I think I figured it out (but it's still not working).
We wanted to make it easier to upload so we manually input a bunch of the fields so now we're only left with 4 things -
Image file name
Image name
Keywords
Verification
When trying to upload this is what I get:
Error uploading image file:
whatever.gif: Image width invalid
whatever.gif: Image heigth invalid (by the way "height" is misspelled here)
Any idea's what would make this happen so I know where to look?