Migrating from Outlook Express to Apple Mail

The other day I arrived home to find my elderly neighbours lugging a rather large large box from their car - on closer inspection I could see it was a brand new iMac. Their 6 year old Dell had died and they had been convinced by their friends to crossover to the Apple ecosystem.

Unfortunately, the so called Apple Genii at the Bondi Junction store were incapable of transferring over their old files as promised so I offered to help. Although the screen was dead on their Dell, it made some whirring and booting noises so I pulled out the HDD to see if I could recover anything. Thankfully the disk seemed fine, I was able to mount it on my windows 7 box and copy off all the files (so much for the skills of the apple genii).

I was able to load the contacts into Windows 7 contacts and export them as vcd files so they could be imported into the mac. The path for the outlook files was a little more convoluted....

This is how I managed to do it.... basically the workflow was Outlook Express Data Files -> Windows Live Mail -> export to eml files -> Import eml files to Thunderbird -> export Thunderbird to mbox -> cleanup mbox files with clean_moz script -> import cleaned mbox files in to Apple Mail.

Here are the details:

I downloaded Windows Live Mail as Outlook Express is not supported on Windows 7. It was able to import the outlook data files once I was able to find them... their location varies depending on the version of windows and outlook express, but from memory I think they were in the Local Settings/ApplicationData directory (this is a hidden folder so you need to enable viewing of hidden files  to see it).

Next I exported the mail in Windows Live Mail format- from memory I think this stores the mail in a folder structure, with each email as an individual eml file

Then I imported the Windows Live mail into Thunderbird, using the thunderbird import export tools plugin.

Then I used the Thunderbird import export plugin to export the mail. Thunderbird stores its mail in the mbox format, which Apple Mail promises to import.

Next, I used the import feature on Apple Mail to import the data in thunderbird format. This took a long while, but somehow only managed to import a single email from each folder. Same result when I imported the mail in mbox format... after some google foo I discovered the Apple Mail import is a bit broken  and does not fully support the mbox format.  Thankfully Trevor Harmon had this problem back in 2004 and wrote an awesome python script to cleanup the mbox files so Apple Mail wouldn't choke.

After cleaning, the files imported perfectly- thanks Trev!