diff --git a/controllers/workspace/devworkspace_controller.go b/controllers/workspace/devworkspace_controller.go
index af22707e2..2565d353e 100644
--- a/controllers/workspace/devworkspace_controller.go
+++ b/controllers/workspace/devworkspace_controller.go
@@ -125,6 +125,12 @@ func (r *DevWorkspaceReconciler) Reconcile(req ctrl.Request) (reconcileResult ct
 
 	// Stop failed workspaces
 	if workspace.Status.Phase == devworkspacePhaseFailing && workspace.Spec.Started {
+		// If debug annotation is present, leave the deployment in place to let users
+		// view logs.
+		if workspace.Annotations[constants.DevWorkspaceDebugStartAnnotation] == "true" {
+			return reconcile.Result{}, nil
+		}
+
 		patch := []byte(`{"spec":{"started": false}}`)
 		err := r.Client.Patch(context.Background(), workspace, client.RawPatch(types.MergePatchType, patch))
 		if err != nil {
diff --git a/pkg/constants/metadata.go b/pkg/constants/metadata.go
index 04a25755d..aab78bf6a 100644
--- a/pkg/constants/metadata.go
+++ b/pkg/constants/metadata.go
@@ -47,6 +47,10 @@ const (
 	// this annotation will be cleared
 	DevWorkspaceStopReasonAnnotation = "controller.devfile.io/stopped-by"
 
+	// DevWorkspaceDebugStartAnnotation enables debugging workspace startup if set to "true". If a workspace with this annotation
+	// fails to start (i.e. enters the "Failed" phase), its deployment will not be scaled down in order to allow viewing logs, etc.
+	DevWorkspaceDebugStartAnnotation = "controller.devfile.io/debug-start"
+
 	// WebhookRestartedAtAnnotation holds the the time (unixnano) of when the webhook server was forced to restart by controller
 	WebhookRestartedAtAnnotation = "controller.devfile.io/restarted-at"