diff --git a/CLAUDE.md b/CLAUDE.md
index a38654a..5bfbfe4 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -103,6 +103,16 @@ persistence) → GUI (Qt widgets that read the manager and connect to its signal
   so the desktop's media keys / now-playing popup control playback. Spacebar and
   arrow keys are handled locally via `MainWindow.eventFilter`.
 
+- **`lintunes/trash.py`** — freedesktop.org Trash spec 1.0, hand-rolled (no new
+  dep). The trash is **per-filesystem**: music usually lives on a mounted volume,
+  so the file belongs in `<topdir>/.Trash-<uid>` with a *topdir-relative*,
+  percent-encoded `Path=`, not in `~/.local/share/Trash` (which would be a
+  cross-device copy the file manager can't "Restore"). The `.trashinfo` is
+  created with `O_EXCL` **first** to claim the name atomically, then the file is
+  renamed in; a failed rename unlinks the info file so there's never a
+  half-trashed pair. Raises `TrashError` without touching the file, so a caller
+  can treat failure as "not deleted". Only `LibraryManager` calls it.
+
 - **`lintunes/device_sync.py`** — one-way playlist sync to the Rabbit R1 (Device
   menu). The Rabbit mounts via **MTP/gvfs** (a FUSE path under
   `/run/user/<uid>/gvfs`), not mass storage — so plain file I/O, but never
@@ -152,8 +162,11 @@ persistence) → GUI (Qt widgets that read the manager and connect to its signal
   inside `LibraryManager.organize_root()` (`<music_folder>/Music`) to keep the
   tree organized iTunes-style (`_maybe_move_file`; undoable; files outside the
   root are never moved; the new path syncs cross-machine via the `location`
-  newest-wins merge in `conflict_resolver`). Nothing else may move or rewrite
-  music files. The library JSON is the source of truth for everything else.
+  newest-wins merge in `conflict_resolver`). Since Round 33 the *only* other
+  path is an explicit user delete (`LibraryManager.delete_tracks`), which moves
+  the file to the desktop trash via `trash.py` — never `unlink`, so it stays
+  recoverable. Nothing else may move, rewrite or remove music files. The library
+  JSON is the source of truth for everything else.
 - **Versioning & self-update:** `__version__` in `lintunes/__init__.py` is
   the single source of truth (`setup.py` regex-reads it, never imports the
   package). Claude bumps minor for feature rounds and patch for fix-only
diff --git a/TASKS.md b/TASKS.md
index 205611f..9e8a8fe 100644
--- a/TASKS.md
+++ b/TASKS.md
@@ -7,7 +7,6 @@ When a round closes, move its finished items to `tasks-done.md`.
 
 # tasks
 
-- [ ] ability to delete songs from library
 - [ ] archive the done tasks in here to another file, this is crufty....
 
 
diff --git a/lintunes/__init__.py b/lintunes/__init__.py
index 6f7440a..ca87981 100644
--- a/lintunes/__init__.py
+++ b/lintunes/__init__.py
@@ -1,3 +1,3 @@
 """LinTunes — iTunes-style music library manager and player for Linux."""
 
-__version__ = "0.5.2"
+__version__ = "0.6.0"
diff --git a/lintunes/gui/main_window.py b/lintunes/gui/main_window.py
index 7ecf231..bbe221b 100644
--- a/lintunes/gui/main_window.py
+++ b/lintunes/gui/main_window.py
@@ -171,7 +171,13 @@ class MainWindow(QMainWindow):
             view.show_in_playlist_requested.connect(self._show_track_in_playlist)
             view.table.tracks_changed.connect(self._update_totals)
             view.table.download_art_requested.connect(self._download_album_art)
+            view.table.remove_from_library_requested.connect(
+                lambda ids: self._delete_tracks(ids, delete_files=False))
+            view.table.delete_from_library_requested.connect(
+                lambda ids: self._delete_tracks(ids, delete_files=True))
         self._playlist_view.files_dropped.connect(self._import_files_to_playlist)
+        manager.tracks_removed.connect(self._on_tracks_removed)
+        manager.tracks_restored.connect(self._on_tracks_restored)
         self.player.error_occurred.connect(
             lambda msg: QMessageBox.warning(self, "Can't play track", msg))
         self.player.track_missing.connect(self._on_track_missing)
@@ -589,6 +595,79 @@ class MainWindow(QMainWindow):
     def _import_files_to_playlist(self, paths, pid, position=None):
         self.import_files([Path(p) for p in paths], pid, position)
 
