale"
 	"github.com/juanfont/headscale/integration/dockertestutil"
@@ -22,7 +24,7 @@ import (
 const (
 	dockerContextPath      = "../."
 	hsicOIDCMockHashLength = 6
-	oidcServerPort         = 10000
+	defaultAccessTTL       = 10 * time.Minute
 )
 
 var errStatusCodeNotOK = errors.New("status code not OK")
@@ -50,7 +52,7 @@ func TestOIDCAuthenticationPingAll(t *testing.T) {
 		"namespace1": len(TailscaleVersions),
 	}
 
-	oidcConfig, err := scenario.runMockOIDC()
+	oidcConfig, err := scenario.runMockOIDC(defaultAccessTTL)
 	if err != nil {
 		t.Errorf("failed to run mock OIDC server: %s", err)
 	}
@@ -87,20 +89,76 @@ func TestOIDCAuthenticationPingAll(t *testing.T) {
 		t.Errorf("failed wait for tailscale clients to be in sync: %s", err)
 	}
 
-	success := 0
+	success := pingAll(t, allClients, allIps)
+	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
 
-	for _, client := range allClients {
-		for _, ip := range allIps {
-			err := client.Ping(ip.String())
-			if err != nil {
-				t.Errorf("failed to ping %s from %s: %s", ip, client.Hostname(), err)
-			} else {
-				success++
-			}
-		}
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func TestOIDCExpireNodes(t *testing.T) {
+	IntegrationSkip(t)
+	t.Parallel()
+
+	shortAccessTTL := 5 * time.Minute
+
+	baseScenario, err := NewScenario()
+	if err != nil {
+		t.Errorf("failed to create scenario: %s", err)
 	}
 
-	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
+	scenario := AuthOIDCScenario{
+		Scenario: baseScenario,
+	}
+
+	spec := map[string]int{
+		"namespace1": len(TailscaleVersions),
+	}
+
+	oidcConfig, err := scenario.runMockOIDC(shortAccessTTL)
+	if err != nil {
+		t.Fatalf("failed to run mock OIDC server: %s", err)
+	}
+
+	oidcMap := map[string]string{
+		"HEADSCALE_OIDC_ISSUER":             oidcConfig.Issuer,
+		"HEADSCALE_OIDC_CLIENT_ID":          oidcConfig.ClientID,
+		"HEADSCALE_OIDC_CLIENT_SECRET":      oidcConfig.ClientSecret,
+		"HEADSCALE_OIDC_STRIP_EMAIL_DOMAIN": fmt.Sprintf("%t", oidcConfig.StripEmaildomain),
+	}
+
+	err = scenario.CreateHeadscaleEnv(
+		spec,
+		hsic.WithTestName("oidcexpirenodes"),
+		hsic.WithConfigEnv(oidcMap),
+		hsic.WithHostnameAsServerURL(),
+	)
+	if err != nil {
+		t.Errorf("failed to create headscale environment: %s", err)
+	}
+
+	allClients, err := scenario.ListTailscaleClients()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	allIps, err := scenario.ListTailscaleClientsIPs()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	err = scenario.WaitForTailscaleSync()
+	if err != nil {
+		t.Errorf("failed wait for tailscale clients to be in sync: %s", err)
+	}
+
+	success := pingAll(t, allClients, allIps)
+	t.Logf("%d successful pings out of %d (before expiry)", success, len(allClients)*len(allIps))
+
+	// await all nodes being logged out after OIDC token expiry
+	scenario.WaitForTailscaleLogout()
 
 	err = scenario.Shutdown()
 	if err != nil {
@@ -143,7 +201,13 @@ func (s *AuthOIDCScenario) CreateHeadscaleEnv(
 	return nil
 }
 
-func (s *AuthOIDCScenario) runMockOIDC() (*headscale.OIDCConfig, error) {
+func (s *AuthOIDCScenario) runMockOIDC(accessTTL time.Duration) (*headscale.OIDCConfig, error) {
+	port, err := dockertestutil.RandomFreeHostPort()
+	if err != nil {
+		log.Fatalf("could not find an open port: %s", err)
+	}
+	portNotation := fmt.Sprintf("%d/tcp", port)
+
 	hash, _ := headscale.GenerateRandomStringDNSSafe(hsicOIDCMockHashLength)
 
