Merge branch 'main' into rerouting

CHANGELOG.md

@@ -7,9 +7,20 @@
 - 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
+### Important Changes
 
 - Added support for Tailscale TS2021 protocol [#738](https://github.com/juanfont/headscale/pull/738)
+- Add experimental support for [SSH ACL](https://tailscale.com/kb/1018/acls/#tailscale-ssh) (see docs for limitations) [#847](https://github.com/juanfont/headscale/pull/847)
+  - Please note that this support should be considered _partially_ implemented
+  - SSH ACLs status:
+    - Support `accept` and `check` (SSH can be enabled and used for connecting and authentication)
+    - Rejecting connections **are not supported**, meaning that if you enable SSH, then assume that _all_ `ssh` connections **will be allowed**.
+    - If you decied to try this feature, please carefully managed permissions by blocking port `22` with regular ACLs or do _not_ set `--ssh` on your clients.
+    - We are currently improving our testing of the SSH ACLs, help us get an overview by testing and giving feedback.
+  - This feature should be considered dangerous and it is disabled by default. Enable by setting `HEADSCALE_EXPERIMENTAL_FEATURE_SSH=1`.
+
+### Changes
+
 - Add ability to specify config location via env var `HEADSCALE_CONFIG` [#674](https://github.com/juanfont/headscale/issues/674)
 - Target Go 1.19 for Headscale [#778](https://github.com/juanfont/headscale/pull/778)
 - Target Tailscale v1.30.0 to build Headscale [#780](https://github.com/juanfont/headscale/pull/780)

Dockerfile.tailscale

@@ -4,14 +4,16 @@ ARG TAILSCALE_VERSION=*
 ARG TAILSCALE_CHANNEL=stable
 
 RUN apt-get update \
-    && apt-get install -y gnupg curl \
+    && apt-get install -y gnupg curl ssh \
     && curl -fsSL https://pkgs.tailscale.com/${TAILSCALE_CHANNEL}/ubuntu/focal.gpg | apt-key add - \
     && curl -fsSL https://pkgs.tailscale.com/${TAILSCALE_CHANNEL}/ubuntu/focal.list | tee /etc/apt/sources.list.d/tailscale.list \
     && apt-get update \
     && apt-get install -y ca-certificates tailscale=${TAILSCALE_VERSION} dnsutils \
     && rm -rf /var/lib/apt/lists/*
 
+RUN adduser --shell=/bin/bash ssh-it-user
+
 ADD integration_test/etc_embedded_derp/tls/server.crt /usr/local/share/ca-certificates/
-RUN chmod 644 /usr/local/share/ca-certificates/server.crt 
+RUN chmod 644 /usr/local/share/ca-certificates/server.crt
 
 RUN update-ca-certificates

Dockerfile.tailscale-HEAD

@@ -1,9 +1,10 @@
 FROM golang:latest
 
 RUN apt-get update \
-    && apt-get install -y ca-certificates dnsutils git iptables \
+    && apt-get install -y ca-certificates dnsutils git iptables ssh \
     && rm -rf /var/lib/apt/lists/*
 
+RUN useradd --shell=/bin/bash --create-home ssh-it-user
 
 RUN git clone https://github.com/tailscale/tailscale.git
 
@@ -18,6 +19,6 @@ RUN cp tailscale /usr/local/bin/
 RUN cp tailscaled /usr/local/bin/
 
 ADD integration_test/etc_embedded_derp/tls/server.crt /usr/local/share/ca-certificates/
-RUN chmod 644 /usr/local/share/ca-certificates/server.crt 
+RUN chmod 644 /usr/local/share/ca-certificates/server.crt
 
 RUN update-ca-certificates

acls.go

@@ -10,10 +10,12 @@ import (
 	"path/filepath"
 	"strconv"
 	"strings"
+	"time"
 
 	"github.com/rs/zerolog/log"
 	"github.com/tailscale/hujson"
 	"gopkg.in/yaml.v3"
+	"tailscale.com/envknob"
 	"tailscale.com/tailcfg"
 )
 
@@ -54,6 +56,8 @@ const (
 	ProtocolFC       = 133 // Fibre Channel
 )
 
