diff --git a/act/container/docker_run.go b/act/container/docker_run.go
index b2266ee8..714c646b 100644
--- a/act/container/docker_run.go
+++ b/act/container/docker_run.go
@@ -895,6 +895,7 @@ func (cr *containerReference) tryReadID(opt string, cbk func(id int)) common.Exe
 			return nil
 		}
 		defer resp.Close()
+		defer context.AfterFunc(ctx, resp.Close)()
 
 		sid, err := resp.Reader.ReadString('\n')
 		if err != nil {
diff --git a/act/container/docker_run_test.go b/act/container/docker_run_test.go
index c1fbaa61..3af5103e 100644
--- a/act/container/docker_run_test.go
+++ b/act/container/docker_run_test.go
@@ -378,6 +378,21 @@ func TestDockerAttachStreamClosesWithItsContext(t *testing.T) {
 	client.AssertExpectations(t)
 }
 
+func TestDockerReadIDStreamClosesWithItsContext(t *testing.T) {
+	conn, peer := net.Pipe()
+	t.Cleanup(func() { _ = peer.Close() })
+	client := &mockDockerClient{}
+	client.On("ExecCreate", mock.Anything, "123", mock.AnythingOfType("client.ExecCreateOptions")).
+		Return(mobyclient.ExecCreateResult{ID: "id"}, nil)
+	client.On("ExecAttach", mock.Anything, "id", mobyclient.ExecAttachOptions{}).
+		Return(mobyclient.ExecAttachResult{HijackedResponse: mobyclient.NewHijackedResponse(conn, "")}, nil)
+	ctx, cancel := context.WithCancel(t.Context())
+	cancel()
+
+	require.NoError(t, (&containerReference{id: "123", cli: client}).tryReadID("-u", func(int) { t.Error("read an ID after cancellation") })(ctx))
+	client.AssertExpectations(t)
+}
+
 func TestDockerWaitFailure(t *testing.T) {
 	ctx := t.Context()
 	statusCh := make(chan container.WaitResponse, 1)
diff --git a/e2e/cli_test.go b/e2e/cli_test.go
index d295701b..97d443ee 100644
--- a/e2e/cli_test.go
+++ b/e2e/cli_test.go
@@ -90,20 +90,29 @@ container:
 type cliDaemon struct {
 	cmd    *exec.Cmd
 	log    *syncBuffer
-	exited chan error
+	exited chan struct{}
+	err    error
 }
 
 func (c *cliRunner) startDaemon(t *testing.T, args ...string) *cliDaemon {
 	t.Helper()
-	d := &cliDaemon{log: &syncBuffer{}, exited: make(chan error, 1)}
+	d := &cliDaemon{log: &syncBuffer{}, exited: make(chan struct{})}
 	d.cmd = exec.Command(c.bin, append([]string{"daemon", "-c", c.cfgFile}, args...)...)
 	d.cmd.Stdout, d.cmd.Stderr = d.log, d.log
 	if err := d.cmd.Start(); err != nil {
 		t.Fatalf("start daemon: %v", err)
 	}
-	go func() { d.exited <- d.cmd.Wait() }()
+	go func() {
+		d.err = d.cmd.Wait()
+		close(d.exited)
+	}()
 	t.Cleanup(func() {
-		_ = d.cmd.Process.Kill() // no-op once the daemon has exited
+		_ = d.cmd.Process.Signal(syscall.SIGTERM)
+		select {
+		case <-d.exited:
+		case <-time.After(30 * time.Second):
+			_ = d.cmd.Process.Kill()
+		}
 	})
 	return d
 }
@@ -112,8 +121,8 @@ func (c *cliRunner) startDaemon(t *testing.T, args ...string) *cliDaemon {
 func (d *cliDaemon) wait(t *testing.T, timeout time.Duration) error {
 	t.Helper()
 	select {
-	case err := <-d.exited:
-		return err
+	case <-d.exited:
+		return d.err
 	case <-time.After(timeout):
 		t.Fatalf("daemon still running after %s\n%s", timeout, d.log)
 		return nil
@@ -140,8 +149,8 @@ func (d *cliDaemon) requireSuccess(t *testing.T, c *cliRunner, runID int64) {
 // testCLIRegisterDaemon drives the built binary the way a user does: register, then daemon.
 func testCLIRegisterDaemon(t *testing.T) {
 	t.Parallel()
-	c := newCLIRunner(t, "e2e-cli", "")
-	d := c.startDaemon(t)
+	c := newCLIRunner(t, "e2e-registered", "")
+	d := c.startDaemon(t, "--labels", "e2e-cli:docker://"+os.Getenv("E2E_JOB_IMAGE"))
 
