Take your Windows Outlook email, contacts, and calendars to your Mac!

Has been recommended by Apple geniuses and The Wall Street Journal's Walter S. Mossberg as a fast and easy way to convert Windows Outlook information to Macintosh formats!

Features Specifications

Just $12.95

for a limited time!

About Us

Little Machines is based the Mission District of San Francisco, California.

We brought you software to help you switch from Windows to Mac, and now we're finding ways to help you connect with your friends.

We're always looking for new opportunities to serve the online and Mac communities. If you have an idea for us, please let us know!



Just fire up Little Machines O2M on your Windows PC, pick the Outlook folders you want to export, and click Start – Little Machines O2M does the rest, automatically exporting your Outlook data into portable files you can import directly into your Apple Mail, Address Book, iCal, Microsoft Entourage, or other Macintosh-compatible programs.

Easy to Use

Little Machines O2M's easy to use wizard will guide you through each step of the way.


Save hours of time and all of your Outlook email, contacts, and calendars for only $12.95!

Downloads in Seconds

Looking for a solution now? Little Machines O2M can be downloaded immediately, and its step-by-step wizard will help you through the process.

Has Configurable Options

Little Machines O2M makes it easy to take exactly what you need, and no more: Specify a Date Range of Emails or Calendar Items to Export, choose what you want to export, and save disk space by excluding large attachments.

Comes with Free Support

Little Machines is at the ready to guide you through your conversion process at no charge. Visit our Support mini-site for frequently asked questions, step-by-step guides, or contact us directly.



Runs on Windows Only. Windows Requirements:

  • Runs on Microsoft Windows 95, 98, Me, NT4, 2000, XP, Vista, 7, 8 or higher running Outlook 97, 98, 2000, 2002, 2003, 2007, 2010, or 2013. Outlook Express is not supported(2)
  • Keyboard, mouse, and 800x600 color display or better recommended
  • Hard disk with 3MB available for Little Machines O2M, plus enough drive space to store exported Outlook files
  • Web browser (optional) for reading Little Machines O2M's accompanying help files

After Little Machines O2M is run on Windows, the files can be imported into your Macintosh. Little Machines O2M can be imported into:

  • Apple Macintosh running OS X (any version, including Jaguar, Panther, Tiger, Leopard, Snow Leopard, Lion, Mountain Lion, or Mavericks)
  • Email, contact, and/or calendar software that supports the mbox, vcf (vCard), and/or ics (iCal) standards – examples include Apple Mail, Address Book, iCal, and Microsoft Entourage
  • Hard disk or other media with sufficient space to hold imported Outlook data
  • Method for transferring exported Outlook files to your Mac – a portable disk, network connection, email, etc.



  • Only U.S./English versions of Windows and Outlook are supported at this time. Little Machines does not guarantee the successful conversion of non-English characters, languages other than English and date formats outside of the United States. Double-byte characters, including Japanese and Chinese language characters are not converted at all. Please see our frequently asked questions for more information on the conversion of files containing languages other than English, date formats and instructions for handling them.
  • Outlook Express is NOT supported. Outlook Express files may be transferred into supported versions of Outlook, and then converted by Little Machines O2M.
  • Note that you must do the importing on your Apple computer yourself – Little Machines O2M will export & convert your Outlook data, but since it's a Windows program, it won't move the data into your Macintosh programs for you.
  • Little Machines O2M has been tested with Windows on Intel & AMD CPUs, plus Apple machines running Virtual PC 5.0 on top of OS X. Also: If your Windows system is equipped with security software or permission settings that prevent programs like Little Machines O2M from accessing Microsoft Outlook, you may need to alter your computer's security settings or permissions.
  • Some mbox, vCard (RFC2426), and iCal (RFC2445) features aren't supported by Outlook and Apple's Mail, Address Book, iCal programs, so transferring data between these applications sometimes requires translation from one type of data to another. If Little Machines O2M finds data in Outlook that can't be exported directly to a data type that Apple supports, it will try to convert the data to the nearest available data type that might be supported by your Macintosh.
  • An error has been reported for Microsoft Vista users that the program cannot create temporary files on the C:\ drive. This problem is often solved by right-clicking the application and running it as the administrator of the machine.

