diff --git a/app/app.py b/app/app.py
index 0f19b9f..33325d6 100644
--- a/app/app.py
+++ b/app/app.py
@@ -2,6 +2,7 @@
 from flask_login import LoginManager
 from functools import wraps
 import yaml
+from file_watcher import Watcher
 import threading
 from markupsafe import escape
 from constants import *
@@ -13,6 +14,13 @@
 import titledb
 
 def init():
+    global watcher
+    # Create and start the file watcher
+    watcher = Watcher([], on_library_change)
+    watcher_thread = threading.Thread(target=watcher.run)
+    watcher_thread.daemon = True
+    watcher_thread.start()
+
     global app_settings
     # load initial configuration
     reload_conf()
@@ -138,6 +146,7 @@ def set_titles_api():
 @app.route('/api/settings/library/paths', methods=['GET', 'POST', 'DELETE'])
 @access_required('admin')
 def library_paths_api():
+    global watcher
     if request.method == 'POST':
         data = request.json
         success, errors = add_library_path_to_settings(data['path'])
@@ -155,6 +164,10 @@ def library_paths_api():
         }    
     elif request.method == 'DELETE':
         data = request.json
+        if watcher.remove_directory(data['path']):
+            print(f"Removed {data['path']} from watchdog monitoring")
+        else:
+            print(f"Failed to remove {data['path']} from watchdog monitoring")
         success, errors = delete_library_path_from_settings(data['path'])
         if success:
             reload_conf()
@@ -272,6 +285,9 @@ def scan_library():
     for library_path in library_paths:
         scan_library_path(library_path, update_library=False)
     
+    # remove missing files
+    remove_missing_files()
+
     # update library
     generate_library()
 
@@ -318,6 +334,8 @@ def scan_library_path(library_path, update_library=True):
             scan_in_progress = False
 
         if update_library:
+            # remove missing files
+            remove_missing_files()
             # update library
             generate_library()
 
@@ -350,7 +368,14 @@ def scan_library_api():
 
 def reload_conf():
     global app_settings
+    global watcher
     app_settings = load_settings()
+    # add library paths to watchdog if necessary
+    library_paths = app_settings['library']['paths']
+    if library_paths:
+        for dir in library_paths:
+            if os.path.exists(dir):
+                watcher.add_directory(dir)
 
 def get_library_status(title_id):
     has_base = False
@@ -388,10 +413,37 @@ def get_library_status(title_id):
     }
     return library_status
 
+def on_library_change(events):
+    libraries_changed = set()
+    with app.app_context():
+        # handle moved files
+        for moved_event in events['moved']:
+            # if the file has been moved outside of the library
+            if not moved_event["dest_path"].startswith(moved_event["directory"]):
+                # remove it from the db
+                print(delete_file_by_filepath(moved_event["src_path"]))
+            else:
+                # update the paths
+                print(update_file_path(moved_event["src_path"], moved_event["dest_path"]))
+
+        for deleted_event in events['deleted']:
+            # delete the file from library if it exists
+            print(delete_file_by_filepath(deleted_event["src_path"]))
+        
+        for created_event in events['created']:
+            libraries_changed.add(created_event["directory"])
+    
+        for library_to_scan in libraries_changed:
+            scan_library_path(library_to_scan, update_library=False)
+        
+        # remove missing files
+        remove_missing_files()
+        generate_library()
+
 
 if __name__ == '__main__':
     init()
-    app.run(debug=True, host="0.0.0.0", port=8465)
+    app.run(debug=False, host="0.0.0.0", port=8465)
 
     # with app.app_context():
     #     get_library_status('0100646009FBE000')
diff --git a/app/db.py b/app/db.py
index 4dda296..e52295b 100644
--- a/app/db.py
+++ b/app/db.py
@@ -1,6 +1,7 @@
 from flask_sqlalchemy import SQLAlchemy
+from sqlalchemy.orm.exc import NoResultFound
 from flask_login import UserMixin
-import json
+import json, os
 
 db = SQLAlchemy()
 
