Updated changelog

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

.github/workflows/release.yml

@@ -65,7 +65,6 @@ jobs:
             type=semver,pattern={{version}}
             type=semver,pattern={{major}}.{{minor}}
             type=semver,pattern={{major}}
-            type=raw,value=latest
             type=sha
       - name: Login to DockerHub
         uses: docker/login-action@v1
@@ -125,13 +124,12 @@ jobs:
             ${{ secrets.DOCKERHUB_USERNAME }}/headscale
             ghcr.io/${{ github.repository_owner }}/headscale
           flavor: |
-            latest=false
+            suffix=-debug,onlatest=true
           tags: |
-            type=semver,pattern={{version}}-debug
-            type=semver,pattern={{major}}.{{minor}}-debug
-            type=semver,pattern={{major}}-debug
-            type=raw,value=latest-debug
-            type=sha,suffix=-debug
+            type=semver,pattern={{version}}
+            type=semver,pattern={{major}}.{{minor}}
+            type=semver,pattern={{major}}
+            type=sha
       - name: Login to DockerHub
         uses: docker/login-action@v1
         with:
@@ -161,69 +159,3 @@ jobs:
         run: |
           rm -rf /tmp/.buildx-cache-debug
           mv /tmp/.buildx-cache-debug-new /tmp/.buildx-cache-debug
-
-  docker-alpine-release:
-    runs-on: ubuntu-latest
-    steps:
-      - name: Checkout
-        uses: actions/checkout@v3
-        with:
-          fetch-depth: 0
-      - name: Set up Docker Buildx
-        uses: docker/setup-buildx-action@v1
-      - name: Set up QEMU for multiple platforms
-        uses: docker/setup-qemu-action@master
-        with:
-          platforms: arm64,amd64
-      - name: Cache Docker layers
-        uses: actions/cache@v2
-        with:
-          path: /tmp/.buildx-cache-alpine
-          key: ${{ runner.os }}-buildx-alpine-${{ github.sha }}
-          restore-keys: |
-            ${{ runner.os }}-buildx-alpine-
-      - name: Docker meta
-        id: meta-alpine
-        uses: docker/metadata-action@v3
-        with:
-          # list of Docker images to use as base name for tags
-          images: |
-            ${{ secrets.DOCKERHUB_USERNAME }}/headscale
-            ghcr.io/${{ github.repository_owner }}/headscale
-          flavor: |
-            latest=false
-          tags: |
-            type=semver,pattern={{version}}-alpine
-            type=semver,pattern={{major}}.{{minor}}-alpine
-            type=semver,pattern={{major}}-alpine
-            type=raw,value=latest-alpine
-            type=sha,suffix=-alpine
-      - name: Login to DockerHub
-        uses: docker/login-action@v1
-        with:
-          username: ${{ secrets.DOCKERHUB_USERNAME }}
-          password: ${{ secrets.DOCKERHUB_TOKEN }}
-      - name: Login to GHCR
-        uses: docker/login-action@v1
-        with:
-          registry: ghcr.io
-          username: ${{ github.repository_owner }}
-          password: ${{ secrets.GITHUB_TOKEN }}
-      - name: Build and push
-        id: docker_build
-        uses: docker/build-push-action@v2
-        with:
-          push: true
-          context: .
-          file: Dockerfile.alpine
-          tags: ${{ steps.meta-alpine.outputs.tags }}
-          labels: ${{ steps.meta-alpine.outputs.labels }}
-          platforms: linux/amd64,linux/arm64
-          cache-from: type=local,src=/tmp/.buildx-cache-alpine
-          cache-to: type=local,dest=/tmp/.buildx-cache-alpine-new
-          build-args: |
-            VERSION=${{ steps.meta-alpine.outputs.version }}
-      - name: Prepare cache for next build
-        run: |
-          rm -rf /tmp/.buildx-cache-alpine
-          mv /tmp/.buildx-cache-alpine-new /tmp/.buildx-cache-alpine

.github/workflows/test-integration-v2-general-auth.yml

@@ -1,35 +0,0 @@
-name: Integration Test v2
-
-on: [pull_request]
-
-jobs:
-  integration-test-v2:
-    runs-on: ubuntu-latest
-
-    steps:
-      - uses: actions/checkout@v2
-        with:
-          fetch-depth: 2
-
-      - name: Set Swap Space
-        uses: pierotofy/set-swap-space@master
-        with:
-          swap-size-gb: 10
-
-      - name: Get changed files
-        id: changed-files
-        uses: tj-actions/changed-files@v14.1
-        with:
-          files: |
-            *.nix
-            go.*
-            **/*.go
-            integration_test/
-            config-example.yaml
-
-      - uses: cachix/install-nix-action@v16
-        if: steps.changed-files.outputs.any_changed == 'true'
-
-      - name: Run general integration tests
-        if: steps.changed-files.outputs.any_changed == 'true'
-        run: nix develop --command -- make test_integration_v2_auth_web_flow

CHANGELOG.md

@@ -5,6 +5,7 @@
 ### BREAKING
 
 - Log level option `log_level` was moved to a distinct `log` config section and renamed to `level` [#768](https://github.com/juanfont/headscale/pull/768)
+- Removed Alpine Linux container image [#962](https://github.com/juanfont/headscale/pull/962)
 
 ### Changes
 
@@ -25,6 +26,7 @@
 - Add `dns_config.override_local_dns` option [#905](https://github.com/juanfont/headscale/pull/905)
 - Fix some DNS config issues [#660](https://github.com/juanfont/headscale/issues/660)
 - Make it possible to disable TS2019 with build flag [#928](https://github.com/juanfont/headscale/pull/928)
+- Fix OIDC registration issues [#960](https://github.com/juanfont/headscale/pull/960) and [#971](https://github.com/juanfont/headscale/pull/971)
 
 ## 0.16.4 (2022-08-21)
 

Dockerfile.alpine

@@ -1,24 +0,0 @@
-# Builder image
-FROM docker.io/golang:1.19.0-alpine AS build
-ARG VERSION=dev
-ENV GOPATH /go
-WORKDIR /go/src/headscale
-
-COPY go.mod go.sum /go/src/headscale/
-RUN apk add gcc musl-dev
-RUN go mod download
-
-COPY . .
-
-RUN CGO_ENABLED=0 GOOS=linux go install -ldflags="-s -w -X github.com/juanfont/headscale/cmd/headscale/cli.Version=$VERSION" -a ./cmd/headscale
-RUN strip /go/bin/headscale
-RUN test -e /go/bin/headscale
-
-# Production image
-FROM docker.io/alpine:latest
-
-COPY --from=build /go/bin/headscale /bin/headscale
-ENV TZ UTC
-
-EXPOSE 8080/tcp
-CMD ["headscale"]

