diff --git a/pkg/cleanup/containers.go b/pkg/cleanup/containers.go
index b49dcb05c6f9..9c2d01b903e3 100644
--- a/pkg/cleanup/containers.go
+++ b/pkg/cleanup/containers.go
@@ -17,6 +17,7 @@ limitations under the License.
 package cleanup
 
 import (
+	"context"
 	"errors"
 	"fmt"
 	"io/fs"
@@ -136,20 +137,20 @@ func (c *containers) stopContainerd() {
 
 func (c *containers) stopAllContainers() error {
 	var msg []error
-	logrus.Debugf("trying to list all pods")
 
 	var pods []string
+	ctx := context.TODO()
 	err := retry.Do(func() error {
+		logrus.Debugf("trying to list all pods")
 		var err error
-		pods, err = c.Config.containerRuntime.ListContainers()
+		pods, err = c.Config.containerRuntime.ListContainers(ctx)
 		if err != nil {
 			return err
 		}
 		return nil
-	})
+	}, retry.Context(ctx), retry.LastErrorOnly(true))
 	if err != nil {
-		logrus.Debugf("failed at listing pods %v", err)
-		return err
+		return fmt.Errorf("failed at listing pods %w", err)
 	}
 	if len(pods) > 0 {
 		if err := removeMount("kubelet/pods"); err != nil {
@@ -162,7 +163,7 @@ func (c *containers) stopAllContainers() error {
 
 	for _, pod := range pods {
 		logrus.Debugf("stopping container: %v", pod)
-		err := c.Config.containerRuntime.StopContainer(pod)
+		err := c.Config.containerRuntime.StopContainer(ctx, pod)
 		if err != nil {
 			if strings.Contains(err.Error(), "443: connect: connection refused") {
 				// on a single node instance, we will see "connection refused" error. this is to be expected
@@ -174,13 +175,13 @@ func (c *containers) stopAllContainers() error {
 				msg = append(msg, fmtError)
 			}
 		}
-		err = c.Config.containerRuntime.RemoveContainer(pod)
+		err = c.Config.containerRuntime.RemoveContainer(ctx, pod)
 		if err != nil {
 			msg = append(msg, fmt.Errorf("failed to remove pod %v: err: %v", pod, err))
 		}
 	}
 
-	pods, err = c.Config.containerRuntime.ListContainers()
+	pods, err = c.Config.containerRuntime.ListContainers(ctx)
 	if err == nil && len(pods) == 0 {
 		logrus.Info("successfully removed k0s containers!")
 	}
diff --git a/pkg/container/runtime/cri.go b/pkg/container/runtime/cri.go
index ea9a50e890e3..3ffa3b97ef46 100644
--- a/pkg/container/runtime/cri.go
+++ b/pkg/container/runtime/cri.go
@@ -32,7 +32,7 @@ type CRIRuntime struct {
 	criSocketPath string
 }
 
-func (cri *CRIRuntime) ListContainers() ([]string, error) {
+func (cri *CRIRuntime) ListContainers(ctx context.Context) ([]string, error) {
 	client, conn, err := getRuntimeClient(cri.criSocketPath)
 	defer closeConnection(conn)
 	if err != nil {
@@ -43,7 +43,7 @@ func (cri *CRIRuntime) ListContainers() ([]string, error) {
 	}
 	request := &pb.ListPodSandboxRequest{}
 	logrus.Debugf("ListPodSandboxRequest: %v", request)
-	r, err := client.ListPodSandbox(context.Background(), request)
+	r, err := client.ListPodSandbox(ctx, request)
 	logrus.Debugf("ListPodSandboxResponse: %v", r)
 	if err != nil {
 		return nil, err
@@ -55,7 +55,7 @@ func (cri *CRIRuntime) ListContainers() ([]string, error) {
 	return pods, nil
 }
 
-func (cri *CRIRuntime) RemoveContainer(id string) error {
+func (cri *CRIRuntime) RemoveContainer(ctx context.Context, id string) error {
 	client, conn, err := getRuntimeClient(cri.criSocketPath)
 	defer closeConnection(conn)
 	if err != nil {
@@ -66,7 +66,7 @@ func (cri *CRIRuntime) RemoveContainer(id string) error {
 	}
 	request := &pb.RemovePodSandboxRequest{PodSandboxId: id}
 	logrus.Debugf("RemovePodSandboxRequest: %v", request)
-	r, err := client.RemovePodSandbox(context.Background(), request)
+	r, err := client.RemovePodSandbox(ctx, request)
 	logrus.Debugf("RemovePodSandboxResponse: %v", r)
 	if err != nil {
 		return err
@@ -75,7 +75,7 @@ func (cri *CRIRuntime) RemoveContainer(id string) error {
 	return nil
 }
 