+var featureEnableSSH = envknob.RegisterBool("HEADSCALE_EXPERIMENTAL_FEATURE_SSH")
+
 // LoadACLPolicy loads the ACL policy from the specify path, and generates the ACL rules.
 func (h *Headscale) LoadACLPolicy(path string) error {
 	log.Debug().
@@ -120,6 +124,20 @@ func (h *Headscale) UpdateACLRules() error {
 	log.Trace().Interface("ACL", rules).Msg("ACL rules generated")
 	h.aclRules = rules
 
+	if featureEnableSSH() {
+		sshRules, err := h.generateSSHRules()
+		if err != nil {
+			return err
+		}
+		log.Trace().Interface("SSH", sshRules).Msg("SSH rules generated")
+		if h.sshPolicy == nil {
+			h.sshPolicy = &tailcfg.SSHPolicy{}
+		}
+		h.sshPolicy.Rules = sshRules
+	} else if h.aclPolicy != nil && len(h.aclPolicy.SSHs) > 0 {
+		log.Info().Msg("SSH ACLs has been defined, but HEADSCALE_EXPERIMENTAL_FEATURE_SSH is not enabled, this is a unstable feature, check docs before activating")
+	}
+
 	return nil
 }
 
@@ -187,6 +205,111 @@ func (h *Headscale) generateACLRules() ([]tailcfg.FilterRule, error) {
 	return rules, nil
 }
 
+func (h *Headscale) generateSSHRules() ([]*tailcfg.SSHRule, error) {
+	rules := []*tailcfg.SSHRule{}
+
+	if h.aclPolicy == nil {
+		return nil, errEmptyPolicy
+	}
+
+	machines, err := h.ListMachines()
+	if err != nil {
+		return nil, err
+	}
+
+	acceptAction := tailcfg.SSHAction{
+		Message:                  "",
+		Reject:                   false,
+		Accept:                   true,
+		SessionDuration:          0,
+		AllowAgentForwarding:     false,
+		HoldAndDelegate:          "",
+		AllowLocalPortForwarding: true,
+	}
+
+	rejectAction := tailcfg.SSHAction{
+		Message:                  "",
+		Reject:                   true,
+		Accept:                   false,
+		SessionDuration:          0,
+		AllowAgentForwarding:     false,
+		HoldAndDelegate:          "",
+		AllowLocalPortForwarding: false,
+	}
+
+	for index, sshACL := range h.aclPolicy.SSHs {
+		action := rejectAction
+		switch sshACL.Action {
+		case "accept":
+			action = acceptAction
+		case "check":
+			checkAction, err := sshCheckAction(sshACL.CheckPeriod)
+			if err != nil {
+				log.Error().
+					Msgf("Error parsing SSH %d, check action with unparsable duration '%s'", index, sshACL.CheckPeriod)
+			} else {
+				action = *checkAction
+			}
+		default:
+			log.Error().
+				Msgf("Error parsing SSH %d, unknown action '%s'", index, sshACL.Action)
+
+			return nil, err
+		}
+
+		principals := make([]*tailcfg.SSHPrincipal, 0, len(sshACL.Sources))
+		for innerIndex, rawSrc := range sshACL.Sources {
+			expandedSrcs, err := expandAlias(
+				machines,
+				*h.aclPolicy,
+				rawSrc,
+				h.cfg.OIDC.StripEmaildomain,
+			)
+			if err != nil {
+				log.Error().
+					Msgf("Error parsing SSH %d, Source %d", index, innerIndex)
+
+				return nil, err
+			}
+			for _, expandedSrc := range expandedSrcs {
+				principals = append(principals, &tailcfg.SSHPrincipal{
+					NodeIP: expandedSrc,
+				})
+			}
+		}
+
+		userMap := make(map[string]string, len(sshACL.Users))
+		for _, user := range sshACL.Users {
+			userMap[user] = "="
+		}
+		rules = append(rules, &tailcfg.SSHRule{
+			RuleExpires: nil,
+			Principals:  principals,
+			SSHUsers:    userMap,
+			Action:      &action,
+		})
+	}
+
+	return rules, nil
+}
+
+func sshCheckAction(duration string) (*tailcfg.SSHAction, error) {
+	sessionLength, err := time.ParseDuration(duration)
+	if err != nil {
+		return nil, err
+	}
+
+	return &tailcfg.SSHAction{
+		Message:                  "",
+		Reject:                   false,
+		Accept:                   true,
+		SessionDuration:          sessionLength,
+		AllowAgentForwarding:     false,
+		HoldAndDelegate:          "",
+		AllowLocalPortForwarding: true,
+	}, nil
+}
+
 func (h *Headscale) generateACLPolicySrcIP(
 	machines []Machine,
 	aclPolicy ACLPolicy,

acls_test.go

@@ -7,6 +7,7 @@ import (
 	"testing"
 