Makefile

@@ -68,17 +68,6 @@ test_integration_v2_general:
 		golang:1 \
 		go test $(TAGS) -failfast ./... -timeout 60m -parallel 6
 
-
-test_integration_v2_auth_web_flow:
-	docker run \
-		-t --rm \
-		-v ~/.cache/hs-integration-go:/go \
-		--name headscale-test-suite \
-		-v $$PWD:$$PWD -w $$PWD/integration \
-		-v /var/run/docker.sock:/var/run/docker.sock \
-		golang:1 \
-		go test ./... -timeout 60m -parallel 6 -run TestAuthWebFlow
-
 coverprofile_func:
 	go tool cover -func=coverage.out
 

cmd/headscale/cli/nodes.go

@@ -134,7 +134,9 @@ var registerNodeCmd = &cobra.Command{
 			return
 		}
 
-		SuccessOutput(response.Machine, fmt.Sprintf("Machine %s registered", response.Machine.GivenName), output)
+		SuccessOutput(
+			response.Machine,
+			fmt.Sprintf("Machine %s registered", response.Machine.GivenName), output)
 	},
 }
 

integration/auth_web_flow_test.go

@@ -10,6 +10,8 @@ import (
 	"net/url"
 	"strings"
 	"testing"
+
+	"github.com/juanfont/headscale/integration/hsic"
 )
 
 var errParseAuthPage = errors.New("failed to parse auth page")
@@ -35,7 +37,7 @@ func TestAuthWebFlowAuthenticationPingAll(t *testing.T) {
 		"namespace2": len(TailscaleVersions),
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("webauthping"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -76,13 +78,16 @@ func TestAuthWebFlowAuthenticationPingAll(t *testing.T) {
 	}
 }
 
-func (s *AuthWebFlowScenario) CreateHeadscaleEnv(namespaces map[string]int) error {
-	err := s.StartHeadscale()
+func (s *AuthWebFlowScenario) CreateHeadscaleEnv(
+	namespaces map[string]int,
+	opts ...hsic.Option,
+) error {
+	headscale, err := s.Headscale(opts...)
 	if err != nil {
 		return err
 	}
 
-	err = s.Headscale().WaitForReady()
+	err = headscale.WaitForReady()
 	if err != nil {
 		return err
 	}
@@ -99,7 +104,7 @@ func (s *AuthWebFlowScenario) CreateHeadscaleEnv(namespaces map[string]int) erro
 			return err
 		}
 
-		err = s.runTailscaleUp(namespaceName, s.Headscale().GetEndpoint())
+		err = s.runTailscaleUp(namespaceName, headscale.GetEndpoint())
 		if err != nil {
 			return err
 		}
@@ -145,8 +150,13 @@ func (s *AuthWebFlowScenario) runTailscaleUp(
 }
 
 func (s *AuthWebFlowScenario) runHeadscaleRegister(namespaceStr string, loginURL *url.URL) error {
+	headscale, err := s.Headscale()
+	if err != nil {
+		return err
+	}
+
 	log.Printf("loginURL: %s", loginURL)
-	loginURL.Host = fmt.Sprintf("%s:8080", s.Headscale().GetIP())
+	loginURL.Host = fmt.Sprintf("%s:8080", headscale.GetIP())
 	loginURL.Scheme = "http"
 
 	httpClient := &http.Client{}
@@ -177,8 +187,10 @@ func (s *AuthWebFlowScenario) runHeadscaleRegister(namespaceStr string, loginURL
 	key := keySep[1]
 	log.Printf("registering node %s", key)
 
-	if headscale, ok := s.controlServers["headscale"]; ok {
-		_, err = headscale.Execute([]string{"headscale", "-n", namespaceStr, "nodes", "register", "--key", key})
+	if headscale, err := s.Headscale(); err == nil {
+		_, err = headscale.Execute(
+			[]string{"headscale", "-n", namespaceStr, "nodes", "register", "--key", key},
+		)
 		if err != nil {
 			log.Printf("failed to register node: %s", err)
 

integration/cli_test.go

@@ -7,6 +7,7 @@ import (
 	"time"
 
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
+	"github.com/juanfont/headscale/integration/hsic"
 	"github.com/stretchr/testify/assert"
 )
 
@@ -36,11 +37,14 @@ func TestNamespaceCommand(t *testing.T) {
 		"namespace2": 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clins"))
+	assert.NoError(t, err)
+
+	headscale, err := scenario.Headscale()
 	assert.NoError(t, err)
 
 	var listNamespaces []v1.Namespace
-	err = executeAndUnmarshal(scenario.Headscale(),
+	err = executeAndUnmarshal(headscale,
 		[]string{
 			"headscale",
 			"namespaces",
@@ -61,7 +65,7 @@ func TestNamespaceCommand(t *testing.T) {
 		result,
 	)
 
-	_, err = scenario.Headscale().Execute(
+	_, err = headscale.Execute(
 		[]string{
 			"headscale",
 			"namespaces",
@@ -75,7 +79,7 @@ func TestNamespaceCommand(t *testing.T) {
 	assert.NoError(t, err)
 
 	var listAfterRenameNamespaces []v1.Namespace
-	err = executeAndUnmarshal(scenario.Headscale(),
+	err = executeAndUnmarshal(headscale,
 		[]string{
 			"headscale",
 			"namespaces",
@@ -114,7 +118,10 @@ func TestPreAuthKeyCommand(t *testing.T) {
 		namespace: 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clipak"))
+	assert.NoError(t, err)
+
+	headscale, err := scenario.Headscale()
 	assert.NoError(t, err)
 
 	keys := make([]*v1.PreAuthKey, count)
@@ -123,7 +130,7 @@ func TestPreAuthKeyCommand(t *testing.T) {
 	for index := 0; index < count; index++ {
 		var preAuthKey v1.PreAuthKey
 		err := executeAndUnmarshal(
-			scenario.Headscale(),
+			headscale,
 			[]string{
 				"headscale",
 				"preauthkeys",
@@ -149,7 +156,7 @@ func TestPreAuthKeyCommand(t *testing.T) {
 
 	var listedPreAuthKeys []v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -202,7 +209,7 @@ func TestPreAuthKeyCommand(t *testing.T) {
 	}
 