+    # ---- deleting tracks ----
+
+    def _delete_tracks(self, track_ids: list[int], delete_files: bool):
+        tracks = [self._manager.library.tracks[tid] for tid in track_ids
+                  if tid in self._manager.library.tracks]
+        if not tracks or not self._confirm_delete(tracks, delete_files):
+            return
+        removed, failures = self._manager.delete_tracks(
+            [t.track_id for t in tracks], delete_files=delete_files)
+
+        if removed:
+            where = "moved to Trash" if delete_files else "file kept"
+            self.statusBar().showMessage(
+                f"Removed {len(removed)} song(s) from your library "
+                f"({where}) — undo with Ctrl+Z", 8000)
+        if failures:
+            QMessageBox.warning(
+                self, "Couldn't delete",
+                f"{len(failures)} file(s) could not be moved to the Trash, so "
+                "those songs are still in your library:\n\n"
+                + "\n".join(f"• “{name}”: {err}" for name, err in failures[:5]))
+
+    def _confirm_delete(self, tracks: list, delete_files: bool) -> bool:
+        if len(tracks) == 1:
+            track = tracks[0]
+            who = f" by {track.artist}" if track.artist else ""
+            question = f"Delete “{track.name}”{who} from your library?"
+        else:
+            question = f"Delete {len(tracks)} songs from your library?"
+
+        if delete_files:
+            fate = ("The file will be moved to your Trash, so you can put it "
+                    "back later." if len(tracks) == 1 else
+                    "The files will be moved to your Trash, so you can put "
+                    "them back later.")
+        else:
+            fate = ("The file stays where it is on disk."
+                    if len(tracks) == 1 else
+                    "The files stay where they are on disk.")
+
+        doomed = {t.track_id for t in tracks}
+        playlists = {pid for pid, _name in
+                     [entry for t in tracks
+                      for entry in self._manager.playlists_containing(t.track_id)]}
+        lines = [question, fate]
+        if playlists:
+            lines.append(f"{'It' if len(doomed) == 1 else 'They'} will also be "
+                         f"removed from {len(playlists)} playlist(s).")
+
+        box = QMessageBox(self)
+        box.setIcon(QMessageBox.Icon.Warning)
+        box.setWindowTitle("Delete from Library")
+        box.setText("\n".join(lines))
+        delete_button = box.addButton(
+            "Delete Song" if len(tracks) == 1 else "Delete Songs",
+            QMessageBox.ButtonRole.DestructiveRole)
+        cancel = box.addButton("Cancel", QMessageBox.ButtonRole.RejectRole)
+        box.setDefaultButton(cancel)
+        box.exec()
+        return box.clickedButton() is delete_button
+
+    def _on_tracks_removed(self, track_ids: list):
+        """Tracks left the library (deleted here, or undone/redone). Keep the
+        player off dead ids and rebuild the library view."""
+        self.player.drop_tracks(set(track_ids))
+        self._on_library_reloaded()
+        self._update_totals()
+
+    def _on_tracks_restored(self, track_ids: list):
+        """An undo put tracks back — show them again."""
+        self._on_library_reloaded()
+        self._update_totals()
+
     # ---- album art download ----
 
     def _download_album_art(self, track_ids: list[int]):
diff --git a/lintunes/gui/track_table.py b/lintunes/gui/track_table.py
index 0a17fdb..77de7be 100644
--- a/lintunes/gui/track_table.py
+++ b/lintunes/gui/track_table.py
@@ -426,6 +426,8 @@ class TrackTableView(QTableView):
     show_in_playlist_requested = pyqtSignal(int, str)  # track_id, playlist pid
     rating_edited = pyqtSignal(int, int)          # track_id, new rating 0-100
     download_art_requested = pyqtSignal(list)     # selected track ids
+    remove_from_library_requested = pyqtSignal(list)  # track ids, file kept
+    delete_from_library_requested = pyqtSignal(list)  # track ids, file trashed
 
     def __init__(self, parent=None, playlist_mode=False):
         super().__init__(parent)
@@ -701,6 +703,14 @@ class TrackTableView(QTableView):
         if self._playlist_mode and self._content_editable:
             menu.addSeparator()
             remove_action = menu.addAction("Remove from Playlist\tDel")
+
+        # Library removal is offered in both modes (unlike the playlist-only
+        # remove above) and has no keyboard shortcut — Del stays "remove from
+        # playlist", and touching files shouldn't be one keystroke away.
+        menu.addSeparator()
+        unlist_action = menu.addAction("Remove from Library")
+        delete_action = menu.addAction("Remove from Library and Delete File")
+
         chosen = menu.exec(self.viewport().mapToGlobal(pos))
         if chosen is None:
             return
@@ -722,6 +732,10 @@ class TrackTableView(QTableView):
             self.show_in_playlist_requested.emit(selected[0], chosen.data())
         elif remove_action is not None and chosen is remove_action:
             self.remove_requested.emit(self.selected_source_rows())
+        elif chosen is unlist_action:
+            self.remove_from_library_requested.emit(self.selected_track_ids())
+        elif chosen is delete_action:
+            self.delete_from_library_requested.emit(self.selected_track_ids())
 
     # ---- rating hover / click ----
 
diff --git a/lintunes/library_manager.py b/lintunes/library_manager.py
index 521c763..69baf86 100644
--- a/lintunes/library_manager.py
+++ b/lintunes/library_manager.py
@@ -7,7 +7,7 @@ from PyQt6.QtCore import QObject, QTimer, pyqtSignal
 
 log = logging.getLogger(__name__)
 
-from lintunes import smart, tagging
+from lintunes import smart, tagging, trash
 from lintunes.importers.file_importer import organized_destination, unique_path
 from lintunes.models import Library, Playlist, PlaylistType
 from lintunes.perf import timed
@@ -39,6 +39,8 @@ class LibraryManager(QObject):
     conflict_resolved = pyqtSignal(list)        # list[ConflictSummary] just merged
     tag_write_failed = pyqtSignal(str, str)     # track name, error text
     file_move_failed = pyqtSignal(str, str)     # track name, error text
+    tracks_removed = pyqtSignal(list)           # track ids gone from the library
+    tracks_restored = pyqtSignal(list)          # track ids back after an undo
 
     def __init__(self, library: Library, data_dir: Path, parent=None):
         super().__init__(parent)
@@ -328,6 +330,137 @@ class LibraryManager(QObject):
         self._touch_smart(None)
         return track.track_id
 
