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January 22, 2009 6:00 AM PST

PC Migration to Mac: Converting Outlook to Mac OS X Mail

by CNET staff

Many PC users migrating to Mac OS X store their emails and other personal organization data (calendars, contacts) in Microsoft Outlook. Although setting up new email accounts is relatively simple, it can be frustrating to migrate previously downloaded emails, contacts, and calendars.

Apple Discussions poster hans.kamp writes:

"I purchased my iMac several months ago after years of Windows experience...How can I move my e-mail history from Outlook 2007 into Mail. I checked the import options in Mail, but have not found a solution."

Apple advertises the Mac as a platform that is easy to migrate to. However, Outlook and some other windows applications are so restricted in their support for universal filetypes that it makes migration rather difficult, especially for downloaded data such as emails that might not be on servers anymore. Fortunately, there are several ways of quickly maintaining workflow on the Mac while users migrate from their PCs.

Microsoft-Based solutions Since modern Macs are built with Windows-compatible hardware, users have the option of installing the programs they use on the PC in the Mac. Apple provides a way to run windows natively using "Boot Camp", but this requires users to restart and not be able to access their Mac files while in Windows. To overcome this, for most office applications users can install a copy of windows to a virtual machine and access it using VMWare Fusion (http://www.vmware.com/products/fusion/) or Parallels Desktop (http://www.parallels.com/). These programs will allow users to run windows and the desired applications nearly seamlessly next to Mac applications in OS X. As such, users can migrate their outlook data to a virtual machine and be able to run it as-is, at least as a temporary solution to stay up and running on their new machines while deciding how to best migrate their data over to native OS X application.

An alternative to virtualization solutions (which require the installation and booting of Windows in the background) is a program called "Crossover", which provides all the resources needed for certain windows applications to run, without actually installing windows itself. Microsoft Outlook is supported in this environment, and can be installed directly into OS X and import the data from Windows machines.

Converting and importing data to Mac OS X Unfortunately, Microsoft Outlook does not support exporting data from Outlook into formats that are easily or properly readable by other email clients. Even Microsoft's Mac mail client "Entourage" does not support importing data directly from Outlook, and as such is not that great of an intermediate step in migrating from Windows to the Mac. Users can do this using Microsoft's products, but it takes a convoluted steps that include installing older versions of Office which users may not have.

While the Microsoft-based solutions using virtualization or crossover will work temporarily for users, a more direct solution is to use the program Outlook 2 Mac which does a good job in converting the Microsoft .pst files used in Outlook to formats that can be installed in Mail, Address Book, and iCal. The program does cost $10, but has positive reviews from users switching from Windows.

Resources

  • hans.kamp
  • "Crossover"
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    Add a Comment (Log in or register) (16 Comments)
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    by lesik--2008 January 22, 2009 7:08 AM PST
    You can use Kerio MailServer for migration of your mail. You should download and install fully functional 30-days trial version for mac or windows, setup an IMAP-account on both mac and windows application and transfer email through IMAP folders. No payment, any email application supports IMAP.
    Reply to this comment
    by info-FFTir January 22, 2009 7:55 AM PST
    For me, I use Thunderbird to import data from outlook on the windows.
    Then, transfering the thunderbird data to the Mac and import it in Mail...



    ---
    Jayce Piel
    http://www.mosx.org/
    Reply to this comment
    by fmarder January 22, 2009 8:34 AM PST
    Another option is Emailchemy which is a Mac program. It will read a .pst and convert it to a Mail importable format. Program is well supported and has been around for quite some time.
    Reply to this comment
    by SkP Helicopters January 22, 2009 8:34 AM PST
    <class="merchant"><span>&#62;</span><div class="datestamp"><i>This is a reply to a previous comment by fmarder</i></div></class><br />
    Emailchemy is perfect.

    No need to keep a PC around, it translates very well the .pst files into .eml format

    I recommend.
    Reply to this comment
    by rclbiz January 22, 2009 10:19 AM PST
    My companion just purchased a MacBook Pro to replace his Dell. We used Little Machines (http://www.littlemachines.com/). It converted all his Outlook data (Calendar, Contacts and Mail) which we imported into OS X. It was easy and flawless. No problems.
    Reply to this comment
    by ready_dotmac January 22, 2009 10:19 AM PST
    <class="merchant"><span>&#62;</span><div class="datestamp"><i>This is a reply to a previous comment by rclbiz</i></div></class><br />
    I have migrated Outlook users to Apple Mail using an Windows application called O2M from www.littlemachines.com. It converts the mail to .mbox type which can then be imported into Apple Mail. I drag and drop the .mbox file into a custom folder I create in Apple Mail and depending on the size of the import the mail shows up after a few minutes.
    Reply to this comment
    by prairiewalker January 22, 2009 10:19 AM PST
    <class="merchant"><span>&#62;&#62;</span><div class="datestamp"><i>This is a reply to a previous comment by ready_dotmac</i></div></class><br />
    I also have used O2M from LittleMachines to migrate Outlook .pst data from Windows systems to Mac Mail and to Entourage 2008 successfully. A great product at a great price.
    Reply to this comment
    by tkessler January 22, 2009 10:19 AM PST
    <class="merchant"><span>&#62;&#62;&#62;</span><div class="datestamp"><i>This is a reply to a previous comment by prairiewalker</i></div></class><br />
    "O2M" is "Outlook 2 Mac", which is referred to in the article...
    Reply to this comment
    by gpell January 22, 2009 10:19 AM PST
    <class="merchant"><span>&#62;&#62;</span><div class="datestamp"><i>This is a reply to a previous comment by ready_dotmac</i></div></class><br />
    I have also used O2M to convert Outlook mail to mbox format. There were some problems, watch carefully what it's doing and don't try converting too many folders at once.

