diff --git a/src/app.py b/src/app.py
index 7859c0b..d8afb2e 100644
--- a/src/app.py
+++ b/src/app.py
@@ -48,6 +48,8 @@ class MainWindow(QMainWindow):
 
         self.playlist_manager = PlaylistManager()
         self._sidebar_visible = True
+        self._pending_playlist_id: str = ""
+        self._pending_playlist_tracks: list = []
 
         self._saved_volume: int = 80
         self._saved_track_path: str = ""
@@ -141,7 +143,9 @@ class MainWindow(QMainWindow):
 
         self.sidebar.tracks_dropped_on_playlist.connect(self._on_tracks_dropped_on_playlist)
         self.sidebar.tracks_dropped_for_nav_transfer.connect(self._on_tracks_dropped_for_nav_transfer)
+        self.sidebar.playlist_dropped_for_nav_transfer.connect(self._on_playlist_dropped_for_nav_transfer)
         self.ipod_tab.tracks_dropped_for_transfer.connect(self._on_tracks_dropped_for_transfer)
+        self.library_tab.transfer_finished.connect(self._on_transfer_finished_for_playlist)
 
     def _on_sidebar_item_selected(self, kind: str, value: str):
         if kind == "tab":
@@ -197,6 +201,55 @@ class MainWindow(QMainWindow):
         self.stack.setCurrentIndex(0)
         self.library_tab.transfer_tracks_by_paths(paths)
 
+    def _on_playlist_dropped_for_nav_transfer(self, playlist_id: str):
+        playlist = self.playlist_manager.get_by_id(playlist_id)
+        if not playlist or not playlist.track_paths:
+            return
+
+        self.stack.setCurrentIndex(0)
+        self._pending_playlist_id = playlist_id
+        self._pending_playlist_tracks = list(playlist.track_paths)
+        self.library_tab.transfer_tracks_by_paths(playlist.track_paths)
+
+    def _on_transfer_finished_for_playlist(self):
+        playlist_id = self._pending_playlist_id
+        track_paths = self._pending_playlist_tracks
+        self._pending_playlist_id = ""
+        self._pending_playlist_tracks = []
+
+        if not playlist_id or not track_paths:
+            return
+
+        mount_point = getattr(self.ipod_tab, "current_mount_point", None)
+        if not mount_point:
+            self.statusBar().showMessage("Cannot create playlist: iPod not mounted", 5000)
+            return
+
+        playlist = self.playlist_manager.get_by_id(playlist_id)
+        if not playlist:
+            return
+
+        self.statusBar().showMessage(f"Creating playlist '{playlist.name}' on iPod...")
+
+        from worker import WorkerThread
+        self._pl_worker = WorkerThread(
+            task_type="create_playlist",
+            mount_point=mount_point,
+            playlist_name=playlist.name,
+            track_paths=track_paths,
+        )
+        self._pl_worker.finished_signal.connect(self._on_playlist_creation_finished)
+        self._pl_worker.start()
+
+    def _on_playlist_creation_finished(self, success, message, result):
+        self.statusBar().showMessage(message, 8000)
+        try:
+            self._pl_worker.quit()
+            self._pl_worker.wait()
+        except Exception:
+            pass
+        self._pl_worker = None
+
     def _load_playlists_into_sidebar(self):
         for pl in self.playlist_manager.get_all():
             self.sidebar.add_playlist_item(pl.id, pl.name)
diff --git a/src/ipod_nano7_db.py b/src/ipod_nano7_db.py
index d810873..ad18a43 100644
--- a/src/ipod_nano7_db.py
+++ b/src/ipod_nano7_db.py
@@ -32,7 +32,7 @@ import sqlite3
 import struct
 import subprocess
 import time
-from typing import Any, Optional
+from typing import Any, Callable, Optional
 
 from mutagen import File as MutagenFile
 from mutagen.easyid3 import EasyID3
@@ -627,6 +627,114 @@ class Nano7Database:
                 deleted += 1
         return deleted
 