Little Machines O2M exports Outlook data from Windows PCs only.

Little Machines O2M is available for download only. No boxed version available yet.


Try it out! Download the trial version of Little Machines O2M (that goes with your version of Outlook) to get started, or buy a copy to take all of your Outlook information to your Mac now!

Little Machines O2M Version 2.0.1

Released on February 09, 2012

* Please note that Little Machines O2M runs on Windows only, and it does not convert Outlook Express or Outlook for Mac.


Buy a copy of Little Machines O2M to take all of your Outlook information to your Mac now!

Only $12.95 lets you move your PC's Outlook email, attachments, calendar appointments, and contacts to your Mac. Price includes all the features, free upgrades, and documentation. We accept secure payment by credit card through PayPal.

Please download Little Machines O2M and run it in "test drive" mode to ensure that it works with your system configuration before making your purchase.

Make sure you download the version of Little Machines O2M that works with your version of Windows Outlook. You will receive an email with your serial number to unlock the software shortly after purchase.

Step 1: download Little Machines O2M.

Little Machines O2M Version 2.0.1

Released on February 09, 2012
  • Download Little Machines O2M for Outlook 2002/2003/XP/2007/2010/2013
  • Download Little Machines O2M for Outlook 2000
  • Download Little Machines O2M for Outlook 97/98

* Please note that Little Machines O2M runs on Windows only, and it does not convert Outlook Express or Outlook running on a Mac.

Contact Us

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  • You've got nothing short of a GREAT piece of software here. I got hubby's Outlook contacts and calendar (he refers to them as His Whole Life) over to a Mac and from there smoothly to the iPhone in about 5 minutes. He's impressed. And you've made me look brilliant. I figure I'll have him moved all the way to his own Mac by year's end. What a BARGAIN!

    Thanks a MILLION!

  • It is truly annoying that Microsoft's Outlook substitute for the Mac, Entourage, has no built-in way to recognize or automatically convert Outlook files from Windows.

    Luckily, there's a third-party program that can do the conversion. It's called Little Machines O2M, from a company called Little Machines, and can be found at www.littlemachines.com. It turns your Outlook data into files that can be imported into Entourage, or into the Mac's built-in email, address book, and calendar programs.

    Walter Mossberg, The Wall Street Journal http://wsj.com →
  • "I wanted to let you know this is a great little utility. I had about 6000 e-mails, 500 addresses, and a ton of appointments....there are alternate ways to achieve the same result, but yours was the easiest and the money spent was well worth the time saved.


  • Purchased your product, although I really wasn't expecting it to work. But I figured the price wasn't too much to spend on an experiment. Your product worked without a hitch. It was fast and simple to use. Great product! It made moving my wife from Outlook to Apple mail a great success.

    T Chester
  • Great software. I've recommended it to everyone I know in IT. You guys definitely saved me from working all weekend. Thanks a million.


  • Subject: Little Machines O2M & the iPhone

    "You've got nothing short of a GREAT piece of software here. I got hubby's Outlook contacts and calendar (he refers to them as His Whole Life) over to a Mac and from there smoothly to the iPhone in about 5 minutes. He's impressed. And you've made me look brilliant. I figure I'll have him moved all the way to his own Mac by year's end. What a BARGAIN!

    Thanks a MILLION!

  • I used your tool to move the owner of our company to a Mac. I was amazed how well it worked.


  • Dear Littles--

    This is the best $10 I have EVER spent.


    Infinite thanks. You have rescued my wife (and me, by extension) from her Dell! I purchased O2M yesterday and used it to migrate all my Outlook 2003 pst files to Entourage 2004 successfully. This product really works and is very easy to use. I also commend your company for the online help knowledge base.

    Regards Desmond
  • thanks a lot for your program ,it was working perfectly. Saved me a lot of time and trouble. Great work.

    best regards

  • I wanted to let you know this is a great little utility. I had about 6000 e-mails, 500 addresses, and a ton of appointments....there are alternate ways to achieve hte same result, but yours was the easiest and the $10 spent was well worth the time saved. Thanks.

  • I just wanted to drop you a quick note to thank you for O2M. Our family is moving to Macs, but my wife really depended on Outlook. Your product has really helped to make the transition rapid and painless. Thanks again!

