I’m an IT Consultant with a good number of years in the business of e-mail systems specifically, and of course am saddled with Exchange on the back-end for my corporate mail for various reasons, the most notable being Blackberry integration.

I’m also a “switcher” having liked the Mac for some time, but having been afraid that it wouldn’t quite do what I needed it to do (with groupware access being high on the list — I saw “groupware” rather than “e-mail” because we’re talking calendars, tasks, and all of the other myriad items that come with doing business). The availability of Entourage and its integration with Exchange was a huge selling point for switching to a Mac last year.

Although I started on Entourage, however, I’ve been back and forth between Entourage and the iApps about three or four times, but think I’ve finally settled back down on the iApps.

The biggest thing that threw me off of Entourage originally was the lack of sync services integration. Everything else on my Mac wants to talk to the address book and calendar. The lack of any kind of decent searching options was another. This would have been around last November that I decided to shut down Entourage and switch back to a combination of Mail.app, iCal, and Address Book. I went away from a Blackberry around the same time, and got an iSync-compatible phone.

When they fixed that in the service pack last March I happily went back to Entourage, since shared calendars and tighter Exchange integration were desirable, and it seemed that Spotlight and Sync Services integration could finally deliver the best of both worlds.

However, Entourage still felt “clunky” compared to the pleasant user experience of using Mail.app, and I wrestled with the decision more than a few times. The final deal-breaker, however, came when I was searching for something that would have been in one of my attachments and came to the realization that Entourage, despite its Spotlight integration, does not do full-text searching of attachments (Mail.app does). The result was that it took me about four times longer to find the mail item I was looking for. Within 24 hours after that I had moved everything back to Mail.app.

The truth is that for Exchange integration, the iApps are not without their options — options that have expanded since my first foray into them a year ago….

1. Naturally, Mail.app will talk IMAP, so as long as those ports are open on your corporate firewall, this works just fine.
2. Exchange Public Folders can even be exposed via IMAP, and in some ways work better than Entourage (there is no support for free-standing documents, or ‘FreeDocs’ in public folders in Entourage — they simply do not appear. Via IMAP, they will at least appear as attachments to blank e-mail messages). Obviously shared calendar and address book folders from Exchange won’t be represented properly in Mail.app, but you will see them as IMAP folders with each entry as a mail-type message.
3. OS X’s built-in Address Book will sync to Exchange quite well, subject to the configuration of Outlook Web Access on the Exchange side (there are a couple of little idiosyncrasies on how Exchange needs to be configured to support this, although it would be fine “out of the box”) Only primary contacts can be synced of course, so any shared address book “public folders” are definitely out here, unfortunately.
4. Snerdware’s GroupCal can be used to synchronize selected iCal calendars with the Exchange calendar. It has improved dramatically in the past six months. When I first tried it last November it was still in beta as far as Tiger support was concerned, and even after release it took until version 3.5 until it was ready for prime time. Shared calendars are also supported from public folders, since each calendar can be given a URL.

In addition, GroupCal will handle the synchronization of tasks to the Exchange server — something that even Entourage inexplicably doesn’t do (Entourage provides local support for tasks, but these are only stored locally). Since I carry a Blackberry and get my tasks synced wirelessly from the Exchange server, the ability to sync those between my desktop and Exchange server is crucial.

The other thing that I found particularly annoying about Entourage was its database. While it’s fair to say that all of the historical problems with database corruption seem to have been resolved (I never had a single issue, even with a 2GB+ database), it’s a nuisance as far as backups are concerned. With Mail.app, my incremental backups end up being much smaller, since only the changed information is coming across. With Entourage, the entire 2Gb database goes into every incremental backup (since it will have generally changed each day). This increases the time that it takes to backup, and of course decreases the number of backups that can be kept (since they’re larger).

To be fair, Entourage does have some features to recommend it, in large part the “Project Centre” and the level of integration that is available between the components (the linking of contacts, tasks, calendar items, and notes to e-mail messages is a nice feature, but much of it can be replicated with the multitude of plug-ins available for Mail.app — I find MailTags , quite specifically, addresses most of the features that Mail.app would otherwise be lacking in this area).

The Project Center was also a nice way of looking at things, but again I found it too confining, when generally a Spotlight search combined with proper use of Mailtags can often provide a more comprehensive view of what I’m looking for.

One other significant advantage of Entourage is that it communicates using the norrmal Outlook Web Access protocols (WebDAV, specifically). This means that as long as Outlook Web Access is available, Entourage will work just fine. My wife uses Entourage on her iBook for that very reason — She’s a teacher, and the school board does not provide any access outside their firewall other than OWA, so IMAP clients are definitely out in the cold. Despite this, however, Entourage still communicates with the Exchange server very effectively and allows her to download her mail and use all of the features of Entourage. Mail.app simply can’t go there due to the IMAP ports being blocked.

At any rate, I just thought I would share my experiences as somebody who has been down the road a few times — in both directions.

Thanks, Jesse. The IT Department where I work would sooner carve their own hearts out with plastic teaspoons than install Microsoft Exchange Server. If things were different, I’d find the tips here especially useful.Entourage, Mail.app, apple mail, switching, exchange server, productivity, groupware, microsoftSimilar Posts:

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