All About Email for Mac OS X


So I’ve upgraded my late-model Powerbook to Tiger, and I’ve decided also to give Apple’s built-in Mail app one more chance. Switching email programs is a risky business—different products store messages on you computer in fundamentally different ways. I myself have been burned more than once, so please allow me to share what I’ve learned…

The email apps that I’ve encountered use one of three basic filesystems: Databases, Mbox and Emix.


These include Microsoft Entourage and Bare Bones’ Mailsmith. I jumped on board with Entourage as soon as I got my copy of the Office 2001 Suite for Mac; though its email functionality is no different than the Mac version of Outlook Express, Entourage could sync my addresses, calendar events and other good stuff with my Palm PDA. The arrangement worked out perfectly, until some cheap RAM on my computer corrupted my mail database, and destroyed all the email I had accrued since my last backup.

Entourage stores your mail in a proprietary database, which you can only access using Entourage. You can compact it, rebuild it and sometimes even repair it from within the program, but if something bad ever happens then there’s little you can do. To be fair, you can export your mail into other readable formats, but if you can’t easily re-import them then what’s the point?

I’ve also downloaded a 30-day trial of Mailsmith, but trashed it as soon as I realized that it too stored mail in a proprietary database. Fool me once…

Enter the Mbox

After my Entourage email disaster, I found myself reunited with an old friend called Eudora. Eudora uses the “mbox” format, just like Mozilla and Thunderbird. The big advantage here is that these mboxes are more or less text files, readable by any word processor. I’ve got archived Eudora mail from eight years ago, and I can still open it with my current version without issue. I can even open a Eudora mailbox in another computer across a network, with the necessary permissions, of course—and that’s pretty cool!

Sadly, Eudora’s interface is anything but. It hasn’t changed all that much since I first started using it, and with Mac OS X’s shiny new buttons it looks downright hideous. So I decided to give Jaguar’s built-in Mail program a try…

Version 1 of Apple’s Mail app also stores mail in mbox format, but with separate preferences and other proprietary files added to the mix. One day I booted up my mail program and got a message that one of these files was corrupt, and that was that. All my mail, gone. I suspect that Apple’s mbox files weren’t really up to standards, as I had a 3MB one sitting on my computer that I couldn’t do a thing with. So back I ran into Eudora’s ugly embrace.


Arguably Apple’s most innovative new feature in its Tiger OS is Spotlight, giving the user the ability to quickly find anything on the computer, including specific email messages. To accomplish this, version 2 of Apple Mail stores each individual message as a separate file, with .emix suffix tacked on to the end. Certainly not your standard file extension, but it works—I’ve tried searching for obscure keywords hidden deep in long emails, and Spotlight has caught each and every one.

For this alone I’m willing to give Apple Mail another chance. If something goes wrong you’ll be sure to hear about it here. In the meantime, if you’re using or thinking of switching to one of the other products mentioned above, hopefully you can learn from my pain and not repeat any of my mistakes!


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15 responses to “All About Email for Mac OS X”

  1. I have also recently gave mail a second chance because its searching ability is so much better than entourage. And now that mail stores each of the individual mails also individual files you can attach spotlight tags which makes it nice for managing projects. I setup project folders inside and now have automator tag emails within those particlar folders (libray/mail/….) and now can just spotlight a particular project title and everything comes up. Very handy.

  2. Hiya Brett… Thanks for the comment!

    Yeah, I’ve been leaving my email on my POP servers while giving another chance, and I think it’s ready for prime time. Here’s hoping, anyway…

  3. Nice post. W.r.t. switching mail programs, for me the ideal solution has been to keep my own IMAP server. Even for a single machine, having a local IMAP server means your email can be stored there, and you can use pretty much any (modern) client to access it.

    I’ve used this mostly on my work Linux machine, because at home (which is where I use my Mac) I have a separate email server. I have put the instructions here:

    I’ve also managed to compile and use dovecot on MacOS X – I may add some notes about that soon.

  4. A local IMAP server? Wow. I’m guessing you can’t do that with Mac OS X without opening a terminal window…


    I should probably point out that most of my actual day to day emailing happens with my hiptop handheld—I just need to know that when I archive my POP mail on my Mac it’ll be both readable and safe for the future.

  5. For those of you who like to glue everything together (myself included) you should try CRM4MAC. It seems to be closest thing out there to the entourage linking feature.

  6. I feel the need to defend Microsoft Entourage. I’m a Mac consultant and I have experience with all the popular email clients on the mac. On my own computer I have to deal with high volumes of email. For many years I used Claris Emailer, then MS Outlook Express and then eventually migrated to MS Entourage. As I said, I’ve dealt with all the email apps for Mac, and I consider Entourage the best choice for email. Yes, the program has had its problems and yes your email database can become corrupted. However, this corruption typically only happens when there is a problem with your computer (usually the kind that cause hard crashes—requiring a forced restart). In my experience, however, Entourage problems are rare and it’s generally very reliable. And, as with anything else to do with computers, having proper backups is essential! I have little sympathy for computer users who do not backup regularly. If you can afford to lose a week’s worth of email, then backup weekly. If you’re like me, however, and you’ll lose valuable time and information by having just a day’s worth of email evaporate, then you should be backing up daily. There are countless ways to automate backups, so there is no excuse not to have such a procedure in place.

  7. By the way, Entourage that comes with Office 2001, Office X and Office 2004 for Mac all export their message folders in teh MBOX format. And it couldn’t be simpler: you just drag the email folder of messages to your desktop (or a particular folder) and voila you have an MBOX archive. Similarly, you can import MBOX archives into Entourage by just dragging them into the list of email folders.

  8. Thanks for the comments, Chris—though I have to disagree on one point…

    Archiving Entourage mail should be easier than dragging individual mailboxes out of the Entourage window and on to the desktop, IMHO. I believe that a truly trustworthy email app will store its native mail files on my hard drive in a format readable by any text editor.

    To be fair, I’ve heard that Entourage databases can be opened by BBEdit… Anyone out there ever tried it?

  9. On the subject of databases, I’m curious… Has anyone out there ever had a corrupted mail database in outlook/outlook express for windows? Are such things common? Fixable?

  10. Use same Entourage database from different Macs in home OSX Server network: Our family shares different Macs at home. Since we don’t have a dedicated machine for each, anyone could be logging on from any machine.
    Will Entourage work off the same Microsoft User folder on the server (User’s Home folder), if I put an alias to it on all the other (client) machines? The intent being, whether I log on the machine running the server software, or another one, when I fire up Entourage I’ll be looking at the same database (mail messages, contacts, calendar appointments).
    Will a plain alias work, or a symlink?

  11. I’m still waiting for Outlook OS X and a pukka Exchange connector…aah the bliss of properly automated back-ups and archive.pst files etc, etc, etc….

  12. Ouch! Sorry for your loss…

    Are you using Mail 2.0, the one that came with Tiger? I believe that it’s more reliable than version 1.x, as it stores each message to a separate file. This is good because I’ve had to re-index my messages on one occasion, and everything came back. The problem, BTW, was caused by a third-party HTTPMail plug-in for Hotmail:

    … Which you certainly don’t need in Entourage!

    If my experience with Apple Mail 2.0 changes, rest assured that I’ll post about it here!

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