 	pushWorkflow(t, c.api, c.repo, "cli.yml")
 	wfRun := waitForRun(t, c.api, c.repo)
@@ -150,6 +159,22 @@ func testCLIRegisterDaemon(t *testing.T) {
 		t.Errorf("job logs are missing the marker:\n%s", logs)
 	}
 
+	runners, err := c.api.Runners(t.Context(), c.repo)
+	if err != nil {
+		t.Fatalf("list runners: %v", err)
+	}
+	var labels []string
+	for _, runner := range runners {
+		if runner.Name == c.repo {
+			for _, label := range runner.Labels {
+				labels = append(labels, label.Name)
+			}
+		}
+	}
+	if !slices.Equal(labels, []string{"e2e-cli"}) {
+		t.Errorf("runner %q has labels %v on the server, want only the --labels override", c.repo, labels)
+	}
+
 	d.terminate(t)
 	if err := d.wait(t, 30*time.Second); err != nil {
 		t.Errorf("daemon did not exit cleanly on SIGTERM: %v\n%s", err, d.log)
@@ -186,36 +211,6 @@ func testCLIOnce(t *testing.T) {
 	}
 }
 
-// testCLILabelsOverride checks that daemon --labels replaces the labels given at registration.
-func testCLILabelsOverride(t *testing.T) {
-	t.Parallel()
-	c := newCLIRunner(t, "e2e-registered", "")
-	d := c.startDaemon(t, "--labels", "e2e-override:docker://"+os.Getenv("E2E_JOB_IMAGE"))
-
-	pushWorkflow(t, c.api, c.repo, "cli_labels.yml")
-	wfRun := waitForRun(t, c.api, c.repo)
-	d.requireSuccess(t, c, wfRun.ID)
-
-	runners, err := c.api.Runners(t.Context(), c.repo)
-	if err != nil {
-		t.Fatalf("list runners: %v", err)
-	}
-	for _, runner := range runners {
-		if runner.Name != c.repo {
-			continue
-		}
-		var labels []string
-		for _, label := range runner.Labels {
-			labels = append(labels, label.Name)
-		}
-		if !slices.Equal(labels, []string{"e2e-override"}) {
-			t.Errorf("runner has labels %v on the server, want only the --labels override", labels)
-		}
-		return
-	}
-	t.Errorf("runner %q not found among %+v", c.repo, runners)
-}
-
 // testCLIShutdownDrains checks that SIGTERM lets a running job finish within shutdown_timeout.
 func testCLIShutdownDrains(t *testing.T) {
 	t.Parallel()
@@ -282,10 +277,6 @@ func testExecArtifacts(t *testing.T) {
 	t.Parallel()
 	ctx := t.Context()
 
-	bin, err := runnerBinary()
-	if err != nil {
-		t.Fatal(err)
-	}
 	workflow, err := os.ReadFile("testdata/workflows/exec_artifact.yml")
 	if err != nil {
 		t.Fatal(err)
@@ -309,11 +300,9 @@ func testExecArtifacts(t *testing.T) {
 	}
 