 	// Test key expiry
-	_, err = scenario.Headscale().Execute(
+	_, err = headscale.Execute(
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -216,7 +223,7 @@ func TestPreAuthKeyCommand(t *testing.T) {
 
 	var listedPreAuthKeysAfterExpire []v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -251,12 +258,15 @@ func TestPreAuthKeyCommandWithoutExpiry(t *testing.T) {
 		namespace: 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clipaknaexp"))
+	assert.NoError(t, err)
+
+	headscale, err := scenario.Headscale()
 	assert.NoError(t, err)
 
 	var preAuthKey v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -273,7 +283,7 @@ func TestPreAuthKeyCommandWithoutExpiry(t *testing.T) {
 
 	var listedPreAuthKeys []v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -313,12 +323,15 @@ func TestPreAuthKeyCommandReusableEphemeral(t *testing.T) {
 		namespace: 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clipakresueeph"))
+	assert.NoError(t, err)
+
+	headscale, err := scenario.Headscale()
 	assert.NoError(t, err)
 
 	var preAuthReusableKey v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -335,7 +348,7 @@ func TestPreAuthKeyCommandReusableEphemeral(t *testing.T) {
 
 	var preAuthEphemeralKey v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",
@@ -355,7 +368,7 @@ func TestPreAuthKeyCommandReusableEphemeral(t *testing.T) {
 
 	var listedPreAuthKeys []v1.PreAuthKey
 	err = executeAndUnmarshal(
-		scenario.Headscale(),
+		headscale,
 		[]string{
 			"headscale",
 			"preauthkeys",

integration/control.go

@@ -13,4 +13,7 @@ type ControlServer interface {
 	CreateNamespace(namespace string) error
 	CreateAuthKey(namespace string) (*v1.PreAuthKey, error)
 	ListMachinesInNamespace(namespace string) ([]*v1.Machine, error)
+	GetCert() []byte
+	GetHostname() string
+	GetIP() string
 }

integration/general_test.go

@@ -6,6 +6,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/juanfont/headscale/integration/hsic"
 	"github.com/rs/zerolog/log"
 )
 
@@ -22,7 +23,7 @@ func TestPingAllByIP(t *testing.T) {
 		"namespace2": len(TailscaleVersions),
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("pingallbyip"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -77,7 +78,7 @@ func TestPingAllByHostname(t *testing.T) {
 		"namespace4": len(TailscaleVersions) - 1,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("pingallbyname"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -144,7 +145,7 @@ func TestTaildrop(t *testing.T) {
 		"taildrop": len(TailscaleVersions) - 1,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("taildrop"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -271,7 +272,7 @@ func TestResolveMagicDNS(t *testing.T) {
 		"magicdns2": len(TailscaleVersions) - 1,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec)
+	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("magicdns"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}

integration/hsic/hsic.go

@@ -1,52 +1,83 @@
 package hsic
 
 import (
-	"archive/tar"
 	"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"
-	"path/filepath"
+	"time"
 
 	"github.com/juanfont/headscale"
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/juanfont/headscale/integration/integrationutil"
 	"github.com/ory/dockertest/v3"
-	"github.com/ory/dockertest/v3/docker"
 )
 
 const (
-	hsicHashLength    = 6
-	dockerContextPath = "../."
-	aclPolicyPath     = "/etc/headscale/acl.hujson"
+	hsicHashLength       = 6
+	dockerContextPath    = "../."
+	aclPolicyPath        = "/etc/headscale/acl.hujson"
+	tlsCertPath          = "/etc/headscale/tls.cert"
+	tlsKeyPath           = "/etc/headscale/tls.key"
+	headscaleDefaultPort = 8080
 )
 
 var errHeadscaleStatusCodeNotOk = errors.New("headscale status code not ok")
 
 type HeadscaleInContainer struct {
 	hostname string
-	port     int
 
 	pool      *dockertest.Pool
 	container *dockertest.Resource
 	network   *dockertest.Network
 
 	// optional config
+	port      int
 	aclPolicy *headscale.ACLPolicy
 	env       []string
+	tlsCert   []byte
+	tlsKey    []byte
 }
 
 type Option = func(c *HeadscaleInContainer)
 
 func WithACLPolicy(acl *headscale.ACLPolicy) Option {
 	return func(hsic *HeadscaleInContainer) {
+		// TODO(kradalby): Move somewhere appropriate
+		hsic.env = append(hsic.env, fmt.Sprintf("HEADSCALE_ACL_POLICY_PATH=%s", aclPolicyPath))
+
 		hsic.aclPolicy = acl
 	}
 }
 
+func WithTLS() Option {
+	return func(hsic *HeadscaleInContainer) {
+		cert, key, err := createCertificate()
+		if err != nil {
+			log.Fatalf("failed to create certificates for headscale test: %s", err)
+		}
+
+		// TODO(kradalby): Move somewhere appropriate
+		hsic.env = append(hsic.env, fmt.Sprintf("HEADSCALE_TLS_CERT_PATH=%s", tlsCertPath))
+		hsic.env = append(hsic.env, fmt.Sprintf("HEADSCALE_TLS_KEY_PATH=%s", tlsKeyPath))
+		hsic.env = append(hsic.env, "HEADSCALE_TLS_CLIENT_AUTH_MODE=disabled")
+
+		hsic.tlsCert = cert
+		hsic.tlsKey = key
+	}
+}
+
 func WithConfigEnv(configEnv map[string]string) Option {
 	return func(hsic *HeadscaleInContainer) {
 		env := []string{}
@@ -59,9 +90,23 @@ func WithConfigEnv(configEnv map[string]string) Option {
 	}
 }
 
+func WithPort(port int) Option {
+	return func(hsic *HeadscaleInContainer) {
+		hsic.port = port
+	}
+}
+
+func WithTestName(testName string) Option {
+	return func(hsic *HeadscaleInContainer) {
+		hash, _ := headscale.GenerateRandomStringDNSSafe(hsicHashLength)
+
+		hostname := fmt.Sprintf("hs-%s-%s", testName, hash)
+		hsic.hostname = hostname
+	}
+}
+
 func New(
 	pool *dockertest.Pool,
-	port int,
 	network *dockertest.Network,
 	opts ...Option,
 ) (*HeadscaleInContainer, error) {
@@ -71,11 +116,10 @@ func New(
 	}
 
 	hostname := fmt.Sprintf("hs-%s", hash)
-	portProto := fmt.Sprintf("%d/tcp", port)
 
 	hsic := &HeadscaleInContainer{
 		hostname: hostname,
-		port:     port,
+		port:     headscaleDefaultPort,
 
 		pool:    pool,
 		network: network,
@@ -85,9 +129,9 @@ func New(
 		opt(hsic)
 	}
 
