I have always been a big fan of Outlook. Why? Because I liked the idea that it was a integrated app for running all my PIM data – email, notes, calendar and contacts. Also, when I switched to another computer, it was as easy as simply moving over a single PST file and all my important information will be ready to use.

In the last year I have switched over to the world of Mac – not that I believe Windows is not worth using. I have used a Thinkpad for Windows 7 (which is a great OS), and of course a Mac for the OS X duties. Steadily over time I have switched more and more of my day to day use to the Mac, but my email archive stayed with Outlook. Why? Because the Macbook is such a great machine to carry around. Unfortunately Outlook is not available for Mac (yet).

Now some of you might tell me to stop and just use Entourage. I am sorry, but Office for Mac is one sorry excuse for an Office suite. It lacks most of the cool features of Office 2007 on PC, and to boot, Microsoft has the balls to go and ask a similar price for it. Why Microsoft would not make the functionality of a import tool from Outlook to Entourage is beyond me. Don’t worry the next version looks a lot better, for one it will have the ribbon interface. The next version of Office for Mac will also bring back Outlook to the Mac.

But enough with the rant – you want to know how to switch Outlook to Apple Mail. It is not super easy, but if you know what to use, it is quite straightforward. Most of the tips I give are based on the idea that you have a lot of email to transfer, I had a 2 gigabyte PST file with a few years of email in there.

1) Clean up your Outlook mailboxes. Why? Because the more mail you have, the longer it will take to transfer. Do you really need to keep that kitten video that is 9 megs? Also, remember to empty your recycle bin / deleted items folder.

2) In Outlook, go to File -> Data File Management. From there, go to each PST file and do the following. Click on the PST file, click settings, and then select Compact Now.

3) Next up you have to go and download Mozillla Thunderbird, and install it on your PC. Yes, I know it’s a pain, but unless you want to spend money on silly little utilities, Thunderbird is your only choice. (You might even find that you like it). I used Thunderbird version 3.

4) Once Thunderbird is installed, fire it up. At first it will ask you to define email login settings, cancel this. Go to the Tools -> and select Import. From here select what you want to transfer. For the purposes of this guide I simply used Mail. It will then ask you which client to import form, select Outlook.

5) If you have a lot of email to transfer, this might take some time. It took me about 15 minutes. Be patient.

6) Once this is complete, you need to transfer all the email over to your other machine. In Thunderbird, go to Tools -> Account Settings. Go to Local folder on the left directory, and then under Message Storage look where your “profile” is being stored. Using Explorer, go find that file. You might find that you need to switch off Hide Files and Folders to get to it. Mine was stored at: C:\Users\Minnaar Pieters\AppData\Roaming\Thunderbird\Profiles\y9e76tao.default

7) Once you find the folder (it typically has a cryptic name and ends with a “default” extension), copy it to some external storage that you can open on your mac. A network folder will do as well. (Its even easier if you are running Windows inside a VM, just share to your host Mac’s drive).

8) Once you have stored the profile folder (that one ending in “default) on your Mac somewhere, its time to fire up Mail. In Mail, go to File -> Import Mailboxes. This will bring up a box where you must select “Thunderbird”.  Click Next, and then it will ask you to feed it that “default” file you saved somewhere on your Mac. Using the finder window that pops up, go and select that folder.

9) Now the Import will start. Again, be prepared to wait a while, especially if it is a lot of email.

10) Once imported, go to the “On My Mac” folder in Mail. A import folder will appear there. Every PST file you had in Outlook will be neatly put there. Once you branch down you will see that Mail thinks you have a lot of unread Mail. Simply right click on each folder and select Mark All Messages as Read. This might take a while to process as well, so be patient. I would recommend you close and reopen Mail every now and then during this step, because it can slow down your machine tremendously (even on my new Macbook Pro).

And there you have it. Now you can enjoy all your heaps of emails on your Mac. If you want to import your email on Entourage, it is quite easy from here as well. Here are the steps:

If you are really someone who enjoys Entourage, go ahead and use it. If however, you have issues with it, you might be happy to know that Snow Leopard has Exchange support built in. So if you have been using Entourage only for the Exchange support, you might want to try to use the built in tools in Mail.

Happy emailing.

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I am a R&D Analyst in Stellenbosch South Africa who has a immense passion for all things tech related. I embrace technology, open source and web standards, and I participate and contribute to the social web.