Transferring all your emails, contacts, and calendar entries from PC to Mac

I’ve recently purchased a new Mac Book Pro and am totally in love with it. Installing programs is real easy, working with it is a pleasure. The one area that is giving me a headache is to transfer my most personal files to the Mac: Thousands of emails, contacts and calendar entries. On my good-old IBM T43 Laptop, I was using Outlook (2007) for all of the above, having a love-hate relationship with a piece of software that has the best feature set and, at the same time, made my laptop half as fast.

On my new Mac, I now have three different programs: Mail, Address Book and iCal. It took me several days of research to find the best ways to migrate everything over, so here’s the results:

1. E-Mails
My email provider is Gmail, so I was lucky enough to have IMAP. It basically synchs all your local mailboxes with your online “master” mailbox (in this instance, Gmail). Which means that everytime I do something in my local mail program, it is automatically reflected on my Gmail account and vice versa. Now, there’s two ways to get ALL your local mail from your PC into your Gmail account.

If you have a regular Gmail account (which means it’s not a Google Apps account), then this is the tutorial for you: http://betapundit.blogspot.com/2006/03/how-to-import-archived-outlook-email.html. If you happen to have a Google Apps account, Gmail makes it even easier, as it provides a nice little program that uploads your mail directly from Outlook into Gmail: http://code.google.com/p/google-email-uploader/. This neat tool will upload all your emails and preserve the folder structure. That being said, it took a full 2 days until all my emails (~30000 emails) were completed.

2. Contacts
For this, I’ve tried a number of different approaches, including using Gmail as the intermediary. I decided against using Gmail as it wasn’t able to import addresses correctly and often times duplicated the address entries within a contact. The absolute easiest solution was Thunderbird, Firefox’ little brother. Thunderbird is the open-source email client created by the same guys that gave us Firefox (the Mozilla Foundation). The advantage of Thunderbird over Outlook iteslf is the usage of standards instead of proprietary formats.
The steps to get your Outlook contacts show up in Address Book are the following:

  1. Download Thunderbird: http://www.mozilla.com/en-US/thunderbird/ and install
  2. Import all your contacts into Thunderbird: Find Tools -> Import. Then, select Addres Book, click Next, and select Outlook.
  3. Export to LDIF: After your import is done, select all contacts in Thunderbird and choose “Tools -> Export”. Save this file and send it to your Mac
  4. In the Mac Address Book Application, select File -> Import -> LDIF and find the file you just sent to yourself

3. Calendar
Surprisingly, this was the easiest part. Using Outlook 2007, go to your Calendar View, click on File -> Save As. In the following dialogue, click on “More Options”, and select “Whole Calendar” in Date Range and “Full Details” in Detail. Then, export that file and send it to your Mac. On your Mac, open iCal and select “File -> Import”.

A couple of notes:

Ideally, I’d like to sync as much as possible with Gmail automatically. Mac’s Address Book has an option to do that, but only if your’re an iPhone or iPod Touch user (see this article for more information: http://lifehacker.com/393810/mac-os-xs-address-book-can-now-sync-google-contacts-update-for-iphone-owners-only-ugh). That limitation doesn’t make sense to me at all.

I’m a Blackberry user, and Blackberry offers a free tool called “PocketMac” (http://na.blackberry.com/eng/services/desktop/mac.jsp). Sadly, this tool is not yet compatible with the Aluminum Mac Book Pro that was releases in October 2008. I’ll keep my fingers crossed they come up with a solution for that soon.