+    # ── playlist creation ────────────────────────────────────────────
+
+    def create_playlist(self, name: str, track_paths: list[str]) -> bool:
+        """Create a user playlist on the iPod.
+
+        Two-pass matching: content hash first, then title+artist+album
+        fallback. Only tracks already present on the iPod will be
+        included in the playlist.
+
+        Args:
+            name: Playlist name.
+            track_paths: Local file paths of the tracks to include.
+
+        Returns:
+            True if the playlist was created, False otherwise.
+        """
+        scanned = self._scan_ipod_files()
+        if not scanned:
+            logger.warning("No tracks on iPod — cannot create playlist")
+            return False
+
+        playlist_created = False
+        self._merge_play_stats(scanned)
+
+        def _build_pl_cb(scanned, tracks):
+            """Build playlist using real db_track_id from TrackInfo."""
+            nonlocal playlist_created
+
+            try:
+                IopPlaylistInfo = _import_iop(
+                    "iTunesDB_Writer.mhyp_writer"
+                ).PlaylistInfo
+            except Exception as e:
+                logger.exception("Failed to import PlaylistInfo: %s", e)
+                return None
+
+            # Pass 1: content_hash → db_track_id
+            hash_to_db_id: dict[str, int] = {}
+            for i, s in enumerate(scanned):
+                ch = s.get("content_hash", "")
+                if ch:
+                    hash_to_db_id[ch] = tracks[i].db_track_id
+
+            found_ids: list[int] = []
+            unmatched: list[str] = []
+
+            for path in track_paths:
+                if not os.path.exists(path):
+                    continue
+                ch = content_hash(path)
+                db_id = hash_to_db_id.get(ch)
+                if db_id is not None:
+                    found_ids.append(db_id)
+                else:
+                    unmatched.append(path)
+
+            hash_matched_count = len(found_ids)
+
+            # Pass 2: metadata fallback
+            if unmatched:
+                scanned_meta = []
+                for i, s in enumerate(scanned):
+                    scanned_meta.append((
+                        s.get("title", "").lower(),
+                        s.get("artist", "").lower(),
+                        (s.get("album") or "").lower(),
+                        tracks[i].db_track_id,
+                    ))
+
+                found_set = set(found_ids)
+                for path in unmatched:
+                    tags = _read_audio_tags(path)
+                    title = (tags.get("title") or "").lower()
+                    artist = (tags.get("artist") or "").lower()
+                    album = (tags.get("album") or "").lower()
+                    if not title or not artist:
+                        continue
+                    for s_title, s_artist, s_album, db_id in scanned_meta:
+                        if (db_id not in found_set
+                                and s_title == title
+                                and s_artist == artist
+                                and s_album == album):
+                            found_ids.append(db_id)
+                            found_set.add(db_id)
+                            break
+
+            if not found_ids:
+                logger.warning(
+                    "No tracks from playlist '%s' found on iPod",
+                    name,
+                )
+                return None
+
+            matched_by_hash = hash_matched_count
+            matched_by_meta = len(found_ids) - hash_matched_count
+            logger.info(
+                "Playlist '%s': %d track(s) matched (%d by hash, %d by metadata)",
+                name, len(found_ids), matched_by_hash, matched_by_meta,
+            )
+            playlist_created = True
+            return [IopPlaylistInfo(name=name, track_ids=found_ids)]
+
+        db_ok = self._write_databases_from_tracks(
+            scanned, build_extra_playlists=_build_pl_cb,
+        )
+        self._cleanup_play_counts_file()
+        return db_ok and playlist_created
+
     # ── sync: regenerate everything via iOpenPod ──────────────────────
 
     def sync_itunescdb(self) -> None:
@@ -694,7 +802,9 @@ class Nano7Database:
             return
 
         self._merge_play_stats(scanned)
-        self._write_databases_from_tracks(scanned)
+        if not self._write_databases_from_tracks(scanned):
+            logger.error("iTunesDB sync failed — play counts not cleaned up")
+            return
         self._cleanup_play_counts_file()
 
     def find_track_by_content_hash(self, content_hash: str) -> dict | None:
@@ -901,7 +1011,9 @@ class Nano7Database:
         self,
         scanned: list[dict],
         artwork_overrides: dict[str, object] | None = None,
-    ) -> None:
+        extra_playlists: list | None = None,
+        build_extra_playlists: Callable | None = None,
+    ) -> bool:
         """Build artwork, convert to TrackInfo, write iTunesDB + SQLite.
 
         Args:
@@ -911,6 +1023,15 @@ class Nano7Database:
                 artwork should come from a local file instead of the iPod file.
                 Use the ``_REMOVE_ARTWORK`` sentinel to explicitly remove
                 artwork for a track.  Omit a key to keep existing iPod artwork.
+            extra_playlists: Pre-built list of PlaylistInfo (ignored when
+                build_extra_playlists is provided).
+            build_extra_playlists: Optional callable(scanned, tracks) → list
+                of PlaylistInfo.  Called after TrackInfo conversion and
+                db_track_id generation, so the callback can use real
+                db_track_id values from TrackInfo objects.
+
+        Returns:
+            True if databases were written successfully.
         """
         artwork_overrides = artwork_overrides or {}
         # 1. Prepare artwork for all tracks
@@ -970,6 +1091,20 @@ class Nano7Database:
         tracks = _scanned_tracks_to_iop(self.mountpoint, scanned, artwork_map)
         logger.info("Built %d iOpenPod TrackInfo objects", len(tracks))
 