 	"gopkg.in/check.v1"
+	"tailscale.com/envknob"
 	"tailscale.com/tailcfg"
 )
 
@@ -73,6 +74,81 @@ func (s *Suite) TestInvalidAction(c *check.C) {
 	c.Assert(errors.Is(err, errInvalidAction), check.Equals, true)
 }
 
+func (s *Suite) TestSshRules(c *check.C) {
+	envknob.Setenv("HEADSCALE_EXPERIMENTAL_FEATURE_SSH", "1")
+
+	namespace, err := app.CreateNamespace("user1")
+	c.Assert(err, check.IsNil)
+
+	pak, err := app.CreatePreAuthKey(namespace.Name, false, false, nil, nil)
+	c.Assert(err, check.IsNil)
+
+	_, err = app.GetMachine("user1", "testmachine")
+	c.Assert(err, check.NotNil)
+	hostInfo := tailcfg.Hostinfo{
+		OS:          "centos",
+		Hostname:    "testmachine",
+		RequestTags: []string{"tag:test"},
+	}
+
+	machine := Machine{
+		ID:             0,
+		MachineKey:     "foo",
+		NodeKey:        "bar",
+		DiscoKey:       "faa",
+		Hostname:       "testmachine",
+		IPAddresses:    MachineAddresses{netip.MustParseAddr("100.64.0.1")},
+		NamespaceID:    namespace.ID,
+		RegisterMethod: RegisterMethodAuthKey,
+		AuthKeyID:      uint(pak.ID),
+		HostInfo:       HostInfo(hostInfo),
+	}
+	app.db.Save(&machine)
+
+	app.aclPolicy = &ACLPolicy{
+		Groups: Groups{
+			"group:test": []string{"user1"},
+		},
+		Hosts: Hosts{
+			"client": netip.PrefixFrom(netip.MustParseAddr("100.64.99.42"), 32),
+		},
+		ACLs: []ACL{
+			{
+				Action:       "accept",
+				Sources:      []string{"*"},
+				Destinations: []string{"*:*"},
+			},
+		},
+		SSHs: []SSH{
+			{
+				Action:       "accept",
+				Sources:      []string{"group:test"},
+				Destinations: []string{"client"},
+				Users:        []string{"autogroup:nonroot"},
+			},
+			{
+				Action:       "accept",
+				Sources:      []string{"*"},
+				Destinations: []string{"client"},
+				Users:        []string{"autogroup:nonroot"},
+			},
+		},
+	}
+
+	err = app.UpdateACLRules()
+
+	c.Assert(err, check.IsNil)
+	c.Assert(app.sshPolicy, check.NotNil)
+	c.Assert(app.sshPolicy.Rules, check.HasLen, 2)
+	c.Assert(app.sshPolicy.Rules[0].SSHUsers, check.HasLen, 1)
+	c.Assert(app.sshPolicy.Rules[0].Principals, check.HasLen, 1)
+	c.Assert(app.sshPolicy.Rules[0].Principals[0].NodeIP, check.Matches, "100.64.0.1")
+
+	c.Assert(app.sshPolicy.Rules[1].SSHUsers, check.HasLen, 1)
+	c.Assert(app.sshPolicy.Rules[1].Principals, check.HasLen, 1)
+	c.Assert(app.sshPolicy.Rules[1].Principals[0].NodeIP, check.Matches, "*")
+}
+
 func (s *Suite) TestInvalidGroupInGroup(c *check.C) {
 	// this ACL is wrong because the group in Sources sections doesn't exist
 	app.aclPolicy = &ACLPolicy{

acls_types.go

@@ -17,6 +17,7 @@ type ACLPolicy struct {
 	ACLs          []ACL         `json:"acls"          yaml:"acls"`
 	Tests         []ACLTest     `json:"tests"         yaml:"tests"`
 	AutoApprovers AutoApprovers `json:"autoApprovers" yaml:"autoApprovers"`
+	SSHs          []SSH         `json:"ssh"           yaml:"ssh"`
 }
 
