Switching to Mac OS X: The Bad

The biggest challenge in the switch is, of course, moving all your data across from Windows to Mac OS X. This is not as simple as it sounds especially if you have been using MS Outlook for email, calender and contacts management for years (as is the case with me). There is no equivalent of MS Outlook on Mac. There is Entourage but I found it rather fiddly to use and was adamant to get away from being bound by the proprietary .pst files that Outlook uses (but that somehow will remain a dream ... see the next post). I decided to use Mail that comes bundled with Mac OS X with a view to using pine in the long run. I was pleased to read in various articles that Mail uses the (sort of) standard mbox format and even had thoughts of interleaving Mail and Pine (I just love the austere simplicity of pine) as described in this post: http://www.oreillynet.com/pub/h/335.

So how does one port several gigabytes of email from MS Outlook (2003 in case you are wondering) to Mail. I searched around on the Internet and found a number of options. One is to use a software from Little Machines that does the conversion for you. It costs only $10. However, a bit of research seemed to indicate that it may not work that well for large mail sizes. Of course, I have no evidence that this is true as I haven't used it myself. The other option is to enable IMAP in googlemail and upload all your email (you will have to create custom labels for all your folders) onto googlemail and then download it using Mail. This seemed reasonable but, again, some research indicated that googlemail has a habit of organising your mail in some clever ways which may mean that you end up having your email in a a bit of a mish-mash (not something you would want with several gigabytes). It wasn't clear whether it is really the case but I didn't want to take the chance. Also, uploading and then downloading several gigabytes on googlemail could take eternity.

From the various options, it seemed the simplest was to install Mozilla Thunderbird on my PC, let it import all my Outlook email and contacts and then import those in turn into Mail on Mac OS X (you can use Eudora as well BTW). This is the option I went for. Thunderbird uses the mbox format. So once all the mail was imported, I transferred it to my Mac and was ready to import into Mail when disaster struck. Each folder would have to be imported individually which would mean recreating the folder hierarchies manually in Mail, something I wasn't prepared to do. So back to some more googling and I found a nifty little utility called Eudora Mailbox Cleaner. The name is historic and it actually converts across a number of mailers on Mac. It can preserve the folder hierarchy. Upon opening Mail you can see the folders but you have to "rebuild" them to see all the emails. The software comes with an Apple Script but it is somewhat temperamental. So I decided to use the convertor and manually rebuild. Sigh. This took hours. I can only thank the author of Eudora Mailbox Cleaner as otherwise I would have spent even longer importing the mailboxes individually.

Did the import work? Yes. Some of the attachments got garbled up but nothing disastrous. Given that I imported several gigabytes of mail, I felt it was pretty good showing (and not sure who was to blame for the garbling: Thunderbird, Eudora Mailbox Cleaner or Mail ... or even Outlook ... with its pst format!).

You can expect to encounter such challenges. I use Microsoft Project and AFAIK there is no version for Mac OS X. So I may end up creating a dual boot to be able to continue using Project which is quite central to the work I do.

Any case, at this point I was pretty excited. Now I could interleave Mail and pine and enjoy the best of both worlds ... the nice GUI of Mail and the simplicity of pine ... whenever I wished. But like the Saracen conquest of Constantinople, it seems it would have to wait for a few centuries.