A little over a week ago, Gmail made it possible to “go offline” and take the contents of your email archive wherever you like. Slate’s technology columnist, Farhad Manjoo, wrote an effusive piece declaring Gmail the victor in a battle between desktop email clients and webmail that’s been raging since the mid-1990s:

“Gmail has bested the Outlooks of the world […] If you’re still tied to a desktop app—whether Outlook, the Mac’s Mail program, or anything else that sees your local hard drive, rather than a Web server, as its brain—then you’re doing it wrong.”

Self-described “pixel-pusher” and member of the greater Twitter Mac cabal, Neven Mrgan, retorted with this gem:

“Well, I’m convinced. I guess I’ll just switch to an email client that doesn’t allow me to drag a goddamn file into the message to attach it.”

While chuckle-worthly, this isn’t strictly true: it’s possible to drag a file onto any file -type input form element in Safari, and the site-specific browser Mailplane makes more general drag-n-drop possible with Gmail on a Mac. Neven’s commment does, however, illustrate the core problem with email clients, desktop or web-based: they’re all utter failures at something.

The Problem With Desktop Email Clients

Manjoo is more than right in claiming that Gmail has bested desktop email clients on most fronts. He talks about Gmail’s speed, its efficiency, that the user doesn’t have to worry about storage, about how its search actually works. Weirdly, though, he doesn’t elaborate on one of Gmail’s best design decisions: conversations.

Gmail presents email threads as one long conversation, starting with the oldest message and ending with the most recent. When coming back to a conversation, older messages are collapsed until you need them. No matter who joins the thread, the conversation will remain one unified, chronological, vertical stack of messages. You can archive entire conversations, and they pop back into your Inbox when continued by new messages.

Anyone who’s given Gmail a fair shake will quickly find conversations indispensable. Going back to any other email client is agonizing and disorienting, like being knocked around and dumped out of the back of a pickup on the outskirts of a strange town. In desktop email clients, new messages arrive completely bereft of context. The only way to orient yourself is to either remember what the conversation was about or read through the mess of quoted text that may or may not be present at the bottom of the message, depending on what kind of email client or prefences the sender has. You could try searching to re-orient yourself, but good luck with that in Outlook or Mail.app.

With conversations, Google has offered the only advancement in the information architecture of email clients in decades. Apple, on the other hand, has given us basically bupkiss, rendering Neven’s defense a bit silly. While they clearly don’t expect many people to use it judging from the attachment toolbar button on the New Message window, it’s lovely of Apple to support drag-n-drop in their Mail.app. But without fundamental improvements like conversations, that’s sort of like bragging about the automatic windows on your car sitting on cinderblocks in the front law: nobody’s impressed anymore, and it’s not going anywhere.

I’ve been trying the beta releases of a desktop email client called Postbox. Other than being a slightly more palatable version of Mozilla Thunderbird, there’s precious little to recommend it. It learns essentially none of the lessons of Gmail, which is probably why one of the top requests from beta testers is a real conversation view. The developers are focusing on nigh-on useless features like social software integration, similar to Apple wasting its last major release of Mail.app on templates, notes that don’t go anywhere, and half-assed RSS reading. It’s one of the only new non-amateur desktop email clients to come out in ages, and it’s no savior.

The problem with desktop email clients is that they’ve gone nowhere, and appear to be going nowhere fast. While Google has delivered solutions that make email less excruciating, Apple, Mozilla, Microsoft, and now Postbox are twiddling their thumbs and staring at the ceiling. The primary recommendation for a desktop email client is that you end up with a copy of your messages on your hard drive, and even that argument is moot. So why do people keep using desktop email clients?

The Problem With Webmail (Really, With Gmail)

First of all, most webmail isn’t Gmail. Most webmail in 2009 is designed to look like a desktop email client. Web interfaces that attempt to mimic desktop software have been perpetual and stunning failures, so it’s baffling as to why they’re still designed this way. I’m not going to waste time tearing down the Yahoo! Mails and Hotmails of the world, or whatever terrible webmail interface your university, company, or ISP forces you to use. They’re abominable, and that’s why Slate has columnists covering Gmail and nobody gives a rip about Yahoo! Mail even though they’re the market leader.

Gmail does everything it possibly can to tastefully straddle the line between web and desktop application. For all its functionality, it still feels more like a web page than a web app. There’s no attempt at drag-n-drop, fake windows, big candy icons, or any of the usual signatures of desktop software. Other than their custom buttons, Gmail tries not to break too many of the web’s rules and conventions in its attempt to provide a fast and efficient interface to one’s email.

Unfortunately, this restraint isn’t enough to keep me from trying desktop clients like Postbox, or even secretly firing up Mail.app once a month to see if I can stand living without conversations for more than two minutes (I can’t).

This is probably heresy coming from a web application developer, but I think web applications are mostly ghastly. I hate using them. When I’m faced with a computing problem, I want to solve it with a polished, stable, native application for my operating system that looks and feels like it belongs on my computer. I don’t believe in Rich Internet Applications — they’re a boogeyman that I keep hoping will disappear.

The problem with Gmail is that it could be a “real” application. While its conversations and search-that-actually-works are (sadly) innovative, they’re not impossible to implement as part of a platform-native email client. I enjoy using Gmail, but I’d enjoy it even more if it obeyed the rules of my operating system, not the rules of the web. The web has a lot to offer certain types of problems, but I’m not convinced that email is one of them.

The Problem, In Summary

The problem with desktop email clients is that they’re not webmail. The problem with webmail is that it’s not a desktop email client.

My hunch is that the very thing geeks seem to like about desktop email clients-that you end up with a copy of our messages on your hard drive-is the very thing that drives most users to webmail. Desktop email clients have to deal with synchronization, and there’s no good way to hide from the user the impedance mismatch of syncing a local and a remote data store. Less technical users get frustrated by the schizophrenic behavior of desktop email clients: messages they thought they moved to a folder never left the Inbox; messages they thought they sent are sitting in their Drafts folder hours later; messages they thought were deleted are still there on the server.

Webmail alleviates this problem by allowing users to interact more directly with the data store that contains their email archive. It’s an illusion, but it’s a more complete illusion than desktop email clients can offer. When using Gmail, you feel like things are actually and really happening when you send an email or archive a conversation. Until, of course, your internet connection falters and you discover that you’ve lost your most recent actions in some local event queue in your browser.

If you’ve managed to make one or another of the current lousy options work for you, congratulations: way to get that car off the cinderblocks. The rest of us loathe our email clients, and would basically kill for something better.

The solution, I think, is to make desktop mail clients more like webmail, and absolutely not the other way around. The more webmail tries to behave “native”, the worse it works. The more desktop mail clients strive to provide an intelligent information architecture and reliable synchronization, the more users win. But before life with email really improves, the major desktop email client vendors need to catch up to Gmail.