  • This not is simply to congratulate you on the development of a great, and simple product that works flawlessly.

    I have a Mac with XP in Parallels and had to transfer all of my Outlook addresses and emails over to the Mac side. The total file size for this was 400Mb. It worked perfectly.

    I was so impressed with it that when helping someone else last week with a similar problem, I suggested we give it a go on his system. This time 900Mb of data transfer. Again it worked perfectly.

    The small fee we both paid to acquire this program save countless hours in data transfer. We didn't have to even have to think about the process, and just let it do its job.

    Fantastic, and congratulations.

  • Downloaded and ran the app on 3 years of mail last night. Worked like a charm! Thanks again, you totally saved my ass.

  • Subject: Your Software Rocks

    Thank you! Just used it for the first time and it worked flawlessly. Keep up the great work.

  • WOW! What a great piece of software. I was able to import my 1900 names in contacts, 216 e-mails, and 3400 calender items from Outlook into my MAC in less then 30 minutes.

    Thanks for the time saver and wonderful piece of software. Subject: Great software!

  • Very well thought out and easy to use! Good job THANKS SO MUCH for you application. After screwing around for about 5 hours trying to migrate my outlook through some convoluted path I found your software and everything came through perfectly with about 2 minutes of config. Finally, I am free of MSFT!!

  • Thank you for creating such an efficient, easy to use program and at a great price. I will only use it the once, to transfer my emails from Pc to Mac - and at only $10 O2M is a bargain really for what it does. You made a stressful exchange easy - and I thank you for it! Jane Sydney, Australia Dear Little machines, My compliments with your O2M program. I transferred 1500 mails successfully. It works perfect. Thanks.

  • That was the best $10 I've ever spent!! Thanks, the process is working flawlessly at this point. I'm transferring my bosses PC Outlook data to Entourage on his new Mac and he saves EVERYTHING. Just doing a folder at time, or several at a time. Probably up to about thirty or so and there's more! The transfer works great though. Once I have them converted it's just drag and drop into Entourage. I do love my mac, now the boss will too. Thanks for the great application.

    Rick Cleveland, Ohio USA
  • Top job!!! Talk about making email migration from PC to Mac a breeze! Keep up the great work!! Thank you for a great little program! Worked a treat today.

  • Subject: Thanks for a great little app!

    I finally migrated from a WinXP laptop to a MacBook and I needed to move a ton of emails out of Office2004, many with attachments. Your app did a killer job and your directions were clear and did the job to move everything in Entourage.

    Thanks much! Well worth the $10.

    D Gorin
  • Purchased your product, although I really wasn't expecting it to work. But I figured $10 wasn't too much to spend on an experiment. Your product worked without a hitch. It was fast and simple to use. Great product! It made moving my wife from Outlook to Apple mail a great success.

    T Chester
  • This piece of software is AWESOME! Subject: Thanks!

    I had a couple of Gigs of archive mail files/folders that I need to bring over from Outlook 2007 to Entourage 2008.

    It couldn't have been easier! Best $10 I've spent! Bravo. you've done a great job. All my attachments, all my contacts, everything! Simply outstanding!

    Jack - Manager
  • I just converted about 5,000 emails, many with attachments, in 20 folders from Outlook on my PC, and they come over perfectly to Mail on my Mac! I don't know that I've ever seen software work so perfectly the way I had hoped! Thank you SO, SO much!!! This program worked GREAT! Wow - what a complete LIFESAVER!!!!!! Thank you.

  • My wife is finally leaving Windows after ten years. Her new iMac arrived on Monday and her old PC started crashing on Tuesday. I was dreading moving her email from Outlook Express to Mail but O2M made the entire process painless. It worked just as advertised and saved me hours of frustration. It's well worth the $10.

    Good luck with it.

    Gary Toronto, Canada
  • Thank you for your reply. O2M worked well: I'm very pleased by the results and I'll certainly recommend it.

    Kind regards from Belgium,

    C. Devilers
  • I purchased your program last night as I was going in circles trying to get my information from Outlook to Mac and it works flawlessly. Thanks for the great program and instructions. I will recommend you to friends.


  • Subject: You ROCK!

