When you open Entourage 2004 does it immediately display the spinning multi-color ball icon? This icon simply indicates that Entourage is thinking, but if this icon never goes away then Entourage is getting stuck while trying to complete a task. There are a number of possible causes but over the past two months I’ve had 5 different clients all report this same problem and in every case the problem was caused by a message being stuck in Entourage’s “Outbox”. The Outbox is where Entourage temporarily stores an email message between when you click the “Send Now” button and when Entourage finishes sending the message. For reasons I haven’t been able to figure out, sometimes Entourage is not able to send the message and it gets stuck trying to send it.

There are two ways to fix this problem. Option 1 – I realized that if I disconnected the Mac from the Internet by either unplugging its ethernet cable or turning off Airport then I could open Entourage and it would not try to send the message. Then, I could simply delete the message in the Outbox. Then, reconnect the ethernet cable or turn Airport back on.

Option 2 – I did some online research and learned that people have been having this problem for years and there is an even easier fix. Simple hold down the shift key while clicking on Entourage’s icon to open it. Holding down the shift key disables the built-in schedule to automatically get for new email messages and to send email messages in the Outbox. This solution came from the Entourage Help Page which has been invaluable over the years when I’ve needed to troubleshoot Entourage issues.

Additional Note: A further curiosity in this situation is that Entourage seems to be frequently getting hung up while specifically trying to send a forwarded copy of an Alaskan Airlines itinerary. I don’t know what is unique or problematic about these emails from Alaska Airlines but I can only guess that Alaska Air has recently changed the contents of their itinerary emails and that one of these changes somehow causes Entourage to get stuck when it is asked to forward these emails.

If you use Entourage 2004 or 2008 then I believe that it’s critically important that you backup your Entourage database daily or even more often.

Entourage stores all of your email messages, your calendar events and your address book contacts in the database file. As this database file gets larger it becomes more and more prone to getting damaged. Some damage can be repaired, but it’s not uncommon for some databases to be damaged beyond repair. At this point there are typically only two ways to deal with the situation. The first option is to manually rebuild your database which is very time consuming and almost certainly ensures that some email messages or other data will be lost. This process requires you to manually export your address book, calendar events and then export each folder one by one into individual mailboxes (mbox). The second option is to restore your Entourage database from a recent backup. Your backup copy of  your Entourage database will still be large and in need of some housekeeping, but hopefully its not damaged and you can do this clean-up and avoid future problems. The more frequent your backups the better since we want to work with a recent database.

I should also emphasize that it’s important to deal with a damaged Entourage database at the earliest sign of problems. In some cases Entourage will display a message indicating that your database is damaged. In other situations you’ll notice problems. Entourage might display multiple copies of the same email message in your inbox. Or, it might display the header information for one email message while displaying the body of a different email message

You can manually start Entourage’s built-in Database Utility by holding down the option key while opening Entourage. It’s recommended that you choose the “Verify” option to check the health of your Entourage database.

Be aware that if you use Entourage 2004 the “rebuild database” option in the Database Utility removes all category information that you’ve assigned to contacts and email messages. I believe it also deletes all of your Notes. These problems were apparently fixed in Entourage 2008 though I haven’t verified that personally.

Entourage stores its database in this location:

/Users/<your username>/Documents/Microsoft User Data/Office Identities 2004/Main Identity    Note: If you’re using Entourage 2008 then the folder name changes to Office Identities 2008.

To backup the database I recommend copying the entire Main Identity folder. Look inside this folder to make sure that the database file inside was modified today. This way you can be more certain that this is your current database. Entourage lets users create multiple Identities so you could have more then one identity folder. If you’ve used the Database Utility to repair your database then you may find more then one database inside the identity folder.