I knew it had to be done, so I was going to be careful about how I migrated my email. I had read in the Missing Manual that there were options with varying degrees of headache and (in one case) cost. David Pogue recommended a consumer application called Outlook2Mac (now called O2M at www.littlemachines.com). It was a simple wizard solution that would do all the heavy lifting and you say which folders to move from Outlook to the Mac. Sounds easy, but it had a price tag of $10 (small price to pay, I know). There were a few simple home-baked solutions recommended as well, including a complicated one using Netscape.
I opted not to go the route of the complicated solutions, but kept my eyes open for a free way as I set up my folders for O2M. I didn’t want to just import all my folders. I wanted to select out the ones that were from friends, and other important emails such as password confirmations, etc. This (including procrastination) took a long time. I had to go through years of old emails and select out the good ones. I also thought I could install Thunderbird on Windows and somehow transfer my mail there and it would be simple to copy that to my Thuderbird in OS X. I quickly gave that up, though, when it didn’t seem workable.
Finally, I was ready to get O2M and get going. The Windows program basically takes all your Outlook content and packages it up for the road. You copy the files over to your Mac and import them into your mail application. The program promises not only to import emails with all their formatting, but also includes attachments, contacts, and calendar. At first I downloaded the trial version (the difference between trial and full versions being a mere unlock code) but after successfully importing a small folder into Apple’s Mail.app, I figured I was ready for the real thing.
Still being a bit gutless, I began by importing Contacts into the Address Book (I’d already done a bit by exporting my Contacts in csv format, so I was actually only updating my Address Book with O2M’s improvements with the same data) and some updates were made (addresses and numbers had been imported as “work” numbers and O2M made them into “home” ones).
Next safe step was iCal (the calendar program in Mac OS X) and I played it even safer by creating a new calendar, separate from my main calendar, in which to import the new events—so I could still delete everything cleanly if it got messed up. It worked flawlessly.
Then, after the program spent some time chugging away at packaging up my emails, I was ready to import them on my Mac. I couldn’t figure how to get any of it into Thunderbird, so I figure as long as I can get it into Mail.app, I’d still be OK. When I got the mail over, I found that I had far fewer emails than I had expected. After I confirmed in Outlook, I realize that O2M was aborting the archiving without telling me. The log acknowledged that there were over 1000 emails in a certain folder, but stopped copying after around 12. What gives? I went to the web site, which was useless. Finally I tried a few experiments and found that it was because of the attachments (including inline graphics that are actually part of the email). After I set it to skip all attachments, I was able to package up all the emails, but I wasn’t happy.
I was able to successfully import all the stripped emails into Mail.app, but I was disappointed at having paid hard-earned money for a program that didn’t work as promised. In the end I guess it’s not a big deal. Emails are just emails. They don’t change the world. But maybe I’ll send the O2M folks a little email of my own and see if that can change something. What do you think?