    Thanks! Your program was easy to use for migrating emails to MS Entourage on MACs. First to MAC mail, then entourage! Is there a way to import Calendars from outlook to Entourage. I was able to make the iCal file and bring it into iCal, but would like to use Entourage as an all purpose machine...regardless of you answer, your product made my life WAY easy when moving to MAC!


  • you have a great program , best 10 i ever spent. i am not a techie but this was a breeze.


  • Subject: Fantastic Product.

    I tried about 2 weeks to get my dad's old Outlook mail from his windows box to his new iMac. The mail was all over the place, the contacts would freeze up when being imported and the calendar program was just plain not working. After about 2 weeks of phone support with my dad, your program took care of everything in about 4 minutes.

    Thank you thank you thank you.

  • Hey, just a quick note to say I did download O2M and yesterday was able move and install all my wife's email on the Mac. I didn't have a single issue the whole time. It's so refreshing when a product works exactly as promised. Hat's off to Little Machines. Cheers. Derek. What a great peice of software! The conversion from Outlook 2007 to Entourage 2008 worked perfectly. Thanks for saving me a lot of hard work. Highly recommended.

  • just wanted to tell you that this is a great product. i just transferred all my emails, contacts, and calendar info from my pc to mac. it was SO easy and fast! thank goodness for little machines!

  • Dear Sirs,

    Thank you so much for your prompt reply and absolutely excellent software - saved my life for sure

  • Hello,

    I just wanted to let you know how much I love this program. I spent a few hours trying to unsuccessfully import contacts (before I learned of your program). Once I read about your program in "Switching to Mac", I downloaded the program and in 5 minutes I had my contacts imported!

    Thank you,

  • Hi there,

    I recently bought your o2m product and I found it very useful. I like your pricing model appealing as well, as i suspect a large proportion of your customers, like myself will be one-time only users....

    Thanks for a good product.

  • I used the software and it worked flawlessly - thanks for making me look like a superstar!

  • Thank you very much. I'm delighted to say that your product worked beautifully, and all of my personal information is now in Entourage.

  • Subject: Great software, thanks a million

    Thanks for this little wonder of a software that saved me lots of headache when I changed from Windows to Mac! It's unbelievably easy to use, even for a tech-idiot like me. Transferred my 6 years of Microsoft Outlook emails to my new Mac in just about 30 minutes!! Would have cost me over a hundred dollars to engage a pro to do exactly the same thing. Great, great great help, it's certainly a Little Machine that is SO useful. You guys are AWESOME!

  • Thanks- it was GREAT and I have all of my emails now!

  • Subject: Wow

    I just had to say thank you I have been surching for several days, and wasted so much time trying different things (even remailing 1000+ mail to my self using a macro tool). This software really is the best 10 Dollars I think I have ever spent.

    Thank you.

  • Awesome little piece of software! Being a Mac guy I was dreading having to figure out a way to transfer 7000 (yes 7000) emails, contacts, calender info from windows xp to a new mac without taking a couple of days and getting even more grey hair. I accomplished all this in less than an hour thanks to your little app. Sweet!

  • Thank you for the product , it worked well for me!

  • Subject: KUDOS!!

    Hello LittleMachines,

    I was made aware of your product 'O2M' via the Apple website. I did the Test Drive and everything seemed to work OK. I then purchased the license and that was a simple and fast process. I am now awaiting my iMac, and once I have that I will transfer my Outlook across.

    I just wanted to say that you have developed and documented a really professional looking utility (O2M) and you deserve praise for making it all so user friendly. I look forward to using it on my whole Outlook file structure.


  • Congratulation and thank you for very good peace of software. It's make my life as IT Support much easier and keeping customers happy.


    Wojtek South Australia
  • Subject: Sweet!

    You guys kick ass! The Ap worked as described and saved me a ton of time. Thanks so much!

  • Just want to say a big THANKS! for this little tool. It saved me countless hours of digging around. Wonderful tool, especially for the price.

  • You saved my day moving metadata from my Outlook 2003 (on XP Pro) to my new Macbook. It was all, or most in Swedish and all strange letters came through OK - as far I have patience to evaluate.

