diff --git a/cheddahbot/scheduler.py b/cheddahbot/scheduler.py
index 5f8e024..2b58cf8 100644
--- a/cheddahbot/scheduler.py
+++ b/cheddahbot/scheduler.py
@@ -385,14 +385,19 @@ class Scheduler:
                 continue
 
             # Respect auto_execute flag — skip tasks that require manual trigger
+            # Unless the task status matches an auto_execute_on_status entry
             mapping = skill_map[task.task_type]
             if not mapping.get("auto_execute", False):
-                log.debug(
-                    "Skipping task '%s' (type=%s): auto_execute is false",
-                    task.name,
-                    task.task_type,
-                )
-                continue
+                status_triggers = mapping.get("auto_execute_on_status", [])
+                if task.status.lower() not in [s.lower() for s in status_triggers]:
+                    hint = mapping.get("trigger_hint", "manual trigger only")
+                    log.info(
+                        "Skipping task '%s' (type=%s): auto_execute is false (%s)",
+                        task.name,
+                        task.task_type,
+                        hint,
+                    )
+                    continue
 
             # Client-side verify: due_date must exist and be within window
             if not task.due_date:
diff --git a/config.yaml b/config.yaml
index 8bed54d..8d36105 100644
--- a/config.yaml
+++ b/config.yaml
@@ -64,6 +64,7 @@ clickup:
     "On Page Optimization":
       tool: "create_content"
       auto_execute: false
+      trigger_hint: "content-cora-inbox file watcher"
       required_fields: [keyword, url]
       field_mapping:
         url: "IMSURL"
@@ -72,6 +73,8 @@ clickup:
     "Content Creation":
       tool: "create_content"
       auto_execute: false
+      auto_execute_on_status: ["outline approved"]
+      trigger_hint: "content-cora-inbox file watcher (Phase 1), outline approved status (Phase 2)"
       field_mapping:
         url: "IMSURL"
         keyword: "Keyword"
@@ -79,6 +82,7 @@ clickup:
     "Link Building":
       tool: "run_link_building"
       auto_execute: false
+      trigger_hint: "cora-inbox file watcher"
       complete_status: "complete"
       error_status: "error"
       field_mapping: