diff --git a/core/automation_engine.py b/core/automation_engine.py
index 1fca397b..28fe623e 100644
--- a/core/automation_engine.py
+++ b/core/automation_engine.py
@@ -345,17 +345,19 @@ class AutomationEngine:
 
             automation_ids = self._event_automations.get(event_type, [])
             if not automation_ids:
+                logger.info(f"Event '{event_type}' — no automations registered in cache. Cache keys: {list(self._event_automations.keys())}")
                 return
 
-            logger.debug(f"Event '{event_type}' — checking {len(automation_ids)} automation(s)")
+            logger.info(f"Event '{event_type}' — checking {len(automation_ids)} automation(s), data={data}")
             for aid in automation_ids:
                 try:
                     auto = self.db.get_automation(aid)
                     if not auto or not auto.get('enabled'):
+                        logger.debug(f"Event '{event_type}' — automation {aid} disabled or not found, skipping")
                         continue
                     config = json.loads(auto.get('trigger_config') or '{}')
                     if self._evaluate_conditions(config, data):
-                        logger.info(f"Event '{event_type}' matched automation '{auto.get('name')}' (id={aid})")
+                        logger.info(f"Event '{event_type}' MATCHED automation '{auto.get('name')}' (id={aid})")
                         # Run in separate thread so delays don't block the event loop
                         threading.Thread(
                             target=self._run_event_automation,
@@ -364,7 +366,7 @@ class AutomationEngine:
                             name=f'automation-exec-{aid}'
                         ).start()
                     else:
-                        logger.debug(f"Event '{event_type}' conditions not met for automation {aid}")
+                        logger.info(f"Event '{event_type}' conditions NOT MET for automation '{auto.get('name')}' (id={aid}), config={config}, data={data}")
                 except Exception as e:
                     logger.error(f"Event automation {aid} error: {e}")
         except Exception as e:
@@ -441,6 +443,12 @@ class AutomationEngine:
         # Inject automation identity for progress tracking
         action_config['_automation_id'] = automation_id
         action_config['_automation_name'] = auto.get('name', '')
+        # Merge event data so action handlers can access trigger context
+        if event_data:
+            action_config['_event_data'] = event_data
+            # Forward playlist_id from event if action config doesn't have one set
+            if not action_config.get('playlist_id') and event_data.get('playlist_id'):
+                action_config['playlist_id'] = event_data['playlist_id']
 
         delay_minutes = action_config.get('delay', 0)
         _delay_already_inited = False
diff --git a/web_server.py b/web_server.py
index c9ba9897..f1119a87 100644
--- a/web_server.py
+++ b/web_server.py
@@ -766,12 +766,14 @@ def _register_automation_handlers():
                     if old_ids != new_ids:
                         added_count = len(new_ids - old_ids)
                         removed_count = len(old_ids - new_ids)
+                        print(f"🔔 [AUTOMATION] Playlist changed: '{pl.get('name', '')}' — {added_count} added, {removed_count} removed (old={len(old_ids)}, new={len(new_ids)})")
                         _update_automation_progress(auto_id,
                             log_line=f'"{pl.get("name", "")}" — {added_count} added, {removed_count} removed', log_type='success')
                         try:
                             if automation_engine:
                                 automation_engine.emit('playlist_changed', {
                                     'playlist_name': pl.get('name', ''),
+                                    'playlist_id': str(pl.get('id', '')),
                                     'old_count': str(len(old_ids)),
                                     'new_count': str(len(new_ids)),
                                     'added': str(added_count),
@@ -780,6 +782,7 @@ def _register_automation_handlers():
                         except Exception:
                             pass
                     else:
+                        print(f"⏭️ [AUTOMATION] No changes: '{pl.get('name', '')}' (tracks={len(old_ids)})")
                         _update_automation_progress(auto_id,
                             log_line=f'No changes: "{pl.get("name", "")}"', log_type='skip')
             except Exception as e:
@@ -27568,8 +27571,10 @@ def _run_playlist_discovery_worker(playlists, automation_id=None):
         # (no point triggering downstream sync if nothing changed)
         try:
             if automation_engine and total_discovered > 0:
+                _disc_pl_id = str(playlists[0]['id']) if len(playlists) == 1 else ''
                 automation_engine.emit('discovery_completed', {
                     'playlist_name': last_playlist_name if len(playlists) == 1 else f'{len(playlists)} playlists',
+                    'playlist_id': _disc_pl_id,
                     'total_tracks': str(total_tracks),
                     'discovered_count': str(total_discovered),
                     'failed_count': str(total_failed),