It all started with our dog having a litter of puppies two years ago. I moved with her up to our holiday house on the central coast an hour's drive north of Sydney. We bought a digital mini-cam and new iMac so that I could make movies of the birth, rearing and weaning of the litter of Collie Rough (Lassie) pups and share these with friends and family back in Sydney. This was my first user experience with Apple products and I must say I was blown away. It was soooo easy over those 4 months to transfer pictures and movie snippets from the cameras to the Macintosh and thence though email to my wife and to our friends back in Sydney. As a life-long Windows user from the very early 80's, I fell in love with Apple.
About the same time, my PC in Sydney began to operate erratically, sometimes booting, sometimes not. Although I had burned CD's of My Documents, I was concerned that I had no backups for my email and contacts which lived in Outlook. I decided to purchase a $10. program called O2M from Little Machines to do the job. O2M runs on Windows. You pick the outlook folders you want and O2M automatically exports Outlook data into portable files which can be imported into Apple's Mail and Address Book applications. As I recall, the mail files went over perfectly and the Contact files not at all. However, enough of my email problem was solved to cause me to forget about it for a while.
Another year went by and my windows PC booted for the last time. I should have bitten the bullet then and there and bought a Mac. Instead, I farted around and found a brand new overstock corporate machine on Ebay for $300. This HP Athelon had XP Professional, 2GB of memory, 160GB disk, keyboard, and mouse and I could not bring myself to spend the extra money on a Mac. This foolishness became apparent when I realized how few original installation disks I had for the software which had been running on the PC. The antivirus software alone was going to cost $200! Since I no longer had access to Microsoft software from work, Office was going to cost $400. By the time I would have finished buying software for my cheap Windows machine, I would easily have touched $1000. At this point I had been living in different houses with different computers for nearly two years. I now had substantial "sent" mail folders living in two locations AND I could not find my O2M license or downloads. This $10. piece of software which I refused to re-buy was my personal environmental tipping point. I swore off commercial software forever and downloaded Ubuntu Linux onto my Windows box. It is from that trip that I now return to the story of getting my g-damn emails out of frigging Microsoft Outlook and into mail.app.
First of all, let me say that everything that is wrong with Microsoft is tied up in Outlook's PST files. Inaccessible, inscrutable, proprietary, arbitrary, non-standard and non-interoperable!!! I read somewhere that you could import PST files into Outlook Express and from there you could export them into a quasi standard format accessible by mail.app. So here's the story:
In Windows, importing PST files into Outlook Express (OE) went great and was very easy. Exporting from OE was equally easy: using Windows Explorer, I created two folders on my desktop: Sent and Contacts. Then, within Outlook Express I highlighted all my sent email and dragged and dropped it into the desktop Sent folder. I ended up with one .eml file for every email message in Outlook Express. Same for contacts except I ended up with one .vcf file in the folder for each contact in OE (vcf is the vCard standard for address information.) I took my exported file to my Mac and I was able to import the vcf folder directly into Address Book on the Mac (version 4.11 on os x 10.5.4.). Not so easy for the .eml email files.
On the Mac, you can double click on one of these .eml files and Mail will kindly open it and display it perfectly. However, you cannot import one or many .eml's into the mail.app file system. There are references to using Microsoft Entourage to convert .eml files to mail.app's mbox format at www.macosxhints.com/article.php?story=20040325164915651 but I wasn't going there! I did find a ruby script that promised to convert eml files into a mbox format. This is at
However, I was not able to import the resultant mbox into mail.app! The 90MB worth of .eml files ended up as one large 90MB email!!!
Thunderbird also uses the mbox format although you cannot import mbox files natively. I saw a reference for an add-in for Thunderbird that allows you to import mbox files at http://nic-nac-project.de/~kaosmos/mboximport-en.html . Back in Sydney I installed Thunderbird on my Ubuntu box and installed this add-in into Thunderbird. I imported the mbox files created by the ruby script into Thunderbird. They appeared as perfectly formed single emails! Since you can import Thunderbird mail directly into mail.app, I tried this via a shared network folder but again ended up with one large blob email. I then tried exporting from Thunderbird and re-importing back into mail.app but ended up again with a one large 90MB email! At this stage, I had mail.app in the same mental catagory as Outlook!
My final solution was a reference to sync (upload) existing Thunderbird email folders with Gmail using Gmail's imap features http:// email.about.com/od/mozillathunderbirdtips/qt/te_get_gmail.htm I did this for my sent mail folder on Thunderbird which I had imported (via the ruby script and the Outlook Express import/export) this all worked and I now had my sent emails from Outlook PST on Gmail! Next, I used another reference showing how to sync (download) Gmail with mail.app using Gmail's POP features http://woss.name/2006/11/20howto-using-mailapp-to-archive-your-gmail/. This reference also showed how to use mail.app rules to plop Gmail's downloaded sent messages automatically into mail.app's sent mail folder. My problem has been solved and I am done with Outlook forever!