How To

Moving email from a PC to the Mac


For the purposes of this guide, I’m going to assume that you were using Outlook or Outlook Express on the PC, and you want to import your messages into the Mail app that ships with Mac OS X. I speak from personal experience with this guide. I had to do this when I switched from a PC to a Mac in September of ’05. I’ve finally solved the last piece of the puzzle, and I wanted to share this information with you so it won’t take you as long as it took me.

I had an email archive that spanned close to 10 years – a fairly complete one at that. I’d been keeping it in Outlook Express, then Outlook, over the years. When I switched to the Mac, I didn’t want to lose it. My wife had an archive that spanned a few years as well, and she kept it in Outlook. We didn’t want to lose those messages, either. As you know, there’s no easy way to import email directly from the PC into the Mac. There’s no nice and easy transfer wizard, for multiple reasons: different operating systems, different file systems, different ways of storing the mail, different applications, etc. Even if there had been a wizard, given my huge mail archive, I’d have probably crashed it.

What didn’t work

Still, I tried to be reasonable. I thought equivalent Microsoft products on the two platforms might be able to import from each other. So I took my PST from my PC, transferred to my Mac, and opened Entourage (the Outlook equivalent on the Mac). The import failed. The two can’t talk to each other. You can’t import between them either way. I thought that was pretty silly. Of all the things Microsoft does wrong, this has to be one of the more obvious ones.

Next I tried the less possible, which was to import from the PST file directly into Mail. That didn’t work, either. I surfed the internet for solutions, and stumbled across a possibility of installing Eudora on the PC, importing from Outlook into it, then copying the library onto the Mac, and using some special utility to do the PC to Mac translation. Well, Eudora failed on the import from Outlook. Again, I had a big PST, I wasn’t surprised. Plus, even when I tried transferring the messages it had managed to copy to the Mac, the utility didn’t do its job. At any rate, I hadn’t put my hopes in Eudora. It might have been all the rage in the early nineties, but it’s pretty useless now. Somebody else suggested using old versions of Netscape Mail. I tried that as well, only to fail again.

I called Apple Support, who were completely clueless about this. Finally, on my second try, the technician suggested I use an IMAP account to transfer the email between the two computers. I saw two problems with that, both related to the size of my archive: one, where am I going to find an IMAP account with more than 4GB of storage, and two, I’m not going to sit there and upload over 4GB of data through my DSL connection. It was going to take days, if not more. Obviously, not a very practical solution.

Updated 1/3/08: Gmail now offers more than 6 GB (and growing) of email storage, and includes both POP and IMAP access.

What worked

Just so I won’t drag this out needlessly, Thunderbird turned out to be the best solution for the transfer. I installed it on the PC, imported from Outlook into it, then transferred the mailbox files to the Mac, where I had to delete the mailbox index files (.msf) files, and only leave the un-indexed data files there. That’s because the Mac version of Thunderbird needs to build its own indexes. So, I located the directory where the email got stored for Thunderbird on my Mac, moved the mailboxes there, and deleted the index files. I then opened up Thunderbird, and after it re-built the indexes, there were my messages! After all the trouble, I was pretty happy!

Next, I wanted to get my email into Mail. This is the step that took the longest for me, and I just solved it yesterday. Granted, I hadn’t been looking very hard since last September… Now, some of you might be asking yourselves why in the world I’d want to switch from Thunderbird to Mail, and I’ve got two reasons: one, and the most important, Spotlight indexes Mail messages, so I can search for what I need from one location, and two, iPhoto sends out photos through Mail, and we email photos a lot; we wanted to have our email messages in one place. Yes, I know, we should share our photos on the web instead, etc…

So, how did I solve it? Certainly not by calling Apple Support, who are were clueless on this issue as well. And I also didn’t solve it by importing from Thunderbird into Mail, which is impossible (not any more), as you might find out if you try it. Version 2.0.7 of Mail crashes miserably, and has done so, reliably, since September of ’05, on my every attempt to import from Thunderbird. I choose Import, then I select the Other or the Netscape/Mozilla option (since Thunderbird isn’t listed as one of the options), then I browse for the location of the message databases, and when I select Import, it crashes like a drunk limousine driver.

Instead, I solved this by doing a search on the Apple Support forums, where intrepid users have posted some great solutions. Among them, I found the Eudora Mailbox Cleaner. It’s a wonderful little utility that will let you drag your Thunderbird message databases onto its icon, and will automatically convert them to Mail message databases. It will also copy them to the proper Mail message library. All you need to do is sit back and wait for it to finish, then rebuild your Mail folders, and all your messages will appear – just follow the directions you’ll find on their website. The best part is that it didn’t crash while it processed my entire archive (over 4GB of messages)! Now that’s a reliable application!

Updated 1/3/08: It turns out, as one of the commenters has pointed out, that Leopard’s version of Mail includes an import function from Thunderbird. Problem solved. Thanks Logan! Now I wonder if a new version of the Eudora Mailbox Cleaner will be released, or whether this new import feature in Mail will negate the need for it.

When I got done, I was ecstatic. All my mail is indexed with Spotlight, and I can instantly find messages and files that are years old without having to do separate searches for each!

