diff --git a/plextraktsync/cli.py b/plextraktsync/cli.py
index 8f3a832a45..601a5391dc 100644
--- a/plextraktsync/cli.py
+++ b/plextraktsync/cli.py
@@ -276,6 +276,29 @@ def unmatched():
     """
 
 
+@command()
+@click.option(
+    "--remove-watched",
+    type=bool,
+    default=False,
+    is_flag=True,
+    help="Remove watched items from playlist",
+)
+@click.option(
+    "--dry-run",
+    "dry_run",
+    type=bool,
+    default=False,
+    is_flag=True,
+    help="Dry run: Do not make changes",
+)
+@click.argument("playlist", nargs=1)
+def update_playlist():
+    """
+    Update playlist: Remove watched items
+    """
+
+
 @command()
 @click.option(
     "--server",
@@ -379,5 +402,6 @@ def config():
 cli.add_command(sync)
 cli.add_command(trakt_login)
 cli.add_command(unmatched)
+cli.add_command(update_playlist)
 cli.add_command(watch)
 cli.add_command(watched_shows)
diff --git a/plextraktsync/commands/update_playlist.py b/plextraktsync/commands/update_playlist.py
new file mode 100644
index 0000000000..14ce208557
--- /dev/null
+++ b/plextraktsync/commands/update_playlist.py
@@ -0,0 +1,44 @@
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
+from plextraktsync.decorators.coro import coro
+from plextraktsync.factory import factory
+from plextraktsync.plex.PlexPlaylist import PlexPlaylist
+
+if TYPE_CHECKING:
+    from plextraktsync.plex.types import PlexPlayable
+
+
+def format_title(p: PlexPlayable):
+    library_title = p._data.attrib.get("librarySectionTitle")
+    title = f"'{p.title}'"
+    if p.year:
+        title += f" ({p.year})"
+
+    if library_title:
+        title += f" (in '{library_title}')"
+    if p.sourceURI:
+        title += f" (on {p.sourceURI})"
+
+    return title
+
+
+@coro
+async def update_playlist(playlist: str, remove_watched: bool, dry_run: bool):
+    print = factory.print
+    print(f"Update playlist: '{playlist}'")
+    print(f"Remove watched from playlist: {remove_watched}")
+    print(f"Dry run: {dry_run}")
+
+    pl = PlexPlaylist(factory.plex_server, playlist)
+    print(f"Playlist: {pl}")
+    items = pl.playlist.items().copy()
+    p: PlexPlayable
+    for p in items:
+        if remove_watched and p.isPlayed:
+            print(f"{'Remove' if not dry_run else 'Would remove'} from playlist: {format_title(p)}")
+            items.remove(p)
+    print(f"Update playlist: {len(pl)} -> {len(items)} items")
+    if not dry_run:
+        pl.update(items)
diff --git a/plextraktsync/plex/PlexPlaylist.py b/plextraktsync/plex/PlexPlaylist.py
index 063200f2d6..e792530c41 100644
--- a/plextraktsync/plex/PlexPlaylist.py
+++ b/plextraktsync/plex/PlexPlaylist.py
@@ -31,6 +31,9 @@ def __len__(self):
     def __contains__(self, m: Media):
         return m.plex_key in self.items
 
+    def __str__(self):
+        return f"PlexPlaylist<name='{self.name}'>"
+
     @cached_property
     def playlist(self) -> Playlist | None:
         try:
diff --git a/plextraktsync/plex/types.py b/plextraktsync/plex/types.py
index b33f136434..66d598fc93 100644
--- a/plextraktsync/plex/types.py
+++ b/plextraktsync/plex/types.py
@@ -5,3 +5,4 @@
 from plexapi.video import Episode, Movie, Show
 
 PlexMedia = Union[Movie, Show, Episode]
+PlexPlayable = Union[Movie, Episode]