Can I get messages off Outlook on my old PC to my shiny new Macbook? There's a catch.

May 4, 2008 6:16 PM

Can I get messages off Outlook on my old PC to my shiny new Macbook? There's a catch.

I save all my work emails because I have a boss who likes to ask the same questions frequently. I use my work webmail to on a day-to-day basis, but the stupid thing deletes old messages after 3 months. I've dealt with this over the past years by just checking my mail with Outlook Express on my personal laptop every once in awhile - it downloads everything onto my computer so I can keep it there and reference it after it's deleted in webmail. I just got a brand new Macbook, and would like to transfer the old messages from Outlook to Mail so I can do the same thing there. Is this even possible? The messages are no longer on the server - they exist only in Outlook. Yikes.

posted by lxs to computers & internet (11 answers total)

Yeah, you can definitely do it, but it'll be a little irritating.

I assume you're going to use Mail.app on your Macbook. Mail can import a lot of different mailbox types, but Outlook (and Outlook Express) isn't on the list.

However, Thunderbird is!

And Thunderbird *can* import Outlook (and Outlook Express) messages. So, what I would do is download Thunderbird on my old PC, import the mailbox files from Outlook, then export them from Thunderbird.

*Then* transfer them over to your Macbook, install Thunderbird, and import them. Then import them from Thunderbird into Mail.

There may be other solutions, but off the top of my head that's the dirty way I would go about it. Ugh.
posted by kbanas at 6:34 PM on May 4, 2008

You want to export everything on the PC laptop to a Personal Folders (.pst) archive. Transfer this archive from your laptop to the Macbook through your favorite mechanism, FTP, local share, thumb drive, whatever. You should be able to open the .pst format from the Mac without too much difficulty.
posted by spatula at 6:39 PM on May 4, 2008

If I understand your setup correctly, you've got a "local" copy of all the emails in Outlook Express on your laptop. If that's correct, then YES you can transfer them from Outlook Express to Mail.app on your new Macbook. It doesn't matter that the messages are not on the server. In fact, it probably makes it somewhat easier.

The most painless way to do this is to have Apple do it for you when you get your new Macbook. If you live near an Apple retail store, take your old (Windows) laptop in when you pickup your new Macbook and they'll do the transfer directly for you. After all, part of that premium Apple price that you're paying is for this sort of "switcher" service. Take advantage of it. I've done this three times with Apple and new converts in my family. It takes about a 1/2 hour or so and I recommend doing it on a workday morning when the store's not terribly busy. Don't even think about it on a weekend.

If you don't live near an Apple store or you're buying online, google something like "import outlook express to mail.app" and you'll find what you need. I'm not going to post a link because your setup can vary on the Outlook Express side, so find something that meets your specific needs.
posted by webhund at 6:43 PM on May 4, 2008

There is an application called o2m or Outlook to Mac that does this.
posted by Gungho at 7:27 PM on May 4, 2008

You do need to be aware that Outlook Express is not Outlook. The two programs are completely different, and use completely different storage formats. If you find yourself looking at any solution involving a .pst file, that's an Outlook solution, and it won't work for Outlook Express. Outlook Express doesn't make .pst files. Make sure whatever you end up using knows that your stuff is coming from Outlook Express.
posted by flabdablet at 9:05 PM on May 4, 2008

It's been awhile since I looked at this issue, but as flabdablet says, Outlook isn't the same as Outlook Express in terms of the format the mail is saved in. And the bad thing about Outlook (as opposed to OE) is that the .pst format which Outlook uses is (last I checked) an undocumented format of Microsoft's. Some people have reverse engineered it, but there's no guarantee that Microsoft won't change something. This matters because Microsoft gives developers access to the Outlook mail via an application programming interface, and because the actual file format is undocumented, that's what application developers (utility developers who make tools for applications like Outlook to back-up mail, convert it to other formats, etc.) use and they do not go to the .pst container file directly. And that matters to you as an end use who wants to use such a tool because using the API means that you have to have Outlook installed and running.

That said, I use an excellent tool called Aid4Mail from Fookes Software (who also makes my favorite notepad replacement, Notetab Pro) which will back-up and cross-convert email to and from Outlook in a variety of formats, including the plain ole UNIX mailbox format or just as individual text files.
posted by Dances with Werewolves at 4:22 AM on May 5, 2008

I have had success transferring mail from Outlook to Mail.app using Thunderbird as the intermediary. That should work with Outlook Express, too. It is mildly annoying, but it does work.

Import from Outlook Express into Thunderbird

Mac OS X Mail: How to import email
posted by andrewraff at 8:24 AM on May 5, 2008

I moved my old Outlook files over to my new MBP only a month ago. So, right off the bat I can say with a high degree of confidence that Mail cannot import .pst files.

