July 15, 2008

A Diverting Entourage/Exchange problem

A user here at work ambled into the geek cave with a problem. We use Exchange here at work, and several people (myself included) access our Exchange using Entourage, the Mac OS X client. His problem was as follows.

He has a Macbook Air which he uses as his primary computer. In addition, he'd just gotten his original iPhone upgraded to firmware 2.0 and set it to talk to our Exchange server. As a result, he realized that the calender information he could see on the iPhone wasn't the same as that on his Macbook. He logged onto the server using our Outlook Web Access (OWA) URL, and found that the iPhone and the OWA system (hence, the server) agreed on his calendar information - but that changes that had been made on his Macbook weren't syncing up to the server.

We began to test.

If I sent him an invitation to a meeting and he accepted it using OWA, it would appear on his OWA calendar and after short delay appear on his Macbook and iPhone.

If I sent him an invitation and he accepted it on his Macbook, it would immediately appear on the Macbook's Entourage calendar but not appear on the OWA (or iPhone) calendars.

If I sent him an invitation and he checked his iPhone, the iPhone would immediately put in a 'tentative' meeting at the proper time. If he then 'accepted' the meeting from the iPhone, it would change to 'confirmed' - but if we checked on the iPhone again after a few minutes, it would have changed back to 'tentative' but the invitation was still gone. It would not show up in OWA.

He can send and receive mail from any of the three clients - Macbook Air, iPhone or OWA. That works fine.

If he sent an invitation to me using OWA and I accepted it using my Mac (and Entourage) it showed up in my OWA and on my Mac.

If he sent an invitation to me using his Macbook and I accepted it using my Mac it would show up in my OWA and on my Mac.

So at this point, it appeared there was something different about his Entourage setup or his Macbook or his Exchange store. Note that I had changed my Entourage account settings to mirror his, and made sure my Mac was on the same wireless network as his prior to the above tests.

Next we created an account for me on his Entourage on his Macbook Air, using my account information. It took around 20 minutes to sync initially (arg) but eventually everything was there. I accepted an invitation using his Macbook Air and his Entourage but my account configuration - and lo and behold, it showed up on my OWA and on my own Macintosh.

At this point, we seem to have narrowed the problem down to either his local datastore on his Macbook Air or his Exchange store on the servers. We discovered that his store was 1.7 GB in size, and that the store that it was residing in has a policy set such that over 1.5 GB it 'blocks send and receive.' However, he can still send and receive mail fine either via WebDAV (Entourage/iPhone) or via OWA.

His store has a large number of items in it, and we noticed that although the appointments did show up on my account (which has many many fewer items, but still several hundred to a thousand) it took some twenty to thirty seconds to sync. We're going to see if his appointments have properly synced by tomorrow. If they have, the next step will be to try to prune his account and see if they sync faster. If they haven't shown up tomorrow, we're going to try to prune his store below 1.5 GB (the limit observed on the server) and see if that allows calendaring as well as mail to work.

Confused, but making progress. Posted by jbz at July 15, 2008 7:57 PM | TrackBack

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