My History of Mail Clients


I’ve been thinking about mail a lot recently. In 1997, I started out in Eudora. I used it all throughout college and for the first year of graduate school.

I was always impressed by Eudora’s unblinking speed when handling mailboxes with thousands of emails. I was also always fond of the interface. I know many thought the interface was horribly outdated, but it made sense to me. I really don’t like the preview pane found in many mail clients; I don’t want to scroll by a message and have it marked read if I don’t open it.

The last killer feature of Eudora is its ability to option-click (I think thats the right combo) on a message and have all of the other messages from that person group around the highlighted one instantly. No fiddling around with sort methods when you need to find other emails from a particular person, just bang!

Anyway, Eudora was the center of my mail universe for a good 5 years. After graduating from college, where a Eudora license was provided for free, I purchased a copy of it for the then new OS X.

A year later, I became displeased with Eudora. My license that I had purchased had run out. An update to Eudora was released (the first major update in more than a year) which finally fixed SSL compatibility with OS X. Qualcomm wanted me to pay for said upgrade. I wrote and complained to them, and to their credit, they extended my license by a couple months. However, my eye had been on Apple Mail for a while.

Apple Mail

During that first year or so of OS X’s existence, I tried Mail a couple of times. Each time, I got fed up with how Mail would choke on my large mailboxes. As much as I liked the idea of a system wide address book and the cool little label on the icon displaying unread emails, I always came running back to Eudora, usually in a matter of days.

The release of OS X 10.2 changed all of that. Mail got faster. Mail got junk mail filtering, which at that point in time was becoming a large problem for me. I switched over to Mail and became relatively happy with it.

Life with Mail was good. OS X 10.3 rolled around and Mail got better. Faster, highlighted threads, etc. At times I felt like I was missing being a “power user,” whatever that means, but Mail did most of what I wanted. I started to play around with running scripts in my mail filters, but it just left me wanting for more.

Recently, I got sick of Mail. I got sick of the interface. It was too much of a fight all the time. That damn mailbox drawer got annoying. Scrolling through messages didn’t have that “just hit the spacebar” feel that Eudora had going for it. Then I read about MailSmith. I already liked BBEdit (though I did skip out on the upgrade to 7, BBEdit 8 is great), so I thought I’d give it a shot.


MailSmith has some neat features. I liked its text-only attitude. I could take or leave the whole distributed filtering paradigm, though it does have fantastic filtering capabilites, as well as most of BBEdit’s text capabilites (mmmm, Regex…) and amazing apple scriptability.

Most importantly, it’s being actively developed. The Eudora development cycle has slowed down considerably in the past few years, and let’s face it, Mail get’s a face lift with every .1 update of OS X, but that’s about it.

That’s not to say that I am completely happy with Mailsmith. Its POP3 only, but I ran my IMAP accounts pretty much like a POP3 accounts anyway. (That’s not to say I don’t want IMAP support in MailSmith – it certainly does make multi-computer use easier). It can also be a bit slow with some tasks. I think the interface could use a bit of tweaking as well.

While Eudora will always hold a warm place in my heart and Mail is a great client for the normal user, I think I will be sticking with MailSmith for the forseeable future.


Recently I’ve played around with Gmail. Its not bad. Certainly better than many of the free web-based email services. Its fast, has lots of space, and has a clean interface. The labeling thing is nice, but the only real difference from traditional mail boxes is that it lets you categorize messages with more than one label at the same time. Perhaps this biggest feature of Gmail is it’s phenomenally fast searching. Of course.

I’m interested in seeing what OS X Tiger’s Mail will be like. Smart folders could end up being very similar in one sense to Gmail’s labels, though even more useful in others. Hopefully this is something other clients will adapt.

Miscellaneous Notes

Two things to state here. First, a mail client I used quite a bit while hopping around from dorm room to lab to home was Pine. I know one can get into quite a debate about the UNIX mail clients, but Pine in conjuction with a couple of IMAP accounts can go a long way. I have a lot of respect for this client.

Secondly, the dreaded spam. When I first started to get a noticeble amount of spam, the University had SpamAssassin already in place. It merely took a filter on my part to trash anything marked as spam. The unfortunate part of this setup was that SpamAssassin never learned from its mistakes.

Mail’s junk filtering was better, but it never really took care of the whole picture. Enter SpamSieve. SpamSieve comes free with the Mailsmith license, and the two are really integrated nicely. Though I’ve never tried it with other clients, SpamSieve is supposed to play nicely with them as well, so I thoroughly recommend checking it out. Since SpamSieve is run locally, one can really tune it to your mail patterns. In the six weeks I’ve been running it, its filtered about 10,000 messages, with an accuracy of 99.1%. Not too bad considering that it was a bit inaccurate at first when I was training it. A really quality product.