 	artifacts := t.TempDir()
-	args := []string{"exec", "-C", workdir, "-W", workflows, "-i", os.Getenv("E2E_JOB_IMAGE"), "--artifact-server-path", artifacts, "--network", fixture.network}
-	cmd := exec.CommandContext(ctx, bin, args...)
-	cmd.Env = slices.DeleteFunc(os.Environ(), func(kv string) bool { return strings.HasPrefix(kv, "ACTIONS_") })
-	if out, err := cmd.CombinedOutput(); err != nil {
-		t.Fatalf("exec: %v\n%s", err, out)
+	stdout, stderr, err := runExec(t, nil, "-C", workdir, "-W", workflows, "-i", os.Getenv("E2E_JOB_IMAGE"), "--artifact-server-path", artifacts, "--network", fixture.network)
+	if err != nil {
+		t.Fatalf("exec: %v\n%s%s", err, stdout, stderr)
 	}
 	if blobs, _ := filepath.Glob(filepath.Join(artifacts, "v4", "*", "*", "blob")); len(blobs) != 2 {
 		t.Fatalf("want one v4 artifact blob per workflow run, got %v", blobs)
diff --git a/e2e/compatibility_test.go b/e2e/compatibility_test.go
index 7fa9331b..6b2f2c0d 100644
--- a/e2e/compatibility_test.go
+++ b/e2e/compatibility_test.go
@@ -37,7 +37,6 @@ func TestCompatibility(t *testing.T) {
 	t.Run("job_timeout", testJobTimeout)
 	t.Run("cli_register_daemon", testCLIRegisterDaemon)
 	t.Run("cli_once", testCLIOnce)
-	t.Run("cli_labels_override", testCLILabelsOverride)
 	t.Run("cli_shutdown_drains", testCLIShutdownDrains)
 	t.Run("cli_shutdown_cancels", testCLIShutdownCancels)
 	t.Run("host_mode", testHostMode)
diff --git a/e2e/gitea_fixture.go b/e2e/gitea_fixture.go
index 3d19da8d..135d14ec 100644
--- a/e2e/gitea_fixture.go
+++ b/e2e/gitea_fixture.go
@@ -80,11 +80,11 @@ func selfNetwork(ctx context.Context, cli mobyclient.APIClient) (string, string,
 	return "", "", false
 }
 
-func StartGitea(ctx context.Context, cli mobyclient.APIClient) (*GiteaFixture, error) {
-	closeClient := true
+func StartGitea(ctx context.Context, cli mobyclient.APIClient) (_ *GiteaFixture, err error) {
+	f := &GiteaFixture{cli: cli}
 	defer func() {
-		if closeClient {
-			_ = cli.Close()
+		if err != nil {
+			_ = f.Close()
 		}
 	}()
 
@@ -123,26 +123,21 @@ func StartGitea(ctx context.Context, cli mobyclient.APIClient) (*GiteaFixture, e
 		return nil, fmt.Errorf("create gitea container: %w", err)
 	}
 
-	f := &GiteaFixture{cli: cli, id: resp.ID, image: image, baseURL: baseURL, network: sharedNet, selfIP: selfIP}
-	closeClient = false
+	f.id, f.image, f.baseURL, f.network, f.selfIP = resp.ID, image, baseURL, sharedNet, selfIP
 
 	if _, err := cli.ContainerStart(ctx, f.id, mobyclient.ContainerStartOptions{}); err != nil {
-		_ = f.Close(ctx)
 		return nil, fmt.Errorf("start gitea container: %w", err)
 	}
 
 	if err := f.waitHealthy(ctx); err != nil {
-		_ = f.Close(ctx)
 		return nil, fmt.Errorf("gitea did not become healthy: %w", err)
 	}
 
 	if err := f.bootstrapAdmin(ctx); err != nil {
-		_ = f.Close(ctx)
 		return nil, fmt.Errorf("bootstrap gitea admin: %w", err)
 	}
 
 	if err := f.readVersion(ctx); err != nil {
-		_ = f.Close(ctx)
 		return nil, fmt.Errorf("read gitea version: %w", err)
 	}
 
@@ -249,6 +244,7 @@ func containerExec(ctx context.Context, cli mobyclient.APIClient, id, user strin
 	if err != nil {
 		return "", err
 	}
+	defer context.AfterFunc(ctx, attached.Close)()
 	defer attached.Close()
 	if stdin != nil {
 		go func() {
@@ -258,7 +254,11 @@ func containerExec(ctx context.Context, cli mobyclient.APIClient, id, user strin
 	}
 
 	var out bytes.Buffer
-	if _, err := stdcopy.StdCopy(&out, &out, attached.Reader); err != nil {
+	_, err = stdcopy.StdCopy(&out, &out, attached.Reader)
+	if ctx.Err() != nil {
+		return "", ctx.Err()
+	}
+	if err != nil {
 		return "", err
 	}
 
