diff --git a/lib/database_cleanup/__init__.py b/lib/database_cleanup/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/lib/database_cleanup/prune_deleted_content.py b/lib/database_cleanup/prune_deleted_content.py
new file mode 100644
index 00000000..80d98eb0
--- /dev/null
+++ b/lib/database_cleanup/prune_deleted_content.py
@@ -0,0 +1,168 @@
+"""
+Tautulli Orphaned History Pruner
+Standalone script to remove watch history entries for media no longer in Plex
+"""
+
+import argparse
+import asyncio
+import logging
+import sqlite3
+from contextlib import contextmanager
+from plexapi.server import PlexServer
+from typing import Set, List
+
+# Configure logging
+logger = logging.getLogger("tautulli-pruner")
+log_handler = logging.StreamHandler()
+log_formatter = logging.Formatter("%(asctime)s - %(levelname)s - %(message)s")
+log_handler.setFormatter(log_formatter)
+logger.addHandler(log_handler)
+
+
+@contextmanager
+def database_connection(db_path: str):
+    """Context manager for SQLite database connections."""
+    conn = sqlite3.connect(db_path)
+    conn.row_factory = sqlite3.Row
+    try:
+        yield conn
+    finally:
+        conn.close()
+
+
+class PlexManager:
+    """Handles Plex server communication with async support"""
+
+    def __init__(self, base_url: str, token: str, server_name: str = None):
+        self.plex = PlexServer(base_url, token)
+        self.server_name = server_name or self.plex.friendlyName
+
+    async def fetch_all_media_ids(self) -> Set[int]:
+        """Fetch all rating keys from relevant Plex libraries"""
+        media_ids = set()
+        loop = asyncio.get_event_loop()
+
+        try:
+            sections = await loop.run_in_executor(None, self.plex.library.sections)
+            for section in sections:
+                if section.type in ("movie", "show"):
+                    try:
+                        items = await loop.run_in_executor(None, section.all)
+                        media_ids.update(item.ratingKey for item in items)
+                        logger.debug(f"Processed {section.title} ({len(items)} items)")
+                    except Exception as e:
+                        logger.error(f"Error processing {section.title}: {e}")
+        except Exception as e:
+            logger.error(f"Plex connection failed: {e}")
+
+        return media_ids
+
+
+class HistoryPruner:
+    """Handles orphaned history detection and removal"""
+
+    def __init__(self, db_path: str):
+        self.db_path = db_path
+
+    def get_watch_history(self) -> List[int]:
+        """Retrieve all rating keys from watch history"""
+        with database_connection(self.db_path) as conn:
+            cursor = conn.cursor()
+            cursor.execute("SELECT rating_key FROM watch_history")
+            return [row["rating_key"] for row in cursor.fetchall()]
+
+    def delete_orphans(self, rating_keys: List[int]):
+        """Batch delete orphaned entries efficiently"""
+        if not rating_keys:
+            logger.info("No orphans to delete")
+            return
+
+        chunk_size = 999  # SQLite parameter limit
+        total_deleted = 0
+
+        with database_connection(self.db_path) as conn:
+            cursor = conn.cursor()
+            try:
+                cursor.execute("BEGIN TRANSACTION")
+                for i in range(0, len(rating_keys), chunk_size):
+                    chunk = rating_keys[i : i + chunk_size]
+                    placeholders = ",".join(["?"] * len(chunk))
+                    cursor.execute(
+                        f"DELETE FROM watch_history WHERE rating_key IN ({placeholders})",
+                        chunk,
+                    )
+                    total_deleted += cursor.rowcount
+                cursor.execute("COMMIT")
+                logger.info(f"Deleted {total_deleted} orphaned entries")
+            except sqlite3.Error as e:
+                cursor.execute("ROLLBACK")
+                logger.error(f"Database error: {e}")
+                raise
+
+
+async def main(args):
+    """Orphan pruning workflow"""
+    logger.setLevel(args.loglevel)
+
+    # Initialize components
+    plex = PlexManager(args.plex_url, args.plex_token, args.plex_server)
+    pruner = HistoryPruner(args.db_path)
+
+    try:
+        # Fetch data from sources
+        logger.info("Fetching Plex media IDs...")
+        plex_ids = await plex.fetch_all_media_ids()
+        logger.info(f"Found {len(plex_ids)} Plex media items")
+
+        logger.info("Fetching Tautulli watch history...")
