Mail of the Species

For as long as I can remember, I’ve had the luxury of unfettered access to my mail server for from wherever I’ve happened to work. This has allowed me to maintain a clean separation between personal and business correspondences, as I’ve always been able to receive POP3 message traffic right into a separate mail database at my office (usually in a different email client from the employer’s official, sanctioned email client), without having to rely on my workplace email address to keep in touch with people.

That’s no longer the case. For security reasons, POP3 traffic is restricted to me during the workday now, so now I have to rely on Web-based email clients, a genre of net software for which I’ve never managed to drum up very much enthusiasm. Managing my email box over the Web is a bit like providing technical support to my mother over the phone; it’s halting and inelegant at best, and frustrating and time-consuming at worst. No matter how many gigabytes of free storage and no matter how much Ajax-goodness is conscripted into the service of the user interface, Web-based mail clients can’t hold a candle to the experience of a desktop email client — even one as convoluted and inscrutable as Microsoft Outlook. And that’s saying a lot.

Webmail Is for Losers

Below: Looking good. The Yahoo Mail beta is better looking than any of its rivals.

However, the beta release of Yahoo Mail comes close. To amend my unfortunate workday exile from POP3, I started to use this stunning online email client last week, thanks to a scarce beta invitation rounded up for me by my friend Richard. Having been in a private beta testing phase since last fall, it’s by now the consensus that this version of Yahoo Mail will be, once it’s released, the best Web client available — I happen to agree.

Yahoo Mail

You’ve probably heard that the new Yahoo Mail goes to extraordinary lengths to approximate the interaction behaviors of a desktop email client. It’s something altogether more amazing, though, when you see it and use it for yourself: messages can be dragged and dropped into folders, email addresses are auto-completed as you compose new messages, and right-clicking produces true and useful contextual menus. It’s a uniformly well-executed experience that’s far and away superior to the whiz-bang eyesore of its most obvious rival, Google’s Gmail. This is due in no small part to the fact that the new Yahoo Mail is hugely more beautiful than all of its competition; its aesthetic is first-rate and realized with aplomb. Fit and finish counts.

Still the Oddpost Out

Of course, this latest version of Yahoo’s mail offering is an assimilated version of Oddpost, arguably the first Web 2.0 application to rise out of the ashes of the dot-com boom, and acquired by the company almost two years ago. What beta users are experiencing is an updated version of Oddpost, but at its core it’s essentially the same as it was before Yahoo broke out its checkbook. So it’s amazing how advanced the user experience remains compared to the raft of online applications that we saw released last year. The only thing it’s truly missing is speed; its performance is acceptable, but it’s still mired by the clunky protocols of remote scripting and American broadband, circa 2006.

If it were just an amazing simulacrum of a desktop email client, though, Yahoo Mail still wouldn’t be the solution for my restricted POP3 access. Thankfully, the company’s exceedingly sharp understanding of what it takes to make a successful online email product wasn’t resigned exclusively to its purchase of Oddpost. Yahoo Mail has always allowed users to retrieve external POP3 email through its interface, but after upgrading to a premium account for US$20 per year, it also allows users to send email from external accounts, too. After a simple authentication process, I can now send messages through Yahoo Mail that, for all intents and purposes, are identical to messages I would otherwise send from my desktop. This allows me to check multiple accounts simultaneously — a feature that is worth the price of admission alone, in my book — while avoiding the paltry webmail feature-set provided by my host.

Hurrah for Yahoo

In the race between Yahoo, Google and Microsoft, I’ve always considered Yahoo to be the likeliest not to come out on top. The company has never had the massive tent-poles of Microsoft’s operating system and boxed software businesses, nor the tremendous and singular mind-share that Google has as the de facto synonym for search. Yet given examples like this Yahoo Mail beta release, I’m beginning to change my mind. It’s obvious that, even in its other products, Yahoo has spent the past several years thinking through its online applications in a way that none of its competitors have; taken as a whole, its suite of online productivity applications are more thoroughly integrated than any of its competitors — they’re far from perfect, but still as close to seamless as anyone can claim at this point in history.

For me, the main sticking point has been that these offerings have never been particularly beautiful, as for years Yahoo had been single-mindedly faithful to its HTML 1.0 aesthetic. But in little ways here and there, that’s been steadily improving, and with this new version of Yahoo Mail, their design sensibility has taken a nontrivial leap forward. Yahoo now has something that Google apparently has no use for and Microsoft handles like a slippery fish: design and aesthetics. I’d like to see the Yahoo Mail beta’s look and feel find its way across all of Yahoo’s offerings — they could certainly use them. And then, wouldn’t it be great if design turns out to be one of the reasons that Yahoo wins?.

  1. Haven’t tried Y!mail myself, but I did have a rather pleasant experience with RoundCube ( If you can live with the limitations (it’s in Alpha stage), you’re looking at a host-it-yourself app, which means that you can keep reading your e-mail (or can Y!mail do POP?).

  2. Well you have it a little better than I do though. At my work they block POP3, IMAP and web based email sites. I am disconnected from the world

  3. Wow – Same exact issue hit me this past week. I just moved into a new office space and my company is now implementing our corporate owner’s policy of no POP3 access. Trying to respond to my various POP accounts is very difficult now! I am currently just using my server’s webmail and my comcast account’s web access. Perhaps I could forward it all to Yahoo!