-	if hsic.aclPolicy != nil {
-		hsic.env = append(hsic.env, fmt.Sprintf("HEADSCALE_ACL_POLICY_PATH=%s", aclPolicyPath))
-	}
+	log.Println("NAME: ", hsic.hostname)
+
+	portProto := fmt.Sprintf("%d/tcp", hsic.port)
 
 	headscaleBuildOptions := &dockertest.BuildOptions{
 		Dockerfile: "Dockerfile.debug",
@@ -95,7 +139,7 @@ func New(
 	}
 
 	runOptions := &dockertest.RunOptions{
-		Name:         hostname,
+		Name:         hsic.hostname,
 		ExposedPorts: []string{portProto},
 		Networks:     []*dockertest.Network{network},
 		// Cmd:          []string{"headscale", "serve"},
@@ -108,7 +152,7 @@ func New(
 	// 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)
+	err = pool.RemoveContainerByName(hsic.hostname)
 	if err != nil {
 		return nil, err
 	}
@@ -123,7 +167,7 @@ func New(
 	if err != nil {
 		return nil, fmt.Errorf("could not start headscale container: %w", err)
 	}
-	log.Printf("Created %s container\n", hostname)
+	log.Printf("Created %s container\n", hsic.hostname)
 
 	hsic.container = container
 
@@ -144,9 +188,25 @@ func New(
 		}
 	}
 
+	if hsic.hasTLS() {
+		err = hsic.WriteFile(tlsCertPath, hsic.tlsCert)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS certificate to container: %w", err)
+		}
+
+		err = hsic.WriteFile(tlsKeyPath, hsic.tlsKey)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS key to container: %w", err)
+		}
+	}
+
 	return hsic, nil
 }
 
+func (t *HeadscaleInContainer) hasTLS() bool {
+	return len(t.tlsCert) != 0 && len(t.tlsKey) != 0
+}
+
 func (t *HeadscaleInContainer) Shutdown() error {
 	return t.pool.Purge(t.container)
 }
@@ -154,8 +214,6 @@ func (t *HeadscaleInContainer) Shutdown() error {
 func (t *HeadscaleInContainer) Execute(
 	command []string,
 ) (string, error) {
-	log.Println("command", command)
-	log.Printf("running command for %s\n", t.hostname)
 	stdout, stderr, err := dockertestutil.ExecuteCommand(
 		t.container,
 		command,
@@ -164,11 +222,11 @@ func (t *HeadscaleInContainer) Execute(
 	if err != nil {
 		log.Printf("command stderr: %s\n", stderr)
 
-		return "", err
-	}
+		if stdout != "" {
+			log.Printf("command stdout: %s\n", stdout)
+		}
 
-	if stdout != "" {
-		log.Printf("command stdout: %s\n", stdout)
+		return "", err
 	}
 
 	return stdout, nil
@@ -183,11 +241,7 @@ func (t *HeadscaleInContainer) GetPort() string {
 }
 
 func (t *HeadscaleInContainer) GetHealthEndpoint() string {
-	hostEndpoint := fmt.Sprintf("%s:%d",
-		t.GetIP(),
-		t.port)
-
-	return fmt.Sprintf("http://%s/health", hostEndpoint)
+	return fmt.Sprintf("%s/health", t.GetEndpoint())
 }
 
 func (t *HeadscaleInContainer) GetEndpoint() string {
@@ -195,17 +249,39 @@ func (t *HeadscaleInContainer) GetEndpoint() string {
 		t.GetIP(),
 		t.port)
 
+	if t.hasTLS() {
+		return fmt.Sprintf("https://%s", hostEndpoint)
+	}
+
 	return fmt.Sprintf("http://%s", hostEndpoint)
 }
 
+func (t *HeadscaleInContainer) GetCert() []byte {
+	return t.tlsCert
+}
+
+func (t *HeadscaleInContainer) GetHostname() string {
+	return t.hostname
+}
+
 func (t *HeadscaleInContainer) WaitForReady() error {
 	url := t.GetHealthEndpoint()
 
 	log.Printf("waiting for headscale to be ready at %s", url)
 
+	client := &http.Client{}
+
+	if t.hasTLS() {
+		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 := http.Get(url) //nolint
+		resp, err := client.Get(url) //nolint
 		if err != nil {
+			log.Printf("ready err: %s", err)
+
 			return fmt.Errorf("headscale is not ready: %w", err)
 		}
 
@@ -292,55 +368,87 @@ func (t *HeadscaleInContainer) ListMachinesInNamespace(
 }
 
 func (t *HeadscaleInContainer) WriteFile(path string, data []byte) error {
-	dirPath, fileName := filepath.Split(path)
+	return integrationutil.WriteFileToContainer(t.pool, t.container, path, data)
+}
 
-	file := bytes.NewReader(data)
+//nolint
+func createCertificate() ([]byte, []byte, error) {
+	// From:
+	// https://shaneutt.com/blog/golang-ca-and-signed-cert-go/
 
-	buf := bytes.NewBuffer([]byte{})
-
-	tarWriter := tar.NewWriter(buf)
-
-	header := &tar.Header{
-		Name: fileName,
-		Size: file.Size(),
-		// Mode:    int64(stat.Mode()),
-		// ModTime: stat.ModTime(),
-	}
-
-	err := tarWriter.WriteHeader(header)
-	if err != nil {
-		return fmt.Errorf("failed write file header to tar: %w", err)
-	}
-
-	_, err = io.Copy(tarWriter, file)
-	if err != nil {
-		return fmt.Errorf("failed to copy file to tar: %w", err)
-	}
-
-	err = tarWriter.Close()
-	if err != nil {
-		return fmt.Errorf("failed to close tar: %w", err)
-	}
-
-	log.Printf("tar: %s", buf.String())
-
-	// Ensure the directory is present inside the container
-	_, err = t.Execute([]string{"mkdir", "-p", dirPath})
-	if err != nil {
-		return fmt.Errorf("failed to ensure directory: %w", err)
-	}
-
-	err = t.pool.Client.UploadToContainer(
-		t.container.Container.ID,
-		docker.UploadToContainerOptions{
-			NoOverwriteDirNonDir: false,
-			Path:                 dirPath,
-			InputStream:          bytes.NewReader(buf.Bytes()),
+	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(30 * time.Minute),
+		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{
+			Organization: []string{"Headscale testing INC"},
+			Country:      []string{"NL"},
+			Locality:     []string{"Leiden"},
+		},
+		IPAddresses:  []net.IP{net.IPv4(127, 0, 0, 1), net.IPv6loopback},
+		NotBefore:    time.Now(),
+		NotAfter:     time.Now().Add(30 * time.Minute),
+		SubjectKeyId: []byte{1, 2, 3, 4, 6},
+		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageClientAuth, x509.ExtKeyUsageServerAuth},
+		KeyUsage:     x509.KeyUsageDigitalSignature,
+	}
+
+	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 err
+		return nil, nil, err
 	}
 