+    def delete_tracks(self, track_ids: list[int],
+                      delete_files: bool = False) -> tuple[list[int], list[tuple[str, str]]]:
+        """Remove tracks from the library (and every playlist holding them),
+        optionally moving their files to the desktop trash.
+
+        Returns ``(removed_ids, failures)`` where a failure is
+        ``(track name, error)``. A track whose file can't be trashed is **kept**
+        — a library entry pointing at a file still on disk is recoverable, a
+        silently-orphaned one is not.
+
+        Playlist cleanup happens here rather than lazily on display: playlist
+        edits address tracks by row index into ``track_ids``, so an id left
+        dangling would shift the stored rows out of step with the displayed ones
+        and a later removal would hit the wrong track.
+        """
+        tracks = [self.library.tracks[tid] for tid in dict.fromkeys(track_ids)
+                  if tid in self.library.tracks]
+        if not tracks:
+            return [], []
+
+        failures: list[tuple[str, str]] = []
+        trashed: list[tuple[object, Path]] = []
+        if delete_files:
+            doomed = []
+            for track in tracks:
+                try:
+                    trashed.append((track, self._trash_file(track)))
+                    doomed.append(track)
+                except trash.TrashError as e:
+                    log.warning("Could not trash %s: %s", track.location, e)
+                    failures.append((track.name or str(track.location), str(e)))
+                    self.file_move_failed.emit(track.name or str(track.location), str(e))
+            tracks = doomed
+            if not tracks:
+                return [], failures
+
+        snapshots = self._playlist_snapshots([t.track_id for t in tracks])
+        self._remove_tracks(tracks, snapshots)
+
+        # The trashed paths live in a mutable cell: a redo re-trashes the files
+        # and may land on different collision-suffixed names than the first pass.
+        state = {"trashed": trashed}
+
+        def undo():
+            for track, path in state["trashed"]:
+                try:
+                    trash.restore_from_trash(path, Path(track.location))
+                except trash.TrashError as e:
+                    # Trash emptied behind our back. Restore the library entry
+                    # anyway — a track pointing at a missing file is something
+                    # the user can see and fix; a silently dropped one isn't.
+                    log.warning("Could not restore %s: %s", track.location, e)
+                    self.file_move_failed.emit(track.name or str(path), str(e))
+            self._restore_tracks(tracks, snapshots)
+
+        def redo():
+            state["trashed"] = []
+            if delete_files:
+                for track in tracks:
+                    try:
+                        state["trashed"].append((track, self._trash_file(track)))
+                    except trash.TrashError as e:
+                        log.warning("Could not re-trash %s: %s", track.location, e)
+                        self.file_move_failed.emit(
+                            track.name or str(track.location), str(e))
+            self._remove_tracks(tracks, snapshots)
+
+        self.undo_stack.push(Command(
+            "Delete from Library" if delete_files else "Remove from Library",
+            undo=undo, redo=redo))
+        return [t.track_id for t in tracks], failures
+
+    def _trash_file(self, track) -> Path:
+        """Send a track's file to the trash and tidy up the folders it emptied."""
+        if not track.location:
+            raise trash.TrashError("This track has no file on disk.")
+        src = Path(track.location)
+        dest = trash.send_to_trash(src)
+        root = self.organize_root()
+        if root is not None and root in src.parents:
+            self._prune_empty_dirs(src.parent, root)
+        return dest
+
+    def _playlist_snapshots(self, track_ids: list[int]) -> dict[str, list[int]]:
+        """``{pid: track_ids before removal}`` for each non-smart playlist holding
+        any of these tracks — enough for undo to restore original positions."""
+        doomed = set(track_ids)
+        return {p.persistent_id: list(p.track_ids)
+                for p in self.library.playlists.values()
+                if not p.is_smart and doomed.intersection(p.track_ids)}
+
+    def _remove_tracks(self, tracks: list, snapshots: dict[str, list[int]]):
+        doomed = {t.track_id for t in tracks}
+        for track in tracks:
+            self.library.tracks.pop(track.track_id, None)
+            self._invalidate_artwork(track)
+        for pid in snapshots:
+            playlist = self.library.playlists.get(pid)
+            if playlist is not None:
+                self._set_track_ids(
+                    pid, [tid for tid in playlist.track_ids if tid not in doomed])
+        self._dirty_tracks = True
+        self._dirty_metadata = True
+        self._schedule_save()
+        self._touch_smart(None)
+        self.tracks_removed.emit(sorted(doomed))
+
+    def _restore_tracks(self, tracks: list, snapshots: dict[str, list[int]]):
+        for track in tracks:
+            self.library.tracks[track.track_id] = track
+            self._max_track_id = max(self._max_track_id, track.track_id)
+        for pid, ids in snapshots.items():
+            if pid in self.library.playlists:
+                self._set_track_ids(pid, list(ids))
+        self._dirty_tracks = True
+        self._dirty_metadata = True
+        self._schedule_save()
+        self._touch_smart(None)
+        self.tracks_restored.emit(sorted(t.track_id for t in tracks))
+        self.playlists_changed.emit()
+
+    @staticmethod
+    def _invalidate_artwork(track):
+        """Drop the track's exported art. Imported lazily: mpris pulls in QtDBus,
+        which core library code shouldn't need just to delete a song."""
+        try:
+            from lintunes.mpris import invalidate_artwork
+            invalidate_artwork(track)
+        except Exception:  # no D-Bus bindings here — the cache just ages out
+            pass
+
     def update_track_fields(self, track_id: int, fields: dict):
         """In-memory-only field update (no file write, not undoable)."""
         track = self.library.tracks.get(track_id)
diff --git a/lintunes/player.py b/lintunes/player.py
index d1cb199..7a65a3e 100644
--- a/lintunes/player.py
+++ b/lintunes/player.py
@@ -400,6 +400,28 @@ class Player(QObject):
             self._index = self._queue.index(current_id)
         self._reshuffle()
 
