Fix organize-by-playlist downloads: library entries, wishlist, and stale Spotify cache

Persist organize_by_playlist on mirrored playlists and run playlist-folder
downloads from the auto-sync pipeline instead of the global wishlist phase.
Register SoulSync library rows after playlist-folder post-processing, route
failed organize batches to the wishlist correctly, and skip sync-time
unmatched wishlist only when organize download handles retries.

Invalidate stale playlist track caches on refresh (Spotify and Deezer ARL),
re-mirror on refetch, and improve standalone playlist modals (re-analysis,
Open in Mirrored). Add filesystem missing-track detection and tests.

Co-authored-by: Cursor <cursoragent@cursor.com>

core/automation/deps.py

@@ -28,7 +28,7 @@ from __future__ import annotations
 
 import threading
 from dataclasses import dataclass, field
-from typing import Any, Callable, Optional
+from typing import Any, Callable, Dict, Optional
 
 
 @dataclass
@@ -105,6 +105,8 @@ class AutomationDeps:
     # --- Playlist pipeline entry points ---
     run_playlist_discovery_worker: Callable[..., Any]
     run_sync_task: Callable[..., Any]
+    run_playlist_organize_download: Callable[..., Dict[str, Any]]
+    missing_download_executor: Any
     load_sync_status_file: Callable[[], dict]
     get_deezer_client: Callable[[], Any]
     parse_youtube_playlist: Callable[[str], Any]

core/automation/handlers/_pipeline_shared.py

@@ -148,9 +148,45 @@ def run_sync_and_wishlist(
         log_type='success' if sync_errors == 0 else 'warning',
     )
 
+    organize_playlists = [pl for pl in playlists if pl.get('organize_by_playlist')]
+    organize_started = 0
+    if organize_playlists and hasattr(deps, 'run_playlist_organize_download'):
+        for pl in organize_playlists:
+            pl_id = pl.get('id')
+            if not pl_id:
+                continue
+            pl_name = pl.get('name', '')
+            try:
+                org_result = deps.run_playlist_organize_download(
+                    mirrored_playlist_id=int(pl_id),
+                    automation_id=automation_id,
+                )
+                if org_result.get('status') == 'started':
+                    organize_started += 1
+                    deps.update_progress(
+                        automation_id,
+                        log_line=f'Organize download started for "{pl_name}"',
+                        log_type='success',
+                    )
+                elif org_result.get('status') == 'skipped':
+                    deps.update_progress(
+                        automation_id,
+                        log_line=f'Organize download skipped for "{pl_name}": {org_result.get("reason", "")}',
+                        log_type='skip',
+                    )
+            except Exception as org_err:  # noqa: BLE001
+                deps.update_progress(
+                    automation_id,
+                    log_line=f'Organize download error for "{pl_name}": {org_err}',
+                    log_type='warning',
+                )
+
+    all_organize = bool(playlists) and len(organize_playlists) == len(playlists)
+    effective_skip_wishlist = skip_wishlist or all_organize
+
     wishlist_queued = run_wishlist_phase(
         deps, automation_id,
-        skip=skip_wishlist,
+        skip=effective_skip_wishlist,
         progress_pct=progress_end + 1,
         wishlist_phase_label=wishlist_phase_label,
         wishlist_phase_start_log=wishlist_phase_start_log,
@@ -161,6 +197,7 @@ def run_sync_and_wishlist(
         'skipped': total_skipped,
         'errors': sync_errors,
         'wishlist_queued': wishlist_queued,
+        'organize_downloads_started': organize_started,
     }
 
 

core/automation/handlers/sync_playlist.py

@@ -180,9 +180,11 @@ def auto_sync_playlist(config: Dict[str, Any], deps: AutomationDeps) -> Dict[str
         log_line=f'Starting sync: {len(tracks_json)} tracks',
         log_type='success',
     )
+    skip_wishlist_add = bool(pl.get('organize_by_playlist'))
     threading.Thread(
         target=deps.run_sync_task,
         args=(sync_id, pl['name'], tracks_json, auto_id, 1, pl.get('image_url', '')),
+        kwargs={'skip_wishlist_add': skip_wishlist_add},
         daemon=True,
         name=f'auto-sync-{playlist_id}',
     ).start()

core/discovery/sync.py

@@ -133,7 +133,17 @@ async def _database_only_find_track(spotify_track, candidate_pool=None):
         return None, 0.0
 
 
-def run_sync_task(playlist_id, playlist_name, tracks_json, automation_id=None, profile_id=1, playlist_image_url='', deps: SyncDeps = None, sync_mode: str = 'replace'):
+def run_sync_task(
+    playlist_id,
+    playlist_name,
+    tracks_json,
+    automation_id=None,
+    profile_id=1,
+    playlist_image_url='',
+    deps: SyncDeps = None,
+    sync_mode: str = 'replace',
+    skip_wishlist_add: bool = False,
+):
     """The actual sync function that runs in the background thread."""
     sync_states = deps.sync_states
     sync_lock = deps.sync_lock
@@ -360,7 +370,14 @@ def run_sync_task(playlist_id, playlist_name, tracks_json, automation_id=None, p
         # Wing It mode — skip wishlist for unmatched tracks
         with sync_lock:
             is_wing_it = sync_states.get(playlist_id, {}).get('wing_it', False)
+        sync_service._skip_unmatched_wishlist = is_wing_it or skip_wishlist_add
         sync_service._skip_wishlist = is_wing_it
+        if skip_wishlist_add:
+            logger.info(
+                "[Organize by Playlist] Skipping sync-time wishlist for '%s' — "
+                "organize download + batch failure handling cover missing tracks",
+                playlist_name,
+            )
 
         # Run the sync (this is a blocking call within this thread)
         result = deps.run_async(sync_service.sync_playlist(playlist, download_missing=False, profile_id=profile_id, sync_mode=sync_mode))

core/downloads/master.py

@@ -343,6 +343,10 @@ def run_full_missing_tracks_process(batch_id, playlist_id, tracks_json, deps: Ma
         batch_is_album = False
         batch_profile_id = 1
         batch_source = 'spotify'
+        batch_playlist_folder_mode = False
+        batch_playlist_name = 'Unknown Playlist'
+        batch_playlist_id = playlist_id
+        batch_source_playlist_ref = ''
         with tasks_lock:
             if batch_id in download_batches:
                 force_download_all = download_batches[batch_id].get('force_download_all', False)
@@ -352,6 +356,29 @@ def run_full_missing_tracks_process(batch_id, playlist_id, tracks_json, deps: Ma
                 batch_artist_context = download_batches[batch_id].get('artist_context')
                 batch_profile_id = download_batches[batch_id].get('profile_id', 1) or 1
                 batch_source = download_batches[batch_id].get('batch_source', 'spotify') or 'spotify'
+                batch_playlist_folder_mode = download_batches[batch_id].get('playlist_folder_mode', False)
+                batch_playlist_name = download_batches[batch_id].get('playlist_name', 'Unknown Playlist')
+                batch_playlist_id = download_batches[batch_id].get('playlist_id', playlist_id)
+                batch_source_playlist_ref = (
+                    download_batches[batch_id].get('source_playlist_ref') or ''
+                ).strip()
+
+        from core.downloads.playlist_folder import (
+            resolve_playlist_folder_mode_for_batch,
+            track_exists_in_playlist_folder_from_track_data,
+        )
+        effective_playlist_folder_mode, effective_playlist_name = resolve_playlist_folder_mode_for_batch(
+            db,
+            playlist_id=str(batch_playlist_id),
+            playlist_name=batch_playlist_name,
+            batch_playlist_folder_mode=batch_playlist_folder_mode,
+            profile_id=batch_profile_id,
+        )
+        if effective_playlist_folder_mode and not batch_playlist_folder_mode:
+            with tasks_lock:
+                if batch_id in download_batches:
+                    download_batches[batch_id]['playlist_folder_mode'] = True
+                    download_batches[batch_id]['playlist_name'] = effective_playlist_name
 
         if force_download_all:
             logger.warning(f"[Force Download] Force download mode enabled for batch {batch_id} - treating all tracks as missing")
@@ -445,6 +472,27 @@ def run_full_missing_tracks_process(batch_id, playlist_id, tracks_json, deps: Ma
                 })
                 continue
 
+            if effective_playlist_folder_mode and not force_download_all:
+                if track_exists_in_playlist_folder_from_track_data(
+                    effective_playlist_name,
+                    track_data,
+                ):
+                    logger.info(
+                        f"[Playlist Folder] '{track_name}' already on disk in playlist folder — skipping download"
+                    )
+                    try:
+                        deps.check_and_remove_track_from_wishlist_by_metadata(track_data)
+                    except Exception as _wl_err:
+                        logger.debug(f"[Playlist Folder] Wishlist removal attempt failed: {_wl_err}")
+                    analysis_results.append({
+                        'track_index': track_index,
+                        'track': track_data,
+                        'found': True,
+                        'confidence': 1.0,
+                        'match_reason': 'playlist_folder_file',
+                    })
+                    continue
+
             # Skip database check if force download is enabled
             if force_download_all:
                 logger.warning(f"[Force Download] Skipping database check for '{track_name}' - treating as missing")
@@ -982,13 +1030,45 @@ def run_full_missing_tracks_process(batch_id, playlist_id, tracks_json, deps: Ma
                         logger.info(f"[Wishlist] Added album context for: '{track_info.get('name')}' -> '{album_ctx['name']}'")
 
 
-                # Add playlist folder mode flag for sync page playlists
-                if batch_playlist_folder_mode:
+                # Add playlist folder mode flag for sync page playlists and wishlist
+                # tracks tied to a mirrored playlist with organize_by_playlist enabled.
+                task_pl_folder_mode = batch_playlist_folder_mode
+                task_pl_name = batch_playlist_name
+                if not task_pl_folder_mode and playlist_id == 'wishlist':
+                    wl_source = track_info.get('source_info') or {}
+                    if isinstance(wl_source, str):
+                        try:
+                            wl_source = json.loads(wl_source)
+                        except (json.JSONDecodeError, TypeError):
+                            wl_source = {}
+                    wl_pl_ref = wl_source.get('playlist_id')
+                    wl_pl_name = wl_source.get('playlist_name')
+                    if wl_pl_ref and hasattr(db, 'resolve_mirrored_playlist'):
+                        wl_mirrored = db.resolve_mirrored_playlist(
+                            wl_pl_ref,
+                            profile_id=batch_profile_id,
+                        )
+                        if wl_mirrored and wl_mirrored.get('organize_by_playlist'):
+                            task_pl_folder_mode = True
+                            task_pl_name = wl_pl_name or wl_mirrored.get('name') or batch_playlist_name
+                if task_pl_folder_mode:
                     track_info['_playlist_folder_mode'] = True
-                    track_info['_playlist_name'] = batch_playlist_name
-                    logger.info(f"[Task Creation] Added playlist folder mode for: {track_info.get('name')} → {batch_playlist_name}")
+                    track_info['_playlist_name'] = task_pl_name
+                    if batch_source_playlist_ref:
+                        track_info['source_info'] = {
+                            'playlist_id': batch_source_playlist_ref,
+                            'playlist_name': task_pl_name,
+                            'source': batch_source,
+                        }
+                    logger.info(
+                        f"[Task Creation] Added playlist folder mode for: "
+                        f"{track_info.get('name')} → {task_pl_name}"
+                    )
                 else:
-                    logger.debug(f"[Debug] Task Creation - playlist folder mode NOT enabled for: {track_info.get('name')}")
+                    logger.debug(
+                        f"[Debug] Task Creation - playlist folder mode NOT enabled for: "
+                        f"{track_info.get('name')}"
+                    )
 
