diff --git a/cheddahbot/tools/content_creation.py b/cheddahbot/tools/content_creation.py
index f2aafae..7202e7e 100644
--- a/cheddahbot/tools/content_creation.py
+++ b/cheddahbot/tools/content_creation.py
@@ -607,9 +607,27 @@ def _run_phase2(
             log.warning("Could not read outline at %s: %s", outline_path, e)
 
     if not outline_text:
+        # Reset task to "to do" so it can be retried after re-running Phase 1
+        if task_id and ctx:
+            client = _get_clickup_client(ctx)
+            if client:
+                try:
+                    reset_status = config.clickup.poll_statuses[0] if config.clickup.poll_statuses else "to do"
+                    client.update_task_status(task_id, reset_status)
+                    client.add_comment(
+                        task_id,
+                        f"⚠️ Outline file not found for keyword '{keyword}'. "
+                        f"Searched: {outline_path or '(no path saved)'}. "
+                        f"Please re-run Phase 1 (create_content) to generate a new outline.",
+                    )
+                except Exception as e:
+                    log.warning("Failed to reset task %s after missing outline: %s", task_id, e)
+                finally:
+                    client.close()
         return (
-            "Error: Could not read the outline file. "
-            f"Expected at: {outline_path or '(no path saved)'}"
+            "Error: Outline file not found. "
+            f"Searched at: {outline_path or '(no path saved)'}. "
+            f"Please re-run Phase 1 (create_content) to generate a new outline."
         )
 
     # Use saved cora_path from state if we don't have one now