Outlook PST files and Mac - conversion time

When I first got my Mac I also made a fundamental shift in the way I manage my e-mail; I switched from Outlook to Gmail. Since I made that switch I've been quite happy; not only does Gmail give me IMAP access so I can get to it from within Mac's Mail, I can also get to it from my little Motorola phone and from any web browser on a public terminal. Sure, Gmail's IMAP implementation leaves much to be desired but the tagging model is really great.

Prior to switching to Gmail I used Outlook for many, many years. I went from version to version, carrying my PST file with me all along the way. Since the newer versions of Outlook didn't have a problem with PST files larger than 2GB I didn't even bother to archive my e-mails. I liked that I could search through my entire e-mail history, dating back to 1996, at any time.

Enter the Problem
So what I've been ignoring for a few months now hit me again yesterday when I had to fire up my Windows XP machine to search for an old e-mail that contained an account number I needed. What I really needed to do was get that 4.1GB PST file into a format that my Mac could read easily.

I did a lot of research and finally found a solution: O2M from Little Machines. This is a little Windows application that sells for $10; it will convert your Outlook  E-mail into MBOX files, which are simply UUEncoded text files that can easily be read by Mac's Mail program. It will also produce vCard (vcf) files for your contacts and iCal (ics) files for your calendar events.

O2M is easily worth the $10, even though for me it's a one shot deal and then I'm done with it. This program is really, really quirky though. It's likely using Microsoft's MAPI interface to scan through the contents of Outlook, which means that if you have an archived PST file you will need to open it in Outlook before it can be exported.

Keep in mind this is a Windows application, not a Mac application, so have a PC (or Windows VM) with Outlook installed and running in order to perform this conversion.

Warning! UI Hazard Ahead!
If you care at all about well designed user interfaces you will need to wear some protective gear when you fire up this application. The UI looks like something that a Visual Basic newbie put together in 1992 without the aid of any standard UI components or even a fully functioning monitor. Don't believe me?

See the control alignment? The completely random whitespace? See those little, itty-bitty checkboxes? You get to manually select every single one of them. Got lots of folders like I do? Enjoy. Fortunately I was able to select the first one and then stand on the Space bar while it cycled through all of the folders.

In spite of the UI it does indeed work, plowing through my gigantic PST file and dutifully popping out scores of MBOX files that can be consumed by Mail or even simply searched in their native form if need be.

It can take a very long time to run, especially if your PST file is very large like mine.  It's something that needs to be casually monitored too because every once in a while it would come across some e-mail and generate an error message about a bad date format and ask whether it should fix the error (Uh, yeah!) or ignore it, or warn me about exporting a digitally signed e-mail.

I ran this on my Windows XP machine with 2GB of RAM and an Intel QX6700 quad core processor. With nothing but Outlook 2007 running it took nearly 4 hours to process my e-mail, extracting 77K messages in 495 folders (now Mailboxes) and 172 Contacts.

Once you're done with the conversion you can select an entire set of folders under the File / Import Mailboxes feature in Mail. It will also take a little while to suck them in, though not nearly as long as it takes to export them from Outlook.

I decided not to import all of my mail though, realizing that large swaths of my messages were really pointless to keep around (most of the old ListServe messages I had are searchable in Google Groups anyway). I now have one less piece of Windows software to depend on.

Yes, I knocked O2M hard on the UI front but it did work fine for me and was well worth the $10 I paid for it. I just wish the Little Machines folks would update the UI on it.


Dean said…
I didn't have quite as much email in my PST file (including archives) as you, so I took a different approach. I just created an IMAP account to GMail in Outlook and moved all my messages from my PSTs to GMail IMAP folders.

I use Mail.app on my Mac, so I can access the Outlook-Gmail messages and copy them to local Mail.app folders if I want.

It's free, but if I had GBs of email locked away in PSTs I might also be tempted to spring for 10 bucks on a program that does it for me.
Wes Hsu said…
I don't use GMail, as I have my own email server, but I did want to convert my 4-5GB of Outlook PSTs (I had one for each year) into Mail.app.

I ended up using a program called Emailchemy (http://www.weirdkid.com/products/emailchemy/index.html)

It's about $30, but it's a cross platform tool that converts from a ton of file formats to RFC-2822. You can then use your target email client to import the data. Or, and this is the cool part, you can run its built-in IMAP server against the exported data, and then point your target email client to it and then move the data into your email client.

While this was a one shot deal for me this time (Outlook to Mail.app), theoretically, I should be able to use this the next time I switch email clients.