                 download_tasks[task_id] = {
                     'status': 'pending', 'track_info': track_info,

core/downloads/playlist_folder.py

@@ -0,0 +1,123 @@
+"""Playlist-folder layout helpers for download analysis and existence checks."""
+
+from __future__ import annotations
+
+import os
+from typing import Any, Dict, List, Optional
+
+from core.downloads.file_finder import AUDIO_EXTENSIONS
+from core.imports.paths import (
+    _get_config_manager,
+    docker_resolve_path,
+    get_file_path_from_template,
+    sanitize_filename,
+)
+
+
+def _first_artist_name(artists: Any) -> str:
+    if not artists:
+        return ''
+    first = artists[0]
+    if isinstance(first, dict):
+        return str(first.get('name', '') or '').strip()
+    return str(first).strip()
+
+
+def candidate_playlist_folder_paths(
+    playlist_name: str,
+    artist: str,
+    title: str,
+) -> List[str]:
+    """Return absolute candidate paths for a track in playlist-folder layout."""
+    if not playlist_name or not title:
+        return []
+
+    artist_name = (artist or 'Unknown Artist').strip()
+    track_name = title.strip()
+    transfer_dir = docker_resolve_path(
+        _get_config_manager().get('soulseek.transfer_path', './Transfer')
+    )
+
+    template_context = {
+        'artist': artist_name,
+        'albumartist': artist_name,
+        'album': track_name,
+        'title': track_name,
+        'playlist_name': playlist_name,
+        'track_number': 1,
+        'disc_number': 1,
+        'year': '',
+        'quality': '',
+        'albumtype': '',
+        '_artists_list': [{'name': artist_name}],
+    }
+
+    candidates: List[str] = []
+    folder_path, filename_base = get_file_path_from_template(template_context, 'playlist_path')
+    if folder_path and filename_base:
+        base = os.path.join(transfer_dir, folder_path, filename_base)
+        for ext in AUDIO_EXTENSIONS:
+            candidates.append(base + ext)
+    else:
+        playlist_name_sanitized = sanitize_filename(playlist_name)
+        playlist_dir = os.path.join(transfer_dir, playlist_name_sanitized)
+        artist_name_sanitized = sanitize_filename(artist_name)
+        track_name_sanitized = sanitize_filename(track_name)
+        stem = f'{artist_name_sanitized} - {track_name_sanitized}'
+        for ext in AUDIO_EXTENSIONS:
+            candidates.append(os.path.join(playlist_dir, stem + ext))
+
+    return candidates
+
+
+def track_exists_in_playlist_folder(
+    playlist_name: str,
+    artist: str,
+    title: str,
+) -> bool:
+    """Return True if any audio file exists at the playlist-folder path for this track."""
+    for path in candidate_playlist_folder_paths(playlist_name, artist, title):
+        if os.path.isfile(path):
+            return True
+    return False
+
+
+def track_exists_in_playlist_folder_from_track_data(
+    playlist_name: str,
+    track_data: Dict[str, Any],
+) -> bool:
+    """Check playlist-folder existence using Spotify-style track payload."""
+    title = track_data.get('name', '') or track_data.get('track_name', '')
+    artist = _first_artist_name(track_data.get('artists', []))
+    if not artist:
+        artist = str(track_data.get('artist_name', '') or '').strip()
+    return track_exists_in_playlist_folder(playlist_name, artist, title)
+
+
+def resolve_playlist_folder_mode_for_batch(
+    db: Any,
+    *,
+    playlist_id: str,
+    playlist_name: str,
+    batch_playlist_folder_mode: bool,
+    profile_id: int = 1,
+) -> tuple[bool, str]:
+    """Merge batch flag with persisted mirrored-playlist preference."""
+    if batch_playlist_folder_mode:
+        return True, playlist_name
+
+    if not hasattr(db, 'resolve_mirrored_playlist'):
+        return False, playlist_name
+
+    mirrored = db.resolve_mirrored_playlist(playlist_id, profile_id=profile_id)
+    if mirrored and mirrored.get('organize_by_playlist'):
+        return True, mirrored.get('name') or playlist_name
+    return False, playlist_name
+
+
+__all__ = [
+    'candidate_playlist_folder_paths',
+    'track_exists_in_playlist_folder',
+    'track_exists_in_playlist_folder_from_track_data',
+    'resolve_playlist_folder_mode_for_batch',
+]

core/imports/pipeline.py

@@ -563,6 +563,26 @@ def post_process_matched_download(context_key, context, file_path, runtime, meta
             record_library_history_download(context)
             record_download_provenance(context)
 
+            try:
+                pf_album_info = build_import_album_info(context, force_album=False)
+                if not pf_album_info or not pf_album_info.get("album_name"):
+                    pf_album_info = {
+                        "is_album": True,
+                        "album_name": playlist_name,
+                        "track_number": track_info.get("track_number", 1) or 1,
+                        "disc_number": track_info.get("disc_number", 1) or 1,
+                        "clean_track_name": get_import_clean_title(
+                            context,
+                            default=get_import_original_search(context).get("title", "Unknown"),
+                        ),
+                        "source": get_import_source(context) or "spotify",
+                    }
+                elif not pf_album_info.get("is_album"):
+                    pf_album_info["is_album"] = True
+                record_soulsync_library_entry(context, artist_context, pf_album_info)
+            except Exception as lib_err:
+                logger.error(f"[Playlist Folder] SoulSync library registration failed: {lib_err}")
+
             task_id = context.get('task_id')
             batch_id = context.get('batch_id')
             if task_id and batch_id:

core/playlists/organize_download.py

@@ -0,0 +1,174 @@
+"""Download missing tracks into playlist-folder layout for mirrored playlists."""
+
+from __future__ import annotations
+
+import json
+import logging
+import uuid
+from typing import Any, Callable, Dict, List, Optional
+
+logger = logging.getLogger(__name__)
+
+
+def mirrored_tracks_to_download_json(tracks: List[Dict[str, Any]]) -> List[Dict[str, Any]]:
+    """Convert mirrored playlist rows to the payload expected by the download master."""
+    out: List[Dict[str, Any]] = []
+    for t in tracks:
+        extra = {}
+        if t.get('extra_data'):
+            try:
+                extra = json.loads(t['extra_data']) if isinstance(t['extra_data'], str) else t['extra_data']
+            except (json.JSONDecodeError, TypeError):
+                extra = {}
+
+        if extra.get('discovered') and extra.get('matched_data'):
+            md = extra['matched_data']
+            album_raw = md.get('album', '')
+            album_obj = album_raw if isinstance(album_raw, dict) else {'name': album_raw or ''}
+            entry = {
+                'name': md.get('name', ''),
+                'artists': md.get('artists', [{'name': t.get('artist_name', '')}]),
+                'album': album_obj,
+                'duration_ms': md.get('duration_ms', 0),
+                'id': md.get('id', ''),
+            }
+            if md.get('track_number'):
+                entry['track_number'] = md['track_number']
+            if md.get('disc_number'):
+                entry['disc_number'] = md['disc_number']
+            out.append(entry)
+            continue
+
+        hint = extra.get('spotify_hint', {})
+        track_image = (t.get('image_url') or '').strip()
+        album_obj = {
+            'name': (t.get('album_name') or '').strip(),
+            'images': [{'url': track_image, 'height': 300, 'width': 300}] if track_image else [],
+        }
+
+        if hint.get('id') and hint.get('name'):
+            hint_artists = hint.get('artists', [])
+            if hint_artists and isinstance(hint_artists[0], str):
+                hint_artists = [{'name': a} for a in hint_artists]
+            elif not hint_artists:
+                hint_artists = [{'name': t.get('artist_name', '')}]
+            out.append({
+                'name': hint['name'],
+                'artists': hint_artists,
+                'album': album_obj,
+                'duration_ms': t.get('duration_ms', 0),
+                'id': hint['id'],
+            })
+        elif t.get('source_track_id') and (t.get('track_name') or '').strip():
+            out.append({
+                'name': t['track_name'].strip(),
+                'artists': [{'name': (t.get('artist_name') or '').strip() or 'Unknown Artist'}],
+                'album': album_obj,
+                'duration_ms': t.get('duration_ms', 0),
+                'id': t['source_track_id'],
+            })
+    return out
+
+
+def run_playlist_organize_download(
+    deps: Any,
+    *,
+    mirrored_playlist_id: int,
+    profile_id: int = 1,
+    get_batch_max_concurrent: Callable[[bool], int],
+    run_full_missing_tracks_process: Callable[..., Any],
+    record_sync_history_start: Optional[Callable[..., Any]] = None,
+    detect_sync_source: Optional[Callable[[str], str]] = None,
+) -> Dict[str, Any]:
+    """Queue a playlist-folder missing-tracks batch for one mirrored playlist."""
+    db = deps.get_database()
+    pl = db.get_mirrored_playlist(int(mirrored_playlist_id))
+    if not pl:
+        return {'status': 'error', 'reason': 'Playlist not found'}
+
+    source_playlist_ref = (pl.get('source_playlist_id') or '').strip()
+    source = (pl.get('source') or 'spotify').strip() or 'spotify'
+
+    tracks = db.get_mirrored_playlist_tracks(int(mirrored_playlist_id))
+    tracks_json = mirrored_tracks_to_download_json(tracks)
+    if not tracks_json:
+        return {'status': 'skipped', 'reason': 'No processable tracks'}
+
+    batch_id = str(uuid.uuid4())
+    playlist_id = str(mirrored_playlist_id)
+    playlist_name = pl.get('name', 'Unknown Playlist')
+
+    download_batches = deps.get_download_batches()
+    tasks_lock = deps.tasks_lock
+
+    with tasks_lock:
+        active_analysis = sum(
+            1 for batch in download_batches.values() if batch.get('phase') == 'analysis'
+        )
+        if active_analysis >= 3:
+            return {'status': 'error', 'reason': 'Too many analysis processes running'}
+
+        download_batches[batch_id] = {
+            'phase': 'analysis',
+            'playlist_id': playlist_id,
+            'playlist_name': playlist_name,
+            'queue': [],
+            'active_count': 0,
+            'max_concurrent': get_batch_max_concurrent(False),
+            'permanently_failed_tracks': [],
+            'cancelled_tracks': set(),
+            'queue_index': 0,
+            'analysis_total': len(tracks_json),
+            'profile_id': profile_id,
+            'analysis_processed': 0,
+            'analysis_results': [],
+            'force_download_all': False,
+            'ignore_manual_matches': False,
+            'playlist_folder_mode': True,
+            'is_album_download': False,
+            'album_context': None,
+            'artist_context': None,
+            'wing_it': False,
+            'batch_source': source,
+            'auto_initiated': False,
+            'organize_by_playlist': True,
+            'source_playlist_ref': source_playlist_ref,
+            'mirrored_playlist_id': int(mirrored_playlist_id),
+        }
+
+    if record_sync_history_start:
+        try:
+            record_sync_history_start(
+                batch_id,
+                playlist_id,
+                playlist_name,
+                tracks_json,
+                False,
+                None,
+                None,
+                True,
+                source_page='automation',
+            )
+        except Exception as hist_err:
+            logger.debug("organize download sync history: %s", hist_err)
+
+    deps.missing_download_executor.submit(
+        run_full_missing_tracks_process,
+        batch_id,
+        playlist_id,
+        tracks_json,
+    )
+    logger.info(
+        "[Organize Download] Started batch %s for mirrored playlist %s (%s tracks)",
+        batch_id,
+        playlist_name,
+        len(tracks_json),
+    )
+    return {
+        'status': 'started',
+        'batch_id': batch_id,
+        'track_count': len(tracks_json),
+    }
+
+
+__all__ = ['mirrored_tracks_to_download_json', 'run_playlist_organize_download']