-func (cri *CRIRuntime) StopContainer(id string) error {
+func (cri *CRIRuntime) StopContainer(ctx context.Context, id string) error {
 	client, conn, err := getRuntimeClient(cri.criSocketPath)
 	defer closeConnection(conn)
 	if err != nil {
@@ -86,7 +86,7 @@ func (cri *CRIRuntime) StopContainer(id string) error {
 	}
 	request := &pb.StopPodSandboxRequest{PodSandboxId: id}
 	logrus.Debugf("StopPodSandboxRequest: %v", request)
-	r, err := client.StopPodSandbox(context.Background(), request)
+	r, err := client.StopPodSandbox(ctx, request)
 	logrus.Debugf("StopPodSandboxResponse: %v", r)
 	if err != nil {
 		return fmt.Errorf("failed to stop pod sandbox: %w", err)
@@ -105,10 +105,9 @@ func getRuntimeClient(addr string) (pb.RuntimeServiceClient, *grpc.ClientConn, e
 }
 
 func getRuntimeClientConnection(addr string) (*grpc.ClientConn, error) {
-	conn, err := grpc.Dial(addr, grpc.WithTransportCredentials(insecure.NewCredentials()), grpc.WithBlock())
+	conn, err := grpc.Dial(addr, grpc.WithTransportCredentials(insecure.NewCredentials()))
 	if err != nil {
-		errMsg := fmt.Errorf("connect endpoint %s, make sure you are running as root and the endpoint has been started: %w", addr, err)
-		logrus.Error(errMsg)
+		return nil, fmt.Errorf("connect endpoint %s, make sure you are running as root and the endpoint has been started: %w", addr, err)
 	} else {
 		logrus.Debugf("connected successfully using endpoint: %s", addr)
 	}
diff --git a/pkg/container/runtime/docker.go b/pkg/container/runtime/docker.go
index 208b38951fbe..0fd118ea4947 100644
--- a/pkg/container/runtime/docker.go
+++ b/pkg/container/runtime/docker.go
@@ -17,6 +17,7 @@ limitations under the License.
 package runtime
 
 import (
+	"context"
 	"fmt"
 	"os/exec"
 	"strings"
@@ -28,7 +29,7 @@ type DockerRuntime struct {
 	criSocketPath string
 }
 
-func (d *DockerRuntime) ListContainers() ([]string, error) {
+func (d *DockerRuntime) ListContainers(context.Context) ([]string, error) {
 	out, err := exec.Command("docker", "--host", d.criSocketPath, "ps", "-a", "--filter", "name=k8s_", "-q").CombinedOutput()
 	if err != nil {
 		return nil, fmt.Errorf("failed to list containers: output: %s: %w", string(out), err)
@@ -36,7 +37,7 @@ func (d *DockerRuntime) ListContainers() ([]string, error) {
 	return strings.Fields(string(out)), nil
 }
 
-func (d *DockerRuntime) RemoveContainer(id string) error {
+func (d *DockerRuntime) RemoveContainer(_ context.Context, id string) error {
 	out, err := exec.Command("docker", "--host", d.criSocketPath, "rm", "--volumes", id).CombinedOutput()
 	if err != nil {
 		return fmt.Errorf("failed to remove container %s: output: %s: %w", id, string(out), err)
@@ -44,7 +45,7 @@ func (d *DockerRuntime) RemoveContainer(id string) error {
 	return nil
 }
 
-func (d *DockerRuntime) StopContainer(id string) error {
+func (d *DockerRuntime) StopContainer(_ context.Context, id string) error {
 	out, err := exec.Command("docker", "--host", d.criSocketPath, "stop", id).CombinedOutput()
 	if err != nil {
 		return fmt.Errorf("failed to stop running container %s: output: %s: %w", id, string(out), err)
diff --git a/pkg/container/runtime/runtime.go b/pkg/container/runtime/runtime.go
index d04d2a0fae92..6758d315971d 100644
--- a/pkg/container/runtime/runtime.go
+++ b/pkg/container/runtime/runtime.go
@@ -16,10 +16,14 @@ limitations under the License.
 
 package runtime
 
+import (
+	"context"
+)
+
 type ContainerRuntime interface {
-	ListContainers() ([]string, error)
-	RemoveContainer(id string) error
-	StopContainer(id string) error
+	ListContainers(ctx context.Context) ([]string, error)
+	RemoveContainer(ctx context.Context, id string) error
+	StopContainer(ctx context.Context, id string) error
 }
 
 func NewContainerRuntime(runtimeType string, criSocketPath string) ContainerRuntime {