Entourage 2008/Outlook 2011 & Exchange 2007 syncing issue

Discussion in 'Mac Apps and Mac App Store' started by zenakitty, Jul 3, 2012.

  1. zenakitty macrumors newbie

    Jul 3, 2012
    Greetings. I have a weird issue with one of my users and using a Mac to check email. We are running Exchange 2007 in a mixed Mac/Windows environment. One of my users reported his Entourage 2008 (Web Services Edition) inbox not syncing. When Entourage checks for new email, it will display "Inbox: Downloading...X/X" emails. ("X" varies according to the number of emails.) It will increment all the way through the numbers of new messages on the mail server, but then nothing will show up in Entourage's inbox. It may loop through this a couple of times, and then stop without having downloaded any email. It will go through this again several minutes later as it tries to sync, and eventually, it will download some of the new emails, but not the latest (e.g., nothing newer than four hours old); this can take anywhere from four to 12 hours after the Exchange server receives the new emails.

    This began around the time the user's two secretaries were added as calendar and mailbox delegates. However, they were unable to tell me if this started immediately after, several hours after, or a couple of days after. All they could tell me is it might have started during the same week as they were added as delegates.

    1. I removed all delegates from the user's account.
    2. I emptied Entourage's cache, and no change. After clearing the cache, Entourage will go out, resync all the folders, download all email--old and new--and then stop syncing.
    3. I uninstalled and reinstalled MS Office on the user's computer, and no change.
    4. I replicated the problem on a different MBP, OS X 10.6.8, Entourage Web Services Edition 2008 (fully updated).
    5. I also replicated the problem on a different iMac running Mac OS X 10.7.4 and Outlook 2011.
    6. I was NOT able to replicate this on a Windows machine. Email syncs fine when checking with Outlook 2007 on Windows (XP and 7) machines, with new messages showing up immediately.
    7. I was also NOT able to replicate this using Outlook Web Access as new messages show up immediately, so I know they are being received and delivered by the Exchange server.

    This problem is affecting only one of hundreds of users. Unfortunately, he also happens to be the District Superintendent!

    I am totally stumped as to what could be causing this. It is affecting only this user, and only when using a Mac and Entourage/Outlook to check email. It works fine with Windows computers and Outlook Web Access.

    Any suggestions or ideas?

    Thank you for your time.

  2. zenakitty thread starter macrumors newbie

    Jul 3, 2012
    Problem resolved

    In case anyone else runs into a problem such as this, it turns out it was caused by an extraordinarily large email attachment in the user's mail queue. I deleted all the mail from the user's inbox via Outlook Web Access, clicked the "Check Messages" button, and viola! Fourteen unseen mail message appeared, including one dated almost a month ago that had a 379MB video attached. I do not know how the video attachment got around our 20MB attachment limit, but once I deleted the email, Entourage 2008 and Outlook 2011 started working as expected. I also don't know why the user didn't notice the problem earlier, but at least it is resolved now and the user is a happy camper.

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