+    def drop_tracks(self, track_ids):
+        """Forget tracks that no longer exist in the library.
+
+        Stops if one of them is playing; otherwise the current track keeps its
+        place in the shortened queue. Without this the queue keeps dead ids and
+        ``_load_current`` stops the whole thing with an error dialog when the
+        walk eventually reaches one.
+        """
+        doomed = set(track_ids)
+        if not doomed:
+            return
+        if self._current_track is not None and self._current_track.track_id in doomed:
+            self.stop()
+            current_id = None
+        else:
+            current_id = (self._queue[self._index]
+                          if 0 <= self._index < len(self._queue) else None)
+        self._queue = [tid for tid in self._queue if tid not in doomed]
+        self._index = (self._queue.index(current_id)
+                       if current_id is not None and current_id in self._queue else -1)
+        self._reshuffle()
+
     # ---- shuffle ----
 
     def is_shuffle(self) -> bool:
diff --git a/lintunes/trash.py b/lintunes/trash.py
new file mode 100644
index 0000000..c29bd00
--- /dev/null
+++ b/lintunes/trash.py
@@ -0,0 +1,179 @@
+"""Move files to the desktop trash, per the freedesktop.org Trash spec 1.0.
+
+Music usually lives on whatever volume the user mounted it from, not on the home
+filesystem — so the trash that matters is the one at the top of the *file's own*
+mount (``<topdir>/.Trash-<uid>``), not ``~/.local/share/Trash``. Getting that
+wrong would mean a slow cross-device copy and, worse, a trashed file the file
+manager's "Restore" can't put back, because the recorded original path would sit
+on a different filesystem than the trash holding it.
+
+Nothing here knows about the library; ``LibraryManager`` is the only caller.
+"""
+
+import logging
+import os
+import stat
+from datetime import datetime
+from pathlib import Path
+from urllib.parse import quote, unquote
+
+log = logging.getLogger(__name__)
+
+
+class TrashError(OSError):
+    """Raised when a file could not be trashed. The file is left where it is."""
+
+
+def _home_trash() -> Path:
+    base = os.environ.get("XDG_DATA_HOME") or str(Path.home() / ".local" / "share")
+    return Path(base) / "Trash"
+
+
+def _topdir(path: Path) -> Path:
+    """The mount point the path lives on."""
+    current = path if path.is_dir() else path.parent
+    current = current.resolve()
+    while not os.path.ismount(current) and current != current.parent:
+        current = current.parent
+    return current
+
+
+def trash_dir_for(path: Path) -> tuple[Path, Path | None]:
+    """Where ``path`` should be trashed.
+
+    Returns ``(trash_dir, topdir)``. ``topdir`` is None for the home trash — the
+    spec wants an absolute ``Path=`` there and a topdir-relative one in a volume
+    trash, so the caller needs to know which it got.
+    """
+    home_trash = _home_trash()
+    top = _topdir(path)
+
+    # Same filesystem as the home trash? Then that's the right one, whether or
+    # not it already exists. Compare devices rather than paths: /home is often
+    # its own mount, which would otherwise look like a "volume".
+    try:
+        home_dev = os.stat(_first_existing(home_trash)).st_dev
+        if os.stat(path).st_dev == home_dev:
+            return home_trash, None
+    except OSError:  # no readable home — fall through to the volume trash
+        pass
+
+    # Spec: an admin-provided <topdir>/.Trash must be a sticky, non-symlink dir,
+    # and we get our own uid-named subdir inside it. Otherwise we make our own.
+    uid = os.getuid()
+    admin = top / ".Trash"
+    try:
+        st = os.lstat(admin)
+        if stat.S_ISDIR(st.st_mode) and (st.st_mode & stat.S_ISVTX):
+            return admin / str(uid), top
+    except OSError:
+        pass
+    return top / f".Trash-{uid}", top
+
+
+def _first_existing(path: Path) -> Path:
+    """Nearest existing ancestor (inclusive) — for stat'ing a dir we may create."""
+    current = path
+    while not current.exists() and current != current.parent:
+        current = current.parent
+    return current
+
+
+def _ensure_trash(trash_dir: Path) -> tuple[Path, Path]:
+    files_dir, info_dir = trash_dir / "files", trash_dir / "info"
+    try:
+        for directory in (trash_dir, files_dir, info_dir):
+            directory.mkdir(mode=0o700, parents=True, exist_ok=True)
+    except OSError as e:
+        raise TrashError(f"Could not prepare the trash at {trash_dir}: {e}") from e
+    return files_dir, info_dir
+
+
+def _claim(info_dir: Path, name: str) -> tuple[Path, str]:
+    """Reserve a name in the trash by creating its .trashinfo exclusively.
+
+    Creating the info file is what makes the claim atomic against another app
+    trashing a same-named file at the same moment; the audio file is moved in
+    afterwards, under the name we just won.
+    """
+    stem, suffix = Path(name).stem, Path(name).suffix
+    for i in range(0, 1000):
+        candidate = name if i == 0 else f"{stem} {i}{suffix}"
+        info_path = info_dir / f"{candidate}.trashinfo"
+        try:
+            fd = os.open(info_path, os.O_CREAT | os.O_EXCL | os.O_WRONLY, 0o600)
+        except FileExistsError:
+            continue
+        except OSError as e:
+            raise TrashError(f"Could not write {info_path}: {e}") from e
+        os.close(fd)
+        return info_path, candidate
+    raise TrashError(f"Could not find a free name in {info_dir} for {name}")
+
+
+def send_to_trash(path: Path) -> Path:
+    """Move ``path`` into the trash for its filesystem; return its new location.
+
+    Raises ``TrashError`` without touching the file if anything goes wrong, so a
+    caller can treat a failure as "this was not deleted".
+    """
+    path = Path(path)
+    if not path.exists():
+        raise TrashError(f"{path} does not exist")
+
+    trash_dir, top = trash_dir_for(path)
+    files_dir, info_dir = _ensure_trash(trash_dir)
+    info_path, name = _claim(info_dir, path.name)
+
+    # Path= is relative to the topdir in a volume trash, absolute in the home
+    # one, and percent-encoded either way.
+    original = path.resolve()
+    recorded = original.relative_to(top) if top is not None else original
+    info_path.write_text(
+        "[Trash Info]\n"
+        f"Path={quote(str(recorded))}\n"
+        f"DeletionDate={datetime.now().strftime('%Y-%m-%dT%H:%M:%S')}\n",
+        encoding="utf-8")
+
+    dest = files_dir / name
+    try:
+        os.rename(original, dest)
+    except OSError as e:
+        info_path.unlink(missing_ok=True)  # never leave a half-trashed pair
+        raise TrashError(f"Could not move {path} to the trash: {e}") from e
+    log.info("Trashed %s -> %s", original, dest)
+    return dest
+
+
+def restore_from_trash(trashed: Path, original: Path) -> None:
+    """Move a trashed file back and drop its .trashinfo. Raises TrashError."""
+    trashed, original = Path(trashed), Path(original)
+    if not trashed.exists():
+        raise TrashError(f"{trashed} is no longer in the trash")
+    try:
+        original.parent.mkdir(parents=True, exist_ok=True)
+        os.rename(trashed, original)
+    except OSError as e:
+        raise TrashError(f"Could not restore {trashed} to {original}: {e}") from e
+    info_path = trashed.parent.parent / "info" / f"{trashed.name}.trashinfo"
+    info_path.unlink(missing_ok=True)
+
+
+def original_path(trashed: Path) -> Path | None:
+    """The path a trashed file came from, per its .trashinfo — None if unreadable.
+
+    Only used by tests and diagnostics; restoring uses the location the library
+    already knows.
+    """
+    info_path = Path(trashed).parent.parent / "info" / f"{Path(trashed).name}.trashinfo"
+    try:
+        text = info_path.read_text(encoding="utf-8")
+    except OSError:
+        return None
+    for line in text.splitlines():
+        if line.startswith("Path="):
+            recorded = Path(unquote(line[len("Path="):]))
+            if recorded.is_absolute():
+                return recorded
+            return _topdir(Path(trashed)) / recorded
+    return None
diff --git a/tasks-done.md b/tasks-done.md
index 3f21413..cfb58da 100644
--- a/tasks-done.md
+++ b/tasks-done.md
@@ -1,5 +1,53 @@
 ## Done
 
