I'm running Lion, connecting to an Exchange 2010 server. Sent messages are stored locally.

Once I've replied to a messages in my Inbox, the "replied" arrow appears to the left of the message, as normal. But when I click on the arrow to see the actual reply it fails roughly 50% of the time. By "fails" I mean that nothing comes up when I click. A message I sent minutes earlier/later can work just fine.

The reply WAS sent using Apple Mail (not my iPhone) and it IS in my sent mail folder. I have re-built my Spotlight index.

  • Fat finger: "the ARROW" appears to the left ...
    – Frankns
    Aug 7, 2011 at 16:17
  • 2
    You can easily edit your own posts by clicking the edit link right underneath the question.
    – NReilingh
    Aug 7, 2011 at 16:39

3 Answers 3


As far as I know, the issue is that Microsoft doesn't provide the Active Sync API to anything other than mobile devices. This is why using Exchange on Mac is a bit buggy.

I would recommend using Microsoft's own Outlook Web App (OWA) for your Exchange emails. Or installing the actual Outlook program for your computer. Those are what I use. :)

Those are probably your two best options if you need your email to be 100% reliable on your Mac.

  • Oops looks like I revived an old thread. For some reason, this was on the main page. Haha sorry. I'll keep my post though incase anyone else finds it helpful :)
    – Vladimir
    Aug 3, 2014 at 18:00

I've experienced the same thing, but only with my company's Exchange server. My other IMAP servers (Gmail, MobileMe a private IMAP) all work fine, 100% of the time.

I'm pretty sure this is a server side Exchange bug.

  • Or possibly a confusion between server sided <sent items> and the local <sent> folder. Not sure. But we have 100's of Mac users converting to Lion/Exchange 2010 and this will be an issue
    – Frankns
    Aug 7, 2011 at 18:50
  • i think it has to do with the general activity of the Exchange Server maybe the Server reaches it's limits.
    – konqui
    Jul 3, 2014 at 5:38

I've seen the same behavior with IMAP accounts in Mail under Lion. I think it's a general bug, and not limited to Exchange (I say this because I have no Exchange accounts).

  • I saw something similar with Mail pre-lion, but completely re-building my accounts solved the problem. I'm wondering if Lion introduced the issue.
    – Frankns
    Aug 8, 2011 at 0:29

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