While I keep some stuff available through IMAP, most of my data is stored locally simply because of the shear volume of data.
Web-JIVE said…
I used a program which worked wonders and was worth what I paid as well. EmailAlchemy.


Another one to add to the arsenal. It will aid in switching amongst Mac mail clients as well if you ever get fed up with Apple Mail.

David Alison said…
@Wes & Eric: Thanks for the tip guys - that looks like a much better solution, though it is 3x the price for what most people will use once I imagine. IT folks that do this all the time would likely be much better off with Emailchemy. I do like the fact that you can use a native Mac application that just opens and works with the PST file directly.

And that IMAP support is pretty damn cool.
Logan Browne said…
I'd suggest using Mozilla Thunderbird on Windows to do the conversion. It creates MBOX files, and it's free. I've used it to migrate 5 GB of PST files to mail.app for my wife and myself.
Charles said…
Emailchemy again. If you have to pull mail from an Exchange server then Apple Mail often won't work for you. In that case you need to use Entourage or a VM and the real Outlook to pull mail. Emailchemy can be run over and over to keep pulling that mail into Apple Mail.
Phillip said…
Dave I recently used O2M and agree the interface is neolithic but it worked fine with one Outlook PST of over 15.5GB with thousands of attachments. The tip I have is that it seems to work better in Apple Mail if you run the exports through Entourage first and clean up the database first before importing into Apple Mail. Major difference in performance.

Mac IT guy
bdavidson said…
I did the same thing Dean outlined... hooked outlook up to Gmail via IMAP and moved all my messages from the local pst fodlers to Gmail folders.
PetieG said…
O2M is a great little product... but I seem to have problems importing the MBOX files it creates that are over ~900MB -- Mail.app crashes...
David Alison said…
@Petieg: O2M does have the ability to select a data range. If the file is too large you may want to try breaking it up into smaller chunks.

you could've done it for free, and pretty easy too ;)

Install Thunderbird on your pc. Have it import your mail from Outlook.

Install Thunderbird on your Mac.

Transfer the Thundebird mail folders to your mac.

Have Mail.app import from Thunderbird.

That's the way I did it, that's the way dad did it, and that's how Denmark does it !

(Sorry, couldn't help myself, I just love the new Ironman movie ;) ).

Anyway, it's how I did it, and it doesn't take that long, plus it's free. Works too.
Ian Thomas said…
sounds like you need a better GTD process - why carry 10 years of communication around your neck?
David Alison said…
@Ian: I don't actually carry it around. As a matter of fact, my inbox rarely has more than 5 or so e-mails parked in it for very long. I like the historical aspect of it, that's all. Sometimes it's nice to find that long forgotten account number from an e-mail from several years ago.
Allan said…
Here's a free solution that worked for me:

1) Install libpst


2) Use the readpst utility installed in step 1) above to convert pst files to Unix mbox format


3) Import into Apple Mail or Mozilla Thunderbird.

It's not 100% perfect (attachments may not be converted properly), but I'm happy if I can get the body text and the names of the senders and recipients.
Anonymous said…
Hi David,

I had as well as PetieG, problems with the mbox files - after using O2M all the Subfolder where shown with the ending .mbox in Apple Mail and only after renaming all Subfolder by deleting the .mbox ending Apple was able to read the content inside the Subfolders.

With more than 1500 Subfolders and not so Computer literate it took me a weekend to do the job manually.

I wasn't happy and still look for another solution to do the conversion with my other archive files yet.
David Alison said…
@HotelNighty: I don't believe the RFC-2822 (MBOX) supports a folder model so if you have lots of sub folders in a PST file you will end up being stuck with lots of MBOX folders files as well.

You may want to consider Emailchemy instead of O2M - based on what people have said in the comments it may be a better solution.
Kim said…
Hi David,
Does the O2M also convert Calendar and Contacts etc from Win Outlook or is it only mail?
I'm looking for a solution to convert the entire lot not just the email...
David Alison said…
@Kim: It does mail, vCard (vcf) files for your contacts and iCal (ics) files for your calendar events.
Derek said…
My problem is my PC has died. I have back-up Outlook.PST and Archive.PST files on my external drive, question is how do I convert them to MBOX without the PC? Very frustrating as I was hoping to move to a Mac but this issue may force me to stay in the PC camp. Damn! Comments please.
David Alison said…
@Derek: You should check out Emailchemy.
Alex said…
I heard about not bad application, Pst fix, it may recover after data file may be damaged by an unexpected power failure, a hardware or network crash and a number of other external factors, program will help you recover your information from a crashed Outlook installation, fix pst file and carry on with your tasks as before – all that done in mere seconds.
Anonymous said…
EmailChemy works on a Mac without needing a pc and outlook installed to convert the PST files you have backed up. I just tested it and I am so glad to see I don't need to use a pc and outlook installed to make it convert. YESSSSSS!


