diff --git a/Dockerfile.tailscale b/Dockerfile.tailscale
index fc02aeaa..adf37ed0 100644
--- a/Dockerfile.tailscale
+++ b/Dockerfile.tailscale
@@ -1,19 +1,16 @@
-FROM ubuntu:latest
+FROM ubuntu:22.04
 
 ARG TAILSCALE_VERSION=*
 ARG TAILSCALE_CHANNEL=stable
 
 RUN apt-get update \
-    && apt-get install -y gnupg curl ssh \
-    && curl -fsSL https://pkgs.tailscale.com/${TAILSCALE_CHANNEL}/ubuntu/focal.gpg | apt-key add - \
+    && apt-get install -y gnupg curl ssh dnsutils ca-certificates \
+    && adduser --shell=/bin/bash ssh-it-user
+
+# Tailscale is deliberately split into a second stage so we can cash utils as a seperate layer.
+RUN curl -fsSL https://pkgs.tailscale.com/${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 \
+    && apt-get install -y tailscale=${TAILSCALE_VERSION} \
+    && apt-get clean \
     && 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 update-ca-certificates
diff --git a/Dockerfile.tailscale-HEAD b/Dockerfile.tailscale-HEAD
index c9a04189..2a3aac76 100644
--- a/Dockerfile.tailscale-HEAD
+++ b/Dockerfile.tailscale-HEAD
@@ -1,7 +1,7 @@
 FROM golang:latest
 
 RUN apt-get update \
-    && apt-get install -y ca-certificates dnsutils git iptables ssh \
+    && apt-get install -y dnsutils git iptables ssh ca-certificates \
     && rm -rf /var/lib/apt/lists/*
 
 RUN useradd --shell=/bin/bash --create-home ssh-it-user
@@ -10,15 +10,8 @@ RUN git clone https://github.com/tailscale/tailscale.git
 
 WORKDIR /go/tailscale
 
-RUN git checkout main
-
-RUN sh build_dist.sh tailscale.com/cmd/tailscale
-RUN sh build_dist.sh tailscale.com/cmd/tailscaled
-
-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 update-ca-certificates
+RUN git checkout main \
+    && sh build_dist.sh tailscale.com/cmd/tailscale \
+    && sh build_dist.sh tailscale.com/cmd/tailscaled \
+    && cp tailscale /usr/local/bin/ \
+    && cp tailscaled /usr/local/bin/
diff --git a/cmd/build-docker-img/main.go b/cmd/build-docker-img/main.go
new file mode 100644
index 00000000..a33ce19f
--- /dev/null
+++ b/cmd/build-docker-img/main.go
@@ -0,0 +1,47 @@
+package main
+
+import (
+	"log"
+
+	"github.com/juanfont/headscale/integration"
+	"github.com/juanfont/headscale/integration/tsic"
+	"github.com/ory/dockertest/v3"
+)
+
+func main() {
+	log.Printf("creating docker pool")
+	pool, err := dockertest.NewPool("")
+	if err != nil {
+		log.Fatalf("could not connect to docker: %s", err)
+	}
+
+	log.Printf("creating docker network")
+	network, err := pool.CreateNetwork("docker-integration-net")
+	if err != nil {
+		log.Fatalf("failed to create or get network: %s", err)
+	}
+
+	for _, version := range integration.TailscaleVersions {
+		log.Printf("creating container image for Tailscale (%s)", version)
+
+		tsClient, err := tsic.New(
+			pool,
+			version,
+			network,
+		)
+		if err != nil {
+			log.Fatalf("failed to create tailscale node: %s", err)
+		}
+
+		err = tsClient.Shutdown()
+		if err != nil {
+			log.Fatalf("failed to shut down container: %s", err)
+		}
+	}
+
+	network.Close()
+	err = pool.RemoveNetwork(network)
+	if err != nil {
+		log.Fatalf("failed to remove network: %s", err)
+	}
+}
diff --git a/integration/scenario.go b/integration/scenario.go
index 2bb7ea66..817ea7c1 100644
--- a/integration/scenario.go
+++ b/integration/scenario.go
@@ -33,6 +33,7 @@ var (
 	tailscaleVersions2021 = []string{
 		"head",
 		"unstable",
+		"1.40.0",
 		"1.38.4",
 		"1.36.2",
 		"1.34.2",
@@ -279,7 +280,7 @@ func (s *Scenario) CreateTailscaleNodesInUser(
 
 			headscale, err := s.Headscale()
 			if err != nil {
-				return fmt.Errorf("failed to create tailscale node: %w", err)
+				return fmt.Errorf("failed to create tailscale node (version: %s): %w", version, err)
 			}
 
 			cert := headscale.GetCert()
diff --git a/integration/tsic/tsic.go b/integration/tsic/tsic.go
index 52a3ff38..520f0f2d 100644
--- a/integration/tsic/tsic.go
+++ b/integration/tsic/tsic.go
@@ -212,7 +212,11 @@ func New(
 		dockertestutil.DockerAllowNetworkAdministration,
 	)
 	if err != nil {
-		return nil, fmt.Errorf("could not start tailscale container: %w", err)
+		return nil, fmt.Errorf(
+			"could not start tailscale container (version: %s): %w",
+			version,
+			err,
+		)
 	}
 	log.Printf("Created %s container\n", hostname)