+        # 2b. Pre-generate db_track_id for all tracks so callbacks can use them
+        generate_db_track_id = _import_iop("iTunesDB_Writer.mhit_writer").generate_db_track_id
+        for track in tracks:
+            if track.db_track_id == 0:
+                track.db_track_id = generate_db_track_id()
+
+        # 2c. Build extra playlists via callback if provided
+        if build_extra_playlists is not None:
+            result = build_extra_playlists(scanned, tracks)
+            if result is not None:
+                extra_playlists = result
+            else:
+                extra_playlists = None
+
         # 3. Determine capabilities for this device
         ipod_device = _import_iop("ipod_device")
         capabilities = None
@@ -998,10 +1133,11 @@ class Nano7Database:
             backup=True,
             capabilities=capabilities,
             master_playlist_name="iPod",
+            playlists=extra_playlists or None,
         )
         if not ok:
             logger.error("iTunesDB write failed")
-            return
+            return False
         logger.info("iTunesDB written (%d tracks)", len(tracks))
 
         # 5. Extract db_pid from the binary DB for SQLite cross-reference
@@ -1029,13 +1165,18 @@ class Nano7Database:
                 capabilities=capabilities,
                 firewire_id=firewire_id,
                 backup=True,
+                playlists=extra_playlists or None,
             )
             if sqlite_ok:
                 logger.info("SQLite databases written")
             else:
                 logger.error("SQLite database write failed")
+                return False
         except Exception as e:
             logger.exception("SQLite write error: %s", e)
+            return False
+
+        return True
 
     def _write_empty_databases(self) -> None:
         """Write minimal empty databases when no tracks exist."""
diff --git a/src/ui/sidebar_widget.py b/src/ui/sidebar_widget.py
index 31b2c85..9ae73b5 100644
--- a/src/ui/sidebar_widget.py
+++ b/src/ui/sidebar_widget.py
@@ -27,6 +27,14 @@ class PlaylistDropListWidget(QListWidget):
         self.setAcceptDrops(True)
         self._hovered_item = None
 
+    def mimeData(self, items):
+        mime = super().mimeData(items)
+        if items:
+            playlist_id = items[0].data(Qt.ItemDataRole.UserRole)
+            if playlist_id:
+                mime.setData("application/x-neopod-playlist", playlist_id.encode())
+        return mime
+
     def dragEnterEvent(self, event: QDragEnterEvent):
         if event.source() is not self and event.mimeData().hasUrls():
             event.acceptProposedAction()
@@ -83,6 +91,7 @@ class PlaylistDropListWidget(QListWidget):
 class NavDropListWidget(QListWidget):
     """QListWidget that accepts external track drops on the iPod nav item."""
     tracks_dropped_for_transfer = pyqtSignal(list)
+    playlist_dropped_for_transfer = pyqtSignal(str)
 
     def __init__(self, parent=None):
         super().__init__(parent)
@@ -95,7 +104,19 @@ class NavDropListWidget(QListWidget):
             return item
         return None
 
+    def _repolish(self):
+        self.style().unpolish(self)
+        self.style().polish(self)
+
     def dragEnterEvent(self, event: QDragEnterEvent):
+        if event.mimeData().hasFormat("application/x-neopod-playlist"):
+            self.setProperty("dndActive", True)
+            self._repolish()
+            pos = event.position().toPoint()
+            if self._target_item_at(pos):
+                event.acceptProposedAction()
+                return
+            # Let default handler accept so dragMoveEvent still fires
         if event.source() is not self and event.mimeData().hasUrls():
             pos = event.position().toPoint()
             if self._target_item_at(pos):
@@ -104,6 +125,7 @@ class NavDropListWidget(QListWidget):
         super().dragEnterEvent(event)
 
     def dragMoveEvent(self, event: QDragMoveEvent):
+        accept = False
         if event.source() is not self and event.mimeData().hasUrls():
             pos = event.position().toPoint()
             item = self._target_item_at(pos)
@@ -115,15 +137,34 @@ class NavDropListWidget(QListWidget):
                     item.setBackground(bg)
             if item:
                 event.acceptProposedAction()
-                return
-        super().dragMoveEvent(event)
+                accept = True
+        if not accept and event.mimeData().hasFormat("application/x-neopod-playlist"):
+            pos = event.position().toPoint()
+            item = self._target_item_at(pos)
+            if item != self._hovered_item:
+                self._clear_hover()
+                if item:
+                    self._hovered_item = item
+                    bg = self.palette().color(self.palette().ColorRole.Highlight)
+                    item.setBackground(bg)
+            if item:
+                event.acceptProposedAction()
+                accept = True
+        if not accept:
+            event.ignore()
 
