The weird and wonderful world of Microsoft’s Exchange Server

The weird and wonderful world of Microsoft’s Exchange Server comes back to haunt me once in a while. We have been heavy users in the past in our ventures, but these days tend to use Google Apps.

However, one member of the family still has an Exchange-based account. Primarily because she a) doesn’t like using Gmail; b) doesn’t like using Mac Mail (we’re all Mac based).

She has had Mac Office 2004 with Entourage running happily on her MacBook Pro for several years, until last weekend when Entourage started to stall and hang a few moments after it started to check for mail from the remote hosted Exchange service.

Here’s some sense of the saga I embarked on to resolve the issue – and how I completely failed. I document it here, like many other such trials and tribulations a) so I have an archive to refer to in the future; b) in case others have experienced the same problems. I researched and came up with a list of ideas to try to fix the issue, it’s clearly similar to other peoples’ experience. So everything listed below came from a forum or other online resource.

Here’s how it panned out:

  • Rebooted the machine. Opened Entourage. I had the Progress window open, it started to to talk to the Exchange server, then after about 5 seconds the pinwheel started to turn and Entourage froze. Had to Force Quit. Tried that a couple of times, including leaving it frozen for half an hour or so in case it just needed more thinking time.
  • Move the machine off the wifi to an ethernet connection in case wifi was a hassle. No dice.
  • Held down Option key when starting Entourage, to open the database manager. Used the Verify feature, which reported the database was fine. No dice.
  • Used the database manager to turn off background database checks. No dice.
  • Started Entourage, and before it hung, went to Preferences and disabled Spotlight indexing. No dice.
  • My personal favourite – locate the oldest message in the Inbox and delete. No dice.
  • Used the database manager to rebuild the database. Left this overnight (because it has to pull a fresh copy of the data down from the remote Exchange server). No dice.
  • Installed all outstanding software updates – I noticed there was a firmware update, and also had noticed that the screen on the MacBook Pro was flickering once or twice every couple of minutes). No dice.
  • I found a reference online that Entourage doesn’t like more than 1,000 messages in an single folder. The main Inbox had 4,400 emails, so I created a set of ‘Archive’ folders under the Inbox and shifted 900 to each folder until I had less than 1,000 left (I was using the web acess (OWA) interface on the Exchange server, so didn’t need Entourage for this). No dice.
  • By now was getting the irrits. I found a copy of Mac Office 2008 in my box of tricks, and upgraded, so we had Entourage 2008. I went to configure a new identity so as to start afresh, lo and behold an error message saying Entourage 2008 Home/Student edition doesn’t have Exchange support. Great. Now I don’t have any email program on the Mac that works with Exchange.
  • Checked online and the current software is Mac Office 2011 – with Outlook 2011, because Entourage for Mac has been replaced by Outlook for Mac. I ran down to the Apple store (so much easier now they opened an Apple Store close by me at Southland) and picked up a copy of Mac Office 2011 for Small Business – because Outlook 2011 Home version doesn’t have Exchange support either.
  • Installed Outlook 2011. Configured it for the Exchange server … and a big fat nothing. Called technical support at our hosting company, who tell me that the particular Exchange server the account is with, is still running Exchange Server 2003, and that Outlook 2011 is not compatible. The only option is to set up IMAP access from Outlook 2011 to Exchange. But this will only cover email, not her Calendars, Contacts etc. I ask about migrating from Exchange 2003 to Exchange 2011 and am told I need to speak to my ‘partner manager’.

And there as of today it stands. I haven’t had time to call my partner manager. We have email running happily, and the user has her iPhone for Calendar and Contacts.

My overall plan is to shift this Exchange account over to Google Apps, and use the Google sync tool so she can continue to use Outlook. But that will take a bunch of time so will have to wait.

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