Can't send photos via MMS

I've had this problem before but after several tries managed to get it through, but won't work at all now.
It's from a picture snapped on the built in camera. Thinking it might be too large I downloaded it to my Mac, opened in Photoshop and downsized it quite a bit. Put it in my iPhoto album, synced with the iPhone and tried again with a file 10% as large. Same problem.
The bar for Sending goes fine but stops just before the end and stays there, eventually timing out. This is over WiFi.

Wi-FI has nothing to do with sending/receiving MMS. SMS/MMS is exchanged over the carrier's cellular network only. A photo or video sent via MMS is resized automatically.
http://support.apple.com/kb/TS2755

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