 // ACL is a basic rule for the ACL Policy.
@@ -50,6 +51,15 @@ type AutoApprovers struct {
 	ExitNode []string            `json:"exitNode" yaml:"exitNode"`
 }
 
+// SSH controls who can ssh into which machines.
+type SSH struct {
+	Action       string   `json:"action"                yaml:"action"`
+	Sources      []string `json:"src"                   yaml:"src"`
+	Destinations []string `json:"dst"                   yaml:"dst"`
+	Users        []string `json:"users"                 yaml:"users"`
+	CheckPeriod  string   `json:"checkPeriod,omitempty" yaml:"checkPeriod,omitempty"`
+}
+
 // UnmarshalJSON allows to parse the Hosts directly into netip objects.
 func (hosts *Hosts) UnmarshalJSON(data []byte) error {
 	newHosts := Hosts{}

api_common.go

@@ -62,6 +62,7 @@ func (h *Headscale) generateMapResponse(
 		DNSConfig:    dnsConfig,
 		Domain:       h.cfg.BaseDomain,
 		PacketFilter: h.aclRules,
+		SSHPolicy:    h.sshPolicy,
 		DERPMap:      h.DERPMap,
 		UserProfiles: profiles,
 		Debug: &tailcfg.Debug{

app.go

@@ -88,6 +88,7 @@ type Headscale struct {
 
 	aclPolicy *ACLPolicy
 	aclRules  []tailcfg.FilterRule
+	sshPolicy *tailcfg.SSHPolicy
 
 	lastStateChange *xsync.MapOf[string, time.Time]
 

integration/cli_test.go

@@ -10,6 +10,7 @@ import (
 
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/juanfont/headscale/integration/hsic"
+	"github.com/juanfont/headscale/integration/tsic"
 	"github.com/stretchr/testify/assert"
 )
 
@@ -39,7 +40,7 @@ func TestNamespaceCommand(t *testing.T) {
 		"namespace2": 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clins"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("clins"))
 	assert.NoError(t, err)
 
 	headscale, err := scenario.Headscale()
@@ -120,7 +121,7 @@ func TestPreAuthKeyCommand(t *testing.T) {
 		namespace: 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clipak"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("clipak"))
 	assert.NoError(t, err)
 
 	headscale, err := scenario.Headscale()
@@ -260,7 +261,7 @@ func TestPreAuthKeyCommandWithoutExpiry(t *testing.T) {
 		namespace: 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clipaknaexp"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("clipaknaexp"))
 	assert.NoError(t, err)
 
 	headscale, err := scenario.Headscale()
@@ -325,7 +326,7 @@ func TestPreAuthKeyCommandReusableEphemeral(t *testing.T) {
 		namespace: 0,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("clipakresueeph"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("clipakresueeph"))
 	assert.NoError(t, err)
 
 	headscale, err := scenario.Headscale()

integration/general_test.go

@@ -7,6 +7,7 @@ import (
 	"time"
 
 	"github.com/juanfont/headscale/integration/hsic"
+	"github.com/juanfont/headscale/integration/tsic"
 	"github.com/rs/zerolog/log"
 )
 
@@ -24,7 +25,7 @@ func TestPingAllByIP(t *testing.T) {
 		"namespace2": len(TailscaleVersions),
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("pingallbyip"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("pingallbyip"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -80,7 +81,7 @@ func TestPingAllByHostname(t *testing.T) {
 		"namespace4": len(TailscaleVersions) - 1,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("pingallbyname"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("pingallbyname"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -148,7 +149,7 @@ func TestTaildrop(t *testing.T) {
 		"taildrop": len(TailscaleVersions) - 1,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("taildrop"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("taildrop"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}
@@ -276,7 +277,7 @@ func TestResolveMagicDNS(t *testing.T) {
 		"magicdns2": len(TailscaleVersions) - 1,
 	}
 
