Adeo Ressi

On Friday, Andy Ruff, Lead Program Manager for Entourage at Microsoft, called to discuss the database import issue that I was experiencing when moving from Entourage 2004 to 2008. Before getting into any details on the "solution," it was very impressive that Andy took the initiative to contact me, especially while working at a large company like Microsoft. As a result, I am going to give Entourage a second chance (in a limited capacity, of course).

Apparently, Microsoft updated the "database" file structure in 2008 with a goal of making the system more "open." The solution to fix a bad import of Entourage 2004 data into Entourage 2008 is as follows:

• Do not delete the Office 2004 applications. If you have, try to recover them from back-up, which I did.
• Ensure that you have enough disk space! You will need around 3x the Entourage database file size in available disk space to proceed. My database was 7.5 Gb, so I required about 25 Gb to get through this. I was deleting movies, songs, etc. I recommend going into /Documents/Microsoft User Data/Office 2004 Identities/ and removing back-ups and databases labeled with "old."
• Open Entourage 2004 and remove any active email accounts associated with it. Entourage 2004 will try to re-download all messages when you re-build the database, and that can take a lot of extra time. The email settings will be lost, so write them down and re-enter then later in the 2008 configuration screen.
• Open the "Database Utility" under the /Microsoft Office 2004/Office/ folder. Choose the top-most database and click "Rebuild database." WARING: my 7.5 Gb database took approximately 5 hours to do, and it generally fails towards the end. Be prepared to go do something else. If the re-build succeeds, proceed. If it fails, call Microsoft and pray.
• Open Entourage 2008 and import a previous Entourage database by clicking Import under the File menu. Expect to wait another 2-3 hours for the import to be complete. It will also take about 30 minutes to load Entourage the first time you launch with the new data. If you have already done some set-up of Entourage, the import action will create a whole new Identity in Entourage which you switch between under the /Entourage/Switch Identity/ menu. The fastest solution is to delete the old Identity and use this new identity as your primary, adding back the account information that you deleted from your 2004 profile. Otherwise you have to do another export and import to merge the Identities!

After countless hours and a lot of work, I got my 2004 Entourage data into the 2008 version, yet I still experienced some strange behavior.

What was the first thing that I did now that it basically worked? Well, I uploaded all of my email archives to Gmail, of course. This was easy:

• Enable IMAP at the Gmail web site through the Settings menu at the top right.
• Connect your Gmail IMAP account to Entourage 2008 by plugging the setting in from Gmail to /Entourage/Account Settings/. Make sure that you uncheck "download complete messages" under the Options tab of the account configuration.
• Then drag mail items and folders from "Folders on My Computer" in Entourage 2008 into your Gmail account. It takes about 45 minutes per 1,000 messages to upload on a high speed connection.
• Last, but not least, I backed up my Entourage 2004 and 2008 database archives from my primary computer before deleting them.

I will continue to use Entourage for day-to-day email composition on a local computer and while traveling. However, I will store vital emails in a nicely searchable context, AKA Gmail. More to come on the overall usability of Entourage 2008.