joefolio

Q: Problems with Mail on Lion with Exchange

Since upgrading to Lion I've encountered intermittent problems with Mail using Exchange with two of my Accounts. I can't find a pattern to the problem but it occurs once or twice every day. One or both of my mailboxes show as empty. If I quit and restart mail the empty box or boxes slowly refill. It's obvious that they are re-downloading from the server. At other, less frequent intervals Mail freezes. It simply stops receiving new mail (this does not occur when the mailbox has been emptyed) and Mail has frozen. After a forced quit and restart everthing works well again until one of the problems re-occurrs.

 

I have the same mail accounts on my MacBook Air (also using Lion) but this prblem des not occur on that unit. Also Mail on my iPhone is working fine.

iMac, Mac OS X (10.7)

Posted on Aug 2, 2011 4:16 AM

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Q: Problems with Mail on Lion with Exchange

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  • by NinjaGreg,

    NinjaGreg NinjaGreg Aug 12, 2011 1:45 PM in response to joefolio
    Level 1 (0 points)
    Aug 12, 2011 1:45 PM in response to joefolio

    Aha! A solution from another thread! https://discussions.apple.com/thread/2140011?threadID=2140011

     

    Summary: use Outlook Web Access, look at your inbox via that, delete any messages that show up there that are not on your mac, and restart Mail.

  • by smoldt,

    smoldt smoldt Aug 29, 2011 3:53 AM in response to NinjaGreg
    Level 1 (0 points)
    Aug 29, 2011 3:53 AM in response to NinjaGreg

    Thanks, NinjaGreg!

     

    This answer finally fixed my problem with the stuck mail.  I had at least one corrupt email stuck in my inbox and, after getting rid of it my mail is working flawlessly.  I was about to have to return to Outlook but now can go forward wth Lion Mail. 

     

    It's still not easy - with over 4,000 emails in my inbox and weeks into using Lion I couldn't just compare all the messages.  Fortunately I noticed that I couldn't expand the messages on a thread that I knew had multiple messages.  I went to Outlook Web Access and deleted all related messages.

     

    Now, I have to go back and add in all the rules I deleted in trying to get rid of the problem.

  • by Ert Dredge,

    Ert Dredge Ert Dredge Sep 20, 2011 8:46 PM in response to NinjaGreg
    Level 1 (0 points)
    Sep 20, 2011 8:46 PM in response to NinjaGreg

    Thanks, NinjaGreg, this appears to have done the trick for me, too.  Touch wood, we'll see how the account is doing in the morning.

     

    I never clean my inbox and have ~6000 messages in it, so I had a bit of a challenge figuring out which message was the offending one.

     

    This is a bit of a long shot, but

    1. If you're in this position with a huge number of messages
    2. Have a second Mail account talking to the server without incident via IMAP, and
    3. Don't mind using Terminal

     

    ...(I realize that's a lot of clauses) this may help you.  To begin:

     

    1. Take your functioning Inbox, and turn off View > Organize by Thread (if you have it on).
    2. Sort the messages by Date Sent
    3. Select all the messages in the functioning Inbox
    4. Select File > Save As...
    5. Choose "Raw Message Source" for Format
    6. Save it to your Desktop, say as "IMAP-messages.rtfd"

     

    (This may appear to complete but take a while before the file shows up, and it will make a huge file -- mine was 1/3 GB)

     

    Do the same thing with the other broken Inbox, saving all your messages to your Desktop as, say, "EWS-messages.rtfd".  (Be careful to select the same first and last message in this second Inbox -- if you had more mail come in while the first save was happening, or if the Exchange connection is stalled, the last message appearing in one Inbox may not be the same as the other.)

     

    Now, open Terminal, and do:

    cd Desktop
    egrep '^Message-ID: ' IMAP-messages.rtfd > IMAP-Message-IDs.txt
    egrep '^Message-ID: ' EWS-messages.rtfd > EWS-Message-IDs.txt
    comm -3 IMAP-Message-IDs.txt EWS-Message-IDs.txt

     

    ...with luck, you'll get a Message-ID of a message that is only in one mailbox and not the other.  Then you can use Terminal again to figure out which message it is.  Say it's Message-ID: <F2DBEF@winops01>, then try:

    grep -A 10 -B 10 'Message-ID: <F2DBEF@winops01>' IMAP-messages.rtfd

     

    ...and you should get the rest of the headers for the offending message.  Then you can search for it in Mail in the IMAP Inbox, delete it, restart Mail, and away you go.

     

    Good luck.

  • by Ert Dredge,

    Ert Dredge Ert Dredge Sep 21, 2011 4:59 AM in response to Ert Dredge
    Level 1 (0 points)
    Sep 21, 2011 4:59 AM in response to Ert Dredge

    Watch out for the line breaks added by discussions.apple.com to the Terminal commands:  Every line starts with either cd, egrep, comm, or grep -- the other stuff is continuation from the previous line.

  • by Peter Resele,

    Peter Resele Peter Resele Nov 4, 2011 9:41 AM in response to joefolio
    Level 1 (4 points)
    Nov 4, 2011 9:41 AM in response to joefolio

    After having the same error ("opening mailbox/changing flags - Requesting latest information" - hang) and fighting for months on my Mac (Lion) to solve it, including writing angry bug reports to Apple - I think I finally found the source of the problem:

     

    There was an old (invalid) certificate installed in Exchange (2007, in my case), enabled for SMTP.

     

    Nobody seems to care about this - including Snow Leopard Mail, Outlook and all iOS devices - but Lion Mail cared, and just stuck. Typically after some time - maybe sleep/wake or just a couple of hours - Mail was stuck and did not receive any new mails anymore, until I Force Quit it.