I like cheap, and like free even better. Therefore, as a longtime Firefox user I went down the Thunderbird route suggested above. It did transfer some of my files — hell, most of my files — but not all of them. Don't know why not. But I tried it multiple times, tweaking my mailbox settings in Outlook each time, but never got it to work properly.

Eventually resorted to buying a copy of Little Machines' O2M (mentioned above) for ~USD$10. It seemed to work just fine, and I was happy that I could get on with coming to grips with my new Mac.

However I was checking through my archives just the other day and realised three months of my girlfriend's emails didn't make the cut. So far I haven't noticed anything else missing, but I haven't been game to really hunt around: I've pretty much exhausted all the methods I could uncover (although I never took my computer in to pay Apple to do it).

Couple of other points —
* For all the 'it just works' talk, I was surprised that Apple haven't created a little application to transfer files across from the most common PC email program. Switching isn't as easy as Apple might have you believe.
* For all the good things that OSX can do, there are still a few things I took for granted in Outlook 2003 that Apple's Mail simply can't do in 2008.
* If you're a big user of To Do lists be aware that Mail seems to have a bug that makes editing alarm times an exercise in frustration.
posted by puffmoike at 8:24 AM on May 5, 2008

Note that puffmoike doesn't make this clear, but the O2M product he mentions, just like every other that I'm aware of, doesn't access the .pst file directly, but runs on your Windows machine, using a functioning installation of Outlook, where your mail resides to export your mail so it's available for importing into another program.

If you want to just be able to copy over your .pst file and have some program get to the mail, it's not going to happen. Any of these programs that do what's been described, including Thunderbird or whatever, access a running Outlook on the same machine to get the mail from it using its API. It's been a few years since I looked into this extensively, because I so badly wanted to get into the .pst directly that I was willing to write my own utility to do so if I could only find information about the file format—but, as I wrote, information on it is scarce because MS has never documented it and doesn't plan to. It's in a special container file format they've developed for Office over the years, but the details of the implementation of Outlook's files in that container format are subject to revision every time MS updates Outlook. That's why no one will risk trying to reverse engineer the .pst file and sell a utility that accesses it directly. MS could break it at any time. Much better, from a developer's point of view, to just use the API to Outlook. The down side is that anyone who needs to get to the contents of the .pst file directly—like someone in the future who has intact .pst files, can read them, but can't install a version of Office—is screwed.

Which underlines the importance of backing-up your Outlook mail into some other format regularly.

Note that all this doesn't apply to Outlook Express as, I'm pretty sure, its .eml format is documented and stable and there are utilities that will work with those files directly. Outlook Express and Office Outlook are, now, two (almost) completely independent products.
posted by Dances with Werewolves at 7:18 PM on May 5, 2008

The .eml format is just the plain text of the mail including all headers, so yes, that's stable and documented. Unfortunately, Outlook Express does not store mails in this format, which is only used for mails you Save As. Internally, OE uses another proprietary Microsoft format called .dbx.

When you use Thunderbird on your Windows box to import Outlook Express mails, Thunderbird does not need to fire up Outlook Express to do the import. This is different from its behavior with Outlook imports. Instead, it processes the .dbx files directly. Unfortunately, Thunderbird provides no way to browse for a .dbx file to process - it assumes that the file you want is in the standard location for OE .dbx files, which is fairly well hidden: "%userprofile%\Local Settings\Application Data\Identities\{guid-hex-characters-and-dashes}\Microsoft\Outlook Express". Note that the Local Settings folder, and the Application Data folder within it, are both hidden by default. If you have multiple Outlook Express identities, giving rise to multiple {guid-hex-characters-and-dashes} entries under ...\Identities, I'm not sure what Thunderbird does.

Once Thunderbird has imported your mails, they will be stored in (loosely standard) mbox format, one file per mail folder,
under "%userprofile%\Application Data\Thunderbird\Profiles\gibberish.default\Mail". You should be able to use those files with these instructions to get your mails into Mail.app without needing install Thunderbird on the Mac.

The Official Apple Way appears to be to use an online IMAP server as an intermediary, rather than fooling about with local file format converters. If I were going to go that way, I'd use a Gmail account rather than a .Mac account to do the IMAP serving. Here are setup guides for IMAP on Gmail for Outlook Express and Apple Mail.
posted by flabdablet at 8:01 PM on May 5, 2008

I'm a recent convert too. I had backlogs of e-mails dating back to 2001, most of which are no longer relevant today but I keep them anyway for historical purposes. If you still refer to your past e-mails regularly, try exporting to/importing from Thunderbird (I haven't but I frantically Googled too and it appeared to be the best solution.) On the other hand, if you're only keeping them around just in case, consider just exporting to an HTML archive, which is guaranteed to be viewable for decades to come.
posted by semi at 6:02 AM on May 7, 2008