-	return nil
+	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
 }

integration/integrationutil/util.go

@@ -0,0 +1,77 @@
+package integrationutil
+
+import (
+	"archive/tar"
+	"bytes"
+	"fmt"
+	"io"
+	"log"
+	"path/filepath"
+
+	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/ory/dockertest/v3"
+	"github.com/ory/dockertest/v3/docker"
+)
+
+func WriteFileToContainer(
+	pool *dockertest.Pool,
+	container *dockertest.Resource,
+	path string,
+	data []byte,
+) error {
+	dirPath, fileName := filepath.Split(path)
+
+	file := bytes.NewReader(data)
+
+	buf := bytes.NewBuffer([]byte{})
+
+	tarWriter := tar.NewWriter(buf)
+
+	header := &tar.Header{
+		Name: fileName,
+		Size: file.Size(),
+		// Mode:    int64(stat.Mode()),
+		// ModTime: stat.ModTime(),
+	}
+
+	err := tarWriter.WriteHeader(header)
+	if err != nil {
+		return fmt.Errorf("failed write file header to tar: %w", err)
+	}
+
+	_, err = io.Copy(tarWriter, file)
+	if err != nil {
+		return fmt.Errorf("failed to copy file to tar: %w", err)
+	}
+
+	err = tarWriter.Close()
+	if err != nil {
+		return fmt.Errorf("failed to close tar: %w", err)
+	}
+
+	log.Printf("tar: %s", buf.String())
+
+	// Ensure the directory is present inside the container
+	_, _, err = dockertestutil.ExecuteCommand(
+		container,
+		[]string{"mkdir", "-p", dirPath},
+		[]string{},
+	)
+	if err != nil {
+		return fmt.Errorf("failed to ensure directory: %w", err)
+	}
+
+	err = pool.Client.UploadToContainer(
+		container.Container.ID,
+		docker.UploadToContainerOptions{
+			NoOverwriteDirNonDir: false,
+			Path:                 dirPath,
+			InputStream:          bytes.NewReader(buf.Bytes()),
+		},
+	)
+	if err != nil {
+		return err
+	}
+
+	return nil
+}

integration/scenario.go

@@ -15,22 +15,28 @@ import (
 	"github.com/juanfont/headscale/integration/hsic"
 	"github.com/juanfont/headscale/integration/tsic"
 	"github.com/ory/dockertest/v3"
+	"github.com/puzpuzpuz/xsync/v2"
 )
 
 const (
 	scenarioHashLength = 6
 	maxWait            = 60 * time.Second
-	headscalePort      = 8080
 )
 
 var (
 	errNoHeadscaleAvailable = errors.New("no headscale available")
 	errNoNamespaceAvailable = errors.New("no namespace available")
-	TailscaleVersions       = []string{
+
+	// Tailscale started adding TS2021 support in CapabilityVersion>=28 (v1.24.0), but
+	// proper support in Headscale was only added for CapabilityVersion>=39 clients (v1.30.0).
+	tailscaleVersions2021 = []string{
 		"head",
 		"unstable",
 		"1.32.1",
 		"1.30.2",
+	}
+
+	tailscaleVersions2019 = []string{
 		"1.28.0",
 		"1.26.2",
 		"1.24.2",
@@ -38,13 +44,20 @@ var (
 		"1.20.4",
 		"1.18.2",
 		"1.16.2",
-
-		// These versions seem to fail when fetching from apt.
-		// "1.14.6",
-		// "1.12.4",
-		// "1.10.2",
-		// "1.8.7",
 	}
+
+	// tailscaleVersionsUnavailable = []string{
+	// 	// These versions seem to fail when fetching from apt.
+	// 	"1.14.6",
+	// 	"1.12.4",
+	// 	"1.10.2",
+	// 	"1.8.7",
+	// }.
+
+	TailscaleVersions = append(
+		tailscaleVersions2021,
+		tailscaleVersions2019...,
+	)
 )
 
 type Namespace struct {
@@ -59,12 +72,14 @@ type Namespace struct {
 type Scenario struct {
 	// TODO(kradalby): support multiple headcales for later, currently only
 	// use one.
-	controlServers map[string]ControlServer
+	controlServers *xsync.MapOf[string, ControlServer]
 
 	namespaces map[string]*Namespace
 
 	pool    *dockertest.Pool
 	network *dockertest.Network
+
+	headscaleLock sync.Mutex
 }
 
 func NewScenario() (*Scenario, error) {
@@ -99,7 +114,7 @@ func NewScenario() (*Scenario, error) {
 	}
 
 	return &Scenario{
-		controlServers: make(map[string]ControlServer),
+		controlServers: xsync.NewMapOf[ControlServer](),
 		namespaces:     make(map[string]*Namespace),
 
 		pool:    pool,
@@ -108,12 +123,17 @@ func NewScenario() (*Scenario, error) {
 }
 
 func (s *Scenario) Shutdown() error {
-	for _, control := range s.controlServers {
+	s.controlServers.Range(func(_ string, control ControlServer) bool {
 		err := control.Shutdown()
 		if err != nil {
-			return fmt.Errorf("failed to tear down control: %w", err)
+			log.Printf(
+				"Failed to shut down control: %s",
+				fmt.Errorf("failed to tear down control: %w", err),
+			)
 		}
-	}
+
+		return true
+	})
 
 	for namespaceName, namespace := range s.namespaces {
 		for _, client := range namespace.Clients {
@@ -150,36 +170,31 @@ func (s *Scenario) Namespaces() []string {
 // Note: These functions assume that there is a _single_ headscale instance for now
 
 // TODO(kradalby): make port and headscale configurable, multiple instances support?
-func (s *Scenario) StartHeadscale() error {
-	headscale, err := hsic.New(s.pool, headscalePort, s.network,
-		hsic.WithACLPolicy(
-			&headscale.ACLPolicy{
-				ACLs: []headscale.ACL{
-					{
-						Action:       "accept",
-						Sources:      []string{"*"},
-						Destinations: []string{"*:*"},
-					},
-				},
-			},
-		),
-	)
-	if err != nil {
-		return fmt.Errorf("failed to create headscale container: %w", err)
+func (s *Scenario) Headscale(opts ...hsic.Option) (ControlServer, error) {
+	s.headscaleLock.Lock()
+	defer s.headscaleLock.Unlock()
+
+	if headscale, ok := s.controlServers.Load("headscale"); ok {
+		return headscale, nil
 	}
 