 	hostname := fmt.Sprintf("hs-oidcmock-%s", hash)
@@ -151,16 +215,17 @@ func (s *AuthOIDCScenario) runMockOIDC() (*headscale.OIDCConfig, error) {
 	mockOidcOptions := &dockertest.RunOptions{
 		Name:         hostname,
 		Cmd:          []string{"headscale", "mockoidc"},
-		ExposedPorts: []string{"10000/tcp"},
+		ExposedPorts: []string{portNotation},
 		PortBindings: map[docker.Port][]docker.PortBinding{
-			"10000/tcp": {{HostPort: "10000"}},
+			docker.Port(portNotation): {{HostPort: strconv.Itoa(port)}},
 		},
 		Networks: []*dockertest.Network{s.Scenario.network},
 		Env: []string{
 			fmt.Sprintf("MOCKOIDC_ADDR=%s", hostname),
-			"MOCKOIDC_PORT=10000",
+			fmt.Sprintf("MOCKOIDC_PORT=%d", port),
 			"MOCKOIDC_CLIENT_ID=superclient",
 			"MOCKOIDC_CLIENT_SECRET=supersecret",
+			fmt.Sprintf("MOCKOIDC_ACCESS_TTL=%s", accessTTL.String()),
 		},
 	}
 
@@ -169,7 +234,7 @@ func (s *AuthOIDCScenario) runMockOIDC() (*headscale.OIDCConfig, error) {
 		ContextDir: dockerContextPath,
 	}
 
-	err := s.pool.RemoveContainerByName(hostname)
+	err = s.pool.RemoveContainerByName(hostname)
 	if err != nil {
 		return nil, err
 	}
@@ -184,11 +249,7 @@ func (s *AuthOIDCScenario) runMockOIDC() (*headscale.OIDCConfig, error) {
 	}
 
 	log.Println("Waiting for headscale mock oidc to be ready for tests")
-	hostEndpoint := fmt.Sprintf(
-		"%s:%s",
-		s.mockOIDC.GetIPInNetwork(s.network),
-		s.mockOIDC.GetPort(fmt.Sprintf("%d/tcp", oidcServerPort)),
-	)
+	hostEndpoint := fmt.Sprintf("%s:%d", s.mockOIDC.GetIPInNetwork(s.network), port)
 
 	if err := s.pool.Retry(func() error {
 		oidcConfigURL := fmt.Sprintf("http://%s/oidc/.well-known/openid-configuration", hostEndpoint)
@@ -215,11 +276,11 @@ func (s *AuthOIDCScenario) runMockOIDC() (*headscale.OIDCConfig, error) {
 	log.Printf("headscale mock oidc is ready for tests at %s", hostEndpoint)
 
 	return &headscale.OIDCConfig{
-		Issuer: fmt.Sprintf("http://%s/oidc",
-			net.JoinHostPort(s.mockOIDC.GetIPInNetwork(s.network), strconv.Itoa(oidcServerPort))),
-		ClientID:         "superclient",
-		ClientSecret:     "supersecret",
-		StripEmaildomain: true,
+		Issuer:                     fmt.Sprintf("http://%s/oidc", net.JoinHostPort(s.mockOIDC.GetIPInNetwork(s.network), strconv.Itoa(port))),
+		ClientID:                   "superclient",
+		ClientSecret:               "supersecret",
+		StripEmaildomain:           true,
+		OnlyStartIfOIDCIsAvailable: true,
 	}, nil
 }
 
@@ -292,6 +353,24 @@ func (s *AuthOIDCScenario) runTailscaleUp(
 	return fmt.Errorf("failed to up tailscale node: %w", errNoNamespaceAvailable)
 }
 
+func pingAll(t *testing.T, clients []TailscaleClient, ips []netip.Addr) int {
+	t.Helper()
+	success := 0
+
+	for _, client := range clients {
+		for _, ip := range ips {
+			err := client.Ping(ip.String())
+			if err != nil {
+				t.Errorf("failed to ping %s from %s: %s", ip, client.Hostname(), err)
+			} else {
+				success++
+			}
+		}
+	}
+
+	return success
+}
+
 func (s *AuthOIDCScenario) Shutdown() error {
 	err := s.pool.Purge(s.mockOIDC)
 	if err != nil {

integration/auth_web_flow_test.go

@@ -141,13 +141,13 @@ func TestAuthWebFlowLogoutAndRelogin(t *testing.T) {
 	}
 
 	for _, client := range allClients {
-		_, _, err = client.Execute([]string{"tailscale", "logout"})
+		err := client.Logout()
 		if err != nil {
 			t.Errorf("failed to logout client %s: %s", client.Hostname(), err)
 		}
 	}
 