+        history_ids = pruner.get_watch_history()
+        logger.info(f"Found {len(history_ids)} watch history entries")
+
+        # Calculate orphans
+        orphans = list(set(history_ids) - plex_ids)
+        logger.info(f"Identified {len(orphans)} orphaned entries")
+
+        pruner.delete_orphans(orphans)
+
+    except Exception as e:
+        logger.error(f"Pruning failed: {e}")
+        raise
+
+
+if __name__ == "__main__":
+    parser = argparse.ArgumentParser(
+        description="Tautulli orphaned history pruner",
+        formatter_class=argparse.ArgumentDefaultsHelpFormatter,
+    )
+
+    # Required arguments
+    parser.add_argument(
+        "--db-path", required=True, help="Path to Tautulli database file (tautulli.db)"
+    )
+    parser.add_argument(
+        "--plex-url", required=True, help="Plex server URL (e.g. http://plex:32400)"
+    )
+    parser.add_argument("--plex-token", required=True, help="Plex authentication token")
+
+    # Optional arguments
+    parser.add_argument("--plex-server", help="Plex server name (if multiple servers)")
+    parser.add_argument(
+        "-v", "--verbose", action="count", default=0, help="Increase logging verbosity"
+    )
+
+    args = parser.parse_args()
+
+    # Set log level based on verbosity
+    args.loglevel = logging.WARNING
+    if args.verbose == 1:
+        args.loglevel = logging.INFO
+    elif args.verbose >= 2:
+        args.loglevel = logging.DEBUG
+
+    try:
+        asyncio.run(main(args))
+    except KeyboardInterrupt:
+        logger.error("Operation cancelled by user")
+    except Exception as e:
+        logger.critical(f"Fatal error: {e}")
+        exit(1)
diff --git a/lib/database_cleanup/tests/__init__.py b/lib/database_cleanup/tests/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/lib/database_cleanup/tests/test_prune_deleted_content.py b/lib/database_cleanup/tests/test_prune_deleted_content.py
new file mode 100644
index 00000000..65765ba0
--- /dev/null
+++ b/lib/database_cleanup/tests/test_prune_deleted_content.py
@@ -0,0 +1,123 @@
+import pytest
+from unittest.mock import MagicMock, patch
+import sqlite3
+
+from lib.database_cleanup.prune_deleted_content import (
+    PlexManager,
+    HistoryPruner,
+    main as pruner_main,
+)
+import logging
+
+
+@pytest.fixture
+def mock_plex():
+    plex = MagicMock()
+    section_movie = MagicMock()
+    section_movie.type = "movie"
+    section_movie.title = "Movies"
+    section_movie.all.return_value = [
+        MagicMock(ratingKey=1001),
+        MagicMock(ratingKey=1002),
+    ]
+
+    section_show = MagicMock()
+    section_show.type = "show"
+    section_show.title = "TV Shows"
+    section_show.all.return_value = [
+        MagicMock(ratingKey=2001),
+        MagicMock(ratingKey=2002),
+    ]
+
+    section_music = MagicMock()
+    section_music.type = "artist"
+    plex.library.sections.return_value = [section_movie, section_show, section_music]
+    return plex
+
+
+@pytest.fixture
+def test_db(tmp_path):
+    db_path = tmp_path / "test.db"
+    conn = sqlite3.connect(db_path)
+    conn.execute(
+        """
+        CREATE TABLE watch_history (
+            id INTEGER PRIMARY KEY,
+            rating_key INTEGER NOT NULL,
+            timestamp INTEGER
+        )
+    """
+    )
+    test_data = [
+        (1001, 1625097600),
+        (1002, 1625184000),
+        (9999, 1625270400),  # Orphan
+        (8888, 1625356800),  # Orphan
+    ]
+    conn.executemany(
+        "INSERT INTO watch_history (rating_key, timestamp) VALUES (?, ?)", test_data
+    )
+    conn.commit()
+    conn.close()
+    return db_path
+
+
+@pytest.mark.asyncio
+async def test_plex_manager_fetch_ids(mock_plex):
+    manager = PlexManager("http://test", "token")
+    with patch("pruner.PlexServer", return_value=mock_plex):
+        ids = await manager.fetch_all_media_ids()
+    assert ids == {1001, 1002, 2001, 2002}
+
+
+def test_history_pruner_get_history(test_db):
+    pruner = HistoryPruner(test_db)
+    assert set(pruner.get_watch_history()) == {1001, 1002, 9999, 8888}
+
+
+def test_delete_orphans(test_db):
+    pruner = HistoryPruner(test_db)
+    pruner.delete_orphans([9999, 8888])
+
+    conn = sqlite3.connect(test_db)
+    remaining = conn.execute("SELECT rating_key FROM watch_history").fetchall()
+    assert len(remaining) == 2
+    assert {r[0] for r in remaining} == {1001, 1002}
+
+
+@pytest.mark.asyncio
+async def test_main_workflow(test_db, mock_plex, caplog):
+    with patch("pruner.PlexManager") as mock_manager:
+        mock_instance = mock_manager.return_value
+        mock_instance.fetch_all_media_ids.return_value = {1001, 1002, 2001, 2002}
+
+        args = MagicMock(
+            db_path=test_db,
+            plex_url="http://test",
+            plex_token="token",
+            plex_server=None,
+            loglevel=logging.INFO,
+        )
+
+        await pruner_main(args)
+
+        # Verify deletions
+        conn = sqlite3.connect(test_db)
+        remaining = conn.execute("SELECT rating_key FROM watch_history").fetchall()
+        assert len(remaining) == 2
+
+        # Verify logs
+        assert "Found 4 watch history entries" in caplog.text
+        assert "Identified 2 orphaned entries" in caplog.text
+        assert "Deleted 2 orphaned entries" in caplog.text
+
+
+def test_empty_database(tmp_path):
+    db_path = tmp_path / "empty.db"
+    conn = sqlite3.connect(db_path)
+    conn.execute("CREATE TABLE watch_history (rating_key INTEGER)")
+    conn.close()
+
+    pruner = HistoryPruner(db_path)
+    assert pruner.get_watch_history() == []
+    pruner.delete_orphans([123])  # Shouldn't error