    Is it possible for you to send me an invitation? 🙂

  4. Gmail also allows you to send email from external accounts. In fact, I use it to manage 7 accounts right now. And it does this for free!

    Also, I can’t live without threaded emails anymore. I cringe at having to use Outlook at work, now.

  5. I myself am a huge fan of Yahoo!Mail both aesthetically and content-wise. Although I don’t need the extraneous accounts feature, I do appreciate its easy-to-use tools and compatability.

    And, as John Kootz said, threaded emails are a must.

  6. I would suggest checking out — I’ve been using it for a number of years and it’s interface is great. There shortcuts to file a message and view the next message in one click are great. I check mail on the road in the browser and use imap and thunderbird at home. All of my mail since 1994 is in that account.

  7. Ward: I’d be glad to end you an invitation, but Yahoo doesn’t make invitations available for beta users to distribute. It seems a touch anachronistic, but this beta is truly a beta — not public, but private. Go figure.

  8. What I dislike in Gmail (eventhough I use it) the lack of rich set of formatting as Outlook Express offers. Also no inline images are supported when composing, but I think Yahoo enabled this feature recently.

    Also I like if the webmail clients offer HTML source access for the mail so I could format my blog posts through webmail.

  9. I’m not completely sold on the new Yahoo email, yet. I haven’t been able to use it first hand (still on the waiting list, apparently).

    My gripes with it, and I could be wrongly informed, but they are:

    – Folders vs. Labels/Tags. It’s increasingly difficult for me to think folder based now that I’ve grown accustomed to tags. It just makes so much more sense that an email could reside in 2 or more places, rather than be cubby holed into one. I use the power of google search with the gmail labels a lot in my email.

    – I generally dislike that they are trying to reproduce the look and feel of an outlook client. I hate Outlook, way too complicated for the simple task of email, I use about 1/50th(at most) of Outlooks features, and I don’t see the need for all of those features to live on the web.

    – Threaded emails. I’m not sure how Yahoo is handling email threads, but I’d be surprised if it was as good as gmails, and I expect it will be more inline with the way Mail on OS X handles it.

    Generally speaking, with the short cut keys, threaded emails, and thoughtful elegance and simplicity with which gmail handles pretty much every aspect of email, I’d be suprised if Yahoo could convince me to switch.

    Plus, I’m Gmail seems to offer pretty much everything that the new Yahoo mail does, but at no cost.

    That said, with all the talk of the new YMail vs. Gmail, I’m particularly interested in Microsofts new Kahuna email web based client.

  10. Depending on how techie you want to get, there are ways to access POP3 accounts by setting up a really basic proxy server. So, for instance, you set up a proxy server on your home workstation that looks for requests at, say port 1110 instead of port 110 (standard POP) but then proxies it to the correct server and port. Thus you’d point your email program to myhomeIP with port 1110 and at home it would redirect it to at port 110. You’d then be downloading what you want to your desktop client.

    SSH Tunneling would also accomplish your objective:

    Thus you could use web clients to get around this, but if you really want to use a desktop client there’s always a way 🙂

  11. This is the first time I’ve actually been interested in the Yahoo! Mail beta. Always in the past, I’ve heard it described, “It’s so great, it looks and acts just like Outlook!” For me, that’s not a selling point at all. I dont like the appearance of Outlook, so automatically I’m turned off. I’m glad you spoke more to the usability of it, rather than just the looks. Maybe I’ll try it out when the time comes for it to be public.

  12. Khoi – thanks anyway! I asked a friend at Yahoo if she could hook me up…she didnt think it was possible.

    Jared – Im not too technical, but are you saying that if my company has closed port 110, there is a way for me to redirect my POP access through a different port that may be open? I’d prefer to use Entourage to read email – would that work with this strategy? Please email me if you get a chance, as I’d love to find out more…

  13. I totally agree with Kyle’s points. Gmail isn’t just webmail with a lot of storage – it’s a different way of using email. I regular have threads with at least 30 emails on them, and it’d be nearly impossible to manage them in another client like Outlook.

  14. I’ve had this problem before. Since I run the pop server I can add another port binding to something high up that isn’t blocked and just change the email client settings to a higher number. Or there are programs that you can use to redirect from one port to another. Even if you dont have access to your pop server you can run something like “redir” on your home machine (it will compile for any linux or the Mac, you’re on your own for windows) even down a dsl line or cable or anything and have it redirect that traffic to the proper port and machine to pick up your pop mail. Course, you might get in trouble 😉

  15. The RSS reader in the new Yahoo! Mail app is pretty nice too.

    And have you noticed you can drag and drop your modules on your My Yahoo! page? For me, this just suddenly became available without any notice. A small thing, but cool anyway.

  16. RE: Jared, ward and James:

    If you have a broadband connection from home you may also want to chek out RealVNC ( or TightVNC ( They both are open-source programs that, similarly to Remote Desktop in Windows, allow you to access your desktop from anywhere. That way you’d have all the convenience of your setup at home available to you at work.

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