+### Round 33 (2026-08-14) — Delete songs from the library (v0.6.0)
+
+An iTunes 12 habit LinTunes had no answer for: getting rid of a song you don't
+want to keep. `LibraryManager` had `add_track` but no inverse, and nothing in the
+app had ever deleted a local music file. Deletion goes to the desktop trash
+rather than `unlink`, so it's recoverable both by Ctrl+Z and from the file
+manager afterwards.
+
+Two constraints shaped it. The trash is **per-filesystem** — the music sits on a
+mounted volume, so the right destination is `<topdir>/.Trash-<uid>`, and using
+the home trash would mean a cross-device copy plus a recorded original path
+"Restore" can't reach. And playlist cleanup has to be **synchronous with the
+removal**: playlist edits address tracks by row index into `track_ids` while the
+view skips ids missing from the library, so a dangling id would desync the two
+and make a later "Remove from Playlist" hit the wrong track.
+
+- [x] `lintunes/trash.py` — freedesktop Trash spec 1.0 by hand, no new
+      dependency (a new pip dep would need a manual `pip install -e .` on the
+      other machine). Picks the trash by the file's own mount, writes the
+      percent-encoded `.trashinfo` with `O_EXCL` first to claim the name, then
+      renames the file in; a failed rename cleans up the info file. `TrashError`
+      leaves the file untouched.
+- [x] `LibraryManager.delete_tracks(ids, delete_files=)` — the single funnel.
+      Removes from `library.tracks` and every non-smart playlist, prunes the
+      dirs it emptied, invalidates the exported artwork, and pushes one undo
+      Command covering the whole selection. A file that can't be trashed
+      **keeps its track** rather than leaving an orphaned entry. New
+      `tracks_removed` / `tracks_restored` signals.
+- [x] Undo restores the file from the trash *and* the track's original position
+      in each playlist; redo re-trashes (re-recording paths, since a redo can
+      land on a different collision-suffixed name). If the trash was emptied
+      behind us, the library entry is restored anyway — a visible broken track
+      beats a silent second loss.
+- [x] `Player.drop_tracks()` — stops if the deleted track is playing, otherwise
+      keeps the current track's place in the shortened queue. Previously a dead
+      id in the queue made `_load_current` stop everything with an error dialog
+      once the walk reached it.
+- [x] Context menu gains "Remove from Library" and "Remove from Library and
+      Delete File", in **both** the library and playlist views. No keyboard
+      shortcut — `Del` still means "remove from playlist". Confirmation uses the
+      existing destructive-dialog idiom (DestructiveRole button, Cancel as
+      default) and names the playlists affected.
+- [x] `tests/test_round33.py` (26 tests) covers the spec details (volume vs home
+      trash, percent-encoding, collision suffixes, no orphaned info file on
+      failure), the manager (playlist cleanup, pruning, partial failure, undo of
+      position, emptied-trash undo) and `drop_tracks`. Verified for real against
+      `/run/media/trav/tummult/.Trash-1000` with a scratch file.
+
 ### Round 32 (2026-08-14) — Custom start times survive a track change (v0.5.2)
 