-	err = scenario.CreateHeadscaleEnv(spec, hsic.WithTestName("magicdns"))
+	err = scenario.CreateHeadscaleEnv(spec, []tsic.Option{}, hsic.WithTestName("magicdns"))
 	if err != nil {
 		t.Errorf("failed to create headscale environment: %s", err)
 	}

integration/hsic/hsic.go

@@ -79,13 +79,9 @@ func WithTLS() Option {
 
 func WithConfigEnv(configEnv map[string]string) Option {
 	return func(hsic *HeadscaleInContainer) {
-		env := []string{}
-
 		for key, value := range configEnv {
-			env = append(env, fmt.Sprintf("%s=%s", key, value))
+			hsic.env = append(hsic.env, fmt.Sprintf("%s=%s", key, value))
 		}
-
-		hsic.env = env
 	}
 }
 

integration/scenario.go

@@ -229,6 +229,7 @@ func (s *Scenario) CreateTailscaleNodesInNamespace(
 	namespaceStr string,
 	requestedVersion string,
 	count int,
+	opts ...tsic.Option,
 ) error {
 	if namespace, ok := s.namespaces[namespaceStr]; ok {
 		for i := 0; i < count; i++ {
@@ -247,6 +248,11 @@ func (s *Scenario) CreateTailscaleNodesInNamespace(
 
 			namespace.createWaitGroup.Add(1)
 
+			opts = append(opts,
+				tsic.WithHeadscaleTLS(cert),
+				tsic.WithHeadscaleName(hostname),
+			)
+
 			go func() {
 				defer namespace.createWaitGroup.Done()
 
@@ -255,8 +261,7 @@ func (s *Scenario) CreateTailscaleNodesInNamespace(
 					s.pool,
 					version,
 					s.network,
-					tsic.WithHeadscaleTLS(cert),
-					tsic.WithHeadscaleName(hostname),
+					opts...,
 				)
 				if err != nil {
 					// return fmt.Errorf("failed to add tailscale node: %w", err)
@@ -341,7 +346,11 @@ 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, opts ...hsic.Option) error {
+func (s *Scenario) CreateHeadscaleEnv(
+	namespaces map[string]int,
+	tsOpts []tsic.Option,
+	opts ...hsic.Option,
+) error {
 	headscale, err := s.Headscale(opts...)
 	if err != nil {
 		return err
@@ -353,7 +362,7 @@ func (s *Scenario) CreateHeadscaleEnv(namespaces map[string]int, opts ...hsic.Op
 			return err
 		}
 
-		err = s.CreateTailscaleNodesInNamespace(namespaceName, "all", clientCount)
+		err = s.CreateTailscaleNodesInNamespace(namespaceName, "all", clientCount, tsOpts...)
 		if err != nil {
 			return err
 		}

integration/scenario_test.go

@@ -6,7 +6,7 @@ import (
 	"github.com/juanfont/headscale/integration/dockertestutil"
 )
 
-// This file is intendet to "test the test framework", by proxy it will also test
+// This file is intended to "test the test framework", by proxy it will also test
 // some Headcsale/Tailscale stuff, but mostly in very simple ways.
 
