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Hard-core techies loved the new look, with its Outlook-like reading pane and advanced features, such as spell-check. But when the company expanded testing in January to include more of its run-of-the-mill Hotmail users, they hit a snag.

Some like it Hotmail
A significant number of testers liked the old version better. "There was this Hotmail loyalist that loved the check boxes," Schackwitz said.

As many as a fifth of the users in some test groups were opting to go back to the old version.

"It could have completely derailed the train," Schackwitz said.

Instead, Microsoft found a compromise. In its latest build, Microsoft decided to add back a "classic mode" option that essentially stripped away most of the new features. The classic mode uses the new architecture behind the scenes, but to consumers, it looks like the same old Hotmail.

But adding the classic interface was sort of a sore spot with some of the Hotmail team.

Product planner Sim likens the new experience to a hot tub. For some users, it was just too hot. With classic mode, he hopes longtime Hotmail users can dip in their toe and discover they like the new bubbles, without immediately taking the plunge. So far, plenty of Hotmail users are happy to stick with the warm bathtub afforded by the classic view.

"When they first dip their toe in, it's way too hot," Sim said. "They sort of have to slowly ease their way in."

For Microsoft, if not for all its users, it is definitely time to move forward. A big part of moving to Windows Live Mail is about trying to keep up with Microsoft's faster-moving rivals, the service's development team said.

Craddock said that before Microsoft started Windows Live Mail, it was "taking a fairly long time to do significant releases," noting that updates might take nine months or a year to arrive.

"Frankly, we didn't think we were smart enough to predict what people want a year in advance," Craddock said. Instead, Microsoft's new mantra is to get new ideas out quickly, see which ones stick and then make tweaks on the fly. "We changed the way we develop software. We now ship a new service to the site every eight weeks," he added.

That approach has brought to light some pitfalls--like the need for classic mode--and some unexpected successes. One big hit was the changeable color schemes that Microsoft added to recent test versions of Windows Live Mail.

"It was actually quite low on our list," Sim said. "The product team just really didn't see much value in it."

Users, on the other hand, felt quite differently. "I didn't realize how much I disliked the old one until I changed color schemes," one tester noted.

Consumer opinions can be very humbling, Sim said. "You feel like you've got...the best engineers building really world-class software," he said. "When you really begin to get user feedback on it, you begin to realize that some of the assumptions that you have were wrong."

Still, Sim is confident that Microsoft has got it right when it comes to the overall shift from Hotmail to Windows Live Mail.

Removing one of the big graphical ads from the in-box is just one step in an effort to create an e-mail service that people will want to use, Sim said. As it stands now, Microsoft plans to jettison the long skinny ad that runs along the side of the in-box in current test versions.

"A lot of it has to do with...users have grown accustomed to expect that you can scroll vertically," Sim said. Having to scroll horizontally is "more of a pain point."

To recoup some of the revenue from the lost ad, Microsoft is looking to sell advertising that would appear at the bottom of e-mail messages sent using the service. In the past, Microsoft has included its own promotional messages, but Microsoft has had talks with some big-name advertisers about buying that prime real estate.

But even as Microsoft seeks to reinvent Hotmail, its competitors forge ahead.

Since first announcing Gmail with 1GB of storage, Google has more than doubled the size of its mailboxes and worked to integrate Gmail with other services, such as instant messaging. Yahoo, meanwhile, has been testing a mail service update that adds an Outlook-like interface and other advanced features, such as the ability to have multiple e-mails open at the same time.

Microsoft, for its part, has an image problem to overcome, Radicati said.

With Gmail, Google managed to launch a service that is "sexy," Radicati said. Hotmail hasn't had anywhere near the same allure.

"Their image is just that they are free," she said.

Perception is important, Radicati said, since free Web e-mail accounts are largely a commodity business. People often sign up on a whim for a new account, but getting committed users is more of a challenge, she said.

In recognition, perhaps, of its diminished coolness, Microsoft is largely abandoning the Hotmail brand it spent so much to acquire--another big gamble. Existing members will be able to keep their Hotmail.com address, but new users will receive Live.com addresses, and Microsoft will stop using the venerable Hotmail brand to tout the service.

In its place, the mail unit is getting a piece of the Windows brand, something that top executives like CEO Steve Ballmer have made clear is a big responsibility.

"Ballmer reminds us of this all the time," Sim said. "We've gifted you with the Windows brand. Don't screw this up."