@@ -291,10 +291,12 @@ func (f *GiteaFixture) doJSON(ctx context.Context, method, path string, reqBody,
 	return api.doJSON(ctx, method, path, reqBody, respBody)
 }
 
-func (f *GiteaFixture) Close(ctx context.Context) error {
+func (f *GiteaFixture) Close() error {
 	if f.id == "" {
 		return f.cli.Close()
 	}
+	ctx, cancel := context.WithTimeout(context.Background(), cleanupTimeout)
+	defer cancel()
 	_, removeErr := f.cli.ContainerRemove(ctx, f.id, mobyclient.ContainerRemoveOptions{Force: true, RemoveVolumes: true})
 	return errors.Join(removeErr, f.cli.Close())
 }
diff --git a/e2e/kubernetes_test.go b/e2e/kubernetes_test.go
index 33a35b05..05a55491 100644
--- a/e2e/kubernetes_test.go
+++ b/e2e/kubernetes_test.go
@@ -55,7 +55,9 @@ func checkClusterLeaks() error {
 	if err != nil {
 		return nil // the tests that needed the cluster already failed
 	}
-	if out, err := containerExec(context.Background(), dockerCLI, cluster.id, "", nil,
+	ctx, cancel := context.WithTimeout(context.Background(), cleanupTimeout)
+	defer cancel()
+	if out, err := containerExec(ctx, dockerCLI, cluster.id, "", nil,
 		"kubectl", "wait", "--for=delete", "pods,secrets", "--selector=app.kubernetes.io/managed-by=gitea-runner", "--timeout=1m",
 	); err != nil {
 		return fmt.Errorf("job pods or secrets left behind: %w: %s", err, out)
@@ -72,7 +74,7 @@ type kubeCluster struct {
 var (
 	k3s            = sync.OnceValues(startK3s) // independent of Gitea, so it can boot alongside it
 	clusterStarted atomic.Bool
-	clusterCleanup []func()
+	clusterCleanup []func(context.Context)
 	sharedCluster  = sync.OnceValues(func() (*kubeCluster, error) {
 		cluster, err := k3s()
 		if err != nil {
@@ -109,7 +111,9 @@ func stopCluster() {
 	}
 	_, _ = k3s()
 	for _, cleanup := range slices.Backward(clusterCleanup) {
-		cleanup()
+		ctx, cancel := context.WithTimeout(context.Background(), cleanupTimeout)
+		cleanup(ctx)
+		cancel()
 	}
 }
 
@@ -138,8 +142,8 @@ func startK3s() (*kubeCluster, error) {
 	if err != nil {
 		return nil, fmt.Errorf("create k3s container: %w", err)
 	}
-	clusterCleanup = append(clusterCleanup, func() {
-		_, _ = cli.ContainerRemove(context.Background(), created.ID, mobyclient.ContainerRemoveOptions{Force: true, RemoveVolumes: true})
+	clusterCleanup = append(clusterCleanup, func(ctx context.Context) {
+		_, _ = cli.ContainerRemove(ctx, created.ID, mobyclient.ContainerRemoveOptions{Force: true, RemoveVolumes: true})
 	})
 	if _, err := cli.ContainerStart(ctx, created.ID, mobyclient.ContainerStartOptions{}); err != nil {
 		return nil, fmt.Errorf("start k3s container: %w", err)
@@ -170,7 +174,9 @@ func startK3s() (*kubeCluster, error) {
 		inspected, inspectErr := cli.ContainerInspect(ctx, created.ID, mobyclient.ContainerInspectOptions{})
 		if inspectErr != nil || !inspected.Container.State.Running || ctx.Err() != nil {
 			var logs bytes.Buffer
-			if reader, logsErr := cli.ContainerLogs(context.Background(), created.ID, mobyclient.ContainerLogsOptions{ShowStdout: true, ShowStderr: true, Tail: "30"}); logsErr == nil {
+			logsCtx, logsCancel := context.WithTimeout(context.Background(), 10*time.Second)
+			defer logsCancel()
+			if reader, logsErr := cli.ContainerLogs(logsCtx, created.ID, mobyclient.ContainerLogsOptions{ShowStdout: true, ShowStderr: true, Tail: "30"}); logsErr == nil {
 				_, _ = stdcopy.StdCopy(&logs, &logs, reader)
 				_ = reader.Close()
 			}
@@ -226,7 +232,7 @@ func preloadImages(ctx context.Context, k3sID string, images ...string) ([]strin
 		if _, err := dockerCLI.ImageTag(ctx, mobyclient.ImageTagOptions{Source: image, Target: alias}); err != nil {
 			return nil, fmt.Errorf("tag %s: %w", image, err)
 		}
-		clusterCleanup = append(clusterCleanup, func() { _, _ = dockerCLI.ImageRemove(context.Background(), alias, mobyclient.ImageRemoveOptions{}) })
+		clusterCleanup = append(clusterCleanup, func(ctx context.Context) { _, _ = dockerCLI.ImageRemove(ctx, alias, mobyclient.ImageRemoveOptions{}) })
 		aliases = append(aliases, alias)
 	}
 	archive, err := dockerCLI.ImageSave(ctx, aliases)
diff --git a/e2e/main_test.go b/e2e/main_test.go
index 5500987c..c746a951 100644
--- a/e2e/main_test.go
+++ b/e2e/main_test.go
@@ -31,6 +31,8 @@ import (
 