-	s.controlServers["headscale"] = headscale
+	headscale, err := hsic.New(s.pool, s.network, opts...)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create headscale container: %w", err)
+	}
 
-	return nil
-}
+	err = headscale.WaitForReady()
+	if err != nil {
+		return nil, fmt.Errorf("failed reach headscale container: %w", err)
+	}
 
-func (s *Scenario) Headscale() *hsic.HeadscaleInContainer {
-	//nolint
-	return s.controlServers["headscale"].(*hsic.HeadscaleInContainer)
+	s.controlServers.Store("headscale", headscale)
+
+	return headscale, nil
 }
 
 func (s *Scenario) CreatePreAuthKey(namespace string) (*v1.PreAuthKey, error) {
-	if headscale, ok := s.controlServers["headscale"]; ok {
+	if headscale, err := s.Headscale(); err == nil {
 		key, err := headscale.CreateAuthKey(namespace)
 		if err != nil {
 			return nil, fmt.Errorf("failed to create namespace: %w", err)
@@ -192,7 +207,7 @@ func (s *Scenario) CreatePreAuthKey(namespace string) (*v1.PreAuthKey, error) {
 }
 
 func (s *Scenario) CreateNamespace(namespace string) error {
-	if headscale, ok := s.controlServers["headscale"]; ok {
+	if headscale, err := s.Headscale(); err == nil {
 		err := headscale.CreateNamespace(namespace)
 		if err != nil {
 			return fmt.Errorf("failed to create namespace: %w", err)
@@ -222,16 +237,36 @@ func (s *Scenario) CreateTailscaleNodesInNamespace(
 				version = TailscaleVersions[i%len(TailscaleVersions)]
 			}
 
+			headscale, err := s.Headscale()
+			if err != nil {
+				return fmt.Errorf("failed to create tailscale node: %w", err)
+			}
+
+			cert := headscale.GetCert()
+			hostname := headscale.GetHostname()
+
 			namespace.createWaitGroup.Add(1)
 
 			go func() {
 				defer namespace.createWaitGroup.Done()
 
 				// TODO(kradalby): error handle this
-				tsClient, err := tsic.New(s.pool, version, s.network)
+				tsClient, err := tsic.New(
+					s.pool,
+					version,
+					s.network,
+					tsic.WithHeadscaleTLS(cert),
+					tsic.WithHeadscaleName(hostname),
+				)
 				if err != nil {
 					// return fmt.Errorf("failed to add tailscale node: %w", err)
-					log.Printf("failed to add tailscale node: %s", err)
+					log.Printf("failed to create tailscale node: %s", err)
+				}
+
+				err = tsClient.WaitForReady()
+				if err != nil {
+					// return fmt.Errorf("failed to add tailscale node: %w", err)
+					log.Printf("failed to wait for tailscaled: %s", err)
 				}
 
 				namespace.Clients[tsClient.Hostname()] = tsClient
@@ -258,7 +293,13 @@ func (s *Scenario) RunTailscaleUp(
 				// TODO(kradalby): error handle this
 				_ = c.Up(loginServer, authKey)
 			}(client)
+
+			err := client.WaitForReady()
+			if err != nil {
+				log.Printf("error waiting for client %s to be ready: %s", client.Hostname(), err)
+			}
 		}
+
 		namespace.joinWaitGroup.Wait()
 
 		return nil
@@ -300,13 +341,8 @@ func (s *Scenario) WaitForTailscaleSync() error {
 // CreateHeadscaleEnv is a conventient method returning a set up Headcale
 // test environment with nodes of all versions, joined to the server with X
 // namespaces.
-func (s *Scenario) CreateHeadscaleEnv(namespaces map[string]int) error {
-	err := s.StartHeadscale()
-	if err != nil {
-		return err
-	}
-
-	err = s.Headscale().WaitForReady()
+func (s *Scenario) CreateHeadscaleEnv(namespaces map[string]int, opts ...hsic.Option) error {
+	headscale, err := s.Headscale(opts...)
 	if err != nil {
 		return err
 	}
@@ -327,7 +363,7 @@ func (s *Scenario) CreateHeadscaleEnv(namespaces map[string]int) error {
 			return err
 		}
 
-		err = s.RunTailscaleUp(namespaceName, s.Headscale().GetEndpoint(), key.GetKey())
+		err = s.RunTailscaleUp(namespaceName, headscale.GetEndpoint(), key.GetKey())
 		if err != nil {
 			return err
 		}

integration/scenario_test.go

@@ -34,12 +34,12 @@ func TestHeadscale(t *testing.T) {
 	}
 
 	t.Run("start-headscale", func(t *testing.T) {
-		err = scenario.StartHeadscale()
+		headscale, err := scenario.Headscale()
 		if err != nil {
 			t.Errorf("failed to create start headcale: %s", err)
 		}
 
-		err = scenario.Headscale().WaitForReady()
+		err = headscale.WaitForReady()
 		if err != nil {
 			t.Errorf("headscale failed to become ready: %s", err)
 		}
@@ -117,12 +117,11 @@ func TestTailscaleNodesJoiningHeadcale(t *testing.T) {
 	}
 
 	t.Run("start-headscale", func(t *testing.T) {
-		err = scenario.StartHeadscale()
+		headscale, err := scenario.Headscale()
 		if err != nil {
 			t.Errorf("failed to create start headcale: %s", err)
 		}
 
-		headscale := scenario.Headscale()
 		err = headscale.WaitForReady()
 		if err != nil {
 			t.Errorf("headscale failed to become ready: %s", err)
@@ -157,7 +156,16 @@ func TestTailscaleNodesJoiningHeadcale(t *testing.T) {
 			t.Errorf("failed to create preauthkey: %s", err)
 		}
 
