Small Dog regularly provides PC to Mac data transfers, and even provides free basic data transfers when you buy a new computer. There are many tools that can be used to perform PC to Mac transfers, one of which is called Outlook2Mac. It’s developed by a company called Little Machines, and is in constant use in our repair facilities.

Late last week, a customer came in with a tired Dell running Windows XP. At check in, the sales staff completed the transfer documentation for me to work off of, and part of the work order was to transfer email from Windows Outlook to Mac Outlook, one component of the just-released Microsoft Office 2011.

I naively removed the hard drive from the PC, thinking that the .pst files from the Outlook application could be imported directly into Mac Outlook. Unfortunately, I found that while our customer was using Outlook, more specifically, it was Outlook Express. Would the new Outlook show me any love? Attempts to import the Outlook Express database were summarily rejected.

Could I attempt to upgrade the older Windows XP unit to Outlook? Unfortunately that was made impossible by a failing optical drive in the unit. What next?

I heard that Thunderbird, the Mozilla mail client (close cousin to Firefox), could be used as a conduit but had never accomplished that before. Time to experiment. I installed Thunderbird on the Dell and imported the mailboxes. I verified that the data was present and a selection of the emails were accessible. Time to pull the drive and hook it back to the Mac.

I pulled the hard drive from the Dell, installed it into a drive sled, and hooked it to the Mac. Try and try as I might, I could not find the Thunderbird Database in the Finder; searches for the database were continually rebuffed, fruitless. I again installed the drive into the Dell and opened Thunderbird; the files were still all there, so why could I not find them? I right clicked on the ‘import folder in Thunderbird and selected ‘Properties.’ The hard path to the mail box looked something like this:

C://Documents and Setting/{UserName} /Application Data/Thunderbird/Profiles/{UniqueProfileID}.default/mail/Local folder/Outlook Express/…

Knowing the path, I again removed the HD and plugged it into the Mac. When I opened up the hard drive in a Finder window, I could find Documents and Setting and the Users folder but no Application Data. Is it a hidden file?

I then opened the Terminal application on the Mac and typed the pathway in to verify that it existed. As I typed a few letters of each level of the directory and pressed the tab, I received confirmation that the file path existed. I guess I may be able to use the Terminal command cp and duplicate the necessary files to the desktop? For fear of not knowing exactly how to ensure all files copy properly with cp I instead choose to alter the Finder so that it displayed the hidden files. Would that reveal hidden files on the Windows file system? My fingers were crossed. The command in Terminal to accomplish the feat is:

defaults write com.apple.Finder AppleShowAllFiles YES

After logging out and back in, I was greeted with a .DS_store and other hidden files on the desktop of the Mac. Opening the Windows drive, previously unseen files and directories were revealed, including the pathway to the Mozilla Thunderbird database. Having already installed Thunderbird on the Mac, I dragged the local folder from the above listed pathway and replaced the the local folder on the Mac at the location:

Macintosh/HD/Users/(username)/Library/Thunderbird/Profiles/{uniqueID}.default/Mail

I restarted the Mac and opened Thunderbird and the Outlook Express mail box showed up Imported Mail in Thunderbird on the Mac. To confirm that it functioned properly, I proceeded to open a selection of messages from the various imported folders.

Next step was to get these messages into Outlook for the Mac. I opened Outlook and selected Import from the Tools. The applications that Outlook supports import from does not include Thunderbird. It was necessary to import Thunderbird Mail into the Apple Mail client first before finally importing into Outlook.

Finally, we have to alter the Finder so the hidden files are hidden once again. That Terminal command is:

defaults write com.apple.finder AppleShowAllFiles FALSE

A day after dropoff, the customer’s new Mac had all of the files and folders perfectly integrated into the iApps, and all the mail and contacts were successfully in Outlook.