I've run a few tests and discovered something even more peculiar. Keeping in mind 99% of my board's file attachments are JPGs, GIFs, and PNGs, if the system returns an error on one image, it won't accept that image on subsequent attempts. If it doesn't return an error on other images, it will accept those images every time.
I've checked the file size I configured for attachments and it's still showing the 2000 KB limit I set. Additionally, my hosting service still shows my board only using 5 GB of space.