    I first tried to convert Outlook mail to a free version of Eudora but it couldn't handle attachments or HTML formated emails so I gave up. 10 USD was much easier to pay after that exercise though! ;-)

    Bye bye from another happy customer! Date: Mon, 29 Dec 2008 13:58:30 +0000 (UTC) Subject: Re: O2M Serial Number and Invoice

    You're product is wonderful. Saved me hours of pain and suffering. Thanks.

  • Subject: O2M Is Brilliant

    I recently made the switch to Mac (whew! it feels GOOD to stop bashing myself over the head with Windows). I struggled with the migration problem and then I happened (through days of searching the web) on your program. For $10 all my problems were solved! One quick set of questions and every contact and calendar event was converted and migrated over to my new Powerbook (and then synched with my new iPhone!) THANK YOU, THANK YOU!

  • Thank you for your prompt and comprehensive response.

    That was the best ten bucks I've spent since my last hazelnut ice- cream knickerbocker parfait!!

    Have a good week-end.

  • Thanks

    The software worked great!

  • Hi there,

    Just wanted to say thanks for such an awesome, fast and efficient tool that works perfectly. Got all my contacts, emails and calendar info on my Mac in no time. Well done!

    Kind regards

    Aafke Johannesburg, South Africa
  • After reading over your site, I decided to try it out. The program copied my different PST folders and allowed me to import them into Entourage very easily. You should put a note in your site saying that entourage users can move their PST based email folders very easily - took me less than 1/2 hour.

    Good program!

  • Hi folks,

    I just wanted to tell you my story of success with O2M: I had read so many critical comments regarding the conversion with other languages than english. I had to convert from German outlook 2000 to entourage 2008 - in German as well. It worked better than I ever would have expected. The only thing to do before converting is to change both computer from German format for figures, dates and digtes into imperial format. Then do the conversion after that change back to German format - that's it. May be, this story gives you a futher cfm for using o2m with other languages than English.

  • Subject: WOW

    Simply Amazing! Well worth the money finally get rid of Outlook! Thank you soooo much. Fantastic App! I will be recommending you to every Window user that has seen the light.

    Have a great weekend!

  • Subject: Great product!!!

    I just wanted to drop you a quick note to let you know how much I liked your O2M product. I recently switched from being a PC user (for years) to a brand new iMac. Your product transferred all of my email messages, calendar entries and contacts from Outlook 2007 to Mail, iCal, Address Book and Entourage 2008 flawlessly.

    Thank you for producing a *very* useful application that does exactly what it says it will with no surprises or glitches...and at a very affordable price, as well!

  • I hope you don't mind a little praise. For $10 your software is fantastic!!! I seemlessly moved everything from our Dell running XP to our new iMac. I had no issues at all. That was probably the best $10 I ever spent. Nice job on a great product!

    Thank you!

    Fantastic little program, well done!!!

  • Thanks for the quick response, I really appreciate and respect that so much. It worked!

    Have a good day,

  • I spent several hours looking at blogs wondering how to get my Outlook email to transfer to my Mac email program. I finally came across this product. WOW, what an easy way to do this and for only $10.

    Saved me the headache and hassle of trying a more laborious method.

    It's very easy to import into Entourage too, you just drag the files into your Inbox, Contacts and Calendar... Very impressed with these guys. I have used the software to import a huge back catalogue of e-mails from Outlook and it worked just fine. I tried some other programs and they did not (despite costing more than your program.)

    Best wishes,

  • Spent two days reading tall tales from pointed-hat mac wizards and gurus about how to transfer pst outlook files to entourage. I thought hackers died out with the 286 and picos! Guess a lot of them moved over to mac. After literally 48 frustrating hours of web drivel about this topic I was ready to return the wife's imac- a beautiful machine- and give her back her pc - when I found a small ad for your program. I downloaded the demo, ten minutes spent the $10 licence fee, and several hours later, she has every file and attachment of over 2gb of outlook email running on her imac. Without a mac hitch- the only delay was outlook itself requesting internet access every 10 minutes. GREAT GREAT GREAT - i'm a computer user going as far back as cobol and fortran- and i used to listen to the big one sing 'Bicycle built for two' (if you are that old you will know what i refer to). You guys have done a great job...

    Thanks again.