-	scenario.waitForTailscaleLogout()
+	scenario.WaitForTailscaleLogout()
 
 	t.Logf("all clients logged out")
 
@@ -259,22 +259,6 @@ func (s *AuthWebFlowScenario) CreateHeadscaleEnv(
 	return nil
 }
 
-func (s *AuthWebFlowScenario) waitForTailscaleLogout() {
-	for _, namespace := range s.namespaces {
-		for _, client := range namespace.Clients {
-			namespace.syncWaitGroup.Add(1)
-
-			go func(c TailscaleClient) {
-				defer namespace.syncWaitGroup.Done()
-
-				// TODO(kradalby): error handle this
-				_ = c.WaitForLogout()
-			}(client)
-		}
-		namespace.syncWaitGroup.Wait()
-	}
-}
-
 func (s *AuthWebFlowScenario) runTailscaleUp(
 	namespaceStr, loginServer string,
 ) error {

integration/control.go

@@ -11,7 +11,7 @@ type ControlServer interface {
 	GetEndpoint() string
 	WaitForReady() error
 	CreateNamespace(namespace string) error
-	CreateAuthKey(namespace string) (*v1.PreAuthKey, error)
+	CreateAuthKey(namespace string, reusable bool, ephemeral bool) (*v1.PreAuthKey, error)
 	ListMachinesInNamespace(namespace string) ([]*v1.Machine, error)
 	GetCert() []byte
 	GetHostname() string

integration/dockertestutil/network.go

@@ -2,6 +2,7 @@ package dockertestutil
 
 import (
 	"errors"
+	"net"
 
 	"github.com/ory/dockertest/v3"
 	"github.com/ory/dockertest/v3/docker"
@@ -60,3 +61,20 @@ func AddContainerToNetwork(
 
 	return nil
 }
+
+// RandomFreeHostPort asks the kernel for a free open port that is ready to use.
+// (from https://github.com/phayes/freeport)
+func RandomFreeHostPort() (int, error) {
+	addr, err := net.ResolveTCPAddr("tcp", "localhost:0")
+	if err != nil {
+		return 0, err
+	}
+
+	listener, err := net.ListenTCP("tcp", addr)
+	if err != nil {
+		return 0, err
+	}
+	defer listener.Close()
+	//nolint:forcetypeassert
+	return listener.Addr().(*net.TCPAddr).Port, nil
+}

integration/general_test.go

@@ -2,6 +2,7 @@ package integration
 
 import (
 	"fmt"
+	"net/netip"
 	"strings"
 	"testing"
 	"time"
@@ -66,6 +67,239 @@ func TestPingAllByIP(t *testing.T) {
 	}
 }
 
