Originally Posted by kovidgoyal
One thing you can try is rebooting both your device and your computer. That rests both MTP stacks and often fixes this kind of issue. Unfortunately, I dont currrently have a Windows 8 system to test with, so I can't comment on whether the problem is generally present with windows 8 or not.
Oddly enough, this actually worked (for Calibre at least). Thanks for the help ^_^