Wife and I both have 5S's running iOS 8.0.2. We both have issues sending iMessages or Text messages. This occurs on messages to people on any platform and on group messages. Steps we've taken to work-around the problem: Uninstalled third party keyboards. This slowed the frequency of failed sent messages. My work around is to restart the phone OR turn off iMessages and wi-fi, then turn them back on and it works. Is anyone else experiencing this? I haven't read this anyways. I would downgrade to iOS 7 if Apple hadn't stopped authorizing iOS 7. It randomly occurs. Here's a screenshot of it happening between myself and a friend with an iPhone. We were both on wifi at the time.