Hot To Trot

The new Hotmail gives Gmail a run for its money.

Hotmail is old. Really old. When Hotmail launched in the summer of 1996 as the first free e-mail system available to everyone, Bill Clinton was running for re-election, the economy was booming, and Lady Gaga, known to her classmates as Stefani Germanotta, had just turned 10. Much of the world wasn’t online; indeed, the idea of being “online,” or of the Internet as a place where we’d soon do much of our shopping and socializing, seemed fantastical. The very prospect of getting mail on your computer struck people as revolutionary. You mean anyone, anywhere, could send you a message? For free? And it would get there instantly? Crazy!

Hotmail was an instant hit—within a year and a half, it had attracted nearly 9 million users. That was a substantial portion of the Internet’s population—AOL, the largest ISP, also had 9 million subscribers at the time. Hotmail’s success inspired a wave of copycats. AOL, Yahoo, and various now-defunct sites launched their own free e-mail systems.

In late 1997, Microsoft bought Hotmail and folded it into MSN. And that seems to be where history stops for Hotmail. The service continued to pick up millions of users—it’s now the world’s largest free e-mail system with more than 360 million users around the world. (Yahoo has more than 300 million and Gmail a little less than 200 million, according to comScore.) But even though it’s grown substantially since its early days, Hotmail hasn’t done much to distinguish itself. It’s long been seen as an e-mail service for people who still use the Web as if it’s 1996—those who don’t get a lot of e-mail, who don’t care much about speed or storage space, and who aren’t itching to use smartphones or iPads. Hotmail, in other words, is an old service for old people, and if you’re still sending messages from a Hotmail account, you might as well be e-mailing from the past.

Microsoft wants to change that perception. Sometime this summer, it will roll out a fantastic new upgrade of Hotmail. I’ve been using a pre-release version of the service for a couple of weeks now, and I’m a huge fan. The new Hotmail is fast, well-designed, and adds a host of features that bring it up to par with other e-mail services, including Gmail. Indeed, it has several features that I wish Gmail included. I’m not switching over yet—I’ve got six years’ of archived mail in Gmail, and I still consider it the best e-mail system on the planet. But that may be just a matter of taste and familiarity. I consider the new Hotmail a very close second, but the more I use it, the more I like it—and I bet loads of people will believe the new version surpasses every other e-mail system around.

Gmail won my heart because it seemed to be designed for power e-mailers—people who get hundreds of messages a day, who use a range of devices to check their messages, and who need (or want) to keep all their e-mail forever. To win that audience, Gmail broke with the past. Not only did it look radically different from other Web e-mail clients; it instituted a range of features—conversation view, “labels” instead of folders, the idea of “archiving” mail instead of deleting it—that diverged widely from the older style of e-mail. The beauty of the new Hotmail is that it’s an old-timey, friendly e-mail system with power features. I think advanced users will like it just fine, but its chief audience will probably be the hundreds of millions of people who want more from their e-mail without having to learn an entirely new e-mail philosophy.

The new Hotmail thus looks pretty similar to every other e-mail system you’ve ever used: Your mail folders are listed on the left side of the screen, and the contents of each folder are displayed in a large well in the center. By default, messages are shown singly—that is, each distinct e-mail occupies its own line in your inbox. But Hotmail has an option to impose a Gmail-like conversation view, which will collect a thread of e-mails with the same subject line into a single box. Hotmail also has an optional preview pane, which lets you see each message below your inbox—not a novel feature in e-mail, of course, but one that isn’t available in Gmail. I suggest turning on both of those options.

My favorite part of the new Hotmail is the way it lets you efficiently sort through e-mail clutter. There are half a dozen “quick view” buttons built into your inbox—click one and you’ll see all the recent messages containing photos, another for all the mail with attachments, another for online shopping shipping notices, and another for “social updates”—the messages we get every day from sites like Twitter, Facebook and LinkedIn. I especially like the button that shows all the messages from people in your address book. This can be invaluable when you first get to your inbox in the morning—it filters out everything but the notes from people you know, which tend to be the most important. (I was able to pull in my contact list and archived e-mail from Gmail. Hotmail, like Gmail, has several ways to connect to and import your data from other online services. I tested it out with several tens of thousands of messages in my inbox, and I found its searching and filtering capabilities just as good as Gmail’s.)

Gmail partisans will point out that Hotmail’s quick views aren’t unique; you could set up many of the same features in Gmail using labels and filters. That’s true, but it misses the point. In Hotmail, you don’t have to do any setup; quick views and other helpful features are there for everyone, by default. The same philosophy carries over to automatic filtering rules. Select several different messages, click “Sweep,” and you’re able to remove those messages—and all future similar messages—from your inbox. Yes, you can do the same thing in Gmail, but the process takes several screens and asks you to go through a bunch of checkboxes. It’s not exactly daunting, but it’s not dead-simple, either.

I also loved the way Hotmail handles attachments. Gmail won’t let you send files larger than 25 MB per message. Hotmail, which integrates with Microsoft’s online storage system SkyDrive, lets you send up to 10 GB of attachments. Select an album of photos to send to your family, for instance, and they will all upload to Skydrive. Your recipients will get a link to an online album, where they can see a slideshow or download all the photos.

With so much to love in the new Hotmail, why aren’t I switching over? First, I’m used to Gmail. I’ve spent a long time tweaking it just to my liking, and even if some of the features take a few more steps to set up than in Hotmail—well, I’ve already set them up. Second, Hotmail includes a big, honking, ever-present graphical ad on the right side of your screen. (You can turn off ads by buying the premium version, which goes for $20 a year.) Gmail’s text ads don’t bother me too much. Sharing my inbox with animations, though, is too much to bear. If Hotmail switches to text ads, I’d seriously consider ditching Gmail. Come on, Microsoft: Aren’t banner ads so 1996?

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