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True Confessions of a Mailsmith Switcher

Email clients are a lot like dogs. Why? Well, for one thing, their owners are in constant denial. The unfortunate passerby may have the dog’s teeth embedded in her shin, with blood running down her leg – the owner will still look her right in the eye and deny that the dog is biting her. (Yes, I’ve actually seen this happen.) Plus, over time a dog and its owner grow increasingly alike, and mutually dependent. And no one can predict what dog an owner will choose and love.

In the same way, I can’t tell you what email client to use. You’re doubtless convinced there’s nothing wrong with the program you’re using now; and the trouble and trepidation of switching, especially when email is your life and the risks are so great, probably seem overwhelming. Besides, what suits me might not suit you. But I can tell you this: One fine day about nine months ago, I, a longtime user and advocate of Eudora, became tired of its shortcomings, switched to Bare Bones Software’s Mailsmith, and have never looked back. Even after all this time, I’m still somewhat stunned by my behavior. Perhaps trying to explain it to you will help me explain it to myself. Perhaps it might lead you to look into Mailsmith as well.




Reasons to Stop Reading — Since the notion that your current email client might need replacing is probably threatening to you, let me help by giving you, up front, some reasons to stop reading this article altogether. You shouldn’t proceed if you absolutely must have IMAP support, or if you like your email as more than text – HTML, format=flowed, or pictures, rendered right in your client program. Mailsmith doesn’t do IMAP at all, and it displays just text: you can easily open attached HTML or images in another program, but you won’t see them within Mailsmith itself. That suits me perfectly, since pure text (plus attachments) is just what I think email should consist of. But if you really need to see email messages with pictures, tiny print, underlines, or funny "quote bars" down the side, don’t consider Mailsmith.

You also shouldn’t read on if you are religiously opposed to an email client that keeps its messages in a database. I actually agree with that position; since email is just text, why over-engineer with a database and all its attendant problems, such as huge file sizes and data you can’t retrieve if things go wrong? This is a prejudice I’ve managed to repress in order to accept Mailsmith; perhaps, after some soul-searching, you could do likewise.

Finally, you shouldn’t read on if you’re trapped in the past. I peeped at Mailsmith 1.0 when it first came out, in the spring of 1998, and, like the groundhog, dove right back into my hole. I don’t remember the details, but I do remember concluding almost immediately that the program didn’t seem to understand anything about how I used email, or even how I used windows.


But when I tried Mailsmith 1.5 last October, I found it greatly changed. This version understood exactly how I use mail. I could view the three essential bits of information – all mailboxes, all messages of one mailbox, the text of one message – in a single tripartite window, in two windows with the mailbox list separate, or in three separate windows. I could easily reply to the sender, or to the sender plus all other recipients. I could have multiple signatures. I could have multiple servers with different settings. I could forward, redirect, or send again. I could encode attachments in five different ways. After composing a message I could save it as a draft, queue it, or send it immediately. I could look right into my POP server and delete or download individual messages. In short, Mailsmith’s mail handling was just great. Add to that its special strengths, and I was soon an addict.

The Iron Triangle — And what are Mailsmith’s special strengths? Naturally, I’ve been giving that question a lot of thought, and I’ve concluded that there are three main ones, that together give Mailsmith its special excellence and character. Here they are:

  • Text Handling. As I’ve said before, in my view email should be just text. Under the hood, Mailsmith’s core is the same as that of Bare Bones’s BBEdit, the best text editor in the business; so, you get all the power of BBEdit’s text handling wrapped up in an email client. That includes terrific quoting and line-wrapping features, along with find-and-replace of text – including regular-expression searching of stored messages, which in Mailsmith 2.0 uses PCRE, the regular-expression gold standard.


  • Scriptability. Mailsmith is almost totally top-to-bottom scriptable with AppleScript. This is no accident; it comes from major planning and forethought. Mailsmith uses scripting internally for much of its communication between the interface and the program’s core (its architecture is "factored"), so its central functionality can then be all the more powerfully exposed to AppleScript. Plus, you can add startup and shutdown scripts that run automatically, utility scripts that appear in a special Script menu, and scripts that modify what happens when you choose a standard menu item.