 func IntegrationSkip(t *testing.T) {

integration/ssh_test.go

@@ -0,0 +1,519 @@
+package integration
+
+import (
+	"fmt"
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/juanfont/headscale"
+	"github.com/juanfont/headscale/integration/hsic"
+	"github.com/juanfont/headscale/integration/tsic"
+	"github.com/stretchr/testify/assert"
+)
+
+var retry = func(times int, sleepInterval time.Duration,
+	doWork func() (string, string, error),
+) (string, string, error) {
+	var result string
+	var stderr string
+	var err error
+
+	for attempts := 0; attempts < times; attempts++ {
+		tempResult, tempStderr, err := doWork()
+
+		result += tempResult
+		stderr += tempStderr
+
+		if err == nil {
+			return result, stderr, nil
+		}
+
+		// If we get a permission denied error, we can fail immediately
+		// since that is something we wont recover from by retrying.
+		if err != nil && strings.Contains(stderr, "Permission denied (tailscale)") {
+			return result, stderr, err
+		}
+
+		time.Sleep(sleepInterval)
+	}
+
+	return result, stderr, err
+}
+
+func TestSSHOneNamespaceAllToAll(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) - 5,
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec,
+		[]tsic.Option{tsic.WithSSH()},
+		hsic.WithACLPolicy(
+			&headscale.ACLPolicy{
+				Groups: map[string][]string{
+					"group:integration-test": {"namespace1"},
+				},
+				ACLs: []headscale.ACL{
+					{
+						Action:       "accept",
+						Sources:      []string{"*"},
+						Destinations: []string{"*:*"},
+					},
+				},
+				SSHs: []headscale.SSH{
+					{
+						Action:       "accept",
+						Sources:      []string{"group:integration-test"},
+						Destinations: []string{"group:integration-test"},
+						Users:        []string{"ssh-it-user"},
+					},
+				},
+			},
+		),
+		hsic.WithConfigEnv(map[string]string{
+			"HEADSCALE_EXPERIMENTAL_FEATURE_SSH": "1",
+		}),
+	)
+	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)
+	}
+
+	_, err = scenario.ListTailscaleClientsFQDNs()
+	if err != nil {
+		t.Errorf("failed to get FQDNs: %s", err)
+	}
+
+	for _, client := range allClients {
+		for _, peer := range allClients {
+			if client.Hostname() == peer.Hostname() {
+				continue
+			}
+
+			assertSSHHostname(t, client, peer)
+		}
+	}
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func TestSSHMultipleNamespacesAllToAll(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) - 5,
+		"namespace2": len(TailscaleVersions) - 5,
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec,
+		[]tsic.Option{tsic.WithSSH()},
+		hsic.WithACLPolicy(
+			&headscale.ACLPolicy{
+				Groups: map[string][]string{
+					"group:integration-test": {"namespace1", "namespace2"},
+				},
+				ACLs: []headscale.ACL{
+					{
+						Action:       "accept",
+						Sources:      []string{"*"},
+						Destinations: []string{"*:*"},
+					},
+				},
+				SSHs: []headscale.SSH{
+					{
+						Action:       "accept",
+						Sources:      []string{"group:integration-test"},
+						Destinations: []string{"group:integration-test"},
+						Users:        []string{"ssh-it-user"},
+					},
+				},
+			},
+		),
+		hsic.WithConfigEnv(map[string]string{
+			"HEADSCALE_EXPERIMENTAL_FEATURE_SSH": "1",
+		}),
+	)
+	if err != nil {
+		t.Errorf("failed to create headscale environment: %s", err)
+	}
+
+	nsOneClients, err := scenario.ListTailscaleClients("namespace1")
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	nsTwoClients, err := scenario.ListTailscaleClients("namespace2")
+	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)
+	}
+
+	_, err = scenario.ListTailscaleClientsFQDNs()
+	if err != nil {
+		t.Errorf("failed to get FQDNs: %s", err)
+	}
+
+	testInterNamespaceSSH := func(sourceClients []TailscaleClient, targetClients []TailscaleClient) {
+		for _, client := range sourceClients {
+			for _, peer := range targetClients {
+				assertSSHHostname(t, client, peer)
+			}
+		}
+	}
+
+	testInterNamespaceSSH(nsOneClients, nsTwoClients)
+	testInterNamespaceSSH(nsTwoClients, nsOneClients)
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func TestSSHNoSSHConfigured(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) - 5,
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec,
+		[]tsic.Option{tsic.WithSSH()},
+		hsic.WithACLPolicy(
+			&headscale.ACLPolicy{
+				Groups: map[string][]string{
+					"group:integration-test": {"namespace1"},
+				},
+				ACLs: []headscale.ACL{
+					{
+						Action:       "accept",
+						Sources:      []string{"*"},
+						Destinations: []string{"*:*"},
+					},
+				},
+				SSHs: []headscale.SSH{},
+			},
+		),
+		hsic.WithTestName("sshnoneconfigured"),
+		hsic.WithConfigEnv(map[string]string{
+			"HEADSCALE_EXPERIMENTAL_FEATURE_SSH": "1",
+		}),
+	)
+	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)
+	}
+
+	_, err = scenario.ListTailscaleClientsFQDNs()
+	if err != nil {
+		t.Errorf("failed to get FQDNs: %s", err)
+	}
+
+	for _, client := range allClients {
+		for _, peer := range allClients {
+			if client.Hostname() == peer.Hostname() {
+				continue
+			}
+
+			assertSSHPermissionDenied(t, client, peer)
+		}
+	}
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func TestSSHIsBlockedInACL(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) - 5,
