Microsoft’s Fresh New Outlook on Webmail

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And the startling news from Microsoft just keeps coming. It’s not just ripping up Windows, selling its own PCs and trying to get consumers to pay for Office as a service. The company is also launching an ambitious new web-based e-mail service–and it’s not simply an update to Hotmail, which remains the most widely used webmail in the world.

Instead, the new service bears another Microsoft brand that’s just as synonymous with e-mail: Outlook. is newsworthy in part because it isn’t Hotmail. More important, it’s the first major webmail in years that makes a no-compromises effort to compete with Gmail as a tool for serious, sophisticated users. (The last time I was this excited by a new webmail service was when I saw Yahoo Mail’s 2005 redesign, which ultimately didn’t live up to its potential.) Microsoft’s service is extremely streamlined and reasonably powerful; it feels like something that a discerning person who wouldn’t be caught dead in Hotmail, Yahoo Mail or AOL Mail might use as his or her primary e-mail interface.

It also brings Microsoft webmail into the modern era by hopping aboard the Metro bandwagon, with a minimalist look and feel that are very close to those of Windows 8. In fact, it has more in common with Windows 8’s Mail app than it does with the upcoming Outlook 2013, which hints at Metro without fully embracing it.

The version Microsoft released on Tuesday at is a preview, and it remains a work in progress. The company is still working on a new calendar feature and built-in Skype video-calling features. I ran across some glitches, including a fraud detector that kept crying wolf. (It even accused e-mail sent by Microsoft of looking phishy.) I also had trouble with features which were supposed to bring my Facebook friends into my Outlook contacts.

Rough edges and all, is the future of Microsoft webmail. At the same time, it’s also clearly derived from the current version of Hotmail, and shares many of its features. But it’s not replacing Hotmail, at least yet. For the immediate future, Hotmail users will be able to switch to Outlook or keep on using Hotmail.

It’s no mystery, of course, why Microsoft is easing the Hotmail name into semi-retirement. Hotmail may have millions of users, but its brand has been hopelessly tarnished for years. It sounds outdated and low-rent, even though the current version, based on a sweeping 2010 redesign, is decent enough. is much better than decent enough. The Metro interface bears little resemblance to Hotmail, and it’s remarkably clean. With their preview panes closed, both Outlook and Gmail squeeze 22 messages into the visible space on my 13″ MacBook Air’s screen. But in Outlook, that looks far lighter and airier than it does in Gmail, in part because there’s no ad above the inbox. That permits the first message to appear nearer the top of the window, allowing for more space between lines.

Unlike Gmail (and Hotmail), Outlook doesn’t bolt on a bar festooned with links to other services its proprietor wants to promote. It’s all about the e-mail, and related features such as built-in chat, in a way that’s very appealing.

The interface isn’t beyond criticism–for instance, if you can tell me why it places the Send button so very far away from the message you just finished typing, I’d love an explanation. Overall, though, I like it better than the current incarnation of Gmail, which remains too cluttered and inconsistent.

Microsoft, which frequently bashes Google as a privacy-invading admonger, hopes that Outlook’s approach to advertising will also help set it apart. Outlook isn’t adopting Gmail’s revenue-generating technology, which scans your e-mail for keywords and displays ads which are allegedly relevant. Instead, it uses the space to the right of your messages to display information about your contacts drawn from Facebook and Twitter.

Outlook does display text ads elsewhere in the interface, such as when you’re in your inbox or reading commercial messages, and it may tailor them based on information it gathers from non-personal email you receive. If you hover over one of these ads, you see an image.

I’m not sure whether many real people are as creeped out by Gmail’s ads as Microsoft thinks we should be. (Me, I just ignore ’em.) But even if’s ads aren’t a major point in the service’s favor, they’re definitely an improvement over the ones in Hotmail, which tend to be cheesy and distracting. doesn’t have anything directly comparable to Gmail’s Priority inbox, which attempts to sort your messages into important and unimportant ones (and in my experience, at least, does a pretty impressive job). It does, however, carry over some Hotmail features that help tame unruly inboxes in other ways. For instance, it automatically creates “Quick view” folders for messages with documents, photos and shipping updates. And the Sweep feature lets you automatically move all messages from particular e-mail addresses to a folder, or deletes them on a schedule you set.

Also brought over from Hotmail are features which let you view photo slideshows and videos without leaving your inbox, as well as integration with Microsoft’s Office Web Apps that lets you edit file attachments. If you want to avoid attachments altogether, you can share files by uploading them to your SkyDrive account.

Oh, and Outlook, like Gmail, has a conversation view which clusters all the e-mails in a thread into one discussion. But it puts the newest messages at the top, which is where they should be. (With Gmail, they’re at the bottom, a design decision that continues to mystify me.)

This new Microsoft e-mail doesn’t compete with Gmail in terms of sheer range of features, and unlike Google’s service, it’s not a rich platform for customization. I’ve tweaked Gmail with a bunch of add-ins from Gmail Labs as well as external services such as Rapportive. I also use third-party services which can access Gmail, such as the Email Game. And Google doesn’t just offer stand-alone Gmail accounts; it also offers the Google Apps variant of the service, designed for business use. Did I mention that the tablet-friendly variant version of Gmail is in some ways superior to the one for desktop browsers?

Right now, at least, doesn’t have any of that richness. (Well, it does have a special version for mobile browsers, but it’s rudimentary compared to Gmail.) For this reason, I don’t have any immediate plan to dump Gmail as my primary e-mail.

What does give you is a nicely-done webmail service which errs on the side of simplicity and modernity, and which carries none of the branding baggage of Hotmail. That’s more than enough to make it worth checking out, even if you’re a happy Gmail user. And you know what? If Microsoft continues to beef up, it may be a boon even for folks who stick with Gmail. I’d love to see what Google would do with its webmail if it had a serious rival which just kept getting better and better.

MORE: My First 12 Questions About the New Microsoft Office