Switching friends (to the Mac)

Last year, I managed to convince 8 people to get Macs who either had not done so in the past, or who were coming back to the Mac from a long hiatus. Although I had for many years not considered myself an evangelist for "the cause", recent changes in Windows, the Mac, and the Internet have brought a change to that neutral position and now I appear to be pretty much a zealot. This despite the fact that I'm one of the few people I know who has both purchased and installed a copy of Vista. So, how do you switch your friends to OS X from XP? Good question, and tonight I've been finding out.

Previously, all of my switching friends could either do it completely themselves or were able to take their PCs in to the Apple Store and get them migrated. Tonight, things are a bit different. My friend, whom we shall call Greg, had a machine running XP which ate itself. Long story short, they are now the proud owners of a brand spanking new iMac.

Unfortunately, without any good assistance nearby, they needed a way to extract their data from their PC to their new Mac. Since I'm into the whole "Macintosh community" thing, I felt like it was a good idea to help out, so Greg sent down the formerly-internal hard drive, and I stuck it in a cheap USB 2.0 case.

The next few steps might actually be interesting to people who are considering doing this themselves, so I've decided to make them public. (Furthermore, I may need to remember what I did...).

The mission:

  • Rescue iTunes purchased songs
  • Rescue iTunes playlists
  • Rescue Outlook Address Book
  • Rescue Outlook Calendar
  • Rescue Outlook mail
  • Make a bootable XP system that could run in parallels as an external drive

Fortunately, I know and love Parallels, so I figured that I'd get started there. Frankly, a lot of this would have been much difficult if I would have been doing it just from the files. Not impossible, but certainly not easy.

Making a bootable XP system from an external drive with Parallels

Starting at the end, let's get the bootable XP system running. Since this system had a copy of XP Professional on it, I needed an XP Pro key to activate the software (relocating a hard disk to an entirely different hardware platform will just about guarantee that you will need to activate). Once I had that, here were the steps:

Warning! This wouldn't be a good process to follow if you have boot camp installed

  1. Start Parallels
  2. Select New VM from the File menu
  3. Select Custom config
  4. Select Windows as the OS Type and Windows XP as the OS Version.
  5. Allocate a reasonable amount of RAM (512MB plus)... I used 512MB, and everything was fine.
  6. When asked to select a virtual hard disk, lie and tell it Use Boot Camp

This boot is going to take a while and you might see some very strange screen effects. At various points, I had to really stretch to figure out how to get my mouse into the right location or how to move to the Next page, but it all worked out in the end.

Parallels will install the drivers it installs for Boot Camp (which are basically the normal drivers) and will create a new boot configuration, which is nice as a backup.

Once you've rebooted, you'll need to dig up that windows activation key because XP's not going to let you progress much further without it. In my case, I couldn't log in without it. However, once that was done, I had a fully functioning, booting version of XP on an external drive.


OK, iTunes is easy, but it's just insanely cool that you can run the Windows version of iTunes flawlessly in Parallels. Since I needed to ship a DVD up to Greg, I decided that the right choice would be to burn the purchased tunes onto a DVD using the build-in backup of iTunes. No muss no fuss, just select Back Up to Disk from the File menu and you're off to the races. Select your DVD burner and tell it you want to save off your purchased tunes.

Once you've waited for the DVD to finish burning, you're ready to grab the playlists. There are two ways to do this, exporting the library or exporting each play list. I did both, because they're slightly different. In either case, you want to use the XML format.

For library export, select Export Library... from the File menu. You'll be prompted for a location and it'll write out a library file with all information about all of your tracks, including # of times played, etc.

For playlist export, select the playlist you want to export (each one individually) and then right-click and select Export... or select Export... from the File menu. Either way, you'll get a window asking you where to put it and what to call it. Save them all to the same folder, so that you can zip them up for safe keeping.

You could also do a full library backup, but I didn't want to spend the time doing it... maybe next time


Outlook is a completely separate problem. Microsoft uses proprietary formats to store all of their data. However, they do have Windows APIs for accessing it, so it's not completely hopeless. Searching the net, I found that most suggestions on getting mail and address book entries out of Outlook involved grabbing the data into something else and exporting it from there. In my case, I figured Thunderbird was the right choice, so I downloaded a copy of the latest Windows release and fired it up. Right on queue, it asked if I wanted to import the information from Outlook and I said "yes".

It took quite a bit of time to move the email, address book entries, and miscellany over to Thunderbird, but in the end, it appears to have worked like a champ.

To export the Address Book, select it and then select Export from the File menu. Tell it to export in LDIF format (a high-value format understood by both Apple's Address Book and Thunderbird) and then give it a file name. When complete, you can drag-copy this file to the Macintosh side and import it by selecting Import LDIF from the File menu. All imported data will be available in your "Last Import" folder.

Exporting email is a bit more interesting, since you don't really export it. Thunderbird stores it's mail inside of a folder named Mail, which is hidden in the Profiles folder in an obscurely named folder. Profiles lives in the Thunderbird folder of the Application Data folder, which in turn is inside of your Documents and Settings folder. You'll probably have to go to the c: drive to figure this one out, but it's not as hard as it sounds. I found it easier to zip the Mail folder rather than try to drag 400MB worth of various folders to the Mac desktop from the Windows one, but I'm not sure that's necessary.

Update: Not quite as easy as it looked. It turns out that you need to use a program such as Eudora Mailbox Cleaner (Freeware) to clean the Thunderbird mailboxes and then load them into Apple Mail. This is apparently necessary because of the use of particular windowsisms in the storage of the messages in something akin to mbox format. If you don't do this, and instead import using Import... from the File menu, then

Last, but not least, is grabbing the Calendar from Outlook. This is actually a bit harder than I would have expected, because outlook can't natively export iCal or vCal formats. Thankfully, there are good instructions and a nice utility on SourceForge for exporting this. I won't go into detail, because you can find outlook2ical at the other end of the link. The resultant .ics file can be easily imported into iCal.

Internet Explorer Shortcuts

These are particularly easy, since Microsoft has a way to export them. Just go to the File menu and select Export and then select all of your bookmarks and name the HTML file that comes out. Drag this one to your desktop and you can import it into Safari using the Import Bookmarks... command from the File menu.

Happy Switching!