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec,
+		[]tsic.Option{tsic.WithSSH()},
+		hsic.WithACLPolicy(
+			&headscale.ACLPolicy{
+				Groups: map[string][]string{
+					"group:integration-test": {"namespace1"},
+				},
+				ACLs: []headscale.ACL{
+					{
+						Action:       "accept",
+						Sources:      []string{"*"},
+						Destinations: []string{"*:80"},
+					},
+				},
+				SSHs: []headscale.SSH{
+					{
+						Action:       "accept",
+						Sources:      []string{"group:integration-test"},
+						Destinations: []string{"group:integration-test"},
+						Users:        []string{"ssh-it-user"},
+					},
+				},
+			},
+		),
+		hsic.WithTestName("sshisblockedinacl"),
+		hsic.WithConfigEnv(map[string]string{
+			"HEADSCALE_EXPERIMENTAL_FEATURE_SSH": "1",
+		}),
+	)
+	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)
+	}
+
+	_, err = scenario.ListTailscaleClientsFQDNs()
+	if err != nil {
+		t.Errorf("failed to get FQDNs: %s", err)
+	}
+
+	for _, client := range allClients {
+		for _, peer := range allClients {
+			if client.Hostname() == peer.Hostname() {
+				continue
+			}
+
+			assertSSHTimeout(t, client, peer)
+		}
+	}
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func TestSSNamespaceOnlyIsolation(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{
+		"namespaceacl1": len(TailscaleVersions) - 5,
+		"namespaceacl2": len(TailscaleVersions) - 5,
+	}
+
+	err = scenario.CreateHeadscaleEnv(spec,
+		[]tsic.Option{tsic.WithSSH()},
+		hsic.WithACLPolicy(
+			&headscale.ACLPolicy{
+				Groups: map[string][]string{
+					"group:ssh1": {"namespaceacl1"},
+					"group:ssh2": {"namespaceacl2"},
+				},
+				ACLs: []headscale.ACL{
+					{
+						Action:       "accept",
+						Sources:      []string{"*"},
+						Destinations: []string{"*:*"},
+					},
+				},
+				SSHs: []headscale.SSH{
+					{
+						Action:       "accept",
+						Sources:      []string{"group:ssh1"},
+						Destinations: []string{"group:ssh1"},
+						Users:        []string{"ssh-it-user"},
+					},
+					{
+						Action:       "accept",
+						Sources:      []string{"group:ssh2"},
+						Destinations: []string{"group:ssh2"},
+						Users:        []string{"ssh-it-user"},
+					},
+				},
+			},
+		),
+		hsic.WithTestName("sshtwonamespaceaclblock"),
+		hsic.WithConfigEnv(map[string]string{
+			"HEADSCALE_EXPERIMENTAL_FEATURE_SSH": "1",
+		}),
+	)
+	if err != nil {
+		t.Errorf("failed to create headscale environment: %s", err)
+	}
+
+	ssh1Clients, err := scenario.ListTailscaleClients("namespaceacl1")
+	if err != nil {
+		t.Errorf("failed to get clients: %s", err)
+	}
+
+	ssh2Clients, err := scenario.ListTailscaleClients("namespaceacl2")
+	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)
+	}
+
+	_, err = scenario.ListTailscaleClientsFQDNs()
+	if err != nil {
+		t.Errorf("failed to get FQDNs: %s", err)
+	}
+
+	// TODO(kradalby,evenh): ACLs do currently not cover reject
+	// cases properly, and currently will accept all incomming connections
+	// as long as a rule is present.
+	//
+	// for _, client := range ssh1Clients {
+	// 	for _, peer := range ssh2Clients {
+	// 		if client.Hostname() == peer.Hostname() {
+	// 			continue
+	// 		}
+	//
+	// 		assertSSHPermissionDenied(t, client, peer)
+	// 	}
+	// }
+	//
+	// for _, client := range ssh2Clients {
+	// 	for _, peer := range ssh1Clients {
+	// 		if client.Hostname() == peer.Hostname() {
+	// 			continue
+	// 		}
+	//
+	// 		assertSSHPermissionDenied(t, client, peer)
+	// 	}
+	// }
+
+	for _, client := range ssh1Clients {
+		for _, peer := range ssh1Clients {
+			if client.Hostname() == peer.Hostname() {
+				continue
+			}
+
+			assertSSHHostname(t, client, peer)
+		}
+	}
+
+	for _, client := range ssh2Clients {
+		for _, peer := range ssh2Clients {
+			if client.Hostname() == peer.Hostname() {
+				continue
+			}
+
+			assertSSHHostname(t, client, peer)
+		}
+	}
+
+	err = scenario.Shutdown()
+	if err != nil {
+		t.Errorf("failed to tear down scenario: %s", err)
+	}
+}
+
+func doSSH(t *testing.T, client TailscaleClient, peer TailscaleClient) (string, string, error) {
+	t.Helper()
+
+	peerFQDN, _ := peer.FQDN()
+
+	command := []string{
+		"ssh", "-o StrictHostKeyChecking=no", "-o ConnectTimeout=1",
+		fmt.Sprintf("%s@%s", "ssh-it-user", peerFQDN),
+		"'hostname'",
+	}
+
+	return retry(10, 1*time.Second, func() (string, string, error) {
+		return client.Execute(command)
+	})
+}
+
+func assertSSHHostname(t *testing.T, client TailscaleClient, peer TailscaleClient) {
+	t.Helper()
+
+	result, _, err := doSSH(t, client, peer)
+	assert.NoError(t, err)
+
+	assert.Contains(t, peer.ID(), strings.ReplaceAll(result, "\n", ""))
+}
+
+func assertSSHPermissionDenied(t *testing.T, client TailscaleClient, peer TailscaleClient) {
+	t.Helper()
+
+	result, stderr, err := doSSH(t, client, peer)
+	assert.Error(t, err)
+
+	assert.Empty(t, result)
+
+	assert.Contains(t, stderr, "Permission denied (tailscale)")
+}
+
+func assertSSHTimeout(t *testing.T, client TailscaleClient, peer TailscaleClient) {
+	t.Helper()
+
+	result, stderr, err := doSSH(t, client, peer)
+	assert.NoError(t, err)
+
+	assert.Empty(t, result)
+
+	assert.Contains(t, stderr, "Connection timed out")
+}

