Upon deeper exploration I have found that this issue only occurs on user roles that have a Role name (ID) of under 3 letters.
Role of Credentials Sub Committee: ID = CSC -> FILE PERMISSIONS DO NOT WORK
Role of Developer: ID = developer -> FILE PERMISSIONS WORK
I tested on all my roles and found this to be true.
Is there any way I can fix this without renaming all of my roles? I have a lot of other logic that works on this naming convention.