diff --git a/src/app/cli.py b/src/app/cli.py
index 5a907ce..d3d3add 100644
--- a/src/app/cli.py
+++ b/src/app/cli.py
@@ -88,7 +88,11 @@ def main(argv: list[str] | None = None) -> int:
         summary = ", ".join(f"{k}:{v}" for k, v in sorted(counts.items()))
         print(f"Playlist {pid}: {len(actions)} actions → {summary}")
         if args.apply and actions:
-            asyncio.run(executor.execute(actions, pl))
+            try:
+                asyncio.run(executor.execute(actions, pl))
+            except DependencyError as e:
+                print(f"ERROR: {e}")
+                return 2
             db.set_playlist_last_sync(pid)
             print(f"Applied actions for {pid}.")
 
diff --git a/src/app/core/sync/executor.py b/src/app/core/sync/executor.py
index c602340..08151ee 100644
--- a/src/app/core/sync/executor.py
+++ b/src/app/core/sync/executor.py
@@ -12,6 +12,7 @@ from ..sync.reorder import safe_multi_rename
 from ..database.db import Database
 from ..utils.yt import extract_playlist_id
 from ..events.event_bus import EventBus
+from ..utils.deps import ensure_ffmpeg_available, ensure_yt_dlp_available
 
 
 class ActionExecutor:
@@ -21,6 +22,8 @@ class ActionExecutor:
         self.bus = event_bus
 
     async def execute(self, actions: Iterable[SyncAction], playlist_cfg: dict) -> None:
+        self._preflight_dependencies(actions, playlist_cfg)
+
         save_path = Path(playlist_cfg.get("save_path", "./downloads")).resolve()
         mode = playlist_cfg.get("download_mode", "audio")
 
@@ -39,6 +42,23 @@ class ActionExecutor:
         # Finally, perform downloads concurrently
         await self._apply_downloads(actions, mode, audio_root, video_root, playlist_cfg)
 
+    def _preflight_dependencies(self, actions: Iterable[SyncAction], playlist_cfg: dict) -> None:
+        """
+        Fail fast on core runtime dependencies before doing any filesystem work.
+
+        This keeps errors consistent regardless of entrypoint (CLI, bootstrap, tests, etc.).
+        """
+        needs_download = any(a.type == SyncActionType.DOWNLOAD for a in actions)
+        if not needs_download:
+            return
+
+        # yt-dlp is required for any download job (Python API usage)
+        ensure_yt_dlp_available()
+
+        # ffmpeg/ffprobe are required for merges and audio extraction; check once up-front
+        ffmpeg_hint = playlist_cfg.get("ffmpeg_path", "ffmpeg")
+        ensure_ffmpeg_available(str(ffmpeg_hint) if ffmpeg_hint is not None else None)
+
     async def _apply_renames(self, actions: Iterable[SyncAction], audio_root: Path, video_root: Path, playlist_cfg: dict) -> None:
         playlist_id = extract_playlist_id(playlist_cfg.get("url", "")) or playlist_cfg.get("url", "")
         audio_renames = []
diff --git a/src/app/main.py b/src/app/main.py
index f2d82fc..2e6a935 100644
--- a/src/app/main.py
+++ b/src/app/main.py
@@ -37,7 +37,11 @@ def bootstrap(db_path: Path | None = None) -> None:
                 print(f"Plan → {summary}")
                 # Execute
                 import asyncio
-                asyncio.run(executor.execute(actions, pl))
+                try:
+                    asyncio.run(executor.execute(actions, pl))
+                except DependencyError as e:
+                    print(f"ERROR: {e}")
+                    continue
                 # Post summary (no DB readback yet)
                 pid = extract_playlist_id(pl.get('url', '')) or pl.get('url', '')
                 db.set_playlist_last_sync(pid)