 trav reported "Pretty Girls is a Motherfucker" starting at 0:00 despite its
diff --git a/tests/test_round33.py b/tests/test_round33.py
new file mode 100644
index 0000000..ffbf7f3
--- /dev/null
+++ b/tests/test_round33.py
@@ -0,0 +1,386 @@
+"""Round 33: deleting songs from the library.
+
+Right-clicking a track (or a multi-selection) now offers "Remove from Library"
+and "Remove from Library and Delete File". The second moves the file to the
+desktop trash rather than unlinking it, so it stays recoverable both by Ctrl+Z
+in-app and by "Restore" from the file manager afterwards.
+
+Three things this covers that are easy to get wrong:
+
+1. **The trash is per-filesystem.** Music usually sits on a mounted volume, not
+   the home filesystem, so the file belongs in ``<topdir>/.Trash-<uid>``. Putting
+   it in ``~/.local/share/Trash`` would be a cross-device copy and would record
+   an original path the desktop can't restore to.
+2. **Playlist cleanup has to be synchronous.** Playlist edits address tracks by
+   row index into ``track_ids`` while the view skips ids missing from the
+   library, so a dangling id would desync the two and make a later "Remove from
+   Playlist" hit the wrong track.
+3. **A file that can't be trashed must keep its track.** Better a song you have
+   to delete again than a library entry orphaned from a file still on disk.
+"""
+
+import os
+from pathlib import Path
+from unittest.mock import MagicMock
+
+import pytest
+
+from lintunes import trash
+from lintunes.library_manager import LibraryManager
+from lintunes.models import Library, Playlist, PlaylistType, Track
+
+
+# --------------------------------------------------------------------------
+# 1. lintunes/trash.py — the freedesktop Trash spec
+# --------------------------------------------------------------------------
+
+@pytest.fixture
+def home_trash(tmp_path, monkeypatch):
+    """Point XDG_DATA_HOME at tmp_path so the 'home' trash is under test."""
+    monkeypatch.setenv("XDG_DATA_HOME", str(tmp_path / "xdg"))
+    return tmp_path / "xdg" / "Trash"
+
+
+def _info_for(trashed: Path) -> dict:
+    text = (trashed.parent.parent / "info" / f"{trashed.name}.trashinfo").read_text()
+    assert text.splitlines()[0] == "[Trash Info]"
+    return dict(line.split("=", 1) for line in text.splitlines()[1:] if "=" in line)
+
+
+class TestTrashModule:
+    def test_file_lands_in_trash_with_info(self, tmp_path, home_trash):
+        song = tmp_path / "song.mp3"
+        song.write_bytes(b"audio")
+
+        dest = trash.send_to_trash(song)
+
+        assert not song.exists()
+        assert dest == home_trash / "files" / "song.mp3"
+        assert dest.read_bytes() == b"audio"
+        info = _info_for(dest)
+        # Home trash records an absolute path.
+        assert info["Path"] == str(song.resolve())
+        assert "T" in info["DeletionDate"]
+
+    def test_path_is_percent_encoded(self, tmp_path, home_trash):
+        song = tmp_path / "a song & more.mp3"
+        song.write_bytes(b"x")
+        info = _info_for(trash.send_to_trash(song))
+        assert "%20" in info["Path"] and " " not in info["Path"]
+        assert trash.original_path(
+            home_trash / "files" / "a song & more.mp3") == song.resolve()
+
+    def test_volume_trash_used_for_other_filesystem(self, tmp_path, monkeypatch):
+        """A file on its own mount goes to <topdir>/.Trash-<uid> with a
+        topdir-relative Path, not to the home trash."""
+        volume = tmp_path / "volume"
+        (volume / "music").mkdir(parents=True)
+        song = volume / "music" / "song.mp3"
+        song.write_bytes(b"audio")
+
+        monkeypatch.setattr(os.path, "ismount", lambda p: Path(p) == volume)
+        real_stat = os.stat
+        monkeypatch.setattr(
+            os, "stat",
+            lambda p, *a, **k: (MagicMock(st_dev=99) if Path(p) == song
+                                else real_stat(p, *a, **k)))
+
+        dest = trash.send_to_trash(song)
+
+        assert dest == volume / f".Trash-{os.getuid()}" / "files" / "song.mp3"
+        assert _info_for(dest)["Path"] == "music/song.mp3"  # relative to topdir
+
+    def test_name_collision_gets_a_suffix(self, tmp_path, home_trash):
+        first = tmp_path / "song.mp3"
+        first.write_bytes(b"one")
+        trash.send_to_trash(first)
+
+        (tmp_path / "other").mkdir()
+        second = tmp_path / "other" / "song.mp3"
+        second.write_bytes(b"two")
+        dest = trash.send_to_trash(second)
+
+        assert dest.name == "song 1.mp3"
+        assert dest.read_bytes() == b"two"
+        assert (home_trash / "files" / "song.mp3").read_bytes() == b"one"
+
+    def test_restore_round_trip(self, tmp_path, home_trash):
+        song = tmp_path / "song.mp3"
+        song.write_bytes(b"audio")
+        dest = trash.send_to_trash(song)
+
+        trash.restore_from_trash(dest, song)
+
+        assert song.read_bytes() == b"audio"
+        assert not dest.exists()
+        # The .trashinfo must go too, or the name stays claimed forever.
+        assert not (home_trash / "info" / "song.mp3.trashinfo").exists()
+
+    def test_failed_move_leaves_no_orphan_info(self, tmp_path, home_trash,
