diff --git a/daemon/exec.go b/daemon/exec.go
index 78a593a6e2184..7ad5c4a17efbc 100644
--- a/daemon/exec.go
+++ b/daemon/exec.go
@@ -22,9 +22,6 @@ import (
 	"github.com/sirupsen/logrus"
 )
 
-// Seconds to wait after sending TERM before trying KILL
-const termProcessTimeout = 10 * time.Second
-
 func (daemon *Daemon) registerExecCommand(container *container.Container, config *exec.Config) {
 	// Storing execs in container in order to kill them gracefully whenever the container is stopped or removed.
 	container.ExecCommands.Add(config.ID, config)
@@ -255,7 +252,10 @@ func (daemon *Daemon) ContainerExecStart(ctx context.Context, name string, stdin
 		CloseStdin: true,
 	}
 	ec.StreamConfig.AttachStreams(&attachConfig)
-	attachErr := ec.StreamConfig.CopyStreams(ctx, &attachConfig)
+	// using context.Background() so that attachErr does not race ctx.Done().
+	copyCtx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+	attachErr := ec.StreamConfig.CopyStreams(copyCtx, &attachConfig)
 
 	// Synchronize with libcontainerd event loop
 	ec.Lock()
@@ -275,18 +275,15 @@ func (daemon *Daemon) ContainerExecStart(ctx context.Context, name string, stdin
 
 	select {
 	case <-ctx.Done():
-		logrus.Debugf("Sending TERM signal to process %v in container %v", name, c.ID)
-		daemon.containerd.SignalProcess(ctx, c.ID, name, int(signal.SignalMap["TERM"]))
-
-		timeout := time.NewTimer(termProcessTimeout)
-		defer timeout.Stop()
-
-		select {
-		case <-timeout.C:
-			logrus.Infof("Container %v, process %v failed to exit within %v of signal TERM - using the force", c.ID, name, termProcessTimeout)
-			daemon.containerd.SignalProcess(ctx, c.ID, name, int(signal.SignalMap["KILL"]))
-		case <-attachErr:
-			// TERM signal worked
+		log := logrus.
+			WithField("container", c.ID).
+			WithField("exec", name)
+		log.Debug("Sending KILL signal to container process")
+		sigCtx, cancelFunc := context.WithTimeout(context.Background(), 30*time.Second)
+		defer cancelFunc()
+		err := daemon.containerd.SignalProcess(sigCtx, c.ID, name, int(signal.SignalMap["KILL"]))
+		if err != nil {
+			log.WithError(err).Error("Could not send KILL signal to container process")
 		}
 		return ctx.Err()
 	case err := <-attachErr:
diff --git a/integration/container/health_test.go b/integration/container/health_test.go
index ad0245c6a80d4..d3851edbb7703 100644
--- a/integration/container/health_test.go
+++ b/integration/container/health_test.go
@@ -2,6 +2,7 @@ package container // import "github.com/docker/docker/integration/container"
 
 import (
 	"context"
+	"fmt"
 	"testing"
 	"time"
 
@@ -93,6 +94,42 @@ while true; do sleep 1; done
 	poll.WaitOn(t, pollForHealthStatus(ctxPoll, client, id, "healthy"), poll.WithDelay(100*time.Millisecond))
 }
 
+// TestHealthCheckProcessKilled verifies that health-checks exec get killed on time-out.
+func TestHealthCheckProcessKilled(t *testing.T) {
+	// FIXME: Broken on Windows + containerd combination
+	defer setupTest(t)()
+	ctx := context.Background()
+	apiClient := testEnv.APIClient()
+
+	cID := container.Run(ctx, t, apiClient, func(c *container.TestContainerConfig) {
+		c.Config.Healthcheck = &containertypes.HealthConfig{
+			Test:     []string{"CMD", "sh", "-c", "sleep 60"},
+			Interval: 100 * time.Millisecond,
+			Timeout:  50 * time.Millisecond,
+			Retries:  1,
+		}
+	})
+	poll.WaitOn(t, pollForHealthCheckLog(ctx, apiClient, cID, "Health check exceeded timeout (50ms)"))
+}
+
+func pollForHealthCheckLog(ctx context.Context, client client.APIClient, containerID string, expected string) func(log poll.LogT) poll.Result {
+	return func(log poll.LogT) poll.Result {
+		inspect, err := client.ContainerInspect(ctx, containerID)
+		if err != nil {
+			return poll.Error(err)
+		}
+		healthChecksTotal := len(inspect.State.Health.Log)
+		if healthChecksTotal > 0 {
+			output := inspect.State.Health.Log[healthChecksTotal-1].Output
+			if output == expected {
+				return poll.Success()
+			}
+			return poll.Error(fmt.Errorf("expected %q, got %q", expected, output))
+		}
+		return poll.Continue("waiting for container healthcheck logs")
+	}
+}
+
 func pollForHealthStatus(ctx context.Context, client client.APIClient, containerID string, healthStatus string) func(log poll.LogT) poll.Result {
 	return func(log poll.LogT) poll.Result {
 		inspect, err := client.ContainerInspect(ctx, containerID)