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Couple of months ago sending messages and making FaceTime calls started to fail from my Mac. I never found the energy to look into this but after upgrading to Yosemite and still seeing the failures I gave up and spent some time on this.

They both started failing at the same time so I think they are somehow connected. I've gone through most of the solutions that the interwebs offer like resetting my timezone and cleaning up the ~/Library/Messages.

Today I checked the message from console as what happens when I try to send a message or initiate a Facetime call.

When I try a FaceTime call then it fails immediately and I see this in the log

FaceTime(10788) deny mach-lookup com.apple.awdd

The full log is at https://gist.github.com/toomasr/1a92803e630f34eb4fb3

And when I try to send a message I get a red exclamation mark immediately (in less than a second) and see the lines in the log

21/10/14 14:40:35,703 imagent[240]: [Warning] Request to send message: IMMessageItem[outgoing: YES sender=(null); service=iMessage; handle=secretEmailAddressThatIChanged@gmail.com; unformatted=(null); country=(null); roomName='(null)'; flags=100005; subject='<< Message Not Loggable >>' text='<< Message Not Loggable >>' messageID: 47 GUID:'F563CCF5-3A9C-4C89-9F8F-167D0131949E' date:'435584435.000000' date-delivered:'0.000000' date-read:'0.000000' date-played:'0.000000' transfer guids: '(null)' empty: NO finished: YES sent: NO read: NO delivered: NO audio: NO played: NO from-me: YES DD results: NO DD Scanned: YES Downgraded: NO emote: NO expirable: NO expire-state: 0 error: 0] to chat: IMDChat: 0x7fed82c76520 GUID: iMessage;-;secretEmailAddressThatIChanged@gmail.com Style: - State: 3 Participants: (
    "[IMDHandle: <secretEmailAddressThatIChanged@gmail.com:(null):(null)>]"
)  Room Name: (null)  Display Name: (null)  Identifier: secretEmailAddressThatIChanged@gmail.com  Unread count: 0  Row ID: 3  Group ID: 9B5305DB-4938-49A0-9129-F3313E82B731  from NIL ID  fromAccount: IDSAccount: 0x7fed82d216e0 [Service: com.apple.madrid  User: myEmailAddress@gmail.com  ID: B7B7962F-E5DE-4991-BB89-F4498794132A  Type: Apple ID  Active: YES  Registration Status: Registered]

Not sure how to move on with this. Any ideas are welcome!

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The best answer so far (weeks after the problem) was at https://discussions.apple.com/message/27149499#27149499 The gist of it is a corrupt keychain. I'll copy paste the steps for a fix here but I advise to read the actual thread over at Apple Discussions and have backups.

Here are the steps:

  1. Open Key Chain Access
  2. Select Login at the top left side
  3. Select All Items on the lower left side
  4. Search for entries of IDS.
  5. Highlight and delete all entries that has IDS. (For me I am going to need to re-install my RSA SecurID Software Token)
  6. Search for entries of FaceTime
  7. Highlight and delete all entries of FaceTime
  8. Search for entries of Messages
  9. Highlight and delete all entries of Messages

I hope this helps.

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