-		err = scenario.RunTailscaleUp(namespace, scenario.Headscale().GetEndpoint(), key.GetKey())
+		headscale, err := scenario.Headscale()
+		if err != nil {
+			t.Errorf("failed to create start headcale: %s", err)
+		}
+
+		err = scenario.RunTailscaleUp(
+			namespace,
+			headscale.GetEndpoint(),
+			key.GetKey(),
+		)
 		if err != nil {
 			t.Errorf("failed to login: %s", err)
 		}

integration/tsic/tsic.go

@@ -12,6 +12,7 @@ import (
 	"github.com/cenkalti/backoff/v4"
 	"github.com/juanfont/headscale"
 	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/juanfont/headscale/integration/integrationutil"
 	"github.com/ory/dockertest/v3"
 	"github.com/ory/dockertest/v3/docker"
 	"tailscale.com/ipn/ipnstate"
@@ -20,13 +21,15 @@ import (
 const (
 	tsicHashLength    = 6
 	dockerContextPath = "../."
+	headscaleCertPath = "/usr/local/share/ca-certificates/headscale.crt"
 )
 
 var (
-	errTailscalePingFailed     = errors.New("ping failed")
-	errTailscaleNotLoggedIn    = errors.New("tailscale not logged in")
-	errTailscaleWrongPeerCount = errors.New("wrong peer count")
-	errTailscaleNotConnected   = errors.New("tailscale not connected")
+	errTailscalePingFailed             = errors.New("ping failed")
+	errTailscaleNotLoggedIn            = errors.New("tailscale not logged in")
+	errTailscaleWrongPeerCount         = errors.New("wrong peer count")
+	errTailscaleCannotUpWithoutAuthkey = errors.New("cannot up without authkey")
+	errTailscaleNotConnected           = errors.New("tailscale not connected")
 )
 
 type TailscaleInContainer struct {
@@ -40,12 +43,51 @@ type TailscaleInContainer struct {
 	// "cache"
 	ips  []netip.Addr
 	fqdn string
+
+	// optional config
+	headscaleCert     []byte
+	headscaleHostname string
+}
+
+type Option = func(c *TailscaleInContainer)
+
+func WithHeadscaleTLS(cert []byte) Option {
+	return func(tsic *TailscaleInContainer) {
+		tsic.headscaleCert = cert
+	}
+}
+
+func WithOrCreateNetwork(network *dockertest.Network) Option {
+	return func(tsic *TailscaleInContainer) {
+		if network != nil {
+			tsic.network = network
+
+			return
+		}
+
+		network, err := dockertestutil.GetFirstOrCreateNetwork(
+			tsic.pool,
+			fmt.Sprintf("%s-network", tsic.hostname),
+		)
+		if err != nil {
+			log.Fatalf("failed to create network: %s", err)
+		}
+
+		tsic.network = network
+	}
+}
+
+func WithHeadscaleName(hsName string) Option {
+	return func(tsic *TailscaleInContainer) {
+		tsic.headscaleHostname = hsName
+	}
 }
 
 func New(
 	pool *dockertest.Pool,
 	version string,
 	network *dockertest.Network,
+	opts ...Option,
 ) (*TailscaleInContainer, error) {
 	hash, err := headscale.GenerateRandomStringDNSSafe(tsicHashLength)
 	if err != nil {
@@ -54,20 +96,38 @@ func New(
 
 	hostname := fmt.Sprintf("ts-%s-%s", strings.ReplaceAll(version, ".", "-"), hash)
 
-	// TODO(kradalby): figure out why we need to "refresh" the network here.
-	// network, err = dockertestutil.GetFirstOrCreateNetwork(pool, network.Network.Name)
-	// if err != nil {
-	// 	return nil, err
-	// }
+	tsic := &TailscaleInContainer{
+		version:  version,
+		hostname: hostname,
+
+		pool:    pool,
+		network: network,
+	}
+
+	for _, opt := range opts {
+		opt(tsic)
+	}
 
 	tailscaleOptions := &dockertest.RunOptions{
 		Name:     hostname,
 		Networks: []*dockertest.Network{network},
-		Cmd: []string{
-			"tailscaled", "--tun=tsdev",
+		// Cmd: []string{
+		// 	"tailscaled", "--tun=tsdev",
+		// },
+		Entrypoint: []string{
+			"/bin/bash",
+			"-c",
+			"/bin/sleep 3 ; update-ca-certificates ; tailscaled --tun=tsdev",
 		},
 	}
 
+	if tsic.headscaleHostname != "" {
+		tailscaleOptions.ExtraHosts = []string{
+			"host.docker.internal:host-gateway",
+			fmt.Sprintf("%s:host-gateway", tsic.headscaleHostname),
+		}
+	}
+
 	// dockertest isnt very good at handling containers that has already
 	// been created, this is an attempt to make sure this container isnt
 	// present.
@@ -88,14 +148,20 @@ func New(
 	}
 	log.Printf("Created %s container\n", hostname)
 
-	return &TailscaleInContainer{
-		version:  version,
-		hostname: hostname,
+	tsic.container = container
 
-		pool:      pool,
-		container: container,
-		network:   network,
-	}, nil
+	if tsic.hasTLS() {
+		err = tsic.WriteFile(headscaleCertPath, tsic.headscaleCert)
+		if err != nil {
+			return nil, fmt.Errorf("failed to write TLS certificate to container: %w", err)
+		}
+	}
+
+	return tsic, nil
+}
+
+func (t *TailscaleInContainer) hasTLS() bool {
+	return len(t.headscaleCert) != 0
 }
 
 func (t *TailscaleInContainer) Shutdown() error {
@@ -113,8 +179,6 @@ func (t *TailscaleInContainer) Version() string {
 func (t *TailscaleInContainer) Execute(
 	command []string,
 ) (string, string, error) {
-	log.Println("command", command)
-	log.Printf("running command for %s\n", t.hostname)
 	stdout, stderr, err := dockertestutil.ExecuteCommand(
 		t.container,
 		command,
@@ -170,7 +234,10 @@ func (t *TailscaleInContainer) UpWithLoginURL(
 		t.hostname,
 	}
 
-	_, stderr, _ := t.Execute(command)
+	_, stderr, err := t.Execute(command)
+	if errors.Is(err, errTailscaleNotLoggedIn) {
+		return nil, errTailscaleCannotUpWithoutAuthkey
+	}
 
 	urlStr := strings.ReplaceAll(stderr, "\nTo authenticate, visit:\n\n\t", "")
 	urlStr = strings.TrimSpace(urlStr)
@@ -314,6 +381,10 @@ func (t *TailscaleInContainer) Ping(hostnameOrIP string) error {
 	})
 }
 
