The application I'm currently working on allows users to upload files to a work directory. Unfortunately, they also need to be able to manually open the directory and manipulate files. The file structure is reflected in the database, which comes to the problem. I need the database and the file system to have the same info, so I'll need to sync the database each time a user makes certain changes (move, delete, new, etc.). I'm not in the least sure how to do this. Any ideas?

You could create a Windows Service that continuously monitors the folder in question and synchronizes with the database whenever a change is triggered. Check out the FileSystemWatcher class here, http://msdn.microsoft.com/en-us/library/system.io.filesystemwatcher.aspx

Thanks, that appears to be exactly what I needed. One of my coworkers told me they'd had issues with the FileSystemWatcher in the past reporting the wrong events, but all my tests came out as expected.