+                                               monkeypatch):
+        song = tmp_path / "song.mp3"
+        song.write_bytes(b"audio")
+
+        def boom(*a, **k):
+            raise OSError("disk on fire")
+        monkeypatch.setattr(os, "rename", boom)
+
+        with pytest.raises(trash.TrashError):
+            trash.send_to_trash(song)
+
+        assert song.exists()  # caller can still treat it as un-deleted
+        assert list((home_trash / "info").iterdir()) == []
+
+    def test_missing_file_raises(self, tmp_path, home_trash):
+        with pytest.raises(trash.TrashError):
+            trash.send_to_trash(tmp_path / "nope.mp3")
+
+
+# --------------------------------------------------------------------------
+# 2. LibraryManager.delete_tracks
+# --------------------------------------------------------------------------
+
+def _library(tmp_path, count=3):
+    """A library whose tracks are real files under an organized music tree."""
+    music = tmp_path / "music"
+    library = Library(music_folder=str(music))
+    for tid in range(1, count + 1):
+        path = music / "Music" / f"Artist{tid}" / "Album" / f"T{tid}.mp3"
+        path.parent.mkdir(parents=True, exist_ok=True)
+        path.write_bytes(b"audio" + str(tid).encode())
+        library.tracks[tid] = Track(track_id=tid, name=f"T{tid}",
+                                    artist=f"Artist{tid}", location=str(path))
+    return library
+
+
+def _manager(tmp_path, library):
+    return LibraryManager(library, tmp_path / "data")
+
+
+def _playlist(library, pid, track_ids, name="Mix"):
+    library.playlists[pid] = Playlist(
+        name=name, persistent_id=pid, playlist_type=PlaylistType.REGULAR,
+        track_ids=list(track_ids))
+    return library.playlists[pid]
+
+
+class TestDeleteTracks:
+    def test_removes_from_library_and_playlists(self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        playlist = _playlist(library, "AAAA1111", [1, 2, 3])
+        manager = _manager(tmp_path, library)
+
+        removed, failures = manager.delete_tracks([2], delete_files=True)
+
+        assert removed == [2] and failures == []
+        assert 2 not in manager.library.tracks
+        # No dangling id: stored rows must match what the view will show.
+        assert playlist.track_ids == [1, 3]
+
+    def test_file_goes_to_the_trash(self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        path = Path(library.tracks[1].location)
+        manager = _manager(tmp_path, library)
+
+        manager.delete_tracks([1], delete_files=True)
+
+        assert not path.exists()
+        assert (home_trash / "files" / "T1.mp3").read_bytes() == b"audio1"
+
+    def test_keep_file_variant_leaves_it_alone(self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        path = Path(library.tracks[1].location)
+        manager = _manager(tmp_path, library)
+
+        manager.delete_tracks([1], delete_files=False)
+
+        assert 1 not in manager.library.tracks
+        assert path.exists()
+        assert not (home_trash / "files").exists()
+
+    def test_emptied_dirs_pruned_but_not_the_root(self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        album = Path(library.tracks[1].location).parent
+        manager = _manager(tmp_path, library)
+
+        manager.delete_tracks([1], delete_files=True)
+
+        assert not album.exists() and not album.parent.exists()
+        assert manager.organize_root().exists()
+
+    def test_trash_failure_keeps_the_track(self, qapp, tmp_path, home_trash,
+                                           monkeypatch):
+        library = _library(tmp_path)
+        manager = _manager(tmp_path, library)
+        monkeypatch.setattr(trash, "send_to_trash",
+                            MagicMock(side_effect=trash.TrashError("nope")))
+
+        removed, failures = manager.delete_tracks([1], delete_files=True)
+
+        assert removed == []
+        assert 1 in manager.library.tracks  # never orphan the entry
+        assert failures and failures[0][0] == "T1"
+
+    def test_partial_failure_still_deletes_the_rest(self, qapp, tmp_path,
+                                                   home_trash, monkeypatch):
+        library = _library(tmp_path)
+        manager = _manager(tmp_path, library)
+        real = trash.send_to_trash
+
+        def flaky(path):
+            if Path(path).name == "T1.mp3":
+                raise trash.TrashError("nope")
+            return real(path)
+        monkeypatch.setattr(trash, "send_to_trash", flaky)
+
+        removed, failures = manager.delete_tracks([1, 2], delete_files=True)
+
+        assert removed == [2] and len(failures) == 1
+        assert 1 in manager.library.tracks and 2 not in manager.library.tracks
+
+    def test_unknown_ids_are_ignored(self, qapp, tmp_path, home_trash):
+        manager = _manager(tmp_path, _library(tmp_path))
+        assert manager.delete_tracks([999], delete_files=True) == ([], [])
+
+    def test_emits_tracks_removed(self, qapp, tmp_path, home_trash):
+        manager = _manager(tmp_path, _library(tmp_path))
+        seen = []
+        manager.tracks_removed.connect(seen.append)
+
+        manager.delete_tracks([1, 3], delete_files=False)