+func TestAuthKeyLogoutAndRelogin(t *testing.T) {
+	IntegrationSkip(t)
+	t.Parallel()
+
+	scenario, err := NewScenario()
+	if err != nil {
+		t.Errorf("failed to create scenario: %s", err)
+	}
+
+	spec := map[string]int{
+		"namespace1": len(TailscaleVersions),
+		"namespace2": len(TailscaleVersions),
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("pingallbyip"))
+	if err != nil {
+		t.Errorf("failed to create headscale environment: %s", err)
+	}
+
+	allClients, err := scenario.ListTailscaleClients()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	err = scenario.WaitForTailscaleSync()
+	if err != nil {
+		t.Errorf("failed wait for tailscale clients to be in sync: %s", err)
+	}
+
+	clientIPs := make(map[TailscaleClient][]netip.Addr)
+	for _, client := range allClients {
+		ips, err := client.IPs()
+		if err != nil {
+			t.Errorf("failed to get IPs for client %s: %s", client.Hostname(), err)
+		}
+		clientIPs[client] = ips
+	}
+
+	for _, client := range allClients {
+		err := client.Logout()
+		if err != nil {
+			t.Errorf("failed to logout client %s: %s", client.Hostname(), err)
+		}
+	}
+
+	scenario.WaitForTailscaleLogout()
+
+	t.Logf("all clients logged out")
+
+	headscale, err := scenario.Headscale()
+	if err != nil {
+		t.Errorf("failed to get headscale server: %s", err)
+	}
+
+	for namespaceName := range spec {
+		key, err := scenario.CreatePreAuthKey(namespaceName, true, false)
+		if err != nil {
+			t.Errorf("failed to create pre-auth key for namespace %s: %s", namespaceName, err)
+		}
+
+		err = scenario.RunTailscaleUp(namespaceName, headscale.GetEndpoint(), key.GetKey())
+		if err != nil {
+			t.Errorf("failed to run tailscale up for namespace %s: %s", namespaceName, err)
+		}
+	}
+
+	err = scenario.WaitForTailscaleSync()
+	if err != nil {
+		t.Errorf("failed wait for tailscale clients to be in sync: %s", err)
+	}
+
+	allClients, err = scenario.ListTailscaleClients()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	allIps, err := scenario.ListTailscaleClientsIPs()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	success := 0
+	for _, client := range allClients {
+		for _, ip := range allIps {
+			err := client.Ping(ip.String())
+			if err != nil {
+				t.Errorf("failed to ping %s from %s: %s", ip, client.Hostname(), err)
+			} else {
+				success++
+			}
+		}
+	}
+
+	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
+
+	for _, client := range allClients {
+		ips, err := client.IPs()
+		if err != nil {
+			t.Errorf("failed to get IPs for client %s: %s", client.Hostname(), err)
+		}
+
+		// lets check if the IPs are the same
+		if len(ips) != len(clientIPs[client]) {
+			t.Errorf("IPs changed for client %s", client.Hostname())
+		}
+
+		for _, ip := range ips {
+			found := false
+			for _, oldIP := range clientIPs[client] {
+				if ip == oldIP {
+					found = true
+
+					break
+				}
+			}
+
+			if !found {
+				t.Errorf("IPs changed for client %s. Used to be %v now %v", client.Hostname(), clientIPs[client], ips)
+			}
+		}
+	}
+
+	t.Logf("all clients IPs are the same")
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func TestEphemeral(t *testing.T) {
+	IntegrationSkip(t)
+	t.Parallel()
+
+	scenario, err := NewScenario()
+	if err != nil {
+		t.Errorf("failed to create scenario: %s", err)
+	}
+
+	spec := map[string]int{
+		"namespace1": len(TailscaleVersions),
+		"namespace2": len(TailscaleVersions),
+	}
+
+	headscale, err := scenario.Headscale(hsic.WithTestName("ephemeral"))
+	if err != nil {
+		t.Errorf("failed to create headscale environment: %s", err)
+	}
+
+	for namespaceName, clientCount := range spec {
+		err = scenario.CreateNamespace(namespaceName)
+		if err != nil {
+			t.Errorf("failed to create namespace %s: %s", namespaceName, err)
+		}
+
+		err = scenario.CreateTailscaleNodesInNamespace(namespaceName, "all", clientCount, []tsic.Option{}...)
+		if err != nil {
+			t.Errorf("failed to create tailscale nodes in namespace %s: %s", namespaceName, err)
+		}
+
+		key, err := scenario.CreatePreAuthKey(namespaceName, true, true)
+		if err != nil {
+			t.Errorf("failed to create pre-auth key for namespace %s: %s", namespaceName, err)
+		}
+
+		err = scenario.RunTailscaleUp(namespaceName, headscale.GetEndpoint(), key.GetKey())
+		if err != nil {
+			t.Errorf("failed to run tailscale up for namespace %s: %s", namespaceName, err)
+		}
+	}
+
+	err = scenario.WaitForTailscaleSync()
+	if err != nil {
+		t.Errorf("failed wait for tailscale clients to be in sync: %s", err)
+	}
+
+	allClients, err := scenario.ListTailscaleClients()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	allIps, err := scenario.ListTailscaleClientsIPs()
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	success := 0
+	for _, client := range allClients {
+		for _, ip := range allIps {
+			err := client.Ping(ip.String())
+			if err != nil {
+				t.Errorf("failed to ping %s from %s: %s", ip, client.Hostname(), err)
+			} else {
+				success++
+			}
+		}
+	}
+
+	t.Logf("%d successful pings out of %d", success, len(allClients)*len(allIps))
+
+	for _, client := range allClients {
+		err := client.Logout()
+		if err != nil {
+			t.Errorf("failed to logout client %s: %s", client.Hostname(), err)
+		}
+	}
+
+	scenario.WaitForTailscaleLogout()
+
+	t.Logf("all clients logged out")
+
+	for namespaceName := range spec {
+		machines, err := headscale.ListMachinesInNamespace(namespaceName)
+		if err != nil {
+			log.Error().
+				Err(err).
+				Str("namespace", namespaceName).
+				Msg("Error listing machines in namespace")
+
+			return
+		}
+
+		if len(machines) != 0 {
+			t.Errorf("expected no machines, got %d in namespace %s", len(machines), namespaceName)
+		}
+	}
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
 func TestPingAllByHostname(t *testing.T) {
 	IntegrationSkip(t)
 	t.Parallel()

