diff --git a/libcontainerd/remote/client.go b/libcontainerd/remote/client.go
index f21076afb2..02930eb852 100644
--- a/libcontainerd/remote/client.go
+++ b/libcontainerd/remote/client.go
@@ -722,9 +722,12 @@ func (c *client) waitServe(ctx context.Context) bool {
 	// `IsServing` will actually block until the service is ready.
 	// However it can return early, so we'll loop with a delay to handle it.
 	for {
-		serving, _ := c.client.IsServing(ctx)
-		if ctx.Err() != nil {
-			return false
+		serving, err := c.client.IsServing(ctx)
+		if err != nil {
+			if errors.Is(err, context.DeadlineExceeded) || errors.Is(err, context.Canceled) {
+				return false
+			}
+			logrus.WithError(err).Warn("Error while testing if containerd API is ready")
 		}
 
 		if serving {
@@ -748,9 +751,16 @@ func (c *client) processEventStream(ctx context.Context, ns string) {
 		ei  libcontainerdtypes.EventInfo
 	)
 
+	// Create a new context specifically for this subscription.
+	// The context must be cancelled to cancel the subscription.
+	// In cases where we have to restart event stream processing,
+	//   we'll need the original context b/c this one will be cancelled
+	subCtx, cancel := context.WithCancel(ctx)
+	defer cancel()
+
 	// Filter on both namespace *and* topic. To create an "and" filter,
 	// this must be a single, comma-separated string
-	eventStream, errC := c.client.EventService().Subscribe(ctx, "namespace=="+ns+",topic~=|^/tasks/|")
+	eventStream, errC := c.client.EventService().Subscribe(subCtx, "namespace=="+ns+",topic~=|^/tasks/|")
 
 	c.logger.Debug("processing event stream")