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I use Messages on mac to iMessage with contacts. Seems to be about 50% of the time I'll send a message and get the red exclamation mark, then click it and it sends. The other half of the time it sends just fine. It also seems to randomly be in sync with my phone, sometimes they are the same and at other times the mac will be like 15 messages behind and after I send a message it will catch up.

Does messages just suck this much or is there something that I might be able to do to fix it.

Note that iMessage on the iPhone/iPad seem to work just fine and stay in sync as I would expect.

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    Are you running Mavericks? – nohillside Jan 8 '14 at 19:50
  • @patrix sorry forgot to mention I'm still on ML – dstarh Jan 8 '14 at 21:40
  • Check this out and see if you have everything set up correctly: apple.stackexchange.com/questions/77157/…. Also, I would try deleting the iMessage account and adding it back. – bassplayer7 Jan 9 '14 at 0:22
  • @bassplayer7 I've got it set up as suggested with the exception of deleting the conversation (which I'd rather not do). As I said in my question, it does sync but it's nowhere near consistent. 20 minutes ago it was synced. Tried to send a message, got the red exclamation mark, clicked it, it sent. 5 minutes later the last 10 or so messages were gone and after switching to messages and waiting for about 45-60 seconds they synced up again. – dstarh Jan 9 '14 at 15:40

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