diff --git a/pkg/reconciler/managed/api.go b/pkg/reconciler/managed/api.go
index 8ab4aeeaf..3a6a3df46 100644
--- a/pkg/reconciler/managed/api.go
+++ b/pkg/reconciler/managed/api.go
@@ -174,7 +174,9 @@ func NewRetryingCriticalAnnotationUpdater(c client.Client) *RetryingCriticalAnno
 // case of a conflict error.
 func (u *RetryingCriticalAnnotationUpdater) UpdateCriticalAnnotations(ctx context.Context, o client.Object) error {
 	a := o.GetAnnotations()
-	err := retry.OnError(retry.DefaultRetry, resource.IsAPIError, func() error {
+	err := retry.OnError(retry.DefaultRetry, func(err error) bool {
+		return !errors.Is(err, context.Canceled)
+	}, func() error {
 		err := u.client.Update(ctx, o)
 		if kerrors.IsConflict(err) {
 			if getErr := u.client.Get(ctx, types.NamespacedName{Name: o.GetName()}, o); getErr != nil {
diff --git a/pkg/reconciler/managed/reconciler.go b/pkg/reconciler/managed/reconciler.go
index 37dc9507c..dbeb8b2f9 100644
--- a/pkg/reconciler/managed/reconciler.go
+++ b/pkg/reconciler/managed/reconciler.go
@@ -1051,10 +1051,9 @@ func (r *Reconciler) Reconcile(ctx context.Context, req reconcile.Request) (resu
 			// issue we'll be requeued implicitly when we update our status with
 			// the new error condition. If not, we requeue explicitly, which will trigger backoff.
 			log.Debug("Cannot create external resource", "error", err)
-			if kerrors.IsConflict(err) {
-				return reconcile.Result{Requeue: true}, nil
+			if !kerrors.IsConflict(err) {
+				record.Event(managed, event.Warning(reasonCannotCreate, err))
 			}
-			record.Event(managed, event.Warning(reasonCannotCreate, err))
 
 			// We handle annotations specially here because it's
 			// critical that they are persisted to the API server.