I have been using Microsoft Entourage 2008 as the email client on my Mac for almost a year now and while it is not perfect, it provides the best Microsoft Exchange support out-of-the-box of any native Mac email application. Mail.app, iCal, and Address Book do not work well enough just yet to use in an enterprise Exchange environment (although I am anxiously awaiting OS X 10.6 which promises native Exchange support in all three applications!). That said, about two weeks ago I had to abandon ship on Entourage. I suffered a major Entourage meltdown, and it frustrated me enough that I made a hard switch over to nothing other than Microsoft Outlook.
Huh? Say that again? Outlook on a Mac? What could I possibly be thinking? How could I be such a traitor to the cult of the Mac? Give me a minute to explain… I am as big of an Apple fan boy as you can get, but put simply Entourage was not delivering a reliable solution for me, and in a work environment that is a non-starter.
The Entourage Identity / Database
If you are an Entourage user, at some point you have probably opened Entourage and seen what I would say is the application’s equivalent of the Windows Blue Screen of Death — a message informing you that something is wrong with your local Identity (also commonly referred to as the database). In essence, your Entourage Identity stores your emails, contacts, and other application data locally on your Mac to improve performance. In theory, there is nothing wrong with that. Lots of applications do the same type of thing.
However in my experience, Entourage’s Identity is fairly susceptible to getting corrupted. In my first month of using Entourage 2008, it got corrupted twice, and I had to use Entourage’s Database Utility to rebuild the database — a process which for my mailbox at least takes a couple hours. Not fun and not very enterprise friendly.
Additionally, the Identity is a bear to back up. Time Machine is hands down one of the greatest features in OS X 10.5, however Microsoft’s Office for Mac team recommends you do not configure Time Machine to back up your Entourage Identity. Why? The actual Identity / database is one big file that appears to Time Machine (or other third-party backup solutions) as a new file anytime it is written to or updated. When Time Machine goes to back up every hour, it therefore makes a full backup of the file as opposed to an incremental one. To put it into an example: if your database was around 5GB in size, then in a day you could eat up 120GB (5GB * 24 hourly backups) on your Time Machine hard drive if you have an active email account. There are some workarounds on how to manage backups, but they require varying degrees of hacking and none in my opinion are scalable enough or appropriate for enterprise use.
The Great Entourage Meltdown of ‘08
So, with that said let’s get back to my story. As I mentioned, my Entourage Identity had corrupted a couple of times early on, but after one service pack and a couple of Office for the Mac patches later, the
developers over at the Mac Business Unit in Microsoft seemed to have
improved the stability of the database. I had a nice stretch without an incident. However, two weeks ago I sat down at my desk at the beginning of the day, got ready to start working, clicked on Entourage, and got the dreaded database error.
Given the backup issues above, I assumed that if something ever seriously went wrong with my Entourage setup, I would first attempt to rebuild the existing Identity, but worst case could just create a new one by syncing with the data on the Exchange server. Therefore, I launched the Database Utility to verify and rebuild my database. Two to three hours later, the Database Utility informed me that my database was fixed. I launched Entourage, and guess what? All my contacts and email were gone. That’s right completely gone.
Still I was not going to panic — I went to plan B and was going to create a new Identity file and re-sync / download all the info from Exchange. Before moving forward with this, I logged onto Outlook Web Access (OWA) which gave me a real-time view of my Exchange account and could not believe what I saw — my entire email, calendar, and contacts were empty outside of a handful of emails that had come in within the last 5 minutes.
I checked with my IT manager and he saw the same from the Exchange side — a mailbox that was barely 20MB in size. What we quickly realized was after I rebuilt the Entourage database, and for whatever reason the rebuild did not do what it was supposed to, the local (now empty) Entourage database synced to Exchange and deleted everything on the Exchange server.
Abandoning Ship…
To cut to the chase, we were able to restore my emails, contacts, and calendar info from a backup, however when you combine Exchange support that is not 100% equivalent to Outlook with the potential to have issues like the above, it is tough for me to “love” Entourage. I recognize there are other preemptive measures I could take in the future to prevent this same sequence of events from occurring, but at the end of the day, you need reliable and scalable applications and systems to run your business and Entourage let me down.
So, I made the move to Outlook. I am using VMWare Fusion which has been on my Mac since day one, but I never really had a reason to use on a daily basis until now. I run Outlook 2003 in a Windows XP virtual machine in Unity mode. So far, I have to say it is working a heck of a lot better than I had originally anticipated. VMWare has a number of features which allow you to share folders across both operating systems, launch Mac apps from Windows and make the integration between the two operating systems work well together.
(Editorial note: It is pretty amazing if you stop to think about this solution for a second. Several years ago doing something like this would have been unthinkable, yet getting this set up literally took minutes. It is a huge credit to Apple’s Mac team for designing a world-class platform.)
Am I in Mac / Exchange email nirvana yet? No. I want to have a native Mac application deliver Exchange integration that really kicks you-know-what. However by moving to Outlook, I now know that: 1) my work day does not have the potential of being randomly interrupted with email problems as a result of my local email application; 2) I have 100% compatibility with the Exchange server and the Windows users in my company; and 3) I am still able to use my Mac in an enterprise environment. Right now Outlook is the only client that can deliver on the three… sorry Entourage and Mail.app 
Let’s all hope that Snow Leopard brings the Exchange integration that Apple has promised and we Mac users need. I am anxious and ready to make the switch back when that happens!