Jorge Arango

*UPDATE – February 24, 2007* – This post was written almost five years ago; some of the applications described here are no longer available. I also believe there are now better ways of achieving this migration, but I wouldn’t know since I haven’t had to do this again since. If you know of another way of migrating your Outlook mail to OSX, please feel free to post it the comments below.

A couple of days ago I managed to finish migrating my email archives from Outlook on Windows to Entourage on Mac OS X. For those of you facing a similar challenge, here is the play-by-play:

1. Import your Outlook mailboxes into Outlook Express.
2. Download oe2mbx.exe. This is an open source command line application that converts OE’s proprietary mail format into the UNIX standard MBOX format. (This application had been offline for a while; thanks to Sasha Svitlica for the updated link.)
3. Using the Windows command line, visit the directory where your Outlook Express mailboxes reside. (You can find them by searching for files with the *.dbx extension.)
4. Run oe2mbx.exe on the .dbx files.
5. Change the resulting files’ extension to .mbox
6. Copy the .mbox files to your Mac.

1. Drag the .mbox files into Entourage’s mail folders pane.

   That’s it. Please drop me a line if you have any problems with this procedure or any suggestions to improve it.

   Note: this technique should also work with Apple’s Mail.app and other mail programs that can read mbox files.

   Another approach

   A lot of folks have written to say that they’ve had issues with the approach presented above. It seems the oe2mbx.exe application is not well documented.

   Although I haven’t used it, Emailchemy is an application that promises to convert mail to and from a variety of formats. Outlook doesn’t seem to be supported, but Outlook Express is, so you could follow the above approach from step 1, replacing Emailchemy for oe2mbx in step 2.

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Just came back from Area2—got to see David Bowie and Moby. Bowie is one of my favorite musicians, and he put on an amazing show. It featured quite a few oldies, including Ziggy Stardust, one of my favorite Bowie tunes. He also sang about half of the songs on Heathen, although he didn’t do Slow Burn which is (IMHO) the best track on the album.

The Moby set was OK. I love Moby’s albums, but his particular brand of tecno-gospel does not translate well to a live show. The man compensates for the lack of real instrumentation by running around the stage like a maniac for no apparent reason. The music is also a lot more aggressive than on the albums, with tons of distorted guitar—which I found to be an unwelcome addition to most of the songs.

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I first saw a Mac in 1985, and it was love at first sight. I didn’t get to actually own one of the little beasts until 1991, when my parents bought me an SE30 for college use. I felt so at home with that machine! It was so personal and… perfect. Hard to describe—it just fit.

After I graduated from college, reality set in: nobody outside of a few select industries (design, video) uses Macs. I grudgingly left the Apple camp behind. (Not that in 1993 the Apple camp was a sexy place to be—John Sculley and his successors managed to turn what was once an amazingly innovative company into another pusher of beige boxes.)

Fast forward to 2002. I am now back in the Apple camp and I’m loving it! They have definitely fixed the biggest complaints, especially the antiquated OS. I have a belief that we should support companies that are doing things right by voting with our dollars. In my book, Apple ca. 2002 is doing things right in a big way. Unix, digital hub, gorgeous hardware, a vision… what is there not to like?

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It seems as though I have run up against a problem that most users migrating from PCs to Macs will face at some point: moving email archives can be a pain in the butt.

I have tried various approaches:

• moving my PC Outlook 2K mail onto PC OE, and importing these PC OE files into Mac OE (No good),
• moving my PC OE mail into PC Eudora and then from PC Eudora into Mac Eudora (No good),
• creating an account on mac.com and moving my PC mail onto their IMAP server, then retrieving this mail from the Mac (Partially works, some mails complain about break formats),
• various combinations of the above.

I am starting to get a bit frustrated. I have over six years of email archives, and whatever platform I stick to needs to give me unhindered access into this information.

I’d like to see this issue addressed by Apple in one of their “Switch” ads. I’m not holding my breath.

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I’ve finished migrating my MP3 collection onto the TiBook. I am tremendously impressed with iTunes 3. It does so many things right! My favorite feature by far is Smart Lists: lists of songs assembled on the fly based on tag searches you establish beforehand. The search criteria are ample enough for the lists to be really “smart” and therefore meaningful.

I have found this to be a consistent feature of Apple software: as a user, you are completely isolated from the complexity unless you intentionally want to be exposed to it. The first time I became aware of this concept was while using HyperCard: the power of a scripting language was there if you wanted to dig, but there was also an easy point-and-click interface for use by most folks.

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