User cannot upload pictures

I have a user who is having problems uploading photo’s. He is receiving an HTTP Error when uploading, he is able to upload some just not all. The photo’s are taken from the same camera and are .jpg’s.

Here’s the funny thing, I have no problems uploading them. He can email them to me and I can turn around; save them, then upload them to WP.

All of his permissions are set the same as the Admin Account that I use.

I don’t know where to begin. Is it his interweb’s? Or is there something wrong internally? Has anyone seen this?