integration/hsic/hsic.go

@@ -316,6 +316,8 @@ func (t *HeadscaleInContainer) CreateNamespace(
 
 func (t *HeadscaleInContainer) CreateAuthKey(
 	namespace string,
+	reusable bool,
+	ephemeral bool,
 ) (*v1.PreAuthKey, error) {
 	command := []string{
 		"headscale",
@@ -323,13 +325,20 @@ func (t *HeadscaleInContainer) CreateAuthKey(
 		namespace,
 		"preauthkeys",
 		"create",
-		"--reusable",
 		"--expiration",
 		"24h",
 		"--output",
 		"json",
 	}
 
+	if reusable {
+		command = append(command, "--reusable")
+	}
+
+	if ephemeral {
+		command = append(command, "--ephemeral")
+	}
+
 	result, _, err := dockertestutil.ExecuteCommand(
 		t.container,
 		command,

integration/scenario.go

@@ -43,11 +43,11 @@ var (
 		"1.24.2",
 		"1.22.2",
 		"1.20.4",
-		"1.18.2",
 	}
 
 	// tailscaleVersionsUnavailable = []string{
 	// 	// These versions seem to fail when fetching from apt.
+	//  "1.18.2",
 	// 	"1.16.2",
 	// 	"1.14.6",
 	// 	"1.12.4",
@@ -194,9 +194,9 @@ func (s *Scenario) Headscale(opts ...hsic.Option) (ControlServer, error) {
 	return headscale, nil
 }
 
-func (s *Scenario) CreatePreAuthKey(namespace string) (*v1.PreAuthKey, error) {
+func (s *Scenario) CreatePreAuthKey(namespace string, reusable bool, ephemeral bool) (*v1.PreAuthKey, error) {
 	if headscale, err := s.Headscale(); err == nil {
-		key, err := headscale.CreateAuthKey(namespace)
+		key, err := headscale.CreateAuthKey(namespace, reusable, ephemeral)
 		if err != nil {
 			return nil, fmt.Errorf("failed to create namespace: %w", err)
 		}
@@ -368,7 +368,7 @@ func (s *Scenario) CreateHeadscaleEnv(
 			return err
 		}
 
-		key, err := s.CreatePreAuthKey(namespaceName)
+		key, err := s.CreatePreAuthKey(namespaceName, true, false)
 		if err != nil {
 			return err
 		}
@@ -469,3 +469,19 @@ func (s *Scenario) ListTailscaleClientsFQDNs(namespaces ...string) ([]string, er
 
 	return allFQDNs, nil
 }
+
+func (s *Scenario) WaitForTailscaleLogout() {
+	for _, namespace := range s.namespaces {
+		for _, client := range namespace.Clients {
+			namespace.syncWaitGroup.Add(1)
+
+			go func(c TailscaleClient) {
+				defer namespace.syncWaitGroup.Done()
+
+				// TODO(kradalby): error handle this
+				_ = c.WaitForLogout()
+			}(client)
+		}
+		namespace.syncWaitGroup.Wait()
+	}
+}

integration/scenario_test.go

@@ -62,7 +62,7 @@ func TestHeadscale(t *testing.T) {
 	})
 
 	t.Run("create-auth-key", func(t *testing.T) {
-		_, err := scenario.CreatePreAuthKey(namespace)
+		_, err := scenario.CreatePreAuthKey(namespace, true, false)
 		if err != nil {
 			t.Errorf("failed to create preauthkey: %s", err)
 		}
@@ -166,7 +166,7 @@ func TestTailscaleNodesJoiningHeadcale(t *testing.T) {
 	})
 
 	t.Run("join-headscale", func(t *testing.T) {
-		key, err := scenario.CreatePreAuthKey(namespace)
+		key, err := scenario.CreatePreAuthKey(namespace, true, false)
 		if err != nil {
 			t.Errorf("failed to create preauthkey: %s", err)
 		}

integration/tailscale.go

@@ -15,6 +15,7 @@ type TailscaleClient interface {
 	Execute(command []string) (string, string, error)
 	Up(loginServer, authKey string) error
 	UpWithLoginURL(loginServer string) (*url.URL, error)
+	Logout() error
 	IPs() ([]netip.Addr, error)
 	FQDN() (string, error)
 	Status() (*ipnstate.Status, error)

integration/tsic/tsic.go

@@ -270,6 +270,15 @@ func (t *TailscaleInContainer) UpWithLoginURL(
 	return loginURL, nil
 }
 