core/wishlist/processing.py

@@ -394,12 +394,17 @@ def resolve_wishlist_source_type_for_batch(batch: Dict[str, Any]) -> str:
 def build_wishlist_source_context(batch: Dict[str, Any], current_time: datetime | None = None) -> Dict[str, Any]:
     """Build the source_context payload used when adding failed tracks back to the wishlist."""
     current_time = current_time or datetime.now()
+    playlist_id = batch.get('source_playlist_ref') or batch.get('playlist_id')
     context = {
         'playlist_name': batch.get('playlist_name', 'Unknown Playlist'),
-        'playlist_id': batch.get('playlist_id', None),
+        'playlist_id': playlist_id,
         'added_from': 'webui_modal',
         'timestamp': current_time.isoformat(),
     }
+    if batch.get('mirrored_playlist_id') is not None:
+        context['mirrored_playlist_id'] = batch.get('mirrored_playlist_id')
+    if batch.get('organize_by_playlist'):
+        context['organize_by_playlist'] = True
     # Preserve album-batch provenance so wishlist requeue has a real signal
     # for album-vs-single routing instead of relying on per-track album dicts
     # that may have been mangled by reconstruction fallbacks.

database/music_database.py

@@ -571,6 +571,7 @@ class MusicDatabase:
 
             # Add explored_at to mirrored_playlists (migration)
             self._add_mirrored_playlist_explored_column(cursor)
+            self._add_mirrored_playlist_organize_column(cursor)
 
             # Add notification columns to automations (migration)
             self._add_automation_notify_columns(cursor)
@@ -970,6 +971,19 @@ class MusicDatabase:
         except Exception as e:
             logger.error(f"Error adding explored_at column to mirrored_playlists: {e}")
 
+    def _add_mirrored_playlist_organize_column(self, cursor):
+        """Add organize_by_playlist preference for playlist-folder downloads."""
+        try:
+            cursor.execute("PRAGMA table_info(mirrored_playlists)")
+            cols = [c[1] for c in cursor.fetchall()]
+            if 'organize_by_playlist' not in cols:
+                cursor.execute(
+                    "ALTER TABLE mirrored_playlists ADD COLUMN organize_by_playlist INTEGER NOT NULL DEFAULT 0"
+                )
+                logger.info("Added organize_by_playlist column to mirrored_playlists table")
+        except Exception as e:
+            logger.error(f"Error adding organize_by_playlist column to mirrored_playlists: {e}")
+
     def _add_automation_notify_columns(self, cursor):
         """Add notification and result columns to automations table."""
         try:
@@ -12171,7 +12185,11 @@ class MusicDatabase:
                     WHERE profile_id = ?
                     ORDER BY updated_at DESC
                 """, (profile_id,))
-                return [dict(row) for row in cursor.fetchall()]
+                return [
+                    self._normalize_mirrored_playlist_row(row)
+                    for row in cursor.fetchall()
+                    if row
+                ]
         except Exception as e:
             logger.error(f"Error getting mirrored playlists: {e}")
             return []
@@ -12198,11 +12216,80 @@ class MusicDatabase:
                 cursor = conn.cursor()
                 cursor.execute("SELECT * FROM mirrored_playlists WHERE id = ?", (playlist_id,))
                 row = cursor.fetchone()
-                return dict(row) if row else None
+                return self._normalize_mirrored_playlist_row(row)
         except Exception as e:
             logger.error(f"Error getting mirrored playlist: {e}")
             return None
 
+    @staticmethod
+    def _normalize_mirrored_playlist_row(row) -> Optional[Dict]:
+        if not row:
+            return None
+        pl = dict(row)
+        pl['organize_by_playlist'] = bool(pl.get('organize_by_playlist', 0))
+        return pl
+
+    def get_mirrored_playlist_by_source(
+        self,
+        source: str,
+        source_playlist_id: str,
+        profile_id: int = 1,
+    ) -> Optional[Dict]:
+        """Return a mirrored playlist by upstream source id."""
+        try:
+            with self._get_connection() as conn:
+                cursor = conn.cursor()
+                cursor.execute(
+                    """
+                    SELECT * FROM mirrored_playlists
+                    WHERE source = ? AND source_playlist_id = ? AND profile_id = ?
+                    """,
+                    (source, str(source_playlist_id), profile_id),
+                )
+                row = cursor.fetchone()
+                return self._normalize_mirrored_playlist_row(row)
+        except Exception as e:
+            logger.error(f"Error getting mirrored playlist by source: {e}")
+            return None
+
+    def resolve_mirrored_playlist(
+        self,
+        playlist_ref: Any,
+        profile_id: int = 1,
+        *,
+        default_source: str = 'spotify',
+    ) -> Optional[Dict]:
+        """Resolve a mirrored playlist from numeric id or upstream source id."""
+        if playlist_ref is None or playlist_ref == '':
+            return None
+        ref = str(playlist_ref).strip()
+        if ref.isdigit():
+            return self.get_mirrored_playlist(int(ref))
+        return self.get_mirrored_playlist_by_source(default_source, ref, profile_id)
+
+    def set_mirrored_playlist_organize_by_playlist(
+        self,
+        playlist_id: int,
+        enabled: bool,
+    ) -> bool:
+        """Persist whether downloads for this playlist use playlist-folder layout."""
+        try:
+            with self._get_connection() as conn:
+                cursor = conn.cursor()
+                cursor.execute(
+                    """
+                    UPDATE mirrored_playlists
+                    SET organize_by_playlist = ?, updated_at = CURRENT_TIMESTAMP
+                    WHERE id = ?
+                    """,
+                    (1 if enabled else 0, playlist_id),
+                )
+                conn.commit()
+                return cursor.rowcount > 0
+        except Exception as e:
+            logger.error(f"Error updating organize_by_playlist for playlist {playlist_id}: {e}")
+            return False
+
     def get_mirrored_playlist_tracks(self, playlist_id: int) -> List[Dict]:
         """Return all tracks for a mirrored playlist ordered by position."""
         try:

services/sync_service.py

@@ -357,8 +357,11 @@ class PlaylistSyncService:
 
             # Auto-add unmatched tracks to wishlist (skip in Wing It mode)
             wishlist_added_count = 0
-            if unmatched_tracks and getattr(self, '_skip_wishlist', False):
-                logger.info(f"[Wing It] Skipping wishlist for {len(unmatched_tracks)} unmatched tracks")
+            if unmatched_tracks and getattr(self, '_skip_unmatched_wishlist', False):
+                logger.info(
+                    "Skipping sync-time wishlist for %s unmatched tracks (wing-it or organize-by-playlist)",
+                    len(unmatched_tracks),
+                )
                 unmatched_tracks = []  # Clear so the loop below doesn't run
             if unmatched_tracks:
                 try:

tests/automation/test_handler_registration.py

@@ -126,6 +126,8 @@ def _build_deps(engine, scan_mgr=None) -> AutomationDeps:
         get_watchlist_scan_state=lambda: {},
         run_playlist_discovery_worker=lambda *a, **k: None,
         run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'skipped'},
+        missing_download_executor=None,
         load_sync_status_file=lambda: {},
         get_deezer_client=lambda: None,
         parse_youtube_playlist=lambda url: None,

tests/automation/test_handlers_maintenance.py

@@ -73,6 +73,8 @@ def _build_deps(**overrides) -> AutomationDeps:
         get_watchlist_scan_state=lambda: {},
         run_playlist_discovery_worker=lambda *a, **k: None,
         run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'skipped'},
+        missing_download_executor=None,
         load_sync_status_file=lambda: {},
         get_deezer_client=lambda: None,
         parse_youtube_playlist=lambda url: None,

tests/automation/test_handlers_personalized_pipeline.py

@@ -47,6 +47,8 @@ def _build_deps(**overrides) -> AutomationDeps:
         get_watchlist_scan_state=lambda: {},
         run_playlist_discovery_worker=lambda *a, **k: None,
         run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'skipped'},
+        missing_download_executor=None,
         load_sync_status_file=lambda: {},
         get_deezer_client=lambda: None,
         parse_youtube_playlist=lambda url: None,

tests/automation/test_handlers_playlist.py

@@ -108,6 +108,8 @@ def _build_deps(**overrides) -> AutomationDeps:
         get_watchlist_scan_state=lambda: {},
         run_playlist_discovery_worker=lambda *a, **k: None,
         run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'skipped'},
+        missing_download_executor=None,
         load_sync_status_file=lambda: {},
         get_deezer_client=lambda: None,
         parse_youtube_playlist=lambda url: None,
@@ -737,6 +739,35 @@ class TestSyncPlaylist:
             time.sleep(0.01)
         assert len(sync_calls) == 1
 
+    def test_organize_by_playlist_passes_skip_wishlist_add(self):
+        discovered_track = {
+            'extra_data': json.dumps({
+                'discovered': True,
+                'matched_data': {
+                    'id': 'spot-1', 'name': 'Track', 'artists': [{'name': 'X'}],
+                    'album': {'name': 'Album'}, 'duration_ms': 200000,
+                },
+            }),
+            'artist_name': 'X',
+        }
+        db = _StubDB(
+            playlists=[{'id': 1, 'name': 'P', 'organize_by_playlist': True}],
+            playlist_tracks={1: [discovered_track]},
+        )
+        sync_calls: List[tuple] = []
+        deps = _build_deps(
+            get_database=lambda: db,
+            run_sync_task=lambda *a, **k: sync_calls.append((a, k)),
+        )
+        auto_sync_playlist({'playlist_id': '1'}, deps)
+        for _ in range(50):
+            if sync_calls:
+                break
+            import time
+            time.sleep(0.01)
+        assert sync_calls
+        assert sync_calls[0][1].get('skip_wishlist_add') is True
+
     def test_unchanged_since_last_sync_returns_skipped(self):
         discovered_track = {
             'extra_data': json.dumps({

tests/automation/test_handlers_simple.py

@@ -60,6 +60,8 @@ def _build_deps(**overrides: Any) -> AutomationDeps:
         get_watchlist_scan_state=lambda: {},
         run_playlist_discovery_worker=lambda *a, **k: None,
         run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'skipped'},
+        missing_download_executor=None,
         load_sync_status_file=lambda: {},
         get_deezer_client=lambda: None,
         parse_youtube_playlist=lambda url: None,