  • Filters. Mailsmith has email filtering to die for. It’s a little complicated, but it’s also incredibly powerful, and with the new 2.0 SpamSieve integration, it’s better than ever (see "Tools We Use: SpamSieve" in TidBITS-667). First, SpamSieve vets incoming mail and eliminates suspected spam; then the incoming mailbox filters take over, and then individual mailboxes get to peruse the incoming messages and move them down the mail folder/mailbox hierarchy. Plus you can manually run filters attached to any mailbox at any time. A filter can contain of an unlimited number of tests, and its action can even be the running of a script. In short, Mailsmith has more than enough power to keep your incoming and outgoing messages categorized just as you want them. (See "Distributed Filtering," a series of two articles beginning in TidBITS-648.) If you buy a new copy of Mailsmith 2.0 directly from Bare Bones on or before 31-Jul-03, Bare Bones will throw in a copy of the $20 SpamSieve for free.

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The Power of 2.0 — Back in October of 2002, I migrated easily but experimentally into the Mailsmith 1.5 demo. After using it for about four days, I realized, in a sudden revelation, that I was hooked, and that I wasn’t going to be abandoning Mailsmith any time soon. All the same, I didn’t feel comfortable about revealing my decision to others; I remained a closet Mailsmith switcher. The trouble was that I couldn’t quite recommend Mailsmith 1.5. It had some interface quirks; it was dog-slow, with the "spinning pizza of death" appearing frequently; and it crashed remarkably often – about once a day – sometimes taking some of my data with it. I really shouldn’t be telling you about that, but unfortunately I can’t tell you why 2.0 is so much better without admitting 1.5’s problems.

The fact is, 2.0 is indeed much better; the problematic aspects of 1.5 are now a thing of the past. The folks at Bare Bones have done a painstaking and thoroughly professional job of revising the program. Menu items and interface elements have been rearranged in a more sensible fashion, threading has been tweaked, just about everything has been sped way up, and bugs have been ruthlessly tracked down and squashed. The result is that Mailsmith 2.0 feels peppy, clean, crisp, and totally reliable. Where I suffered through Mailsmith 1.5’s drawbacks to take advantage of its special strengths, 2.0 is in every respect a delight to use.

Sweating the Small Stuff — I haven’t yet mentioned many aspects of Mailsmith that deserve attention. It has great drag & drop support and great use of contextual menus. The new PGP (Pretty Good Privacy) integration is excellent. The new support for Apple’s Address Book has me using that program for the first time; it serves as a "whitelist" for SpamSieve and allows auto-completion when typing an addressee’s name. Searching is fast – not quite as fast as Eudora, but on the same order of magnitude (contrast Entourage, which I had to stop using after a week’s flirtation, years ago, because searching was glacially slow; see "Entourage: The Grand Tour" in TidBITS-550). I could mention lots more, but this paragraph would soon become a features list, and for that you can consult the Mailsmith Web site.


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Mailsmith does contain some things that still annoy me. You can elect to leave large messages on the POP server; a "stub" message appears in your inbox, and you use this to delete or download the real message later. That’s great, but if you download it, the stub is replaced by the real message, and nothing then informs you that the original is still sitting on the server.

Date sorting of messages sometimes works oddly. Glossary entries and signatures can contain references to special placeholder items, whose values are substituted when messages are sent, but there’s no helpful interface for listing and inserting these placeholders (you have to consult the manual and type them by hand). The glossary mechanism itself is clumsy; you can’t just insert a glossary item by typing its name, as in Microsoft Word. Many common simple actions, such as deleting a message, can’t be reversed by Undo.

Navigating to a message’s enclosing mailbox list doesn’t select that message, which is silly because the reason you navigated there is surely to find it in context. Option-Command-Delete deletes a message permanently (rather than moving it to the Trash mailbox), but Option-clicking the Delete button does not, which is confusing. There is spell-checking, but it isn’t inline, which many folks prefer. The Connection window, which is supposed to alert you that a server transaction is in process, often doesn’t come far enough forward to be visible.

Conclusions — Despite such nitpicking, this version of Mailsmith puts the program in a whole new category. Mailsmith 1.5 was usable but flawed; it had a coterie of devoted followers, but they seemed mostly to be fanatics. Mailsmith 2.0, on the other hand, is simply a great program, and deserves wide and serious consideration. It has been worth the wait. If you’ve wondered what the fuss is about, now is the right time to give Mailsmith a second look – or a first look.

Mailsmith requires at least Mac OS X 10.1.5, and some features require Mac OS X 10.2 Jaguar, with 10.2.6 strongly recommended. A 30-day demo is available as a 13 MB download and can be converted to permanency by purchasing a license. Mailsmith 2.0 costs $100, with a $20 academic and cross-upgrade discount. Mailsmith 1.5 owners can upgrade for free until 15-Sep-03; owners of version 1.0 or 1.1 can upgrade for $50.

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