 const runTimeout = 3 * time.Minute
 
+const cleanupTimeout = 2 * time.Minute
+
 var nonRepoChars = regexp.MustCompile(`[^a-zA-Z0-9._-]+`)
 
 var fixture *GiteaFixture
@@ -42,8 +44,10 @@ var binDir string
 var dockerCLI mobyclient.APIClient
 
 var runnerBinary = sync.OnceValues(func() (string, error) {
+	ctx, cancel := context.WithTimeout(context.Background(), runTimeout)
+	defer cancel()
 	bin := filepath.Join(binDir, "gitea-runner")
-	if out, err := exec.Command(cmp.Or(os.Getenv("GO"), "go"), "build", "-o", bin, "..").CombinedOutput(); err != nil {
+	if out, err := exec.CommandContext(ctx, cmp.Or(os.Getenv("GO"), "go"), "build", "-o", bin, "..").CombinedOutput(); err != nil {
 		return "", fmt.Errorf("build runner: %w\n%s", err, out)
 	}
 	return bin, nil
@@ -80,7 +84,7 @@ func runSuite(m *testing.M) int {
 		return 1
 	}
 	fixture = f
-	defer func() { _ = fixture.Close(context.Background()) }()
+	defer func() { _ = fixture.Close() }()
 
 	fmt.Fprintf(os.Stderr, "gitea fixture: image=%s version=%s\n", fixture.image, fixture.version)
 
diff --git a/e2e/modes_test.go b/e2e/modes_test.go
index 72841b1f..e46a3b6a 100644
--- a/e2e/modes_test.go
+++ b/e2e/modes_test.go
@@ -9,6 +9,7 @@ import (
 	"bufio"
 	"bytes"
 	"cmp"
+	"context"
 	"encoding/json"
 	"errors"
 	"os"
@@ -138,14 +139,31 @@ func daemonWorkflow(t *testing.T, m mode, spec workflowSpec) *workflowResult {
 	return result
 }
 