tests/automation/test_playlist_pipeline_folder_mode.py

@@ -0,0 +1,117 @@
+"""Tests for organize-by-playlist integration in the playlist pipeline tail."""
+
+from unittest.mock import MagicMock
+
+from core.automation.deps import AutomationDeps, AutomationState
+from core.automation.handlers._pipeline_shared import run_sync_and_wishlist
+import threading
+
+
+def _minimal_deps(**overrides):
+    base = dict(
+        engine=MagicMock(),
+        state=AutomationState(),
+        config_manager=MagicMock(),
+        update_progress=lambda *a, **k: None,
+        logger=MagicMock(),
+        get_database=lambda: MagicMock(),
+        spotify_client=None,
+        tidal_client=None,
+        web_scan_manager=None,
+        process_wishlist_automatically=lambda **k: None,
+        process_watchlist_scan_automatically=lambda **k: None,
+        is_wishlist_actually_processing=lambda: False,
+        is_watchlist_actually_scanning=lambda: False,
+        get_watchlist_scan_state=lambda: {},
+        run_playlist_discovery_worker=lambda *a, **k: None,
+        run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'started', 'batch_id': 'b1'},
+        missing_download_executor=None,
+        load_sync_status_file=lambda: {},
+        get_deezer_client=lambda: None,
+        parse_youtube_playlist=lambda url: None,
+        get_sync_states=lambda: {},
+        set_db_update_automation_id=lambda v: None,
+        get_db_update_state=lambda: {},
+        db_update_lock=threading.Lock(),
+        db_update_executor=None,
+        run_db_update_task=lambda *a, **k: None,
+        run_deep_scan_task=lambda *a, **k: None,
+        get_duplicate_cleaner_state=lambda: {},
+        duplicate_cleaner_lock=threading.Lock(),
+        duplicate_cleaner_executor=None,
+        run_duplicate_cleaner=lambda: None,
+        get_quality_scanner_state=lambda: {},
+        quality_scanner_lock=threading.Lock(),
+        quality_scanner_executor=None,
+        run_quality_scanner=lambda *a, **k: None,
+        download_orchestrator=None,
+        run_async=lambda coro: None,
+        tasks_lock=threading.Lock(),
+        get_download_batches=lambda: {},
+        get_download_tasks=lambda: {},
+        sweep_empty_download_directories=lambda: 0,
+        get_staging_path=lambda: '/staging',
+        docker_resolve_path=lambda p: p,
+        get_current_profile_id=lambda: 1,
+        get_watchlist_scanner=lambda spc: None,
+        get_app=lambda: None,
+        get_beatport_data_cache=lambda: {'cache_lock': threading.Lock(), 'homepage': {}},
+        init_automation_progress=lambda *a, **k: None,
+        record_progress_history=lambda *a, **k: None,
+        build_personalized_manager=lambda: None,
+    )
+    base.update(overrides)
+    return AutomationDeps(**base)  # type: ignore[arg-type]
+
+
+def test_all_organize_playlists_skips_wishlist():
+    wishlist_calls = []
+
+    def sync_one(_pl):
+        return {'status': 'skipped', 'reason': 'unchanged'}
+
+    deps = _minimal_deps(
+        process_wishlist_automatically=lambda **k: wishlist_calls.append(k),
+    )
+    playlists = [
+        {'id': 1, 'name': 'A', 'organize_by_playlist': True},
+    ]
+    result = run_sync_and_wishlist(
+        deps,
+        'auto-1',
+        playlists,
+        sync_one_fn=sync_one,
+        sync_id_for_fn=lambda pl: f'mirror_{pl["id"]}',
+        skip_wishlist=False,
+    )
+    assert result['wishlist_queued'] == 0
+    assert result['organize_downloads_started'] == 1
+    assert wishlist_calls == []
+
+
+def test_mixed_playlists_still_runs_wishlist():
+    wishlist_calls = []
+
+    deps = _minimal_deps(
+        process_wishlist_automatically=lambda **k: wishlist_calls.append(1),
+        is_wishlist_actually_processing=lambda: False,
+    )
+    playlists = [
+        {'id': 1, 'name': 'Organized', 'organize_by_playlist': True},
+        {'id': 2, 'name': 'Normal', 'organize_by_playlist': False},
+    ]
+
+    def sync_one(_pl):
+        return {'status': 'skipped'}
+
+    result = run_sync_and_wishlist(
+        deps,
+        None,
+        playlists,
+        sync_one_fn=sync_one,
+        sync_id_for_fn=lambda pl: f'mirror_{pl["id"]}',
+    )
+    assert result['organize_downloads_started'] == 1
+    assert result['wishlist_queued'] == 1
+    assert len(wishlist_calls) == 1

tests/automation/test_progress_callbacks.py

@@ -46,6 +46,8 @@ def _build_deps(**overrides) -> AutomationDeps:
         get_watchlist_scan_state=lambda: {},
         run_playlist_discovery_worker=lambda *a, **k: None,
         run_sync_task=lambda *a, **k: None,
+        run_playlist_organize_download=lambda **k: {'status': 'skipped'},
+        missing_download_executor=None,
         load_sync_status_file=lambda: {},
         get_deezer_client=lambda: None,
         parse_youtube_playlist=lambda url: None,

tests/downloads/test_playlist_folder_exists.py

@@ -0,0 +1,88 @@
+"""Tests for playlist-folder existence detection."""
+
+import os
+from unittest.mock import patch
+
+import pytest
+
+from core.downloads.playlist_folder import (
+    candidate_playlist_folder_paths,
+    resolve_playlist_folder_mode_for_batch,
+    track_exists_in_playlist_folder,
+)
+
+
+class _FakeDB:
+    def __init__(self, mirrored=None):
+        self._mirrored = mirrored
+
+    def resolve_mirrored_playlist(self, playlist_ref, profile_id=1, default_source='spotify'):
+        return self._mirrored
+
+
+def test_track_exists_in_playlist_folder_finds_file(tmp_path):
+    playlist_dir = tmp_path / 'My Playlist'
+    playlist_dir.mkdir()
+    track_file = playlist_dir / 'Artist A - Song One.flac'
+    track_file.write_bytes(b'x')
+
+    with patch('core.downloads.playlist_folder._get_config_manager') as cfg:
+        cfg.return_value.get.return_value = str(tmp_path)
+        with patch('core.downloads.playlist_folder.docker_resolve_path', side_effect=lambda p: p):
+            with patch(
+                'core.downloads.playlist_folder.get_file_path_from_template',
+                return_value=('', ''),
+            ):
+                assert track_exists_in_playlist_folder('My Playlist', 'Artist A', 'Song One')
+
+
+def test_track_exists_in_playlist_folder_missing(tmp_path):
+    with patch('core.downloads.playlist_folder._get_config_manager') as cfg:
+        cfg.return_value.get.return_value = str(tmp_path)
+        with patch('core.downloads.playlist_folder.docker_resolve_path', side_effect=lambda p: p):
+            with patch(
+                'core.downloads.playlist_folder.get_file_path_from_template',
+                return_value=('', ''),
+            ):
+                assert not track_exists_in_playlist_folder('My Playlist', 'Artist A', 'Song One')
+
+
+def test_candidate_paths_template_layout(tmp_path):
+    with patch('core.downloads.playlist_folder._get_config_manager') as cfg:
+        cfg.return_value.get.return_value = str(tmp_path)
+        with patch('core.downloads.playlist_folder.docker_resolve_path', side_effect=lambda p: p):
+            with patch(
+                'core.downloads.playlist_folder.get_file_path_from_template',
+                return_value=('Cool Mix', 'Artist - Title'),
+            ):
+                paths = candidate_playlist_folder_paths('Cool Mix', 'Artist', 'Title')
+                assert any(p.endswith('.flac') for p in paths)
+                assert all('Cool Mix' in p for p in paths)
+
+
+def test_resolve_playlist_folder_mode_from_mirrored():
+    db = _FakeDB(mirrored={
+        'id': 5,
+        'name': 'Rekordbox Set',
+        'organize_by_playlist': True,
+    })
+    enabled, name = resolve_playlist_folder_mode_for_batch(
+        db,
+        playlist_id='37i9dQZF1',
+        playlist_name='Other Name',
+        batch_playlist_folder_mode=False,
+    )
+    assert enabled is True
+    assert name == 'Rekordbox Set'
+
+
+def test_resolve_playlist_folder_mode_batch_flag():
+    db = _FakeDB()
+    enabled, name = resolve_playlist_folder_mode_for_batch(
+        db,
+        playlist_id='1',
+        playlist_name='Batch Name',
+        batch_playlist_folder_mode=True,
+    )
+    assert enabled is True
+    assert name == 'Batch Name'

tests/imports/test_import_pipeline.py

@@ -202,7 +202,12 @@ def test_post_process_matched_download_forwards_separate_metadata_runtime(tmp_pa
     monkeypatch.setattr(import_pipeline, "emit_track_downloaded", lambda *args, **kwargs: None)
     monkeypatch.setattr(import_pipeline, "record_library_history_download", lambda *args, **kwargs: None)
     monkeypatch.setattr(import_pipeline, "record_download_provenance", lambda *args, **kwargs: None)
-    monkeypatch.setattr(import_pipeline, "record_soulsync_library_entry", lambda *args, **kwargs: None)
+    library_calls = []
+
+    def _record_library(context, artist_context, album_info):
+        library_calls.append((context, artist_context, album_info))
+
+    monkeypatch.setattr(import_pipeline, "record_soulsync_library_entry", _record_library)
     monkeypatch.setattr(import_pipeline, "check_and_remove_from_wishlist", lambda *args, **kwargs: None)
     monkeypatch.setattr(import_pipeline, "record_retag_download", lambda *args, **kwargs: None)
 
@@ -221,6 +226,8 @@ def test_post_process_matched_download_forwards_separate_metadata_runtime(tmp_pa
     )
 
     assert seen["runtime"] is metadata_runtime
+    assert len(library_calls) == 1
+    assert library_calls[0][2]["album_name"] == "Album"
 
 
 # ---------------------------------------------------------------------------

tests/wishlist/test_processing.py

@@ -177,6 +177,22 @@ def test_build_wishlist_source_context_minimal_batch_skips_album_provenance():
     assert "artist_context" not in context
 
 
+def test_build_wishlist_source_context_uses_source_playlist_ref_for_organize_batches():
+    batch = {
+        "playlist_name": "Summer Mix",
+        "playlist_id": "42",
+        "source_playlist_ref": "spotifyPlaylistId123",
+        "mirrored_playlist_id": 42,
+        "organize_by_playlist": True,
+    }
+
+    context = processing.build_wishlist_source_context(batch)
+
+    assert context["playlist_id"] == "spotifyPlaylistId123"
+    assert context["mirrored_playlist_id"] == 42
+    assert context["organize_by_playlist"] is True
+
+
 def test_build_wishlist_source_context_preserves_album_context_for_album_batches():
     """Album batches must carry album_context/artist_context through to the
     wishlist row so a later requeue has authoritative routing data instead

web_server.py

@@ -1084,6 +1084,8 @@ def _register_automation_handlers():
         get_watchlist_scan_state=lambda: watchlist_scan_state,
         run_playlist_discovery_worker=_run_playlist_discovery_worker,
         run_sync_task=_run_sync_task,
+        run_playlist_organize_download=_run_playlist_organize_download,
+        missing_download_executor=missing_download_executor,
         load_sync_status_file=_load_sync_status_file,
         get_deezer_client=_get_deezer_client,
         parse_youtube_playlist=parse_youtube_playlist,
@@ -18788,6 +18790,23 @@ def start_missing_tracks_process(playlist_id):
     if playlist_folder_mode:
         logger.info(f"[Playlist Folder] Enabled for playlist: '{playlist_name}'")
 