     def dragLeaveEvent(self, event: QDragLeaveEvent):
         self._clear_hover()
+        if self.property("dndActive"):
+            self.setProperty("dndActive", False)
+            self._repolish()
         super().dragLeaveEvent(event)
 
     def dropEvent(self, event: QDropEvent):
         self._clear_hover()
+        if self.property("dndActive"):
+            self.setProperty("dndActive", False)
+            self._repolish()
         if event.source() is not self and event.mimeData().hasUrls():
             pos = event.position().toPoint()
             if self._target_item_at(pos):
@@ -133,6 +174,14 @@ class NavDropListWidget(QListWidget):
                     self.tracks_dropped_for_transfer.emit(paths)
                     event.acceptProposedAction()
                     return
+        if event.mimeData().hasFormat("application/x-neopod-playlist"):
+            pos = event.position().toPoint()
+            if self._target_item_at(pos):
+                playlist_id = bytes(event.mimeData().data("application/x-neopod-playlist")).decode()
+                if playlist_id:
+                    self.playlist_dropped_for_transfer.emit(playlist_id)
+                    event.acceptProposedAction()
+                    return
         super().dropEvent(event)
 
     def _clear_hover(self):
@@ -146,6 +195,7 @@ class SidebarWidget(QWidget):
     playlist_selected = pyqtSignal(str)
     tracks_dropped_on_playlist = pyqtSignal(str, list)
     tracks_dropped_for_nav_transfer = pyqtSignal(list)
+    playlist_dropped_for_nav_transfer = pyqtSignal(str)
 
     def __init__(self, parent=None):
         super().__init__(parent)
@@ -205,6 +255,9 @@ class SidebarWidget(QWidget):
             QListWidget::item:hover:!selected {{
                 background: {hl_light_name};
             }}
+            #navList[dndActive="true"]::item:hover:!selected {{
+                background: transparent;
+            }}
         """)
 
     def _build_ui(self):
@@ -292,6 +345,7 @@ class SidebarWidget(QWidget):
         layout.addWidget(line2)
 
         self._nav_list = NavDropListWidget()
+        self._nav_list.setObjectName("navList")
         items = [
             ("🎸  iPod", "ipod"),
             ("⚙️  Settings", "settings"),
@@ -303,6 +357,7 @@ class SidebarWidget(QWidget):
             self._nav_list.addItem(item)
         self._nav_list.itemClicked.connect(self._on_nav_item_clicked)
         self._nav_list.tracks_dropped_for_transfer.connect(self._on_tracks_dropped_for_nav_transfer)
+        self._nav_list.playlist_dropped_for_transfer.connect(self._on_playlist_dropped_for_transfer)
         layout.addWidget(self._nav_list)
 
         self._playlist_items: dict = {}
@@ -396,6 +451,9 @@ class SidebarWidget(QWidget):
     def _on_tracks_dropped_for_nav_transfer(self, paths: list):
         self.tracks_dropped_for_nav_transfer.emit(paths)
 
+    def _on_playlist_dropped_for_transfer(self, playlist_id: str):
+        self.playlist_dropped_for_nav_transfer.emit(playlist_id)
+
     def _on_playlists_reordered(self):
         order = self.get_playlist_order_ids()
         self.item_selected.emit("playlist_reorder", "|".join(order))
diff --git a/src/worker.py b/src/worker.py
index d89ed99..80a6de2 100644
--- a/src/worker.py
+++ b/src/worker.py
@@ -44,6 +44,7 @@ class WorkerThread(QThread):
                 "delete_tracks": self._run_delete_tracks,
                 "remove_duplicates": self._run_remove_duplicates,
                 "sync_metadata": self._run_sync_metadata,
+                "create_playlist": self._run_create_playlist,
             }
             handler = handlers.get(self.task_type)
             if handler:
@@ -362,6 +363,26 @@ class WorkerThread(QThread):
         self.progress_signal.emit(100, msg)
         self.finished_signal.emit(synced > 0, msg, {"synced": synced, "errors": errors})
 
+    def _run_create_playlist(self):
+        mount_point = self.kwargs.get("mount_point")
+        name = self.kwargs.get("playlist_name", "")
+        track_paths = self.kwargs.get("track_paths", [])
+
+        if not mount_point or not name:
+            self.finished_signal.emit(False, "Missing parameters for playlist creation", None)
+            return
+
+        from ipod_nano7_db import Nano7Database
+        db = Nano7Database(mount_point)
+
+        self.progress_signal.emit(0, f"Creating playlist '{name}' on iPod...")
+        success = db.create_playlist(name, track_paths)
+
+        if success:
+            self.finished_signal.emit(True, f"Playlist '{name}' created on iPod", None)
+        else:
+            self.finished_signal.emit(False, f"Failed to create playlist '{name}'", None)
+
     def stop(self):
         self.is_running = False
         self.wait()