integration/tailscale.go

@@ -7,6 +7,7 @@ import (
 	"tailscale.com/ipn/ipnstate"
 )
 
+//nolint
 type TailscaleClient interface {
 	Hostname() string
 	Shutdown() error
@@ -20,4 +21,5 @@ type TailscaleClient interface {
 	WaitForReady() error
 	WaitForPeers(expected int) error
 	Ping(hostnameOrIP string) error
+	ID() string
 }

integration/tsic/tsic.go

@@ -47,6 +47,7 @@ type TailscaleInContainer struct {
 	// optional config
 	headscaleCert     []byte
 	headscaleHostname string
+	withSSH           bool
 }
 
 type Option = func(c *TailscaleInContainer)
@@ -83,6 +84,12 @@ func WithHeadscaleName(hsName string) Option {
 	}
 }
 
+func WithSSH() Option {
+	return func(tsic *TailscaleInContainer) {
+		tsic.withSSH = true
+	}
+}
+
 func New(
 	pool *dockertest.Pool,
 	version string,
@@ -176,6 +183,10 @@ func (t *TailscaleInContainer) Version() string {
 	return t.version
 }
 
+func (t *TailscaleInContainer) ID() string {
+	return t.container.Container.ID
+}
+
 func (t *TailscaleInContainer) Execute(
 	command []string,
 ) (string, string, error) {
@@ -215,6 +226,10 @@ func (t *TailscaleInContainer) Up(
 		t.hostname,
 	}
 
+	if t.withSSH {
+		command = append(command, "--ssh")
+	}
+
 	if _, _, err := t.Execute(command); err != nil {
 		return fmt.Errorf("failed to join tailscale client: %w", err)
 	}

machine.go

@@ -745,7 +745,11 @@ func (h *Headscale) toNode(
 
 		KeepAlive:         true,
 		MachineAuthorized: !machine.isExpired(),
-		Capabilities:      []string{tailcfg.CapabilityFileSharing},
+		Capabilities: []string{
+			tailcfg.CapabilityFileSharing,
+			tailcfg.CapabilityAdmin,
+			tailcfg.CapabilitySSH,
+		},
 	}
 
 	return &node, nil