Microsoft Outlook to Mozilla Thunderbird: A Migration Buggily (And Unhappily) Deferred

A year ago, I told you that I was planning on sooner-or-later transitioning from Microsoft Outlook 2000 to Mozilla Thunderbird as my PIM (personal information management, i.e. email, calendar, contacts and tasks) client. And two days ago, I decided to take the plunge. Since I’m no longer using a Windows Mobile O/S-based phone, and since Google is now my nexus for email, calendar, contact and task data, I have no particular need to stick with Outlook. And since I’m now using OS X-based Macs as my primary computers, a Windows-centric PIM is sub-optimal. VMware Fusion’s virtualization is functionally solid but it’s not particularly speedy, especially with an application that makes heavy use of the virtualized HDD, such as Outlook with its centralized PST database file. And the each-hour NewsGator Inbox RSS sessions put a heavy strain on the virtualized CPU, too.

Tuesday morning, after staring at one too many lengthy Outlook 2000-induced Windows XP hourglasses, I decided to defect. Thunderbird v3 had gone gold; in fact, version 3.0.3 had recently been released. My first step was to export my Google Reader feed list to Thunderbird in the form of an OPML file. Here’s where I encountered my initial problem; the first time I tried to import the OPML into Thunderbird, only some of the feed subscriptions appeared, and for only some of them were the settings screens correctly appearing. Manually deleting the appropriate files from my Thunderbird profile and then re-attempting the OPML import produced an error message indicating that the OPML was invalid, and both re-launching Thunderbird and rebooting the system produced no relief. Deleting and re-installing Thunderbird, then re-attempting the import, finally resulted in seeming success…though I noticed yesterday afternoon that the settings for some of the subscriptions had once again disappeared.

Next, I set up my various email accounts; two based on the POP3 protocol, one using IMAP, and the fourth (Gmail) initially set up with IMAP so that if I encountered any problems with Thunderbird, I wouldn’t lose my messages since copies would remain on the server until I explicitly deleted them. This process went fairly smoothly, although Thunderbird didn’t always guess the right server URLs, ports, and security schemes, forcing me to manually enter the necessary settings in some cases. And speaking of settings (and their display disappearance), I subsequently ran into what appeared to be an XML parsing issue here, resulting in on-screen garbage characters which application restarts and computer reboots didn’t fix. Again, an uninstall and reinstall of Thunderbird 3.0.3 rectified the situation, fortunately without forcing me to recreate the user profile I’d just crafted.

My ultimate aspiration, as you may recall, was to migrate my decade-plus old Outlook database into Thunderbird (a task that will hopefully be more straightforward in the future now that Microsoft has pledged to open up the PST format specification). The OS X version of the program doesn’t directly import Outlook data, but the Windows version of Thunderbird v3 does. So I installed TB v3.0.3 on my MSI Wind U100 netbook PC and used it to create the folder hierarchy that I’d subsequently migrate to my Apple MacBook Air. The first few times I attempted to import Outlook into Thunderbird, after having first pulled the messages from Outlook’s ARCHIVE.PST back into OUTLOOK.PST, the operation completed with an error (and an incomplete import) on one particular folder which no amount of experimentation on my part (copying the folder contents to a new folder, then deleting the old one, and converting all of the necessary emails from HTML to ASCII text format, etc) would work around. Eventually, I figured out that AVG AntiVirus Free Edition was invalidly flagging one of the emails as containing a virus in the midst of the import, and temporarily disabling AVG enabled the import to completely succeed, preserving its original hierarchy to boot. I then moved the imported Outlook data from the Thunderbird profile on the netbook to the one on the Mac, and the next time I launched the OS X version of Thunderbird v3.0.3, the additional messages and folder structure appeared there as well, in the Local Folders tree.

As of late yesterday afternoon, Thunderbird seemed to be running stably, so I deleted the Gmail IMAP account profile and created a new one using POP3 (I could find no way to migrate the existing profile from IMAP to POP3). I then downloaded a day’s worth of accumulated email from the Gmail account to Thunderbird. When I left for a couple of hours to go cross-country skiing, Thunderbird was busily indexing all of the imported Outlook messages. When I returned home, the indexing operation seemed to be complete, yet Thunderbird had not done an RSS (supposedly every hour) download session. I manually downloaded email and then initiated a manual RSS download…and Thunderbird crashed hard. It hasn’t yet fully resurrected itself.

Attempts to launch Thunderbird produce, after a few seconds’ worth of startup activity, a nebulous Crash Reporter message:

When I try to run Thunderbird in safe mode, here’s what happens:

And believe it or not, Crash Reporter itself then crashes:

Manually deleting the imported Outlook file and folder hierarchy, I’ve just discovered, enables Thunderbird to launch. And strangely enough, copying my entire Thunderbird profile (including the seeming offensive Outlook-sourced messages) to a Windows XP-based version of Thunderbird v3.0.3 seems to work just fine. So I seem to have stumbled across an OS X-specific bug, and if it’s any consolation, I don’t appear to be the only one having this particular problem.

So I guess I’m going back to Outlook 2000 for now, having lost roughly one day’s worth of email in the process (and having already proven to myself that the v3.1 initial beta doesn’t fix my problem). It’s too bad; although I stumbled across a few other minor glitches with the program beyond those mentioned above, there was a lot to like about Thunderbird. And I found some great extensions (Lightning plus Provider For Google Calendar, Manually Sort Folders, and ThunderBrowse…plus a few others I hadn’t had a chance to try out yet) that (as with Mozilla’s Firefox browser) further enriched the program’s capabilities. To wit, the ability to browse directly within Thunderbird was quite compelling, even though ThunderBrowse certainly won’t completely replace Firefox in my particular case (among other reasons, because it doesn’t yet support syncing bookmarks via Xmarks or Weave).

I’m working with Mozilla’s PR representative to set up some time with Thunderbird’s developers, in the hopes of sorting out and rectifying whatever seemingly went awry when the OS X version of the program was indexing my imported Outlook messages and folder tree. Until then, content yourself with the following writeups:

• Review: Thunderbird 3 takes flight with tabs, enhanced search (Ars Technica)
• Mozilla Messaging building nest for Thunderbird 3.1 (Ars Technica)
• Mozilla Thunderbird 3 Released (Slashdot)
• French Military Contributes to Thunderbird 3 (Slashdot)
• Geek to Live: Eight killer Thunderbird extensions (Lifehacker)
• Run Google Wave Inside Thunderbird 3 (Lifehacker)
• Make Thunderbird 3 Your Ultimate Online/Offline Message Hub (Lifehacker)
• WAT For Thunderbird Lets You Open URLs In New Tabs (Lifehacker)
• 10 must-have Thunderbird Addons (+ 25 more)
• Google Calendar in Thunderbird tabs