this happened on my iPhone 5 when i jailbroke it too. i try to send a picture through iMessage and it won't go through, if i send it as a text message it will work but not iMessage. anyone know how to fix this?
Is it giving you the failure message and exclamation point?
Mine does it to, but they are actually going through to the other person. When I sign out of iMessage on my iPad mini it fixes it. I'm assuming it has something to do with one being on iOS 6 and the other on iOS 7. But I haven't found a real reason for it.