     

    I got the hint from another forum (somebody suggested changing the properties in the locally installed certificates in Lion - but this was not the solution) and after seeing the question popping up once in Mail Preferences (do you want to trust this (old) certificate).

     

    After removing the old certificate from Exchange (good luck with this admin user interface - no wonder we did not notice it) - everything works ok for me, already a day without any hangs.

     

    Hope it helps! (Let us know the outcome...)

  • by patrickvb,

    patrickvb patrickvb Nov 27, 2011 8:53 AM in response to joefolio
    Level 1 (6 points)
    Nov 27, 2011 8:53 AM in response to joefolio

    On Friday I upgraded to Lion on my G5.

    All went well except for the mail program. I have had similar difficulties that have already been mentioned. The short story is the mail program was "migrating" data for over 15 hours.

     

    I followed the suggestions:

    (1) Delete anything with envelope in the ~/Library/Preferences/apple.mail.com  of Mail folders.

     

    (2) I then went into my Time Capsule backup prior to the Lion upgrade and dragged out the Mail folder, saving it to my Desktop

     

    (3) I tried several times to open and "migrate" the file into mail - it continued to "hang" for hours, i.e., with no resolution

     

    (4) In the meantime I checked my email via my Firefox for my three mail accounts - a bit of a hassel but its a work around and my archives stayed intact with all three accounts - mostly.

     

    (5) Next I highlighted my Mail Folder which I had copied to my desktop, see (2) above. I clicked on "File" and "Get Info" and studied my options - out of curiousity and with nothing to lose in the "Get Info" window I checked a box that said "use 32 bit". I then closed the window.

     

    (6) I shutdown the computer and even unplugged it for 60 seconds trying to get a full reset.

     

    (7) Powering back up, I clicked on the Mail Icon selected Continue for install and then the migration happened very quickly and I heard the "ding" that the migration was in process or complete(?)

     

    (8) The Mail program window opened looking very familiar and for about another 30 minutes the migration of data populated into the program. I did not try to compose emails. I wanted to allow the program to run and populate the archive of the various email accounts. Everything is intact at this time.

     

    Now I am sending, receiving emails without difficulty.

     

    I do not know which step really solved this issue - it may have been the full reboot, which is more absolute than the computer restarting after the update. It may have been the "32 bit" box checked in Get Info while the Mail Folder on my Desktop was highlighted. The Genius' in this forum may be laughing at that strategy, its okay, I am just glad it worked. And I empathize with those whose Mail program is still not working.

     

    I hope something here helps.

     

    *Apple really needs to make this crystal clear and be transparent about the issues when offering an upgrade. This is not the first time an OSX upgrade has caused problems with the Mail Program. My suggestion is that Apple upgrade the Mail Program first then add all the sexy bells and whistles. If we don't have a Mail Program that integrate withing the upgrade - "Houston, or rather Cupertino, we have a problem!"

     

    Good luck people.

  • by beemboy,

    beemboy beemboy Apr 4, 2012 2:52 PM in response to NinjaGreg
    Level 1 (0 points)
    Apr 4, 2012 2:52 PM in response to NinjaGreg

    Thanks - this was a helpful hint. I canceled the pending operations, and my non-syncing Exchange account continued to sync. I'll keep a watch out for this account.

  • by everettfrommission viejo,

    everettfrommission viejo everettfrommission viejo May 12, 2012 1:50 PM in response to Peter Resele
    Level 1 (0 points)
    May 12, 2012 1:50 PM in response to Peter Resele

    Peter Resele,

    Let me get this straight. Exchange 2007 had an expired certificate, not the Mac OS X 10.7 client computer? I don't have access to the Exch server, just the Mac. Forgive my ignorance, but there isn't an SMTP connection set up in Apple Mail when accessing Exchange using EWS, is there? I'm having the exact problem as described and no email moves in or out for about 10-60 minutes after the computer is moved to another network. As in going from work to home. All other email servers deliver as usual (iCloud and POP), but the Exchange account hangs. The IT for the colocated 2007 service just says to use Outlook for Mac. Stonewalls. Any help?

     

    Thanks and Cheers All.

  • by Matt Crawford2,

    Matt Crawford2 Matt Crawford2 Feb 11, 2013 1:31 PM in response to Ert Dredge
    Level 1 (102 points)
    Mac OS X
    Feb 11, 2013 1:31 PM in response to Ert Dredge

    I took my Exchange account offline in Mail and added an IMAP account for the same mailboxes on the same server. (Holding down the Option key while clicking Continue on the first page of account-creation was a key trick in this. Otherwise it would only create another Exchange account.)

     

    I set the view, saved all the messages to raw source from both accounts. I had to sort the extracted Message-ID lines before "comm" would give me s short, clean result. That done, I did find there were  8 messages in the Exchange account inbox and not the IMAP inbox. The most suspicious of those message were clustered in two days.

     

    I deleted them all. One vanished on its own when I clicked it. Time will tell if this solves the problem.

  • by Matt Crawford2,

    Matt Crawford2 Matt Crawford2 Feb 27, 2013 11:00 AM in response to Matt Crawford2
    Level 1 (102 points)
    Mac OS X
    Feb 27, 2013 11:00 AM in response to Matt Crawford2

    Time has told. I got the same symptom ("changing flags / requesting latest information") today. I recreated the IMAP account tied to the same Exchange acount and dumped the two views of the Inbox. This time, there were no messages in one but not the other.

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