+    # Persist organize-by-playlist preference on the mirrored playlist row
+    try:
+        profile_id = get_current_profile_id()
+        db_pref = get_database()
+        mirrored_pl = db_pref.resolve_mirrored_playlist(
+            playlist_id,
+            profile_id=profile_id,
+            default_source='spotify',
+        )
+        if mirrored_pl and mirrored_pl.get('id'):
+            db_pref.set_mirrored_playlist_organize_by_playlist(
+                int(mirrored_pl['id']),
+                bool(playlist_folder_mode),
+            )
+    except Exception as pref_err:
+        logger.debug(f"[Playlist Folder] Could not persist mirrored preference: {pref_err}")
+
     # Limit concurrent analysis processes to prevent resource exhaustion
     with tasks_lock:
         active_analysis_count = sum(1 for batch in download_batches.values() 
@@ -23615,11 +23634,38 @@ def _build_sync_deps():
     )
 
 
-def _run_sync_task(playlist_id, playlist_name, tracks_json, automation_id=None, profile_id=1, playlist_image_url='', sync_mode='replace'):
+def _run_sync_task(
+    playlist_id,
+    playlist_name,
+    tracks_json,
+    automation_id=None,
+    profile_id=1,
+    playlist_image_url='',
+    sync_mode='replace',
+    skip_wishlist_add=False,
+):
     return _discovery_sync.run_sync_task(
         playlist_id, playlist_name, tracks_json, automation_id, profile_id, playlist_image_url,
         _build_sync_deps(),
         sync_mode=sync_mode,
+        skip_wishlist_add=skip_wishlist_add,
+    )
+
+
+def _run_playlist_organize_download(mirrored_playlist_id, automation_id=None, profile_id=None):
+    """Start a playlist-folder missing-tracks batch for automation / pipeline."""
+    from core.playlists.organize_download import run_playlist_organize_download
+
+    if profile_id is None:
+        profile_id = get_current_profile_id()
+    return run_playlist_organize_download(
+        _automation_deps,
+        mirrored_playlist_id=int(mirrored_playlist_id),
+        profile_id=profile_id,
+        get_batch_max_concurrent=_get_batch_max_concurrent,
+        run_full_missing_tracks_process=_run_full_missing_tracks_process,
+        record_sync_history_start=_record_sync_history_start,
+        detect_sync_source=_downloads_history.detect_sync_source,
     )
 
 
@@ -31664,6 +31710,55 @@ def update_mirrored_playlist_source_ref_endpoint(playlist_id):
         return jsonify({"error": str(e)}), 500
 
 
+@app.route('/api/mirrored-playlists/<int:playlist_id>/preferences', methods=['PATCH'])
+def update_mirrored_playlist_preferences_endpoint(playlist_id):
+    """Update per-playlist download preferences (e.g. organize by playlist folder)."""
+    try:
+        data = request.get_json() or {}
+        if 'organize_by_playlist' not in data:
+            return jsonify({"error": "organize_by_playlist is required"}), 400
+
+        database = get_database()
+        playlist = database.get_mirrored_playlist(playlist_id)
+        if not playlist:
+            return jsonify({"error": "Playlist not found"}), 404
+
+        enabled = bool(data.get('organize_by_playlist'))
+        ok = database.set_mirrored_playlist_organize_by_playlist(playlist_id, enabled)
+        if not ok:
+            return jsonify({"error": "Failed to update preferences"}), 500
+
+        updated = database.get_mirrored_playlist(playlist_id) or {}
+        return jsonify({"success": True, "playlist": updated})
+    except Exception as e:
+        logger.error(f"Error updating mirrored playlist preferences: {e}")
+        return jsonify({"error": str(e)}), 500
+
+
+@app.route('/api/mirrored-playlists/resolve', methods=['GET'])
+def resolve_mirrored_playlist_endpoint():
+    """Resolve mirrored playlist by numeric id or upstream source id (e.g. Spotify playlist id)."""
+    try:
+        playlist_ref = request.args.get('ref') or request.args.get('playlist_id')
+        source = request.args.get('source', 'spotify')
+        profile_id = get_current_profile_id()
+        if not playlist_ref:
+            return jsonify({"error": "ref or playlist_id query param required"}), 400
+
+        database = get_database()
+        playlist = database.resolve_mirrored_playlist(
+            playlist_ref,
+            profile_id=profile_id,
+            default_source=source,
+        )
+        if not playlist:
+            return jsonify({"found": False, "playlist": None})
+        return jsonify({"found": True, "playlist": playlist})
+    except Exception as e:
+        logger.error(f"Error resolving mirrored playlist: {e}")
+        return jsonify({"error": str(e)}), 500
+
+
 def _playlist_pipeline_state_key(playlist_id):
     return f"mirrored_{int(playlist_id)}"
 

webui/static/auto-sync.js

@@ -675,6 +675,7 @@ function autoSyncWeeklyCardHtml(playlist, schedule) {
                     ${_esc(playlist.name)}
                 </div>
                 <div class="auto-sync-scheduled-meta">${_esc(autoSyncSourceLabel(playlist.source))} &middot; ${playlist.track_count || 0} tracks</div>
+                ${autoSyncOrganizeToggleHtml(playlist)}
                 <div class="auto-sync-scheduled-timing">
                     <span>${_esc(label)}</span>
                     <small>${_esc(tz)}</small>
@@ -1576,6 +1577,34 @@ function autoSyncAutomationCardHtml(auto, playlists) {
     `;
 }
 
+function autoSyncOrganizeToggleHtml(playlist) {
+    const checked = playlist.organize_by_playlist ? 'checked' : '';
+    return `
+        <label class="auto-sync-organize-toggle" onclick="event.stopPropagation();" title="Download missing tracks into a playlist-named folder (artist - track)">
+            <input type="checkbox" ${checked} onchange="setAutoSyncOrganizeByPlaylist(${playlist.id}, this.checked)">
+            <span>Organize by playlist</span>
+        </label>
+    `;
+}
+
+async function setAutoSyncOrganizeByPlaylist(playlistId, enabled) {
+    try {
+        const res = await fetch(`/api/mirrored-playlists/${playlistId}/preferences`, {
+            method: 'PATCH',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({ organize_by_playlist: !!enabled }),
+        });
+        const data = await res.json();
+        if (!res.ok || data.error) throw new Error(data.error || 'Failed to update preference');
+        const pl = _autoSyncScheduleState.playlists.find(p => parseInt(p.id, 10) === parseInt(playlistId, 10));
+        if (pl) pl.organize_by_playlist = !!enabled;
+        showToast(enabled ? 'Auto-Sync will use playlist folders' : 'Auto-Sync will use standard download layout', 'success');
+    } catch (err) {
+        showToast(`Error: ${err.message}`, 'error');
+        await refreshAutoSyncScheduleModal();
+    }
+}
+
 function autoSyncScheduledCardHtml(playlist, schedule) {
     const enabled = schedule?.enabled !== false;
     const nextLabel = schedule?.next_run ? autoSyncNextRunLabel(schedule.next_run) : '';
@@ -1592,6 +1621,7 @@ function autoSyncScheduledCardHtml(playlist, schedule) {
                     ${_esc(playlist.name)}
                 </div>
                 <div class="auto-sync-scheduled-meta">${_esc(autoSyncSourceLabel(playlist.source))} &middot; ${playlist.track_count || 0} tracks</div>
+                ${autoSyncOrganizeToggleHtml(playlist)}
                 <div class="auto-sync-scheduled-timing">
                     <span>${_esc(autoSyncIntervalLabel(schedule?.hours || 24))}</span>
                     ${nextLabel ? `<small>${_esc(nextLabel)}</small>` : ''}

webui/static/core.js

@@ -521,6 +521,7 @@ function handleServiceStatusUpdate(data) {
     _isSoulsyncStandalone = isSoulsyncStandalone;
     document.querySelectorAll('.sync-to-server-btn, [id$="-sync-btn"], [onclick*="startPlaylistSync"], [onclick*="syncPlaylistToServer"], [onclick*="startDecadeSync"]').forEach(btn => {
         if (btn.id === 'stats-sync-btn') return; // React stats page owns this control now.
+        if (btn.classList.contains('soulsync-standalone-action')) return;
         if (isSoulsyncStandalone) {
             btn.dataset.hiddenByStandalone = '1';
             btn.style.display = 'none';

webui/static/downloads.js

@@ -2449,8 +2449,9 @@ async function startMissingTracksProcess(playlistId) {
         const forceDownloadAll = forceDownloadCheckbox ? forceDownloadCheckbox.checked : false;
 
         // Check if playlist folder mode toggle is enabled (only for sync page playlists)
-        const playlistFolderModeCheckbox = document.getElementById(`playlist-folder-mode-${playlistId}`);
-        const playlistFolderMode = playlistFolderModeCheckbox ? playlistFolderModeCheckbox.checked : false;
+        const playlistFolderMode = typeof isPlaylistOrganizeEnabled === 'function'
+            ? isPlaylistOrganizeEnabled(playlistId)
+            : (document.getElementById(`playlist-folder-mode-${playlistId}`)?.checked ?? false);
 
         // Hide the force download toggle during processing
         const forceToggleContainer = forceDownloadCheckbox ? forceDownloadCheckbox.closest('.force-download-toggle-container') : null;
@@ -4425,20 +4426,34 @@ async function startPlaylistSync(playlistId, syncModeOverride = null) {
     }
 
     // Ensure we have the full track list before starting
+    const playlistMeta = spotifyPlaylists.find(p => p.id === playlistId);
     let tracks = playlistTrackCache[playlistId];
-    if (!tracks) {
+    const cacheStale = typeof playlistTrackCacheIsStale === 'function'
+        && playlistTrackCacheIsStale(playlistId, playlistMeta);
+    if (!tracks || cacheStale) {
         const trackFetchStart = Date.now();
-        console.log(`🔄 [${new Date().toTimeString().split(' ')[0]}] Cache miss - fetching tracks for playlist ${playlistId}`);
+        console.log(`🔄 [${new Date().toTimeString().split(' ')[0]}] ${cacheStale ? 'Cache stale' : 'Cache miss'} - fetching tracks for playlist ${playlistId}`);
         try {
-            // Use the right endpoint based on playlist source
-            const fetchUrl = playlistId.startsWith('deezer_arl_')
-                ? `/api/deezer/arl-playlist/${playlistId.replace('deezer_arl_', '')}`
-                : `/api/spotify/playlist/${playlistId}`;
-            const response = await fetch(fetchUrl);
-            const fullPlaylist = await response.json();
-            if (fullPlaylist.error) throw new Error(fullPlaylist.error);
-            tracks = fullPlaylist.tracks;
-            playlistTrackCache[playlistId] = tracks; // Cache it
+            if (cacheStale && typeof invalidatePlaylistTrackCache === 'function') {
+                invalidatePlaylistTrackCache(playlistId);
+            }
+            if (playlistId.startsWith('deezer_arl_') && typeof fetchAndCacheDeezerArlPlaylistTracks === 'function') {
+                const deezerId = playlistId.replace('deezer_arl_', '');
+                const fullPlaylist = await fetchAndCacheDeezerArlPlaylistTracks(playlistId, deezerId);
+                tracks = fullPlaylist.tracks;
+            } else if (typeof fetchAndCacheSpotifyPlaylistTracks === 'function' && !playlistId.startsWith('deezer_arl_')) {
+                const fullPlaylist = await fetchAndCacheSpotifyPlaylistTracks(playlistId);
+                tracks = fullPlaylist.tracks;
+            } else {
+                const fetchUrl = playlistId.startsWith('deezer_arl_')
+                    ? `/api/deezer/arl-playlist/${playlistId.replace('deezer_arl_', '')}`
+                    : `/api/spotify/playlist/${playlistId}`;
+                const response = await fetch(fetchUrl);
+                const fullPlaylist = await response.json();
+                if (fullPlaylist.error) throw new Error(fullPlaylist.error);
+                tracks = fullPlaylist.tracks;
+                playlistTrackCache[playlistId] = tracks;
+            }
             const trackFetchTime = Date.now() - trackFetchStart;
             console.log(`✅ [${new Date().toTimeString().split(' ')[0]}] Fetched and cached ${tracks.length} tracks (took ${trackFetchTime}ms)`);
         } catch (error) {

webui/static/shared-helpers.js

@@ -961,6 +961,322 @@ function setAlbumDownloadingStatus(albumId, downloaded = 0, total = 0) {
 // in artists.js but used broadly across the app.
 // ----------------------------------------------------------------------------
 