-func execWorkflow(t *testing.T, m mode, spec workflowSpec) *workflowResult {
+func runExec(t *testing.T, env []string, args ...string) (stdout, stderr []byte, err error) {
 	t.Helper()
-	ctx := t.Context()
-
 	bin, err := runnerBinary()
 	if err != nil {
 		t.Fatal(err)
 	}
+	ctx, cancel := context.WithTimeout(t.Context(), runTimeout)
+	defer cancel()
+	cmd := exec.CommandContext(ctx, bin, append([]string{"exec"}, args...)...)
+	cmd.Env = append(slices.DeleteFunc(os.Environ(), func(kv string) bool { return strings.HasPrefix(kv, "ACTIONS_") }), env...)
+	cmd.Cancel = func() error { return cmd.Process.Signal(os.Interrupt) }
+	cmd.WaitDelay = cleanupTimeout
+	var stdoutBuf, stderrBuf bytes.Buffer
+	cmd.Stdout, cmd.Stderr = &stdoutBuf, &stderrBuf
+	err = cmd.Run()
+	if ctx.Err() != nil {
+		t.Fatalf("exec did not finish within %s\n%s%s", runTimeout, stdoutBuf.Bytes(), stderrBuf.Bytes())
+	}
+	return stdoutBuf.Bytes(), stderrBuf.Bytes(), err
+}
+
+func execWorkflow(t *testing.T, m mode, spec workflowSpec) *workflowResult {
+	t.Helper()
+	ctx := t.Context()
+
 	workdir := t.TempDir()
 	workflows := filepath.Join(workdir, ".gitea", "workflows")
 	if err := os.MkdirAll(workflows, 0o755); err != nil {
@@ -170,12 +188,12 @@ func execWorkflow(t *testing.T, m mode, spec workflowSpec) *workflowResult {
 		}
 	}
 
-	args := []string{"exec", "--json", "-C", workdir, "-W", workflows, "--artifact-server-path", t.TempDir(), "--artifact-server-port", "0"}
-	env := slices.DeleteFunc(os.Environ(), func(kv string) bool { return strings.HasPrefix(kv, "ACTIONS_") })
+	args := []string{"--json", "-C", workdir, "-W", workflows, "--artifact-server-path", t.TempDir(), "--artifact-server-port", "0"}
+	var env []string
 	if m.kubernetes {
 		cluster := requireCluster(t)
 		args = append(args, "-i", "kubernetes://"+cluster.jobImage)
-		env = append(env, "KUBECONFIG="+cluster.kubernetes.Kubeconfig)
+		env = []string{"KUBECONFIG=" + cluster.kubernetes.Kubeconfig}
 	} else {
 		args = append(args, "-i", os.Getenv("E2E_JOB_IMAGE"), "--network", fixture.network)
 	}
@@ -185,21 +203,17 @@ func execWorkflow(t *testing.T, m mode, spec workflowSpec) *workflowResult {
 			args = append(args, "--input", name+"="+value)
 		}
 	}
-	cmd := exec.CommandContext(ctx, bin, append(args, spec.execArgs...)...)
-	cmd.Env = env
-	var stdout, stderr bytes.Buffer
-	cmd.Stdout, cmd.Stderr = &stdout, &stderr
-	runErr := cmd.Run()
+	stdout, stderr, runErr := runExec(t, env, append(args, spec.execArgs...)...)
 	var exitErr *exec.ExitError
 	if runErr != nil && !errors.As(runErr, &exitErr) {
-		t.Fatalf("exec: %v\n%s", runErr, stderr.String())
+		t.Fatalf("exec: %v\n%s", runErr, stderr)
 	}
 
 	result := &workflowResult{conclusion: "success", jobs: map[string]string{}}
 	if runErr != nil {
 		result.conclusion = "failure"
 	}
-	scanner := bufio.NewScanner(&stdout)
+	scanner := bufio.NewScanner(bytes.NewReader(stdout))
 	scanner.Buffer(nil, 1<<20)
 	for scanner.Scan() {
 		var entry struct {
@@ -220,8 +234,8 @@ func execWorkflow(t *testing.T, m mode, spec workflowSpec) *workflowResult {
 			}
 		}
 	}
-	if result.conclusion != "success" && len(result.jobs) == 0 {
-		t.Fatalf("exec ran no job: %v\n%s", runErr, stderr.String())
+	if len(result.jobs) == 0 {
+		t.Fatalf("exec ran no job: %v\n%s", runErr, stderr)
 	}
 	return result
 }
diff --git a/e2e/testdata/workflows/cli_labels.yml b/e2e/testdata/workflows/cli_labels.yml
deleted file mode 100644
index dfc4eb7c..00000000
--- a/e2e/testdata/workflows/cli_labels.yml
+++ /dev/null
@@ -1,7 +0,0 @@
-name: cli-labels
-on: push
-jobs:
-  hello:
-    runs-on: e2e-override
-    steps:
-      - run: echo e2e-override-ran