KevinTheJedi I would think that too.. but I think I updated every file size setting I could find..
User attachments..

Agent attachments...

PHP.ini...

.. and the IIS config..

The server is restarted nightly, so it's a fresh load of the web server, just to make sure all the settings were set properly. I've disabled and re-enabled the local file storage plugin..
There's got to be something I'm not setting..