+function playlistDetailsOrganizeCheckboxId(playlistRef) {
+    return `playlist-organize-${playlistRef}`;
+}
+
+/** Map UI playlist ids (e.g. deezer_arl_123) to mirrored-playlist resolve refs. */
+function normalizePlaylistOrganizeRef(playlistRef, source = 'spotify') {
+    const ref = String(playlistRef || '').trim();
+    if (source === 'deezer' && ref.startsWith('deezer_arl_')) {
+        return ref.slice('deezer_arl_'.length);
+    }
+    return ref;
+}
+
+function playlistOrganizeToggleHtml(playlistRef, source = 'spotify') {
+    const safeRef = String(playlistRef).replace(/'/g, "\\'");
+    const safeSource = String(source).replace(/'/g, "\\'");
+    return `
+        <label class="playlist-modal-organize-toggle" title="Download into a playlist-named folder (Artist - Track) under your transfer path">
+            <input type="checkbox" id="${playlistDetailsOrganizeCheckboxId(playlistRef)}"
+                onchange="onPlaylistOrganizePreferenceChange('${safeRef}', this.checked, '${safeSource}')">
+            <span>Organize by playlist</span>
+        </label>
+    `;
+}
+
+function syncPlaylistOrganizeCheckboxes(playlistRef, enabled) {
+    const detailsCb = document.getElementById(playlistDetailsOrganizeCheckboxId(playlistRef));
+    const downloadMissingCb = document.getElementById(`playlist-folder-mode-${playlistRef}`);
+    if (detailsCb) detailsCb.checked = !!enabled;
+    if (downloadMissingCb) downloadMissingCb.checked = !!enabled;
+}
+
+function isPlaylistOrganizeEnabled(playlistRef) {
+    const detailsCb = document.getElementById(playlistDetailsOrganizeCheckboxId(playlistRef));
+    if (detailsCb) return detailsCb.checked;
+    const downloadMissingCb = document.getElementById(`playlist-folder-mode-${playlistRef}`);
+    return downloadMissingCb ? downloadMissingCb.checked : false;
+}
+
+async function fetchMirroredOrganizePreference(playlistRef, source = 'spotify') {
+    try {
+        const resolveRef = normalizePlaylistOrganizeRef(playlistRef, source);
+        const res = await fetch(
+            `/api/mirrored-playlists/resolve?ref=${encodeURIComponent(resolveRef)}&source=${encodeURIComponent(source)}`
+        );
+        const data = await res.json();
+        return !!(data.found && data.playlist?.organize_by_playlist);
+    } catch (err) {
+        console.debug('Could not load organize-by-playlist preference:', err);
+        return false;
+    }
+}
+
+async function setMirroredOrganizePreference(playlistRef, enabled, source = 'spotify') {
+    try {
+        const resolveRef = normalizePlaylistOrganizeRef(playlistRef, source);
+        const res = await fetch(
+            `/api/mirrored-playlists/resolve?ref=${encodeURIComponent(resolveRef)}&source=${encodeURIComponent(source)}`
+        );
+        const data = await res.json();
+        if (!data.found || !data.playlist?.id) {
+            return false;
+        }
+        const patchRes = await fetch(`/api/mirrored-playlists/${data.playlist.id}/preferences`, {
+            method: 'PATCH',
+            headers: { 'Content-Type': 'application/json' },
+            body: JSON.stringify({ organize_by_playlist: !!enabled }),
+        });
+        const patchData = await patchRes.json();
+        if (!patchRes.ok || patchData.error) {
+            return false;
+        }
+        syncPlaylistOrganizeCheckboxes(playlistRef, !!enabled);
+        return true;
+    } catch (err) {
+        console.debug('Could not save organize-by-playlist preference:', err);
+        return false;
+    }
+}
+
+async function loadPlaylistOrganizePreferenceIntoModal(playlistRef, source = 'spotify') {
+    const enabled = await fetchMirroredOrganizePreference(playlistRef, source);
+    syncPlaylistOrganizeCheckboxes(playlistRef, enabled);
+}
+
+async function onPlaylistOrganizePreferenceChange(playlistRef, enabled, source = 'spotify') {
+    syncPlaylistOrganizeCheckboxes(playlistRef, enabled);
+    const ok = await setMirroredOrganizePreference(playlistRef, enabled, source);
+    if (!ok) {
+        showToast('Could not save playlist folder preference (mirror this playlist first)', 'warning');
+    }
+}
+
+async function applyMirroredOrganizePreference(playlistRef, source = 'spotify') {
+    await loadPlaylistOrganizePreferenceIntoModal(playlistRef, source);
+}
+
+function playlistTrackCacheIsStale(playlistId, playlist) {
+    const cached = playlistTrackCache[playlistId];
+    if (!cached) {
+        return false;
+    }
+    const expected = playlist?.track_count;
+    if (expected != null && Number(expected) !== cached.length) {
+        return true;
+    }
+    return false;
+}
+
+function clearPlaylistDownloadProcess(playlistId) {
+    const proc = activeDownloadProcesses?.[playlistId];
+    if (!proc) {
+        return;
+    }
+    if (proc.poller) {
+        clearInterval(proc.poller);
+        proc.poller = null;
+    }
+    if (proc.modalElement) {
+        proc.modalElement.remove();
+    }
+    delete activeDownloadProcesses[playlistId];
+}
+
+/** True when Spotify list or track cache changed since the last Download Missing run. */
+function isPlaylistDownloadProcessStale(playlistId, playlistMeta) {
+    if (typeof playlistTrackCacheIsStale === 'function'
+        && playlistTrackCacheIsStale(playlistId, playlistMeta)) {
+        return true;
+    }
+    const proc = activeDownloadProcesses?.[playlistId];
+    if (!proc) {
+        return false;
+    }
+    const expected = playlistMeta?.track_count;
+    if (expected != null && Array.isArray(proc.tracks)
+        && Number(expected) !== proc.tracks.length) {
+        return true;
+    }
+    // Refresh clears the track cache but can leave a completed modal from the old run.
+    if (!playlistTrackCache[playlistId] && proc.status === 'complete') {
+        return true;
+    }
+    return false;
+}
+
+function invalidatePlaylistTrackCache(playlistId = null) {
+    if (playlistId) {
+        delete playlistTrackCache[playlistId];
+        if (currentModalPlaylistId === playlistId) {
+            currentPlaylistTracks = [];
+        }
+        clearPlaylistDownloadProcess(playlistId);
+        return;
+    }
+    playlistTrackCache = {};
+    currentPlaylistTracks = [];
+    const ids = new Set();
+    if (typeof spotifyPlaylists !== 'undefined' && Array.isArray(spotifyPlaylists)) {
+        for (const p of spotifyPlaylists) {
+            if (p?.id) {
+                ids.add(p.id);
+            }
+        }
+    }
+    if (typeof deezerArlPlaylists !== 'undefined' && Array.isArray(deezerArlPlaylists)) {
+        for (const p of deezerArlPlaylists) {
+            const arlId = String(p.id || '').startsWith('deezer_arl_')
+                ? p.id
+                : `deezer_arl_${p.id}`;
+            ids.add(arlId);
+        }
+    }
+    for (const id of ids) {
+        clearPlaylistDownloadProcess(id);
+    }
+}
+
+function mirrorPlaylistTracksForSource(source, sourcePlaylistId, fullPlaylist) {
+    if (typeof mirrorPlaylist !== 'function' || !fullPlaylist?.tracks) {
+        return;
+    }
+    mirrorPlaylist(source, sourcePlaylistId, fullPlaylist.name, fullPlaylist.tracks.map(t => ({
+        track_name: t.name,
+        artist_name: (t.artists && t.artists[0])
+            ? (typeof t.artists[0] === 'object' ? t.artists[0].name : t.artists[0])
+            : '',
+        album_name: t.album ? (typeof t.album === 'object' ? t.album.name : t.album) : '',
+        duration_ms: t.duration_ms || 0,
+        image_url: t.album && typeof t.album === 'object' && t.album.images && t.album.images[0]
+            ? t.album.images[0].url
+            : null,
+        source_track_id: t.id || t.spotify_track_id || '',
+    })), {
+        description: fullPlaylist.description,
+        owner: fullPlaylist.owner,
+        image_url: fullPlaylist.image_url,
+    });
+}
+
+/** @deprecated Use mirrorPlaylistTracksForSource */
+function mirrorSpotifyPlaylistTracks(playlistId, fullPlaylist) {
+    mirrorPlaylistTracksForSource('spotify', playlistId, fullPlaylist);
+}
+
+async function fetchAndCachePlaylistTracks(cacheKey, fetchUrl, mirrorSource, mirrorSourceId) {
+    const response = await fetch(fetchUrl);
+    const fullPlaylist = await response.json();
+    if (fullPlaylist.error) {
+        throw new Error(fullPlaylist.error);
+    }
+    playlistTrackCache[cacheKey] = fullPlaylist.tracks;
+    mirrorPlaylistTracksForSource(mirrorSource, mirrorSourceId, fullPlaylist);
+    return fullPlaylist;
+}
+
+async function fetchAndCacheSpotifyPlaylistTracks(playlistId) {
+    return fetchAndCachePlaylistTracks(
+        playlistId,
+        `/api/spotify/playlist/${playlistId}`,
+        'spotify',
+        playlistId,
+    );
+}
+
+async function fetchAndCacheDeezerArlPlaylistTracks(arlPlaylistId, deezerPlaylistId) {
+    return fetchAndCachePlaylistTracks(
+        arlPlaylistId,
+        `/api/deezer/arl-playlist/${deezerPlaylistId}`,
+        'deezer',
+        deezerPlaylistId,
+    );
+}
+
+/**
+ * Footer actions for Spotify/Deezer playlist details modals.
+ * Standalone SoulSync has no media-server playlist sync — show Mirrored + re-analysis instead.
+ */
+function playlistModalDownloadSyncFooterHtml(playlistId, options = {}) {
+    const {
+        hasCompletedProcess = false,
+        isSyncing = false,
+        source = 'spotify',
+        closeBeforeDownload = false,
+    } = options;
+    const openDm = closeBeforeDownload
+        ? `closeDeezerArlPlaylistDetailsModal(); openDownloadMissingModal('${playlistId}')`
+        : `openDownloadMissingModal('${playlistId}')`;
+    const downloadBtns = hasCompletedProcess
+        ? `<button class="playlist-modal-btn playlist-modal-btn-tertiary" onclick="${openDm}">📊 View Last Results</button>
+           <button class="playlist-modal-btn playlist-modal-btn-tertiary soulsync-standalone-action" onclick="restartPlaylistDownloadMissing('${playlistId}')">🔄 Download Missing (New)</button>`
+        : `<button class="playlist-modal-btn playlist-modal-btn-tertiary" onclick="${openDm}">📥 Download Missing Tracks</button>`;
+
+    if (_isSoulsyncStandalone) {
+        return `${downloadBtns}
+            <button class="playlist-modal-btn playlist-modal-btn-secondary soulsync-standalone-action" onclick="navigateToMirroredPlaylist('${playlistId}', '${source}')">📂 Open in Mirrored</button>`;
+    }
+
+    return `${downloadBtns}
+        <select id="sync-mode-${playlistId}" class="playlist-modal-sync-mode" title="Replace overwrites the server playlist; Append only adds new tracks (preserves user-added)">
+            <option value="replace" selected>Replace</option>
+            <option value="append">Append only</option>
+        </select>
+        <button id="sync-btn-${playlistId}" class="playlist-modal-btn playlist-modal-btn-primary" onclick="startPlaylistSync('${playlistId}')" ${isSyncing ? 'disabled' : ''}>${isSyncing ? '⏳ Syncing...' : 'Sync Playlist'}</button>`;
+}
+
+async function restartPlaylistDownloadMissing(playlistId) {
+    const proc = activeDownloadProcesses[playlistId];
+    if (proc?.poller) {
+        clearInterval(proc.poller);
+    }
+    if (proc?.modalElement) {
+        proc.modalElement.remove();
+    }
+    delete activeDownloadProcesses[playlistId];
+    if (typeof closePlaylistDetailsModal === 'function') {
+        closePlaylistDetailsModal();
+    }
+    if (typeof closeDeezerArlPlaylistDetailsModal === 'function') {
+        closeDeezerArlPlaylistDetailsModal();
+    }
+    await openDownloadMissingModal(playlistId);
+}
+
+async function navigateToMirroredPlaylist(playlistRef, source = 'spotify') {
+    if (typeof navigateToPage === 'function') {
+        navigateToPage('sync');
+    }
+    const mirroredBtn = document.querySelector('.sync-tab-button[data-tab="mirrored"]');
+    if (mirroredBtn) {
+        mirroredBtn.click();
+    }
+    try {
+        const resolveRef = normalizePlaylistOrganizeRef(playlistRef, source);
+        const res = await fetch(
+            `/api/mirrored-playlists/resolve?ref=${encodeURIComponent(resolveRef)}&source=${encodeURIComponent(source)}`
+        );
+        const data = await res.json();
+        if (!data.found || !data.playlist?.id) {
+            if (typeof loadMirroredPlaylists === 'function') {
+                await loadMirroredPlaylists();
+            }
+            showToast('Playlist not mirrored yet — open it once from Sync to create the mirror.', 'warning');
+            return;
+        }
+        if (typeof loadMirroredPlaylists === 'function') {
+            await loadMirroredPlaylists();
+        }
+        if (typeof openMirroredPlaylistModal === 'function') {
+            await openMirroredPlaylistModal(data.playlist.id);
+        }
+    } catch (err) {
+        showToast(`Could not open mirrored playlist: ${err.message}`, 'error');
+    }
+}
+
 async function openDownloadMissingModalForArtistAlbum(virtualPlaylistId, playlistName, spotifyTracks, album, artist, showLoadingOverlayParam = true, contextType = 'artist_album') {
     if (showLoadingOverlayParam) {
         showLoadingOverlay('Loading album...');
@@ -3200,6 +3516,7 @@ async function fetchAndUpdateServiceStatus() {
         _isSoulsyncStandalone = isSoulsyncStandalone2;
         document.querySelectorAll('.sync-to-server-btn, [id$="-sync-btn"], [onclick*="startPlaylistSync"], [onclick*="syncPlaylistToServer"], [onclick*="startDecadeSync"]').forEach(btn => {
             if (btn.id === 'stats-sync-btn') return; // React stats page owns this control now.
+            if (btn.classList.contains('soulsync-standalone-action')) return;
             if (isSoulsyncStandalone2) {
                 btn.dataset.hiddenByStandalone = '1';
                 btn.style.display = 'none';