  • Subject: O2M on WPR

    Take a listen to [WISCONSIN RADIO: http://clipcast.wpr.org:8080/ramgen/wpr/mlr/mlr090803f.rm] at about the 32 minute mark... I had great results with your product and passed the word along...


  • Subject: Love you man!

    Don't do this often - send praise. But I was in a real bind - having to leave my field post but still work on my files and correspondence for a couple months - of course my office was pc (Outlook), I'm on mac. So I was pulling my hair out trying to get a zillion emails to migrate to Entourage. You saved the day! I did a little search and saw a few conversations that mentioned Outlook2mac. The best ten bucks I ever spent! Thanks a ton! Patrick (in Kyrgyzstan, Central Asia doing development work) Even was able to download over our questionable service and bandwidth!

  • Subject: Praise

    Hello from Switzerland, A Mac shop tried to transfer my outlook files without using your software and its was a disaster. Half was missing!

    As soon as I did that with your 02M product it worked perfectly, calendar and Contacts alike. Your software is GREAT !!!!! More people in Switzerland should know about it - especially the people selling Macs!!!!

  • Last night I imported the .pst files into Outlook 2007. Then today, I downloaded O2M and did a test run without buying. Worked perfect and very simple. So I bought a $10 license. I am currently in the process of converting my huge amount of Outlook email.

    I must say that I am highly impressed with this nifty little program!

    You have my gratitude for fixing a mess for me.


  • Subject: Thank you!!

    For the money, this is one of the best business applications I have ever used!!!! Saved me days of work!!!

  • Subject: Ecstatically Happy Customer

    What a f*cking awesome little program!!

    Brilliant! Fantastic! So quick and easy! You have made the transition from the hell of Microsoft to the promised land of Apple amazingly easy.

    ...Everybody needs to know about you. Best $10 I ever spent.

  • This is what we call a solution. A successful migration form Windows to Mac within a few seconds.

  • Subject: thank you

    Thanks for a great piece of software! My PC is now an official piece of landfill. I have been waiting to transfer my old emails and contacts to my Mac. Your software worked great and your on-line guides made the whole process painless. BTW, Found you by Googling my need, not the name of your company or software.

    Thank you Just wanted to thank you guys I tried three other more expensive products (Techhit, Transend and Aid4Mail) before I tried O2M, they did not work -not even a little bit. O2M was intuative and even when Outlook crashed during the export, your log files made it easy for me to grab the delta. Thanks for a great product at a great price.

  • Subject: works just great


    purchased your o2m yesterday and used it right away on a friend's laptop- very nice tool!

    kind regards,

  • Subject: Great!

    it all worked proparly and i was able (i=B4m not an expert in computer = stuff) to handle it all in 5 minutes...

    Thank you so much!!

  • Subject: Cudos

    Excellent software - ecerything transferred without a hitch - perfectly.

  • Best thing I've bought in a long while. Thanks, and I'll have others order this as well.

  • Thanks so much. I love this program

  • Hi

    Just to let you know how impressed I am with this little programme. I have spent hours trying work out how to convert my outlook 2000 files to mac and this does it in no time and with no errors. Great product!

  • thank you, this worked and have been transferring all of my contacts, calendar and email to my new iMac. great tool!

  • Great software, it is very easy to handle and I am so happy that I can "save" all my e-mails from my old laptop!

    Thank you again and kind regards

  • Hello,

    A great tool that saved me lot of time from a even greater company. These guys truly are a service oriented company.

    Thanks a lot again.

    Kind regards,

  • I downloaded the program and it worked perfectly. What a great product.

    Thanks for the responding to my question and such a great product.

  • Subject: Awesome!

    The transfer from my PC to my new 27 IM AC was a piece of cake. I'm not computer literate but Little Machines made the transfer from a 2003 Outlook to the new MAC so simple. Even a greenhorn like me made it happen. Thanks Little Machines for a simple transfer.

  • Brilliant "little" programme, very happy!

    Best regards,

  • Thank you.. The program functioned as designed.. The user guide was very helpful and concise..

  • I bought the product and it worked great. I didn't know how to get all of my old email messages from Outlook into an Mbox format and this tool did the trick. Nice product!!

  • Thank you for sending the serial number. The program worked great and I am very pleased.