diff --git a/integration/tsic/tsic.go b/integration/tsic/tsic.go
new file mode 100644
index 00000000..40a0e693
--- /dev/null
+++ b/integration/tsic/tsic.go
@@ -0,0 +1,217 @@
+package tsic
+
+import (
+	"errors"
+	"fmt"
+	"log"
+	"net/netip"
+	"strings"
+
+	"github.com/juanfont/headscale"
+	"github.com/juanfont/headscale/integration/dockertestutil"
+	"github.com/ory/dockertest/v3"
+	"github.com/ory/dockertest/v3/docker"
+)
+
+const tsicHashLength = 6
+const dockerContextPath = "../."
+
+var errTailscalePingFailed = errors.New("ping failed")
+
+type TailscaleInContainer struct {
+	version  string
+	Hostname string
+
+	pool      *dockertest.Pool
+	container *dockertest.Resource
+	network   *dockertest.Network
+}
+
+func New(
+	pool *dockertest.Pool,
+	version string,
+	network *dockertest.Network) (*TailscaleInContainer, error) {
+	hash, err := headscale.GenerateRandomStringDNSSafe(tsicHashLength)
+	if err != nil {
+		return nil, err
+	}
+
+	hostname := fmt.Sprintf("ts-%s-%s", 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
+	// }
+
+	tailscaleOptions := &dockertest.RunOptions{
+		Name:     hostname,
+		Networks: []*dockertest.Network{network},
+		Cmd: []string{
+			"tailscaled", "--tun=tsdev",
+		},
+	}
+
+	// dockertest isnt very good at handling containers that has already
+	// been created, this is an attempt to make sure this container isnt
+	// present.
+	err = pool.RemoveContainerByName(hostname)
+	if err != nil {
+		return nil, err
+	}
+
+	container, err := pool.BuildAndRunWithBuildOptions(
+		createTailscaleBuildOptions(version),
+		tailscaleOptions,
+		dockertestutil.DockerRestartPolicy,
+		dockertestutil.DockerAllowLocalIPv6,
+		dockertestutil.DockerAllowNetworkAdministration,
+	)
+	if err != nil {
+		return nil, fmt.Errorf("could not start tailscale container: %w", err)
+	}
+	log.Printf("Created %s container\n", hostname)
+
+	return &TailscaleInContainer{
+		version:  version,
+		Hostname: hostname,
+
+		pool:      pool,
+		container: container,
+		network:   network,
+	}, nil
+}
+
+func (t *TailscaleInContainer) Shutdown() error {
+	return t.pool.Purge(t.container)
+}
+
+func (t *TailscaleInContainer) Up(
+	loginServer, authKey string,
+) error {
+	command := []string{
+		"tailscale",
+		"up",
+		"-login-server",
+		loginServer,
+		"--authkey",
+		authKey,
+		"--hostname",
+		t.Hostname,
+	}
+
+	log.Println("Join command:", command)
+	log.Printf("Running join command for %s\n", t.Hostname)
+	_, _, err := dockertestutil.ExecuteCommand(
+		t.container,
+		command,
+		[]string{},
+	)
+	if err != nil {
+		return err
+	}
+	log.Printf("%s joined\n", t.Hostname)
+
+	return nil
+}
+
+func (t *TailscaleInContainer) IPs() ([]netip.Addr, error) {
+	ips := make([]netip.Addr, 0)
+
+	command := []string{
+		"tailscale",
+		"ip",
+	}
+
+	result, _, err := dockertestutil.ExecuteCommand(
+		t.container,
+		command,
+		[]string{},
+	)
+	if err != nil {
+		return []netip.Addr{}, err
+	}
+
+	for _, address := range strings.Split(result, "\n") {
+		address = strings.TrimSuffix(address, "\n")
+		if len(address) < 1 {
+			continue
+		}
+		ip, err := netip.ParseAddr(address)
+		if err != nil {
+			return nil, err
+		}
+		ips = append(ips, ip)
+	}
+
+	return ips, nil
+}
+
+func (t *TailscaleInContainer) Ping(ip netip.Addr) error {
+	command := []string{
+		"tailscale", "ping",
+		"--timeout=1s",
+		"--c=10",
+		"--until-direct=true",
+		ip.String(),
+	}
+
+	result, _, err := dockertestutil.ExecuteCommand(
+		t.container,
+		command,
+		[]string{},
+	)
+	if err != nil {
+		return err
+	}
+
+	if !strings.Contains(result, "pong") {
+		return errTailscalePingFailed
+	}
+
+	return nil
+}
+
+func createTailscaleBuildOptions(version string) *dockertest.BuildOptions {
+	var tailscaleBuildOptions *dockertest.BuildOptions
+	switch version {
+	case "head":
+		tailscaleBuildOptions = &dockertest.BuildOptions{
+			Dockerfile: "Dockerfile.tailscale-HEAD",
+			ContextDir: dockerContextPath,
+			BuildArgs:  []docker.BuildArg{},
+		}
+	case "unstable":
+		tailscaleBuildOptions = &dockertest.BuildOptions{
+			Dockerfile: "Dockerfile.tailscale",
+			ContextDir: dockerContextPath,
+			BuildArgs: []docker.BuildArg{
+				{
+					Name:  "TAILSCALE_VERSION",
+					Value: "*", // Installs the latest version https://askubuntu.com/a/824926
+				},
+				{
+					Name:  "TAILSCALE_CHANNEL",
+					Value: "unstable",
+				},
+			},
+		}
+	default:
+		tailscaleBuildOptions = &dockertest.BuildOptions{
+			Dockerfile: "Dockerfile.tailscale",
+			ContextDir: dockerContextPath,
+			BuildArgs: []docker.BuildArg{
+				{
+					Name:  "TAILSCALE_VERSION",
+					Value: version,
+				},
+				{
+					Name:  "TAILSCALE_CHANNEL",
+					Value: "stable",
+				},
+			},
+		}
+	}
+
+	return tailscaleBuildOptions
+}