@@ -86,6 +87,29 @@ def add_to_titles_db(library, file_info):
 
     db.session.commit()
 
+def update_file_path(old_path, new_path):
+    try:
+        # Find the file entry in the database using the old_path
+        file_entry = Files.query.filter_by(filepath=old_path).one()
+        
+        # Extract the new folder and root_dir from the new_path
+        new_folder = "/" + os.path.basename(os.path.dirname(new_path))
+
+        # Update the file entry with the new path values
+        file_entry.filepath = new_path
+        file_entry.folder = new_folder
+        
+        # Commit the changes to the database
+        db.session.commit()
+
+        return f"File path updated successfully from {old_path} to {new_path}."
+    
+    except NoResultFound:
+        return f"No file entry found for the path: {old_path}."
+    except Exception as e:
+        db.session.rollback()  # Roll back the session in case of an error
+        return f"An error occurred while updating the file path: {str(e)}"
+
 def get_all_titles_from_db():
     # results = db.session.query(Files.title_id).distinct()
     # return [row[0] for row in results]
@@ -126,4 +150,48 @@ def delete_files_by_library(library_path):
             'path': 'library/paths',
             'error': f"An error occurred: {e}"
         })
-        return success, errors
\ No newline at end of file
+        return success, errors
+
+def delete_file_by_filepath(filepath):
+    try:
+        # Find file with the given filepath
+        file_to_delete = Files.query.filter_by(filepath=filepath).one()
+        
+        # Delete file
+        db.session.delete(file_to_delete)
+        
+        # Commit the changes
+        db.session.commit()
+        
+        return f"File '{filepath}' has been deleted."
+    except Exception as e:
+        # If there's an error, rollback the session
+        db.session.rollback()
+        return f"An error occurred while deleting the file path: {str(e)}"
+
+def remove_missing_files():
+    try:
+        # Query all entries in the Files table
+        files = Files.query.all()
+        
+        # List to keep track of IDs to be deleted
+        ids_to_delete = []
+        
+        for file_entry in files:
+            # Check if the file exists on disk
+            if not os.path.exists(file_entry.filepath):
+                # If the file does not exist, mark this entry for deletion
+                ids_to_delete.append(file_entry.id)
+                print(f"File not found, marking file for deletion: {file_entry.filepath}")
+        
+        # Delete all marked entries from the database
+        if ids_to_delete:
+            Files.query.filter(Files.id.in_(ids_to_delete)).delete(synchronize_session=False)
+            db.session.commit()
+            print(f"Deleted {len(ids_to_delete)} files from the database.")
+        else:
+            print("No files were deleted. All files are present on disk.")
+    
+    except Exception as e:
+        db.session.rollback()  # Rollback in case of an error
+        print(f"An error occurred while removing missing files: {str(e)}")
\ No newline at end of file
diff --git a/app/file_watcher.py b/app/file_watcher.py
new file mode 100644
index 0000000..807c712
--- /dev/null
+++ b/app/file_watcher.py
@@ -0,0 +1,140 @@
+from constants import *
+import time, os
+from watchdog.observers import Observer
+from watchdog.events import FileSystemEventHandler
+import threading
+from functools import wraps
+
+
+def is_dict_in_list(dict_list, dictionary):
+    for item in dict_list:
+        if item == dictionary:
+            return True
+    return False
+
+def debounce(wait):
+    """Decorator that postpones a function's execution until after `wait` seconds
+    have elapsed since the last time it was invoked."""
+    def decorator(fn):
+        @wraps(fn)
+        def debounced(*args, **kwargs):
+            def call_it():
+                fn(*args, **kwargs)
+            if hasattr(debounced, '_timer'):
+                debounced._timer.cancel()
+            debounced._timer = threading.Timer(wait, call_it)
+            debounced._timer.start()
+        return debounced
+    return decorator
+
+class Watcher:
+    def __init__(self, directories, callback):
+        self.directories = set(directories)  # Use a set to store directories
+        self.callback = callback
+        self.event_handler = Handler(self.callback)
+        self.observer = Observer()
+        self.scheduler_map = {}
+
+    def run(self):
+        for directory in self.directories:
+            task = self.observer.schedule(self.event_handler, directory, recursive=True)
+            self.scheduler_map[directory] = task
+        self.observer.start()
+        
+        try:
+            while True:
+                time.sleep(1)
+        except KeyboardInterrupt:
+            self.observer.stop()
+        self.observer.join()
+
+    def add_directory(self, directory):
+        if directory not in self.directories:
+            print(f'add directory {directory} to watchdog')
+            task = self.observer.schedule(self.event_handler, directory, recursive=True)
+            self.scheduler_map[directory] = task
+            self.directories.add(directory)
+            self.event_handler.add_directory(directory)
+            return True
+        return False
+    
+    def remove_directory(self, directory):
+        if directory in self.directories:
+            if directory in self.scheduler_map:
+                self.observer.unschedule(self.scheduler_map[directory])
+                del self.scheduler_map[directory]
+            self.directories.remove(directory)
+            return True
+        return False
+
+class Handler(FileSystemEventHandler):
+    def __init__(self, callback, debounce_time=5):
+        self._raw_callback = callback  # The actual callback passed to the handler
+        self.directories = []
+        self.debounce_time = debounce_time
+        self.events_to_process = {
+            'modified': [],
+            'created': [],
+            'deleted': [],
+            'moved': []
+        }
+        self.debounced_process_events = self.debounce_callback(self._process_collected_events, debounce_time)
+
+    def add_directory(self, directory):
+        if directory not in self.directories:
+            self.directories.append(directory)
+
+    def debounce_callback(self, callback, wait):
+        @debounce(wait)
+        def debounced_callback():
+            callback()
+        return debounced_callback
+
+    def _process_collected_events(self):
+        if any(self.events_to_process.values()):  # Check if any list has events
+            self._raw_callback(self.events_to_process)
+            # Reset the events_to_process dictionary
+            self.events_to_process = {
+                'modified': [],
+                'created': [],
+                'deleted': [],
+                'moved': []
+            }
+
+    def collect_event(self, event, directory):
+        if event.is_directory:
+            return
+
+        if event.event_type in ['deleted', 'moved', 'created']:
+            file_extension = os.path.splitext(event.src_path)[1][1:]
+            if file_extension not in ALLOWED_EXTENSIONS:
+                return
+
+            event_slim = {
+                'directory': directory,
+                'dest_path': event.dest_path,
+                'src_path': event.src_path
+            }
+            if not is_dict_in_list(self.events_to_process[event.event_type], event_slim):
+                self.events_to_process[event.event_type].append(event_slim)
+                self.debounced_process_events()  # Trigger the debounce mechanism
+
+    def on_modified(self, event):
+        for directory in self.directories:
+            if event.src_path.startswith(directory):
+                self.collect_event(event, directory)
+
+    def on_created(self, event):
+        for directory in self.directories:
+            if event.src_path.startswith(directory):
+                self.collect_event(event, directory)
+
+    def on_deleted(self, event):
+        for directory in self.directories:
+            if event.src_path.startswith(directory):
+                self.collect_event(event, directory)
+
+    def on_moved(self, event):
+        for directory in self.directories:
+            if event.src_path.startswith(directory):
+                self.collect_event(event, directory)
diff --git a/app/settings.py b/app/settings.py
index da100d6..b93292f 100644
--- a/app/settings.py
+++ b/app/settings.py
@@ -83,7 +83,6 @@ def delete_library_path_from_settings(path):
     settings = load_settings()
     library_paths = settings['library']['paths']
     if library_paths:
-        print(library_paths)
         if path in library_paths:
             library_paths.remove(path)
             settings['library']['paths'] = library_paths
diff --git a/requirements.txt b/requirements.txt
index e7f3010..155eb52 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -4,6 +4,7 @@ flask-sqlalchemy==3.1.1
 PyYAML==6.0.1
 requests==2.31.0
 unzip_http==0.4
+watchdog==4.0.1
 Werkzeug==3.0.1
 
 # NSTools