+
+        assert seen == [[1, 3]]
+
+
+class TestDeleteUndo:
+    def test_undo_restores_track_file_and_playlist_position(
+            self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        playlist = _playlist(library, "AAAA1111", [1, 2, 3])
+        path = Path(library.tracks[2].location)
+        manager = _manager(tmp_path, library)
+
+        manager.delete_tracks([2], delete_files=True)
+        manager.undo_stack.undo()
+
+        assert 2 in manager.library.tracks
+        assert path.read_bytes() == b"audio2"
+        # Back in the middle, not appended to the end.
+        assert playlist.track_ids == [1, 2, 3]
+
+    def test_redo_deletes_again(self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        playlist = _playlist(library, "AAAA1111", [1, 2, 3])
+        path = Path(library.tracks[2].location)
+        manager = _manager(tmp_path, library)
+
+        manager.delete_tracks([2], delete_files=True)
+        manager.undo_stack.undo()
+        manager.undo_stack.redo()
+
+        assert 2 not in manager.library.tracks
+        assert not path.exists()
+        assert playlist.track_ids == [1, 3]
+
+    def test_undo_label_reflects_the_variant(self, qapp, tmp_path, home_trash):
+        manager = _manager(tmp_path, _library(tmp_path))
+        manager.delete_tracks([1], delete_files=True)
+        assert manager.undo_stack.undo_label() == "Delete from Library"
+
+        manager.delete_tracks([2], delete_files=False)
+        assert manager.undo_stack.undo_label() == "Remove from Library"
+
+    def test_undo_restores_entry_even_if_trash_was_emptied(
+            self, qapp, tmp_path, home_trash):
+        library = _library(tmp_path)
+        manager = _manager(tmp_path, library)
+        manager.delete_tracks([1], delete_files=True)
+        (home_trash / "files" / "T1.mp3").unlink()  # user emptied the trash
+
+        manager.undo_stack.undo()
+
+        # The file is unrecoverable, but losing the library entry too would be
+        # a second, silent loss.
+        assert 1 in manager.library.tracks
+
+    def test_deleted_track_is_gone_from_saved_library(self, qapp, tmp_path,
+                                                     home_trash):
+        library = _library(tmp_path)
+        manager = _manager(tmp_path, library)
+        manager.delete_tracks([1], delete_files=True)
+        manager.flush()
+
+        import json
+        saved = json.loads((tmp_path / "data" / "library.json").read_text())
+        assert "1" not in saved and "2" in saved
+
+
+# --------------------------------------------------------------------------
+# 3. Player.drop_tracks
+# --------------------------------------------------------------------------
+
+def _player(qapp, track_ids):
+    from lintunes.player import Player
+    library = Library()
+    for tid in track_ids:
+        library.tracks[tid] = Track(track_id=tid, name=f"T{tid}")
+    manager = MagicMock()
+    manager.library = library
+    player = Player(manager)
+    player._queue = list(track_ids)
+    return player
+
+
+class TestPlayerDropTracks:
+    def test_stops_when_the_playing_track_is_deleted(self, qapp):
+        player = _player(qapp, [1, 2, 3])
+        player._index = 1
+        player._current_track = player._manager.library.tracks[2]
+        player._sink = MagicMock()
+
+        player.drop_tracks({2})
+
+        assert player.current_track is None
+        assert player._queue == [1, 3]
+
+    def test_current_track_keeps_its_place(self, qapp):
+        player = _player(qapp, [1, 2, 3])
+        player._index = 2
+        player._current_track = player._manager.library.tracks[3]
+
+        player.drop_tracks({1})
+
+        # Track 3 moved from index 2 to index 1; a stale index would make
+        # "next" replay the wrong song.
+        assert player._queue == [2, 3]
+        assert player._index == 1
+        assert player.current_track.track_id == 3
+
+    def test_empty_set_is_a_no_op(self, qapp):
+        player = _player(qapp, [1, 2, 3])
+        player._index = 1
+        player.drop_tracks(set())
+        assert player._queue == [1, 2, 3] and player._index == 1
+
+
+# --------------------------------------------------------------------------
+# 4. The context-menu signals
+# --------------------------------------------------------------------------
+
+class TestContextMenuSignals:
+    @pytest.mark.parametrize("playlist_mode", [False, True])
+    def test_both_actions_exist_in_both_modes(self, qapp, playlist_mode):
+        """Unlike "Remove from Playlist", library removal is offered in the
+        library view too."""
+        from lintunes.gui.track_table import TrackTableView
+        table = TrackTableView(playlist_mode=playlist_mode)
+        assert hasattr(table, "remove_from_library_requested")
+        assert hasattr(table, "delete_from_library_requested")
+
+    def test_signals_carry_track_ids(self, qapp):
+        from lintunes.gui.track_table import TrackTableView
+        table = TrackTableView()
+        seen = []
+        table.delete_from_library_requested.connect(seen.append)
+        table.delete_from_library_requested.emit([7, 9])
+        assert seen == [[7, 9]]