    Also be aware that there is a bug in Apple Mail when importing mail from mbox files. If the text in any one of the messages within a folder in the import happens to have a line that starts with "from " then the import folder will be empty. Watch out for that.
    Reply to this comment
    by silverst January 22, 2009 1:10 PM PST
    See this article:
    http://www.macosxhints.com/article.php?story=20040325164915651
    Reply to this comment
    by MacTech_MT January 22, 2009 1:23 PM PST
    I heartily recommend the affordable program "emailchemy" ( www.weirdkid.com/products/emailchemy/index.html ). It can translate among multiple email formats, and is the only Mac program I've found that can RELIABLY deal with the .pst format used by Outlook. I've tried every free and shareware alternative out there over the years, and this is by far the best.
    Reply to this comment
    by jonparshall January 22, 2009 3:15 PM PST
    Thanks for the mention of CrossOver--we appreciate it. I have about a zillion years of email bundled up on .pst files, so I know the pain there. Fortunately, Outlook *does* run under our mojo, so I've managed not to have to ween myself off those .pst files yet.

    Cheers,

    -jon parshall-
    COO
    www.codeweavers.com
    Reply to this comment
    by Matthew Rosen January 22, 2009 11:30 PM PST
    For transferring mail, use an IMAP account as a "conduit."

    Add the account details to Outlook on the PC. (If you don't have one, sign up for a GMail account. They should grant you enough space to do the tranistion).

    Sync/drag the contents of the respective Outlook mailboxes, i.e. In, Sent, to the IMAP folders.

    Wait.

    When completed, add the same IMAP account details to the Mac e-mail client and sync. Wait some more.

    For contacts, I believe Outlook can export to plain text, csv, tab-delimited, v-card, etc. formatted files that can be imported into Address Book.

    I've never done a calendar swap.

    Can mass .ics files be exported a la V-cards for contacts?
    Reply to this comment
    by Mike - macguy January 23, 2009 7:06 AM PST
    Got a slight variation to this dilemma. Have a few users sticking with G5 Macs so Outlook 2001 will still run. Why you ask.... They, instead of using the Personal Folder inside Outlook, dragged individual emails to the Mac desktop, folders, servers, etc. For 5 years. I have these files burned on CDs and filed all over the place on the server.

    That is fine if you still have Classic and Outlook. Just double click this file and it opens up in Outlook looking just it did when it was in Outlook.

    The problem: Intel Macs do not run Classic, hence they do not run Outlook 2001. These files are unopenable. So glad MS owns Entourage, it won't even open or import these files. If you get info on them, the Kind is listed as "MSMLServer Document".

    I can open them in Word, but them they are 30 pages of formatting junk with the actual info buried in there. Not user friendly. I am currently in the process to see if a text cleaner app can open and clean these up.

    I will look at the apps mentioned on this post to see what they can do.
    Please let me know if anyone has had experience with this.

    Thanks,

    Mike
    Reply to this comment
    by fmarder January 23, 2009 7:06 AM PST
    <class="merchant"><span>&#62;</span><div class="datestamp"><i>This is a reply to a previous comment by Mike - macguy</i></div></class><br />
    I believe Microsoft has a migration tool to go from Outlook 2001 to Entourage.
    Reply to this comment
    by July 17, 2009 3:08 PM PDT
    First, I tried using Thunderbird on my PC to convert my Outlook 2007 mail, based on another post I found by Anuj Gakhar on his blog. I've kept over 10 years' worth of emails in PST files and wanted to do the migration for free. While Thunderbird did convert all the PST files to mbox format, I checked one of the imported folders in Thunderbird and it had embedded HTML in many of the emails, so that was not going to work for me.

    I used a trail version of O2M to do the same thing for the same PST file, and copied the resulting mbox file over to my MacBook and opened it up in Mac Mail. No embedded HTML, everything looked good. So I purchased the software and began the long process of converting all my Outlook folders over. It loads Outlook 2007 in the process and as it converts messages, Outlook eats more and more memory (my PC has Vista Business BTW) and several times, it froze after hitting a memory usage amount of 250MB or so. Also, I forgot to instruct O2M to keep attachments like .exe, .msg, .zip, etc. So I had to start over a few times.

    I found what worked great was to boot up in Safe Mode and launch O2M that way, and convert 10-15 folders from Outlook at a time rather than 5-6 like before. It was quite fast even while preserving the attachments! Once I had all of the mbox files done, I linked to the share drive on the PC from my MacBook using Finder and used Mac Mail to import each mbox file. I was pretty satisfied with the results and consider the money well spent. Now I have all those emails organized the way I want them in Mac Mail.
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