+func (t *TailscaleInContainer) Logout() error {
+	_, _, err := t.Execute([]string{"tailscale", "logout"})
+	if err != nil {
+		return err
+	}
+
+	return nil
+}
+
 func (t *TailscaleInContainer) IPs() ([]netip.Addr, error) {
 	if t.ips != nil && len(t.ips) != 0 {
 		return t.ips, nil

machine.go

@@ -153,9 +153,15 @@ func (machine *Machine) isOnline() bool {
 	return machine.LastSeen.After(time.Now().Add(-keepAliveInterval))
 }
 
+// isEphemeral returns if the machine is registered as an Ephemeral node.
+// https://tailscale.com/kb/1111/ephemeral-nodes/
+func (machine *Machine) isEphemeral() bool {
+	return machine.AuthKey != nil && machine.AuthKey.Ephemeral
+}
+
 func containsAddresses(inputs []string, addrs []string) bool {
 	for _, addr := range addrs {
-		if contains(inputs, addr) {
+		if containsStr(inputs, addr) {
 			return true
 		}
 	}
@@ -386,7 +392,7 @@ func (h *Headscale) GetMachineByGivenName(namespace string, givenName string) (*
 // GetMachineByID finds a Machine by ID and returns the Machine struct.
 func (h *Headscale) GetMachineByID(id uint64) (*Machine, error) {
 	m := Machine{}
-	if result := h.db.Preload("Namespace").Find(&Machine{ID: id}).First(&m); result.Error != nil {
+	if result := h.db.Preload("AuthKey").Preload("Namespace").Find(&Machine{ID: id}).First(&m); result.Error != nil {
 		return nil, result.Error
 	}
 
@@ -398,7 +404,7 @@ func (h *Headscale) GetMachineByMachineKey(
 	machineKey key.MachinePublic,
 ) (*Machine, error) {
 	m := Machine{}
-	if result := h.db.Preload("Namespace").First(&m, "machine_key = ?", MachinePublicKeyStripPrefix(machineKey)); result.Error != nil {
+	if result := h.db.Preload("AuthKey").Preload("Namespace").First(&m, "machine_key = ?", MachinePublicKeyStripPrefix(machineKey)); result.Error != nil {
 		return nil, result.Error
 	}
 
@@ -410,7 +416,7 @@ func (h *Headscale) GetMachineByNodeKey(
 	nodeKey key.NodePublic,
 ) (*Machine, error) {
 	machine := Machine{}
-	if result := h.db.Preload("Namespace").First(&machine, "node_key = ?",
+	if result := h.db.Preload("AuthKey").Preload("Namespace").First(&machine, "node_key = ?",
 		NodePublicKeyStripPrefix(nodeKey)); result.Error != nil {
 		return nil, result.Error
 	}
@@ -423,7 +429,7 @@ func (h *Headscale) GetMachineByAnyKey(
 	machineKey key.MachinePublic, nodeKey key.NodePublic, oldNodeKey key.NodePublic,
 ) (*Machine, error) {
 	machine := Machine{}
-	if result := h.db.Preload("Namespace").First(&machine, "machine_key = ? OR node_key = ? OR node_key = ?",
+	if result := h.db.Preload("AuthKey").Preload("Namespace").First(&machine, "machine_key = ? OR node_key = ? OR node_key = ?",
 		MachinePublicKeyStripPrefix(machineKey),
 		NodePublicKeyStripPrefix(nodeKey),
 		NodePublicKeyStripPrefix(oldNodeKey)); result.Error != nil {
@@ -683,7 +689,15 @@ func (h *Headscale) toNode(
 	}
 	primaryPrefixes := Routes(primaryRoutes).toPrefixes()
 
-	allowedIPs = append(allowedIPs, primaryPrefixes...)
+	machineRoutes, err := h.GetMachineRoutes(&machine)
+	if err != nil {
+		return nil, err
+	}
+	for _, route := range machineRoutes {
+		if route.Enabled && (route.IsPrimary || route.isExitRoute()) {
+			allowedIPs = append(allowedIPs, netip.Prefix(route.Prefix))
+		}
+	}
 
 	var derp string
 	if machine.HostInfo.NetInfo != nil {
@@ -844,6 +858,7 @@ func getTags(
 func (h *Headscale) RegisterMachineFromAuthCallback(
 	nodeKeyStr string,
 	namespaceName string,
+	machineExpiry *time.Time,
 	registrationMethod string,
 ) (*Machine, error) {
 	nodeKey := key.NodePublic{}
@@ -877,6 +892,10 @@ func (h *Headscale) RegisterMachineFromAuthCallback(
 			registrationMachine.NamespaceID = namespace.ID
 			registrationMachine.RegisterMethod = registrationMethod
 