webui/static/style.css

@@ -12088,6 +12088,21 @@ body.helper-mode-active #dashboard-activity-feed:hover {
     line-height: 1.3;
 }
 
+.auto-sync-organize-toggle {
+    display: flex;
+    align-items: center;
+    gap: 6px;
+    margin-top: 6px;
+    font-size: 11px;
+    color: rgba(255, 255, 255, 0.72);
+    cursor: pointer;
+    user-select: none;
+}
+
+.auto-sync-organize-toggle input {
+    margin: 0;
+}
+
 .auto-sync-scheduled-timing {
     display: flex;
     flex-wrap: wrap;
@@ -18728,6 +18743,24 @@ body.helper-mode-active #dashboard-activity-feed:hover {
 .playlist-modal-footer-right {
     display: flex;
     gap: 12px;
+    flex-wrap: wrap;
+    justify-content: flex-end;
+}
+
+.playlist-modal-organize-toggle {
+    display: flex;
+    align-items: center;
+    gap: 8px;
+    font-size: 13px;
+    color: rgba(255, 255, 255, 0.85);
+    cursor: pointer;
+    user-select: none;
+    max-width: 100%;
+}
+
+.playlist-modal-organize-toggle input {
+    margin: 0;
+    flex-shrink: 0;
 }
 
 .playlist-modal-btn {

webui/static/sync-services.js

@@ -2438,6 +2438,11 @@ async function loadDeezerArlPlaylists() {
             throw new Error(error.error || 'Failed to fetch Deezer playlists');
         }
         deezerArlPlaylists = await response.json();
+        if (typeof invalidatePlaylistTrackCache === 'function') {
+            invalidatePlaylistTrackCache();
+        } else {
+            playlistTrackCache = {};
+        }
         renderDeezerArlPlaylists();
         deezerArlPlaylistsLoaded = true;
 
@@ -2525,25 +2530,25 @@ async function openDeezerArlPlaylistDetailsModal(event, playlistId) {
     showLoadingOverlay(`Loading playlist: ${playlist.name}...`);
 
     try {
-        if (playlistTrackCache[arlPlaylistId]) {
+        const playlistMeta = { ...playlist, track_count: playlist.track_count ?? playlist.tracks?.length };
+        const cacheStale = typeof playlistTrackCacheIsStale === 'function'
+            && playlistTrackCacheIsStale(arlPlaylistId, playlistMeta);
+        if (playlistTrackCache[arlPlaylistId] && !cacheStale) {
             const fullPlaylist = { ...playlist, id: arlPlaylistId, tracks: playlistTrackCache[arlPlaylistId] };
             showDeezerArlPlaylistDetailsModal(fullPlaylist, playlistId);
         } else {
-            const response = await fetch(`/api/deezer/arl-playlist/${playlistId}`);
-            const fullPlaylist = await response.json();
-            if (fullPlaylist.error) throw new Error(fullPlaylist.error);
-
-            playlistTrackCache[arlPlaylistId] = fullPlaylist.tracks;
-
-            // Auto-mirror
-            mirrorPlaylist('deezer', playlistId, fullPlaylist.name, fullPlaylist.tracks.map(t => ({
-                track_name: t.name,
-                artist_name: (t.artists && t.artists[0]) ? (typeof t.artists[0] === 'object' ? t.artists[0].name : t.artists[0]) : '',
-                album_name: t.album ? (typeof t.album === 'object' ? t.album.name : t.album) : '',
-                duration_ms: t.duration_ms || 0,
-                source_track_id: t.id || ''
-            })), { description: fullPlaylist.description, owner: fullPlaylist.owner, image_url: fullPlaylist.image_url });
-
+            if (cacheStale && typeof invalidatePlaylistTrackCache === 'function') {
+                invalidatePlaylistTrackCache(arlPlaylistId);
+            }
+            const fullPlaylist = typeof fetchAndCacheDeezerArlPlaylistTracks === 'function'
+                ? await fetchAndCacheDeezerArlPlaylistTracks(arlPlaylistId, playlistId)
+                : await (async () => {
+                    const response = await fetch(`/api/deezer/arl-playlist/${playlistId}`);
+                    const data = await response.json();
+                    if (data.error) throw new Error(data.error);
+                    playlistTrackCache[arlPlaylistId] = data.tracks;
+                    return data;
+                })();
             showDeezerArlPlaylistDetailsModal({ ...fullPlaylist, id: arlPlaylistId }, playlistId);
         }
     } catch (error) {
@@ -2608,15 +2613,20 @@ function showDeezerArlPlaylistDetailsModal(playlist, originalDeezerPlaylistId) {
             </div>
 
             <div class="playlist-modal-footer">
-                <button class="playlist-modal-btn playlist-modal-btn-secondary" onclick="closeDeezerArlPlaylistDetailsModal()">Close</button>
-                <button class="playlist-modal-btn playlist-modal-btn-tertiary" onclick="closeDeezerArlPlaylistDetailsModal(); openDownloadMissingModal('${playlistId}')">
-                    ${hasCompletedProcess ? '📊 View Download Results' : '📥 Download Missing Tracks'}
-                </button>
-                <select id="sync-mode-${playlistId}" class="playlist-modal-sync-mode" title="Replace overwrites the server playlist; Append only adds new tracks (preserves user-added)" ${_isSoulsyncStandalone ? 'style="display:none"' : ''}>
-                    <option value="replace" selected>Replace</option>
-                    <option value="append">Append only</option>
-                </select>
-                <button id="sync-btn-${playlistId}" class="playlist-modal-btn playlist-modal-btn-primary" onclick="startPlaylistSync('${playlistId}')" ${isSyncing ? 'disabled' : ''} ${_isSoulsyncStandalone ? 'style="display:none"' : ''}>${isSyncing ? '⏳ Syncing...' : 'Sync Playlist'}</button>
+                <div class="playlist-modal-footer-left">
+                    ${typeof playlistOrganizeToggleHtml === 'function' ? playlistOrganizeToggleHtml(playlistId, 'deezer') : ''}
+                </div>
+                <div class="playlist-modal-footer-right">
+                    <button class="playlist-modal-btn playlist-modal-btn-secondary" onclick="closeDeezerArlPlaylistDetailsModal()">Close</button>
+                    ${typeof playlistModalDownloadSyncFooterHtml === 'function'
+                        ? playlistModalDownloadSyncFooterHtml(playlistId, {
+                            hasCompletedProcess,
+                            isSyncing,
+                            source: 'deezer',
+                            closeBeforeDownload: true,
+                        })
+                        : `<button class="playlist-modal-btn playlist-modal-btn-tertiary" onclick="closeDeezerArlPlaylistDetailsModal(); openDownloadMissingModal('${playlistId}')">📥 Download Missing Tracks</button>`}
+                </div>
             </div>
         </div>
     `;
@@ -2633,6 +2643,9 @@ function showDeezerArlPlaylistDetailsModal(playlist, originalDeezerPlaylistId) {
     }
 
     modal.style.display = 'flex';
+    if (typeof loadPlaylistOrganizePreferenceIntoModal === 'function') {
+        void loadPlaylistOrganizePreferenceIntoModal(playlistId, 'deezer');
+    }
 }
 
 function closeDeezerArlPlaylistDetailsModal() {

webui/static/sync-spotify.js

@@ -1610,6 +1610,11 @@ async function loadSpotifyPlaylists() {
             throw new Error(error.error || 'Failed to fetch playlists');
         }
         spotifyPlaylists = await response.json();
+        if (typeof invalidatePlaylistTrackCache === 'function') {
+            invalidatePlaylistTrackCache();
+        } else {
+            playlistTrackCache = {};
+        }
         renderSpotifyPlaylists();
         spotifyPlaylistsLoaded = true;
 
