I've done allot of searching but found no answer and haven't been able to get to the Apple store yet. For about 2 weeks now (I didn't know about it until I saw him in person) that for the 2 previous days that he wasn't receiving my messages. I am able to receive his messages, face times, and calls (and I can call him, FaceTime with no issues). iMessages works with everyone else on my contacts, it's just him. The messages after I click send shows "Delivered" and shows up on my iPhone 4, iPad 3 and rMBP 2012. Steps I've taken to resolve this are logged off messages on all my devices and VM's (I could think of) Deleted his contact info had hind delete my contact info So anyone else have this issue and any ideas? I need to communicate with my boss and need to resolve this ASAP.