+func (t *TailscaleInContainer) WriteFile(path string, data []byte) error {
+	return integrationutil.WriteFileToContainer(t.pool, t.container, path, data)
+}
+
 func createTailscaleBuildOptions(version string) *dockertest.BuildOptions {
 	var tailscaleBuildOptions *dockertest.BuildOptions
 	switch version {

oidc.go

@@ -76,19 +76,54 @@ func (h *Headscale) RegisterOIDC(
 ) {
 	vars := mux.Vars(req)
 	nodeKeyStr, ok := vars["nkey"]
-	if !ok || nodeKeyStr == "" {
-		log.Error().
-			Caller().
-			Msg("Missing node key in URL")
-		http.Error(writer, "Missing node key in URL", http.StatusBadRequest)
+
+	log.Debug().
+		Caller().
+		Str("node_key", nodeKeyStr).
+		Bool("ok", ok).
+		Msg("Received oidc register call")
+
+	if !NodePublicKeyRegex.Match([]byte(nodeKeyStr)) {
+		log.Warn().Str("node_key", nodeKeyStr).Msg("Invalid node key passed to registration url")
+
+		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
+		writer.WriteHeader(http.StatusUnauthorized)
+		_, err := writer.Write([]byte("Unauthorized"))
+		if err != nil {
+			log.Error().
+				Caller().
+				Err(err).
+				Msg("Failed to write response")
+		}
 
 		return
 	}
 
-	log.Trace().
-		Caller().
-		Str("node_key", nodeKeyStr).
-		Msg("Received oidc register call")
+	// We need to make sure we dont open for XSS style injections, if the parameter that
+	// is passed as a key is not parsable/validated as a NodePublic key, then fail to render
+	// the template and log an error.
+	var nodeKey key.NodePublic
+	err := nodeKey.UnmarshalText(
+		[]byte(NodePublicKeyEnsurePrefix(nodeKeyStr)),
+	)
+
+	if !ok || nodeKeyStr == "" || err != nil {
+		log.Warn().
+			Err(err).
+			Msg("Failed to parse incoming nodekey in OIDC registration")
+
+		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
+		writer.WriteHeader(http.StatusBadRequest)
+		_, err := writer.Write([]byte("Wrong params"))
+		if err != nil {
+			log.Error().
+				Caller().
+				Err(err).
+				Msg("Failed to write response")
+		}
+
+		return
+	}
 
 	randomBlob := make([]byte, randomByteSize)
 	if _, err := rand.Read(randomBlob); err != nil {
@@ -103,7 +138,7 @@ func (h *Headscale) RegisterOIDC(
 	stateStr := hex.EncodeToString(randomBlob)[:32]
 
 	// place the node key into the state cache, so it can be retrieved later
-	h.registrationCache.Set(stateStr, nodeKeyStr, registerCacheExpiration)
+	h.registrationCache.Set(stateStr, NodePublicKeyStripPrefix(nodeKey), registerCacheExpiration)
 
 	// Add any extra parameter provided in the configuration to the Authorize Endpoint request
 	extras := make([]oauth2.AuthCodeOption, 0, len(h.cfg.OIDC.ExtraParams))
@@ -405,8 +440,8 @@ func (h *Headscale) validateMachineForOIDCCallback(
 	claims *IDTokenClaims,
 ) (*key.NodePublic, bool, error) {
 	// retrieve machinekey from state cache
-	machineKeyIf, machineKeyFound := h.registrationCache.Get(state)
-	if !machineKeyFound {
+	nodeKeyIf, nodeKeyFound := h.registrationCache.Get(state)
+	if !nodeKeyFound {
 		log.Error().
 			Msg("requested machine state key expired before authorisation completed")
 		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
@@ -419,20 +454,38 @@ func (h *Headscale) validateMachineForOIDCCallback(
 				Msg("Failed to write response")
 		}
 
-		return nil, false, errOIDCInvalidMachineState
+		return nil, false, errOIDCNodeKeyMissing
 	}
 
 	var nodeKey key.NodePublic
-	nodeKeyFromCache, nodeKeyOK := machineKeyIf.(string)
+	nodeKeyFromCache, nodeKeyOK := nodeKeyIf.(string)
+	if !nodeKeyOK {
+		log.Error().
+			Msg("requested machine state key is not a string")
+		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
+		writer.WriteHeader(http.StatusBadRequest)
+		_, err := writer.Write([]byte("state is invalid"))
+		if err != nil {
+			log.Error().
+				Caller().
+				Err(err).
+				Msg("Failed to write response")
+		}
+
+		return nil, false, errOIDCInvalidMachineState
+	}
+
 	err := nodeKey.UnmarshalText(
 		[]byte(NodePublicKeyEnsurePrefix(nodeKeyFromCache)),
 	)
 	if err != nil {
 		log.Error().
+			Str("nodeKey", nodeKeyFromCache).
+			Bool("nodeKeyOK", nodeKeyOK).
 			Msg("could not parse node public key")
 		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
 		writer.WriteHeader(http.StatusBadRequest)
-		_, werr := writer.Write([]byte("could not parse public key"))
+		_, werr := writer.Write([]byte("could not parse node public key"))
 		if werr != nil {
 			log.Error().
 				Caller().
@@ -443,21 +496,6 @@ func (h *Headscale) validateMachineForOIDCCallback(
 		return nil, false, err
 	}
 
-	if !nodeKeyOK {
-		log.Error().Msg("could not get node key from cache")
-		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
-		writer.WriteHeader(http.StatusInternalServerError)
-		_, err := writer.Write([]byte("could not get node key from cache"))
-		if err != nil {
-			log.Error().
-				Caller().
-				Err(err).
-				Msg("Failed to write response")
-		}
-
-		return nil, false, errOIDCNodeKeyMissing
-	}
-
 	// retrieve machine information if it exist
 	// The error is not important, because if it does not
 	// exist, then this is a new machine and we will move

protocol_common.go

@@ -490,6 +490,7 @@ func (h *Headscale) handleNewMachineCommon(
 		Bool("noise", machineKey.IsZero()).
 		Str("machine", registerRequest.Hostinfo.Hostname).
 		Msg("The node seems to be new, sending auth url")
+
 	if h.oauth2Config != nil {
 		resp.AuthURL = fmt.Sprintf(
 			"%s/oidc/register/%s",
@@ -528,6 +529,7 @@ func (h *Headscale) handleNewMachineCommon(
 	log.Info().
 		Caller().
 		Bool("noise", machineKey.IsZero()).
+		Str("AuthURL", resp.AuthURL).
 		Str("machine", registerRequest.Hostinfo.Hostname).
 		Msg("Successfully sent auth url")
 }
@@ -726,7 +728,7 @@ func (h *Headscale) handleMachineExpiredCommon(
 	if h.oauth2Config != nil {
 		resp.AuthURL = fmt.Sprintf("%s/oidc/register/%s",
 			strings.TrimSuffix(h.cfg.ServerURL, "/"),
-			NodePublicKeyStripPrefix(registerRequest.NodeKey))
+			registerRequest.NodeKey)
 	} else {
 		resp.AuthURL = fmt.Sprintf("%s/register/%s",
 			strings.TrimSuffix(h.cfg.ServerURL, "/"),