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The redesign effort, even its more ambitious aspects, is not a total wash, however.
Both the classic and full modes sit atop a far more modern engine, the internal part of the mail system. With Hotmail, Microsoft was at the end of its development rope. Every new feature basically had to be "hacked" into the code.
The new code can support multiple interfaces, not just Hotmail's classic and full modes, and can support sending mail information to other Microsoft properties as well as potentially to third parties.
Already, Microsoft has said it will use the new mail engine to power Office Live mail accounts as well as a new Windows Live @ Edu effort, in which Microsoft is trying to get universities and public-school systems to allow it to power their mail.
Microsoft acquires Hotmail and its 8 million users.
Hotmail tops 30 million users.
Hotmail hits 52 million users.
Google announces Gmail.
Microsoft demos improved Hotmail (code-named Kahuna) at a conference for financial analysts. It starts public testing of the product.
Yahoo launches a limited U.S. beta of its improved Yahoo Mail service with features like drag-and-drop organization and a built-in RSS reader.
Microsoft announces Windows Live, including plans to rename Hotmail as Windows Live Mail.
Amid pushback from users, "classic" mode is made the default for the revamped Hotmail.
Windows Live Mail drops its beta tag in the Netherlands but remains in testing in the United States and elsewhere.
Microsoft announces that a Web mail initiative called Windows Live Hotmail.
Windows Live Hotmail loses its beta tag worldwide.
For those who really want a more Outlook-like experience, Microsoft has another option: Outlook. Microsoft plans to make available in a couple of weeks a new test version of its Outlook connector software that will enable anyone with a copy of Outlook 2003 or Outlook 2007 to use the software to access Windows Live Hotmail messages and contacts.
Microsoft also plans to offer a separate Windows program, Windows Live Mail, which is similar to the Windows Live Mail desktop program that the company has been testing. That software, set to run on Windows XP and Windows Vista, is designed to work with Hotmail as well as e-mail accounts from rivals. It will feature contextual advertising tied to the contents of users' e-mail, though users will be able to turn off the "active search" feature.
Windows Live Mail will be one of Microsoft's first desktop programs to include advertising, though the company is considering making other consumer programs available in an ad-supported fashion.
Kevin Doerr, the Windows Live general manager in charge of the redesign, likens Microsoft's lesson of going too far with the Hotmail redesign to that of New Coke. In 1985, Coca-Cola changed the formula of its namesake soda, only to find that most people hated the new taste. The company was forced to revert to the old formula, which became known as Coca-Cola Classic.
"Even in software, you can go broke underestimating how little change people want to experience," Doerr said.
Microsoft isn't alone in its challenges trying to get Web mail right. Yahoo's redesigned mail is still in beta, as is Google's Gmail. Yahoo plans to drop the beta moniker in the coming months, while Google would not say just when it will move out of beta.
Yahoo has also found that some users want to use check boxes, adding back the boxes in its most recent test version, which is being rolled out to current users.
"We thought it would be a natural enough experience for users that they would be able to drag and drop, and use keyboard shortcuts," Yahoo spokeswoman Karen Mahon said. "The feedback we heard from our users is, they were lost without the check boxes, so we put them back."
In some ways, Microsoft's failures worked to its advantage. Few workers would have been excited by the prospect of building a new mail engine rather than leaving the interface largely unchanged. It might have also proved a tougher sell to get the resources needed for a ground-up rewrite.
Even Sim, who joined the Hotmail effort in August 2004, said it might have been a tougher sell for him, had he known how much would have to stay the same.
"I came thinking I would change the way people would communicate online," Sim said.
Indeed, that's the same draw Gmail product manager Keith Coleman sees in his job. "It's really exciting to do that because you can change the way people's lives work," he said. "The risk, of course, is something like what it sounds like Hotmail is seeing. If you take too big a leap, people get lost."
The Hotmail team believes that, despite taking a circuitous route, it has found a happy medium. But it doesn't plan on staying in the realm of the comfortable forever.
"That doesn't mean you shouldn't continue pushing," Doerr said. "It means you need to understand that and honor that and figure out a way to transition them from where they are today to where they should be."
What will now become the primary interface for hundreds of millions of Web mail users was originally designed as a fallback.
The first version of what is now Windows Live Hotmail's default "classic" view was rushed out to offer a better option than what some beta users were getting--an error message saying the new Hotmail didn't work with their browser.
"We just shipped immediately anything we could ship," program manager Ellie Powers-Boyle said. "You could view mail. You could send mail. You couldn't forward mail because we didn't have time to add that button."
Not too much later, Microsoft decided that it needed not only something for older browsers, but also an option for those who didn't want as radical a makeover as the new Web 2.0-style mail program.
Months later, it decided that there were more of those people than those who wanted the new version. The company shifted the bulk of its engineers to work on the classic mode, completing its transformation from Hotmail's stepchild to its poster child.
And, yes, the Forward button works just fine.
Hotmail goes retro
Just a basic version at the start, "classic" mode has become the default for the redesigned e-mail program. May 7, 2007
As Microsoft gets set to launch its revamped Web mail service, here's a peek at how its look evolved. May 7, 2007
Web mail repairman
Microsoft's Mike Schackwitz works under the hood on the veteran Hotmail service.April 26, 2006
Editors: Anne Dujmovic, Mike Ricciuti
Design: Andrew Ballagh
Production: Jessica Kashiwabara
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