diff --git a/cli/command/container/run.go b/cli/command/container/run.go
index 2c4e8d41ea8f..0da127c46379 100644
--- a/cli/command/container/run.go
+++ b/cli/command/container/run.go
@@ -186,7 +186,11 @@ func runContainer(ctx context.Context, dockerCli command.Cli, runOpts *runOption
 		defer closeFn()
 	}
 
-	statusChan := waitExitOrRemoved(ctx, apiClient, containerID, copts.autoRemove)
+	// New context here because we don't to cancel waiting on container exit/remove
+	// when we cancel attach, etc.
+	statusCtx, cancelStatusCtx := context.WithCancel(context.WithoutCancel(ctx))
+	defer cancelStatusCtx()
+	statusChan := waitExitOrRemoved(statusCtx, apiClient, containerID, copts.autoRemove)
 
 	// start the container
 	if err := apiClient.ContainerStart(ctx, containerID, container.StartOptions{}); err != nil {
diff --git a/cli/command/container/utils.go b/cli/command/container/utils.go
index 9662ac027ffe..794c0db60949 100644
--- a/cli/command/container/utils.go
+++ b/cli/command/container/utils.go
@@ -36,6 +36,7 @@ func waitExitOrRemoved(ctx context.Context, apiClient client.APIClient, containe
 
 	statusC := make(chan int)
 	go func() {
+		defer close(statusC)
 		select {
 		case <-ctx.Done():
 			return
diff --git a/e2e/container/run_test.go b/e2e/container/run_test.go
index cffd1aeb8d46..fa8ea72b0334 100644
--- a/e2e/container/run_test.go
+++ b/e2e/container/run_test.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"strings"
 	"testing"
+	"time"
 
 	"github.com/docker/cli/e2e/internal/fixtures"
 	"github.com/docker/cli/internal/test/environment"
@@ -34,6 +35,22 @@ func TestRunAttachedFromRemoteImageAndRemove(t *testing.T) {
 	golden.Assert(t, result.Stderr(), "run-attached-from-remote-and-remove.golden")
 }
 
+// Regression test for https://github.com/docker/cli/issues/5053
+func TestRunInvalidEntrypointWithAutoremove(t *testing.T) {
+	environment.SkipIfDaemonNotLinux(t)
+
+	result := make(chan *icmd.Result)
+	go func() {
+		result <- icmd.RunCommand("docker", "run", "--rm", fixtures.AlpineImage, "invalidcommand")
+	}()
+	select {
+	case r := <-result:
+		r.Assert(t, icmd.Expected{ExitCode: 127})
+	case <-time.After(4 * time.Second):
+		t.Fatal("test took too long, shouldn't hang")
+	}
+}
+
 func TestRunWithContentTrust(t *testing.T) {
 	skip.If(t, environment.RemoteDaemon())