Let’s review

  1. Install Thunderbird on PC, import from Outlook/Outlook Express into it.
  2. Install Thunderbird on Mac, note storage location for mail files.
  3. Copy message databases onto Mac, in the specific directory where mail is stored, delete index files, then start up Thunderbird and let it rebuild the indexes.
  4. Use the Eudora Mailbox Cleaner to export to Mail. (only for OS X Tiger)
  5. Rebuild mailboxes in Mail, then relax, because you’re done! (only for OS X Tiger)
  6. If you have Leopard, skip steps 4 and 5, and use Mail’s import function to get your messages out of Thunderbird. (only for OS X Leopard)

💡 Thunderbird and the Eudora Mailbox Cleaner are free software. If you find them helpful, please don’t forget to donate to them, even if it’s just a few dollars. It’s the right thing to do if you want to support the efforts of their developers. Here is a donation link for Mozilla (the maker of Thunderbird), and here is a donation link for the Eudora Mailbox Cleaner.


New Hotmail shows Microsoft still playing catchup

I’ve been a user of Hotmail for several years, probably since 1998. I can’t remember the date very well, but it’s been a long time. The point is, I had a Hotmail account long before Gmail came out. Why do I say this? Because I stuck with Hotmail through the years. That’s not to say I wasn’t fed up with the service before – I had it up to my neck with the never-ending ads that overwhelmed the page.

What the Hotmail folks did recently is to move the service to the Live platform without regard for the users. While Hotmail worked fine on different browsers before, now it just doesn’t. Unless I use IE and only IE, the site doesn’t work properly. The functionality is stunted. I can choose between two modes, Classic and Live, and no matter which one I choose, unless I use IE, it just won’t work right. Just a few examples of the shortcomings: I can’t select multiple emails to designate them as Spam, I can’t empty my Junk Mail folder with one click, the site looks weird… The Live portal seems to do okay, but not Hotmail.

And while the Microsoft folks made a big deal about doing away with one of the ads on the page inside Hotmail, I still see two, and it’s still very annoying.

What’s worse, I can’t help playing the comparison game with Gmail. I love my Gmail account. I get barely any spam, and when I do, it’s sorted nicely in my Spam folder. Once in a while, a random message makes it to my inbox, only to be dispatched to its cyberspace grave. In Hotmail, unless I set my Spam filter to exclusive, spammers make it to my Inbox most every day. And if the filter’s set to exclusive, I run the risk of having legitimate emails end up in the Junk Email folder. I have to constantly check it and be barraged with ads for erectile dysfunction or penile enlargement and other such things. And the volume of spam that makes it to my Hotmail account is… voluminous, whereas at Gmail, it’s just a few every day. Hotmail obviously doesn’t have a very good spam filtering system, no matter what Bill Gates may say.

I also can’t help looking at my Gmail account’s size limit (now over 2GB), and Hotmail is still at 250MB. Let’s not forget that before Gmail came out, Hotmail was at 2MB. Not 20MB, not even 10MB, but 2MB! Pathetic… I had to constantly delete emails from my Inbox. If I hadn’t been able to POP into my Hotmail account with Outlook Express and download my messages, I’d have had to delete years’ worth of emails. That just wasn’t right.

While I’m on the subject, let me not forget that Gmail has worked cross-browser from the start. That includes IE, Firefox, Netscape, Mozilla, Camino, Safari, and I believe Konqueror. With Hotmail, and now with Live Mail, it’s IE or you’re guaranteed a less than full functionality experience. You’d think Microsoft, with all of its talent, could come up with something better, but no, they can’t… or won’t.

So, let’s see, Vista disappointed, Hotmail disappoints… Is there any other conclusion to draw, other than Microsoft is still playing catchup?


Inbox Zero: better practices for staying (near) zero

From 43 Folders:

“This post is part of the Inbox Zero series. You’ve doubtless already discovered your inbox won’t stay at zero — and it shouldn’t. As I said yesterday, this is a process, not some miraculous one-time event like a tonsillectomy or a Jandek concert. And you can’t just wave a magic wand every couple weeks and make it all go away. Why not use the august occasion of your newly empty inbox as the chance to start mending your ways going forward?”

I can tell you from personal experience it feels pretty darn good to have an empty Inbox, but it takes constant work. It IS worth the effort though! Here is the link.

How To

Mac OS X tip of the week: sending huge attachments

From Apple Hot News: “Chances are your email server puts a limit on the size of the attachments you can send. So what do you do when you want to send an attachment that exceeds that limit? Try iChat. [Apr 19, 2006]” Here is the link.


clearTXT: text messaging for online learning systems

clearTXT is a really cool product that works in conjunction with online learning systems like Blackboard, or by itself, and allows for permission-based text messaging to those who want to get up to date information right away on their cellphones. I’ve used it in conjunction with Blackboard, and it’s a great product! The sign-up is easy: students pick their mobile provider, enter their number, choose what level of messages they want to receive (announcements, course-level alerts/news, special vendor offers/coupons) and they’re done!

For Schools: clearTXT delivers important school and class information such as announcements, schedule changes, emergency alerts, campus news, and grades directly to student and instructor cell phones and email addresses. Plus, schools can generate revenue from messages by striking ad deals with local vendors.

For Marketers: when working together with schools, can send marketing information, coupons, and discounts to college students interested in their products and services for just pennies per message.

For Government Agencies: allows people to select the types of information they want from a particular agency and have it delivered right to their mobile phones.

They’ve even got a completely free product called alphaTXT, that enables schools to deliver time-sensitive notifications, emergency alerts, and other important information directly to the mobile phones of teachers and students.

Cool stuff!