Anonymous said…
I, too, was hoping to switch to a Mac and was concerned about losing my *.pst files. From this discussion it appears that emailchemy is the way to go. the real reason I want to save the .pst files is to preserve the attachments. Can anyone confirm that the attachments will be more-or-less unaffected?
kvf said…
No. You have to pay for that Emailchemy or what ever that thing is called. Using the free software from Mozilla or that "http://alioth.debian.org/projects/libpst/" is the way to go. THEY ARE FREE! and THEY WORK BETTER! I have explored all the options listed in this forum, and the thunderbird route is def the way to go! simple, easy and reletively fast (depending on the size of said pst file). just do it already!
Alex said…
Know good similar tool which recover data-pst recovery programs,as far as I know is free,it can process PST and OST files and extract all critical data, no need to wait, it is very fast,supports all Microsoft Windows operating systems, starting from Windows 98 to Windows Vista,working with Outlook pst data recovery software and .pst recovery program,will recreate folder structure and all messages, which are found in your mailbox,preview the results and make sure, that all emails are successfully repaired.
Hendrikd said…
I tried O2M and MessageSave without success. EmailChemy works many times better (and keeps the folder structure intact)

Cheers, H.
Maglor said…
Hi, that's all very nice indeed, but what if all I really want is my notes and contacts and calendar from the PST file? How can I convert that to entourage?
Mike said…
Thank you David, I am a Microsoft Outlook user. Few days ago, I got an error in outlook. I was unable to open outlook. I tried Inbox repair tool to fix outlook file, but it could not help me. After that I contacted with Repair Outlook PST file. They are Outlook pst expert, they repaired my pst file.
Anonymous said…
I did want to convert my 7 GB PST to mbox format, so try with multiple utility but not able to do successfully,at last one of my friend suggest me to try PST Converter Pro and i try that with demo version it will convert all without any error,i use this utility it is really useful and you cant compare with all existing email conversion utility,its really too much high in rank and cost wise only $10,thanks to PST COnverter Pro team to create such a great tool.

Keep it up guys.....
Anonymous said…
I had some big pst files, and I used PstExporter from www.arrowbit.com. It is an all Mac application so It does not need access to Windows nor Outlook. Check their quick video tutorials to see how it works.
Anonymous said…
Mark says: I love the site byline that says we are entitled to your opinion!
Nick said…
I used PST Converter Pro for outlook to mac conversion, It worked nicely.
Aaron Bentley said…
There is lot of recovery software with different characteristics and specifications. Diskdoctors is one of them, provide a wide range of recovery,pst file size limit and other type of software.

J. Kenneth Leap said…
I started with a web search: "How can I retain my folder structure when I migrate my email from Outlook to Mail?" I purchased O2M after looking at all of the other options. My emails migrated alright but my file structure of a nested tree of folders was replaced with one folder, "imported", and 500 individual folders inside of that with the individual emails intact inside of them. Rebuilding the file tree involves renaming all of these folders individually and re-nesting them again to recreate the folder hierarchy. I'm only a 1/4 of the way through now so I have come to vent! What a pain in the butt.
I couldn't find any other resource that would tell me if it was even possible to maintain the folder structure aside from purchasing Outlook for MAC which inconveniently now is ONLY available in the Office Professional bundle. Currently $250 and what's the point since I'm moving to MAC I don't want to repurchase all of my old Microsoft programs again. That's how they get you. I would love it if someone could point me to a good article on managing and archiving emails for a one-man business. I have 7 years of emails that I would like to keep searchable because you never know when you have to look up an old supplier or remind yourself what you last said to a client.
David Alison said…
@Ken: I'm a big folder user as well (in my case it's actually Gmail labels that are mapped via IMAP to the native Mail application on my Macs). The search capability of Mail is actually decent; since these are all older emails, maybe letting them all sit in that imported folder structure is OK and you can just use a search to find them?
Stiven Mendoza said…
Here is the complete solution available for all PST file corruption issues which can easily repair Outlook PST file and resolve all corruption issues without any data modification. This PST Recovery software application is a secure and user-friendly tool that performs Outlook recovery in all instances of PST file corruption. The tool also saves recovered data into Outlook PST and other files like MSG, DBX and MBOX format.
Learn more details, here:- https://goo.gl/1VcvS4
Jennifer Martin said…
I do believe that OST to PST Converter software allows migration of corrupted OST files to PST so that various folders like inbox, drafts can be retrievable.

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