When you open Entourage 2004 does it immediately display the spinning multi-color ball icon? This icon simply indicates that Entourage is thinking. However, 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. 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 the time 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 on the way out.

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 and 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. Simply hold down the shift key while clicking on Entourage’s icon to open it. Holding down the shift key disables the built-in schedule that automatically gets new email messages and sends email messages in the Outbox.

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. 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 asked to forward these emails.