diff --git a/src/get_playlists_v2.py b/src/get_playlists_v2.py
index 5e530dd..8e039c9 100644
--- a/src/get_playlists_v2.py
+++ b/src/get_playlists_v2.py
@@ -454,6 +454,18 @@ def update_playlist_if_needed(config, playlist_dir, media_dir):
             return playlist_file
         else:
             logger.info("✓ Playlist is up to date")
+            # Even when the playlist version matches, ensure media files exist locally.
+            # The media folder might be empty (e.g. fresh install or deleted files).
+            logger.info("📥 Checking for missing media files...")
+            ssl_manager = auth.ssl_manager if config.get('use_https', True) else None
+            server_url = auth.auth_data.get('server_url', '')
+            downloaded = download_media_files(
+                server_data.get('playlist', []), media_dir, ssl_manager, server_url
+            )
+            if downloaded:
+                server_data['playlist'] = downloaded
+                # Re-save playlist with updated URLs if needed
+                save_playlist(server_data, playlist_dir)
             return playlist_file
     
     except Exception as e:
diff --git a/src/main.py b/src/main.py
index ce16dd0..1449a94 100644
--- a/src/main.py
+++ b/src/main.py
@@ -1522,6 +1522,9 @@ class SignagePlayer(Widget):
     def _on_video_eos(self, instance):
         """Callback when video reaches end of stream"""
         Logger.debug("SignagePlayer: Video finished playing (EOS)")
+        # Unschedule any pending timer and advance to next media
+        Clock.unschedule(self.next_media)
+        Clock.schedule_once(self.next_media, 0.5)
     
     def _on_video_loaded(self, instance, value):
         """Callback when video is loaded - log video information"""
diff --git a/windows/development-track.md b/windows/development-track.md
index 72b7267..12cb0c9 100644
--- a/windows/development-track.md
+++ b/windows/development-track.md
@@ -99,12 +99,22 @@
 - **Files:** `windows/run_win.py`, `windows/cef_browser.py`
 
 ### [BUG-008] Intro video and media files not found at runtime
-- **Status:** 🟡 **Known** 2026-07-24
+- **Status:** ✅ **Fixed** 2026-07-24
 - **Symptom:** `[ERROR] [Image] Error loading <...intro1.mp4>` — intro
   broken. Also `❌ Media file not found` for playlist items.
-- **Root cause:** Media files are not bundled in .exe — must be downloaded
-  from server. Player connects (v16 received) but hasn't downloaded files.
-- **Fix:** Verify server is sending media content and player downloads it.
+- **Root cause:** Media download only ran when `server_version > local_version`.
+  When versions matched (v16 == v16), `download_media_files` was never called
+  → media folder stayed empty.
+- **Fix:** Added download check in the "up to date" branch — now downloads
+  missing media files even when playlist version hasn't changed.
+
+### [BUG-009] Video never advances to next item (EOS handler empty)
+- **Status:** ✅ **Fixed** 2026-07-24
+- **Symptom:** Video plays but never advances to the next playlist item.
+- **Root cause:** `_on_video_eos()` callback was a stub — just logged
+  "Video finished playing (EOS)" but never called `next_media()`.
+- **Fix:** Added `Clock.unschedule(self.next_media)` + `Clock.schedule_once`
+  to advance after 0.5s when a video reaches end of stream.
 
 ---