+			if machineExpiry != nil {
+				registrationMachine.Expiry = machineExpiry
+			}
+
 			machine, err := h.RegisterMachine(
 				registrationMachine,
 			)

oidc.go

@@ -236,7 +236,7 @@ func (h *Headscale) OIDCCallback(
 		return
 	}
 
-	if err := h.registerMachineForOIDCCallback(writer, namespace, nodeKey); err != nil {
+	if err := h.registerMachineForOIDCCallback(writer, namespace, nodeKey, idToken.Expiry); err != nil {
 		return
 	}
 
@@ -679,10 +679,12 @@ func (h *Headscale) registerMachineForOIDCCallback(
 	writer http.ResponseWriter,
 	namespace *Namespace,
 	nodeKey *key.NodePublic,
+	expiry time.Time,
 ) error {
 	if _, err := h.RegisterMachineFromAuthCallback(
 		nodeKey.String(),
 		namespace.Name,
+		&expiry,
 		RegisterMethodOIDC,
 	); err != nil {
 		log.Error().

platform_config.go

@@ -255,7 +255,7 @@ func (h *Headscale) ApplePlatformConfig(
 		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
 		writer.WriteHeader(http.StatusBadRequest)
 		_, err := writer.Write(
-			[]byte("Invalid platform, only ios and macos is supported"),
+			[]byte("Invalid platform. Only ios, macos-app-store and macos-standalone are supported"),
 		)
 		if err != nil {
 			log.Error().

protocol_common.go

@@ -622,6 +622,20 @@ func (h *Headscale) handleMachineLogOutCommon(
 			Caller().
 			Err(err).
 			Msg("Failed to write response")
+
+		return
+	}
+
+	if machine.isEphemeral() {
+		err = h.HardDeleteMachine(&machine)
+		if err != nil {
+			log.Error().
+				Err(err).
+				Str("machine", machine.Hostname).
+				Msg("Cannot delete ephemeral machine from the database")
+		}
+
+		return
 	}
 
 	log.Info().

protocol_common_poll.go

@@ -664,7 +664,11 @@ func (h *Headscale) scheduledPollWorker(
 				Str("machine", machine.Hostname).
 				Bool("noise", isNoise).
 				Msg("Sending keepalive")
-			keepAliveChan <- data
+			select {
+			case keepAliveChan <- data:
+			case <-ctx.Done():
+				return
+			}
 
 		case <-updateCheckerTicker.C:
 			log.Debug().
@@ -674,7 +678,11 @@ func (h *Headscale) scheduledPollWorker(
 				Msg("Sending update request")
 			updateRequestsFromNode.WithLabelValues(machine.Namespace.Name, machine.Hostname, "scheduled-update").
 				Inc()
-			updateChan <- struct{}{}
+			select {
+			case updateChan <- struct{}{}:
+			case <-ctx.Done():
+				return
+			}
 		}
 	}
 }

routes_test.go

@@ -6,6 +6,7 @@ import (
 
 	"gopkg.in/check.v1"
 	"tailscale.com/tailcfg"
+	"tailscale.com/types/key"
 )
 
