I'm using a CLR because I don't know if there are file(s) or not, nor do I know what their names would be. All I know is the path they should be at if they exist.
So far I've:
Set the assembly to have EXTERNAL_ACCESS (though I didn't sign it, I set the DB to trustworthy and had whatever the permission set I needed to do it)
The access is via sql server authentication at the moment, I tried using windows authentication just to see if it would make a difference, but didn't seem to help (at the very least I still wasn't finding the correct account to give permissions to)
I'll read up on that link and get back to y'all though.
(Thank you very much for your kind replies)