Freeing My Email: Open Source And Industry Standard As A Matter Of Course

Three weeks back, with a two-week-back follow-up, I shared with you my initial steps at breaking away from a Microsoft Outlook PIM lock. At this point, my contacts and calendar are in two interlocking ‘clouds’, Google and Apple’s MobileMe, with the Address Book and iCal applications running on my Apple laptop as their bridging intermediary. Google Calendar and Contacts directly feed my Windows Mobile smartphone via Exchange, while MobileMe automatically keeps my iPod touch updated, along with my other Macs. And if I ever get around to migrating Outlook beyond the 2000-era iteration I’m currently running, MobileMe can keep its calendar and contacts data current, too.

But I frankly don’t think I’ll get around to upgrading to Outlook 2003 or 2007, because I’m leaning towards dropping Outlook entirely. Right now, the bulk of the computer systems I use on a regular basis are Macs, and therefore my only means of running Outlook-on-Windows on them are through Wine emulation (in which case I don’t think my RSS plugin would work) or via Boot Camp or virtualization. Emulation, however, is hit-and-miss, Boot Camp’s been buggy for me, and virtualization is both slower than native mode and feature-incomplete. Plus, all three of these options are only possible for my Intel-based MacBook and MacBook Air; my PowerPC-fueled Power Macs are SOL.

Part of my motivation to ‘jump ship’, I admit, is also a ‘freedom of information’ matter of principle. Microsoft made it hard enough to extract calendar and contacts data from Outlook, as my previous writeups have exemplified, but migrating stored emails elsewhere (heaven forbid, to a standard format like mbox) is darn near impossible without hefty third-party assistance. The company doesn’t even (for perhaps obvious reasons) enable you to import your Outlook PST database into the functionally equivalent Microsoft Entourage for OS X (unless you are running Outlook 2000 or older, as I am, and also happen to have an ancient copy of Entourage 2001 lying around along with Mac hardware that supports Classic mode). Conversely, and ironically, Outlook natively supports numerous email import capabilities. How’s that Eagle’s song lyric go…

You can check out any time you like, but you can never leave…

I took on Microsoft’s roadblocks as challenges to be surmounted, and I’m happy to report that my efforts were ultimately successful. Note that since I already extracted calendar and contacts entries from Outlook via other means, I didn’t re-attempt these particular operations with the tools I’ll mention; I focused only on my 12+ year email archive. Speaking of archive, any of you who want to follow in my footsteps will first need to manually pull emails out of archive.pst and back into outlook.pst, since migration utilities only focus their attention on the latter, primary database. This is a straightforward albeit tedious task; open the archive file within Outlook and then drag groups of emails folder-by-folder into their primary database equivalents.

The first utility I tried was Outlook2Mac by Little Machines. At $10, the price was certainly right, and the program worked as advertised although the end result wasn’t particularly optimal for me; those of you with simpler Outlook setups will likely find O2M more palatable. It runs under Windows, in conjunction with an also-running copy of Outlook. The setup Wizard enables you to specify numerous export parameters; my biggest grumble about it was the lack of a ’select all’ button, thereby forcing me to checkbox-click each of my 1400+ nested Outlook folders in a tedious and mouse finger-cramping one-by-one fashion.

More than just a simple iterative email folder-to-mbox script, O2M will alert you if it finds emails with missing or invalid dates (which happened in my case with messages originating with first program I used after joining EDN, Eudora, and which I subsequently got into Outlook 97 via Outlook Express):

Outlook will also alert you if you attempt to export digitally signed emails:

Along with a corresponding O2M pop-up:

As you can see, the Outlook-plus-O2M combo makes resouce-efficient use of my HyperThreaded 1.6 GHz Atom CPU-based netbook (the performance pauses are caused by the above user guidance prompts):

Continue reading with Part 2, ‘Freeing My Email: Import Discord And A Mozilla Outcome‘…