Microsoft Entourage is not Outlook for Mac. There is now an Outlook for Mac included in the 2011 release of Microsoft Office.

However, prior to that Entourage was the only option for supporting Exchange servers and their email/calendar/contacts syncing and sharing. 1

Entourage is not without its problems and as any experienced Mac users or technicians know, Entourage has a duo of fatal flaws.

The Problems with Entourage

It keeps everything in one database file.

Where is my database file?

Entourage stores the file inside the Documents folders in a folder called Microsoft User Data/Office 2008 Identities. There should be a folder called Main Identity by default. Inside it, there is a file called “database.”

What exactly is in the database file?

Your rules, mailing lists, signatures, messages, data, schedules, contacts, tasks, notes, calendar are in your database.

Why is that bad?

The problem with this is the file will continue to grow and become unstable. How big can the database get before it becomes unstable? The Entourage 2004 & 2008 database has no size limit, just a limit to the number of items in the Entourage database: 2 million database items.

Due to the way the database handles messages, the limit is about 1 million email messages. This may seem like a lot but I’ve seen databases going back a decade or more that can contain far more than this.

How can I tell if my database is corrupted?

The signs of database corruption are:
* Problems viewing and opening items
* Big grey blank of about 3-4 lines in Inbox which if I click on it, freezes the screen and or makes app close down
* Blank E-mails with no text
* Messages that won’t delete
* Crash and freeze when opening

Why not archive messages and old data out of the Entourage to keep the database file small and stable? This brings me to the second flaw in Entourage.

There is no way to Auto Archiving for messages.

Outlook users have enjoyed the ability to automatically archive their messages since at least Outlook ’97, Entourage never gained parity.

How do I auto-archive my messages?

You can’t. 2

How do I manually archive my messages?

There are a few ways to archive Entourage data but none of them are easy and some of them are downright hostile.

In order to back up your Entourage database you must quit all Microsoft applications.

  • This means Entourage, Word, Excel, PowerPoint, My Day, Office Reminders, Microsoft Database daemon and Messenger must be closed before you can begin and remain closed until the process is complete.

Now that all of those applications are closed and remain closed for the duration of your backup, here are the choices to back up.

  1. Create an MBOX file
    This is best for backing up a single folder as it will not keep the file structure of sub folders. Ideally, to use this method, create a rule to move all the items to archive into a single folder.
    To create the MBOX file simply drag the folder from Entourage to your desktop. Depending on the size of the folder, this can take a long time so be patient.
    When it’s done, you will have a file you can drag back into Entourage or open with a text editor.

  2. Create an Entourage Archive (rge file)
    The benefit to the rge file is that it can export multiple folders with sub folders along with calendar items, contacts, notes and tasks.
    Once you’ve exported your rge file, you can import it back into Entourage and it will show up with folder structure intact. This is particularly helpful if you’re going to make a separate identity to keep your archives.

  3. Create a separate identity.
    The new identity will be empty upon creation. Since this identity is not for sending receiving email, I would recommend not setting up an email account with it. Instead, this is the perfect place to import the rge or mbox file you exported.
    Setting up a live email account in this identity will lead to the same problem as the main identity. All of the email on the server will still take up space in your database and lead to instability.
    Think of this second identity as your backup. This is your attic where you keep the holiday decorations. You don’t visit it everyday but it’s there when you need it.
    Over time, it would be good to create multiple identities to keep you ever-growing archive of email. Separating the identities by year should be more than enough to keep everything tidy and stable.

  4. Time Machine other backup software
    Using Time Machine or another backup software such as SuperDuper! you can keep backup copies of your database in the event it become irreparably unstable, you can restore it from an older copy.
    There is a series of scripts available which can make the process easier.

How can I keep Entourage happy and healthy?

The most important lesson in keeping a happy, healthy mailbox is delete your email. If you are never going to look at a message again, delete it. If you think you’ll need it later then archive it. If you need it for a project then tag or file or until the project ends, then delete or archive it.

I am as bad about this as anyone since I constantly have a flow of conversations about support calls, outage reports and other emails flying at me at all hours.

The solution I have found is to block off the last hour of a Friday each month and go through my email. By doing this monthly, I don’t allow the pile to grow too large. If it takes more than the hour I have scheduled then I may try to tidy my mailbox during the week or wait for the next scheduled Friday.
If one hour is not enough, take 90 minutes or am hour every other Friday. If Fridays are bad, pick a time when your schedule is usually lighter. A little time spent on keeping a tidy mailbox will save you from catastrophe down the road.

What if I can’t delete my email?

There are certain professions or government agencies which require retention of email. If your organization had such a policy, they should also have a backup of archive policy as well. Ask your local IT technician or call your Help Desk if you don’t know what they are.

If you have no policy for retention of email but want to keep it then develop a system for doing so. Archive it using a method I described above. If you have access to upgrade To Outlook, I highly recommend doing so. If your workplace offers a remote terminal setup where you could access the Windows version of Outlook and keep archived email there, that is also a good solution.

The point is that keeping these messages in Entourage will eventually lead to a database failure. If the database fails, you wot have to worry about your emails because they will all be gone.

Lets say this again. If your Entourage database fails, there is no recovery options for your emails.

Take the time to put a system in place and use it. Block out the time in your calendar now so you know to keep it clear. Setup reminders do you don’t have to remember it.

This truly is a case where an ounce of prevention is worth a pound of cure.

Further Reading

  1. Snow Leopard shipped with Exchange support in, iCal and Address Book but required Exchange Server 2007 or later to run leaving Exchange Server 2003 with Entourage as the only option. 

  2. There are ways to archive semi-automatically but they all require third-party software and I’ll get to those later.