How To

Moving email from a PC to the Mac

Background

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.

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Reviews

Google just made AJAX development easier

Google Web ToolkitGoogle released what looks to be a very useful piece of software around noon today: the Google Web Toolkit. Bret Taylor broke the news on the Google Blog. As those of us who work in web development know, AJAX is a pain to code and deploy. With the Google Web Toolkit, you can write the code in Java, then convert it to browser-compliant JavaScript and HTML on the fly. Nice!

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Reviews

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?

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Thoughts

Congress readies new digital copyright bill

I find this unbelievable, yet Congress seems poised to pass another revision of the DMCA, expanding the reach of this already-controversial bill. It only goes to show the power that special-interest groups have in Washington.

For example, under this new law, if Sony’s rootkit malware were removed by anti-virus software, Sony would have the right to sue those companies! Sounds very silly, doesn’t it!

Just talking about or attempting to bypass copyright protection on anything can land you in jail for up to 10 years! This parallels a French law that their legislature wanted to pass late last year.

I am left to ponder whether lack of forethought and absence of logic have hopped on the back of the bird flu swans and have now infected our politicians… Maybe they’ve been here all along, ever since the 1st version of the DMCA was passed years ago.

Here’s a link to the CNET News article.

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Reviews

Caveat Emptor: TurboTax is a pain

Before I start, I should say I’ve been a user of TurboTax for several years – can’t remember exactly how many, but for more than 5 years for sure. I couldn’t imagine doing my taxes without it in the past, but after this year’s experience, I’m seriously thinking about switching to something else, just so I don’t end up banging my head on the wall out of utter frustration!

I should also mention that I waited since 4/17 to post this entry in order to cool off. I would have been much more critical if I wrote this last week…

I’ve been using the online version of TurboTax since it came out about two years ago. When I started using it this year, I noticed that it had changed a lot – the graphics were slicker, the site looked nicer, etc. That’s where the good points stopped! The rest of the changes were horrible:

  • Gone was the wonderful screen-by-screen contextual help, with audio and video walk-throughs. Instead, now I had some horrible pop-up help that didn’t help much at all and at times referred me to dig through the IRS site for some form or other such thing.
  • Gone was the easy navigation to specific pages. Now, if I wanted to access a specific screen, I had to start from the beginning of the section and go through e-v-e-r-y little page I didn’t care about, making sure I didn’t mess up my previously answered fields… Horrible, just horrible! This was the single biggest time-waster of this year’s tax season!
  • Gone was the simple, easy to use interface. Now I had a slick but clunky interface, where I had to guess how things were organized. I had this weird dichotomy of thought – on the one hand, I wanted to take a sharp pencil and run it across the screen in anguish, doodling in despair, and on the other hand, the buttons looked so nice… Ugh!
  • Did any of you notice the ridiculous wait times to get to chat live with a rep? For me, it was 50 minutes! Do I have 50 minutes to sit in front of my computer, only to wait for some tired and frazzled rep to answer my question perfunctorily? I think not.

I can’t describe the agony of doing my taxes this year. It was a nightmare. I must have wasted over 10 hours because of TurboTax ‘s horrible navigation and clunkiness! Still, I would have been willing to pull the cover over all these glaring shortcomings if only TurboTax would have been able to do its most basic function, which is… to file my taxes correctly! But no, it had to go and mess that up, too!

I chose to file my taxes electronically this year, and to send in a hand-signed form. I was supposed to get notified by TurboTax when my taxes were electronically accepted by the IRS, so I could come back online and print out the form, sign it, and mail it. Sounds simple, right? Well, they never notified me! My wife and I sat there wondering when it would happen, and come tax day (4/17), we still weren’t notified!

That afternoon, I decided to log back into my account to check the status, and I couldn’t! I kept getting this error, telling me TurboTax couldn’t retrieve my submission status. Well, gosh darn it, why did I pay for this piece of software? No matter how many times I tried, even after logging out, emptying my cache, jumping on one foot, throwing salt over my shoulder, whatever, TurboTax couldn’t retrieve my submission status, and it was getting really, really late – I mean, like 10 minutes before 5 pm late!

Finally, I started looking through the TurboTax help files to see how this error could be addressed – because, of course, TurboTax didn’t provide a link to the specific help page addressing this error next to the error message (duh!). After 10 minutes of digging around and mumbling all sorts of unwell thoughts about TurboTax , I stumbled across some number (not toll-free) I could call to check my status over the phone. When I called, I had to listen to a pre-recorded message telling me how I could check my status online… Would I be calling if I could do that?! So anyway, after navigating through a needless phone menu, I was able to get my information, and to find out that my return had been accepted by the IRS several days earlier. Peachy, or so I thought!

I logged back into my TurboTax acount to print out the special one-page form, but of course, I couldn’t print it because the stinking program couldn’t retrieve my status. Aargh! So I went to the IRS site and printed the form, then filled it in by hand – again, I couldn’t help asking myself why I paid for TurboTax if I had to fill out forms by hand (?!) – only to find out… and it gets better, folks… that it was too late. I was supposed to sign and send the form within 24 hours of the electronic acceptance by the IRS!

At this point, I think steam must have been coming out of my ears! I tell you, I was NOT thinking nice, friendly thoughts about TurboTax , and for good reason! They didn’t notify me the IRS had received my taxes! They were able to do it last year, but not this year!

In the end, I ended up having to print my entire tax forms set from TurboTax and send it into the IRS once more, hoping that they’ll accept it in paper format even though I’d sent it in electronically already… I included the special signature form, for good measure. I hope I won’t get in trouble with the IRS. If I do, I have TurboTax to thank for it!

So, there you have it, my entire, horrible, not to be repeated, experience with TurboTax , which this year, was a dreadful, “pull your hair out” piece of software. You be the judge of whether you want to use it to do your taxes. My take: tax time is stressful enough already without having to deal with buggy, hard to use software.

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