@@ -1833,35 +1838,35 @@ async function openPlaylistDetailsModal(event, playlistId) {
     showLoadingOverlay(`Loading playlist: ${playlist.name}...`);
 
     try {
-        // --- CACHING LOGIC START ---
-        if (playlistTrackCache[playlistId]) {
+        const cacheStale = typeof playlistTrackCacheIsStale === 'function'
+            && playlistTrackCacheIsStale(playlistId, playlist);
+        if (playlistTrackCache[playlistId] && !cacheStale) {
             console.log(`Cache HIT for playlist ${playlistId}. Using cached tracks.`);
-            // Use the cached tracks instead of fetching
             const fullPlaylist = { ...playlist, tracks: playlistTrackCache[playlistId] };
             showPlaylistDetailsModal(fullPlaylist);
         } else {
-            console.log(`Cache MISS for playlist ${playlistId}. Fetching from server...`);
-            // Fetch from the server if not in cache
-            const response = await fetch(`/api/spotify/playlist/${playlistId}`);
-            const fullPlaylist = await response.json();
-            if (fullPlaylist.error) throw new Error(fullPlaylist.error);
-
-            // Store the fetched tracks in the cache
-            playlistTrackCache[playlistId] = fullPlaylist.tracks;
+            if (cacheStale) {
+                console.log(`Cache STALE for playlist ${playlistId} — refetching tracks.`);
+                if (typeof invalidatePlaylistTrackCache === 'function') {
+                    invalidatePlaylistTrackCache(playlistId);
+                } else {
+                    delete playlistTrackCache[playlistId];
+                }
+            } else {
+                console.log(`Cache MISS for playlist ${playlistId}. Fetching from server...`);
+            }
+            const fullPlaylist = typeof fetchAndCacheSpotifyPlaylistTracks === 'function'
+                ? await fetchAndCacheSpotifyPlaylistTracks(playlistId)
+                : await (async () => {
+                    const response = await fetch(`/api/spotify/playlist/${playlistId}`);
+                    const data = await response.json();
+                    if (data.error) throw new Error(data.error);
+                    playlistTrackCache[playlistId] = data.tracks;
+                    return data;
+                })();
             console.log(`Cached ${fullPlaylist.tracks.length} tracks for playlist ${playlistId}.`);
-
-            // Auto-mirror this Spotify playlist
-            mirrorPlaylist('spotify', playlistId, fullPlaylist.name, fullPlaylist.tracks.map(t => ({
-                track_name: t.name, artist_name: (t.artists && t.artists[0]) ? (typeof t.artists[0] === 'object' ? t.artists[0].name : t.artists[0]) : '',
-                album_name: t.album ? (typeof t.album === 'object' ? t.album.name : t.album) : '',
-                duration_ms: t.duration_ms || 0,
-                image_url: t.album && typeof t.album === 'object' && t.album.images && t.album.images[0] ? t.album.images[0].url : null,
-                source_track_id: t.id || t.spotify_track_id || ''
-            })), { description: fullPlaylist.description, owner: fullPlaylist.owner, image_url: fullPlaylist.image_url });
-
             showPlaylistDetailsModal(fullPlaylist);
         }
-        // --- CACHING LOGIC END ---
 
     } catch (error) {
         showToast(`Error: ${error.message}`, 'error');
@@ -1929,22 +1934,27 @@ function showPlaylistDetailsModal(playlist) {
             </div>
             
             <div class="playlist-modal-footer">
-                <button class="playlist-modal-btn playlist-modal-btn-secondary" onclick="closePlaylistDetailsModal()">Close</button>
-                <button class="playlist-modal-btn playlist-modal-btn-tertiary" onclick="openDownloadMissingModal('${playlist.id}')">
-                    ${hasCompletedProcess
-            ? '📊 View Download Results'
-            : '📥 Download Missing Tracks'}
-                </button>
-                <select id="sync-mode-${playlist.id}" class="playlist-modal-sync-mode" title="Replace overwrites the server playlist; Append only adds new tracks (preserves user-added)" ${_isSoulsyncStandalone ? 'style="display:none"' : ''}>
-                    <option value="replace" selected>Replace</option>
-                    <option value="append">Append only</option>
-                </select>
-                <button id="sync-btn-${playlist.id}" class="playlist-modal-btn playlist-modal-btn-primary" onclick="startPlaylistSync('${playlist.id}')" ${isSyncing ? 'disabled' : ''} ${_isSoulsyncStandalone ? 'style="display:none"' : ''}>${isSyncing ? '⏳ Syncing...' : 'Sync Playlist'}</button>
+                <div class="playlist-modal-footer-left">
+                    ${typeof playlistOrganizeToggleHtml === 'function' ? playlistOrganizeToggleHtml(playlist.id, 'spotify') : ''}
+                </div>
+                <div class="playlist-modal-footer-right">
+                    <button class="playlist-modal-btn playlist-modal-btn-secondary" onclick="closePlaylistDetailsModal()">Close</button>
+                    ${typeof playlistModalDownloadSyncFooterHtml === 'function'
+                        ? playlistModalDownloadSyncFooterHtml(playlist.id, {
+                            hasCompletedProcess,
+                            isSyncing,
+                            source: 'spotify',
+                        })
+                        : `<button class="playlist-modal-btn playlist-modal-btn-tertiary" onclick="openDownloadMissingModal('${playlist.id}')">📥 Download Missing Tracks</button>`}
+                </div>
             </div>
         </div>
     `;
 
     modal.style.display = 'flex';
+    if (typeof loadPlaylistOrganizePreferenceIntoModal === 'function') {
+        void loadPlaylistOrganizePreferenceIntoModal(playlist.id, 'spotify');
+    }
 }
 
 function closePlaylistDetailsModal() {
@@ -2184,19 +2194,36 @@ async function openDownloadMissingModal(playlistId) {
     showLoadingOverlay('Loading playlist...');
 
     // **NEW**: Check if a process is already active for this playlist
-    if (activeDownloadProcesses[playlistId]) {
+    const playlistMeta = spotifyPlaylists.find(p => p.id === playlistId);
+    const processStale = typeof isPlaylistDownloadProcessStale === 'function'
+        ? isPlaylistDownloadProcessStale(playlistId, playlistMeta)
+        : (typeof playlistTrackCacheIsStale === 'function'
+            && playlistTrackCacheIsStale(playlistId, playlistMeta));
+
+    if (activeDownloadProcesses[playlistId] && !processStale) {
         console.log(`Modal for ${playlistId} already exists. Showing it.`);
-        closePlaylistDetailsModal(); // Close playlist details modal even when reusing existing modal
+        closePlaylistDetailsModal();
         const process = activeDownloadProcesses[playlistId];
         if (process.modalElement) {
-            // Show helpful message if it's a completed process
             if (process.status === 'complete') {
-                showToast('Showing previous results. Close this modal to start a new analysis.', 'info');
+                showToast('Showing previous results. Use "Download Missing (New)" for a fresh run.', 'info');
             }
             process.modalElement.style.display = 'flex';
         }
         hideLoadingOverlay();
-        return; // Don't create a new one
+        return;
+    }
+    if (processStale && activeDownloadProcesses[playlistId]) {
+        if (typeof restartPlaylistDownloadMissing === 'function') {
+            await restartPlaylistDownloadMissing(playlistId);
+            hideLoadingOverlay();
+            return;
+        }
+        if (typeof clearPlaylistDownloadProcess === 'function') {
+            clearPlaylistDownloadProcess(playlistId);
+        } else if (typeof invalidatePlaylistTrackCache === 'function') {
+            invalidatePlaylistTrackCache(playlistId);
+        }
     }
 
     console.log(`📥 Opening Download Missing Tracks modal for playlist: ${playlistId}`);
@@ -2210,16 +2237,29 @@ async function openDownloadMissingModal(playlistId) {
     }
 
     let tracks = playlistTrackCache[playlistId];
-    if (!tracks) {
+    const needFreshTracks = !tracks || (
+        typeof playlistTrackCacheIsStale === 'function'
+        && playlistTrackCacheIsStale(playlistId, playlist)
+    );
+    if (needFreshTracks) {
         try {
-            const fetchUrl = playlistId.startsWith('deezer_arl_')
-                ? `/api/deezer/arl-playlist/${playlistId.replace('deezer_arl_', '')}`
-                : `/api/spotify/playlist/${playlistId}`;
-            const response = await fetch(fetchUrl);
-            const fullPlaylist = await response.json();
-            if (fullPlaylist.error) throw new Error(fullPlaylist.error);
-            tracks = fullPlaylist.tracks;
-            playlistTrackCache[playlistId] = tracks;
+            if (playlistId.startsWith('deezer_arl_')) {
+                const fetchUrl = `/api/deezer/arl-playlist/${playlistId.replace('deezer_arl_', '')}`;
+                const response = await fetch(fetchUrl);
+                const fullPlaylist = await response.json();
+                if (fullPlaylist.error) throw new Error(fullPlaylist.error);
+                tracks = fullPlaylist.tracks;
+                playlistTrackCache[playlistId] = tracks;
+            } else if (typeof fetchAndCacheSpotifyPlaylistTracks === 'function') {
+                const fullPlaylist = await fetchAndCacheSpotifyPlaylistTracks(playlistId);
+                tracks = fullPlaylist.tracks;
+            } else {
+                const response = await fetch(`/api/spotify/playlist/${playlistId}`);
+                const fullPlaylist = await response.json();
+                if (fullPlaylist.error) throw new Error(fullPlaylist.error);
+                tracks = fullPlaylist.tracks;
+                playlistTrackCache[playlistId] = tracks;
+            }
         } catch (error) {
             showToast(`Failed to fetch tracks: ${error.message}`, 'error');
             hideLoadingOverlay();
@@ -2335,10 +2375,7 @@ async function openDownloadMissingModal(playlistId) {
                             <input type="checkbox" id="force-download-all-${playlistId}">
                             <span>Force Download All</span>
                         </label>
-                        <label class="force-download-toggle">
-                            <input type="checkbox" id="playlist-folder-mode-${playlistId}">
-                            <span>Organize by Playlist (Downloads/Playlist/Artist - Track.ext)</span>
-                        </label>
+                        <input type="checkbox" id="playlist-folder-mode-${playlistId}" class="playlist-folder-mode-sync" hidden>
                     </div>
                     <button class="download-control-btn primary" id="begin-analysis-btn-${playlistId}" onclick="startMissingTracksProcess('${playlistId}')">
                         Begin Analysis
@@ -2361,6 +2398,7 @@ async function openDownloadMissingModal(playlistId) {
     `;
 
     applyProgressiveTrackRendering(playlistId, tracks.length);
+    await applyMirroredOrganizePreference(playlistId, 'spotify');
     modal.style.display = 'flex';
     hideLoadingOverlay();
 }