[rstark18]

Now this is just plain strange. When I logged into iCloud.com, I notice three contacts didn't have the pics I assigned on the iPhone. At that point I noticed that changes made to the contact from the iPhone didn't push to iCloud.com. I finally thought I narrowed it down to a corrupt contacts pic. Whenever I had that pic assigned it halted all updates to iCloud.com. Fair enough I thought, I'll just take a screen shot of the pic and use the screen shot for the contact pic. That didn't work. Any other picture will work except the one that I suspect is corrupt. But a screen shot IS a new picture. How could it not work???

[rstark18]

Well after playing around with this way too much I really think it's a bug in iOS/iCloud.

It seems any picture from a third party camera that needs rotating to orient it correctly, completely screws up the contacts/iCloud link. The picture un-rotated works perfectly but rotating it anywhere else (on the iPhone, in Photoshop, in Windows) completely breaks the link. I also tried changing the file type to PNG, BMP, TIFF and neither of those work.

The thing that completely baffles me is taking a screen shot of the image breaks the link (that one I just can't figure out).

On top of that my battery started to drain very fast when this error state happens. I would be more than happy to send anyone some sample pics if they want to try and tackle this.