 func (s *Suite) TestGetRoutes(c *check.C) {
@@ -352,3 +353,102 @@ func (s *Suite) TestSubnetFailover(c *check.C) {
 	c.Assert(err, check.IsNil)
 	c.Assert(len(routes), check.Equals, 2)
 }
+
+// TestAllowedIPRoutes tests that the AllowedIPs are correctly set for a node,
+// including both the primary routes the node is responsible for, and the
+// exit node routes if enabled.
+func (s *Suite) TestAllowedIPRoutes(c *check.C) {
+	namespace, err := app.CreateNamespace("test")
+	c.Assert(err, check.IsNil)
+
+	pak, err := app.CreatePreAuthKey(namespace.Name, false, false, nil, nil)
+	c.Assert(err, check.IsNil)
+
+	_, err = app.GetMachine("test", "test_enable_route_machine")
+	c.Assert(err, check.NotNil)
+
+	prefix, err := netip.ParsePrefix(
+		"10.0.0.0/24",
+	)
+	c.Assert(err, check.IsNil)
+
+	prefix2, err := netip.ParsePrefix(
+		"150.0.10.0/25",
+	)
+	c.Assert(err, check.IsNil)
+
+	prefixExitNodeV4, err := netip.ParsePrefix(
+		"0.0.0.0/0",
+	)
+	c.Assert(err, check.IsNil)
+
+	prefixExitNodeV6, err := netip.ParsePrefix(
+		"::/0",
+	)
+	c.Assert(err, check.IsNil)
+
+	hostInfo1 := tailcfg.Hostinfo{
+		RoutableIPs: []netip.Prefix{prefix, prefix2, prefixExitNodeV4, prefixExitNodeV6},
+	}
+
+	nodeKey := key.NewNode()
+	discoKey := key.NewDisco()
+	machineKey := key.NewMachine()
+
+	now := time.Now()
+	machine1 := Machine{
+		ID:             1,
+		MachineKey:     MachinePublicKeyStripPrefix(machineKey.Public()),
+		NodeKey:        NodePublicKeyStripPrefix(nodeKey.Public()),
+		DiscoKey:       DiscoPublicKeyStripPrefix(discoKey.Public()),
+		Hostname:       "test_enable_route_machine",
+		NamespaceID:    namespace.ID,
+		RegisterMethod: RegisterMethodAuthKey,
+		AuthKeyID:      uint(pak.ID),
+		HostInfo:       HostInfo(hostInfo1),
+		LastSeen:       &now,
+	}
+	app.db.Save(&machine1)
+
+	err = app.processMachineRoutes(&machine1)
+	c.Assert(err, check.IsNil)
+
+	err = app.EnableRoutes(&machine1, prefix.String())
+	c.Assert(err, check.IsNil)
+
+	// We do not enable this one on purpose to test that it is not enabled
+	// err = app.EnableRoutes(&machine1, prefix2.String())
+	// c.Assert(err, check.IsNil)
+
+	err = app.EnableRoutes(&machine1, prefixExitNodeV4.String())
+	c.Assert(err, check.IsNil)
+
+	err = app.EnableRoutes(&machine1, prefixExitNodeV6.String())
+	c.Assert(err, check.IsNil)
+
+	err = app.handlePrimarySubnetFailover()
+	c.Assert(err, check.IsNil)
+
+	enabledRoutes1, err := app.GetEnabledRoutes(&machine1)
+	c.Assert(err, check.IsNil)
+	c.Assert(len(enabledRoutes1), check.Equals, 3)
+
+	peer, err := app.toNode(machine1, "headscale.net", nil)
+	c.Assert(err, check.IsNil)
+
+	c.Assert(len(peer.AllowedIPs), check.Equals, 3)
+
+	foundExitNodeV4 := false
+	foundExitNodeV6 := false
+	for _, allowedIP := range peer.AllowedIPs {
+		if allowedIP == prefixExitNodeV4 {
+			foundExitNodeV4 = true
+		}
+		if allowedIP == prefixExitNodeV6 {
+			foundExitNodeV6 = true
+		}
+	}
+
+	c.Assert(foundExitNodeV4, check.Equals, true)
+	c.Assert(foundExitNodeV6, check.Equals, true)
+}

templates/apple.html

@@ -24,7 +24,7 @@
       <li>
         ALT + Click the Tailscale icon in the menu and hover over the Debug menu
       </li>
-      <li>Under "Custm Login Server", select "Add Account..."</li>
+      <li>Under "Custom Login Server", select "Add Account..."</li>
       <li>
         Enter "{{.URL}}" of the headscale instance and press "Add Account"
       </li>
@@ -68,7 +68,16 @@
     <!--
 		<pre><code>curl {{.URL}}/apple/ios</code></pre>
 		-->
-    <pre><code>curl {{.URL}}/apple/macos</code></pre>
+    <ul>
+      <li>
+        for app store client:
+        <code>curl {{.URL}}/apple/macos-app-store</code>
+      </li>
+      <li>
+        for standalone client:
+        <code>curl {{.URL}}/apple/macos-standalone</code>
+      </li>
+    </ul>
 
     <h2>Profiles</h2>
 

utils.go

@@ -269,6 +269,16 @@ func stringToIPPrefix(prefixes []string) ([]netip.Prefix, error) {
 	return result, nil
 }
 
+func containsStr(ts []string, t string) bool {
+	for _, v := range ts {
+		if v == t {
+			return true
+		}
+	}
+
+	return false
+}
+
 func contains[T string | netip.Prefix](ts []T, t T) bool {
 	for _, v := range ts {
 		if reflect.DeepEqual(v, t) {