Please log out of iMessages on your iPad. Log back in and attempt to send a picture to someone via iMessages. Does the pic go through as normal or do you get an error message? This is the issue I've been having on my iPad and iPhone using multiple (3) Apple IDs. I cannot send pictures via iMessages (suddenly). I was on the phone with Apple support for 2 hours and got sent all the way up to the engineer who has no clue why I'm having the issue. I'd like to for someone to test the above scenario to see they receive the error and that their pic does not get received. I've had 2 other friends confirm that after logging out they received the same error. Weird. My iPhone is jb, my iPad is not, never has been. Thanks.