I am troubleshooting mobile messages stuck on FSM 6 iOS mobile. I have seen that error before where messages get stuck in Waiting or Ready in the device and the only solution is to reinitialize, which loses all the data that was stuck. Please note that this is not caused by messages in Error.
In the past I have seen it happening two times. One was a mobile customization problem and the other one was a product bug. The latter was caused by buggy sync code that set some messages in a group in Waiting, but they were not really waiting for anything. Consequently they never got an answer and got stuck in Waiting.
Have you seen any of that recently? The message getting stuck is always an attachment and it is stuck in Ready. I looked into the mobile and server logs and there are not exception matching that time stamp. The only thing strange about those messages is that they attachment_log.attachment file is NULL, which makes me think it is either a bug or they tried to attach a blank file. I am still investigating that.