Microsoft Vista was a stumble that exposed weakness

The year was 2006, and Microsoft was hoping for a big splash with its Windows Vista operating system—but the rollout had the opposite effect.

“I thought, ‘This stuff is really bad,’” Peter Gutmann, a computer scientist at the University of Auckland, New Zealand, and early Vista critic, told IT Brew of the operating system’s debut. “It’s just not going to work. You can’t do it like this.”

He wasn’t the only one. Wes Miller, a former Microsoft product manager, told IT Brew that the concerns he had with Vista, developed under the code name Longhorn, led to his parting ways with the corporation.

“The fundamental reason I left was because Longhorn was not going to work in the enterprise,” Miller, who today works as a research analyst with independent IT planning firm Directions on Microsoft, said.

Steve Ballmer, Microsoft CEO from 2000 to 2014, called the Vista experience his “biggest regret” in an interview with ZDNet around the time he was leaving the company.

“The thing I regret most is the, what shall I call it, the loopedy-loo that we did that was sort of Longhorn to Vista,” Ballmer said. “I would say that's probably the thing I regret most. And you know, there are side effects of that when you tie up a big team to do something that doesn’t prove to be as valuable.”

Backstory. Development of Vista was a tricky process. In a 2018 retrospective on the platform’s release, Ben Fathi, who was Microsoft’s corporate VP of the security technology unit when Vista was released, wrote that the company’s disorganization was part of the problem.

“At the time, the Windows development environment was a mishmash of tools stitched together over many years,” Fathi wrote. “Teams couldn’t simply build and test their own component without having to spend many hours compiling the universe from scratch to make sure they hadn’t missed an undetected header file dependency.”

For Robert Scoble, a former “evangelist” at Microsoft whose job it was during the run up to Vista to hype the new platform, the development process led to a lot of on-the-fly backing off of prior promises of what would be delivered.

“It went on for months—oh, this feature is disappearing, oh, this feature is disappearing,” Scoble told IT Brew.

Challenged. With the wildly successful Windows already acting as the dominant operating system in both consumer and enterprise environments, innovation wasn’t considered a priority. Rather, the company added to the existing infrastructure incrementally—a process that meant there was added complexity to the system and made it “harder to leapfrog the competition,” Fathi wrote.

Further, the new software was asking a lot of older hardware, and needed newer, up-to-date machines to run properly. This introduced a major issue for consumers who were less than enthusiastic about purchasing new computers for the newer operating system, as former Microsoft CVP for Office Development Terry Crowley wrote a decade later.

“An important part of what was happening here was a deeper problem — the basic sufficiency of the desktop form factor for the jobs it was being asked to do,” Crowley explained. “The basic use cases — productivity (mostly Office), communications, browsing (including search, websites, and web applications), custom internal line-of-business applications, front ends to custom devices (think of your dentist’s X-ray machine) had mostly stabilized by 2000 and have not changed much since then.”

What did this mean for Vista? Well, most existing hardware—not the newest computers and laptops, but the older ones that were still ubiquitous—was built for software that the new platform would largely render obsolete. And that meant that while Vista would run on older devices, it wouldn’t run well.

“To be fair to Vista, when you install it on a new PC, it actually had a pretty good experience,” Miller said. “The problem for people like me who were in the enterprise space was we’d already just asked people to get new PCs for XP a few years prior. So, companies in particular were not enthusiastic.”

Future imperfect. Miller, looking back on the release, said that while the company may have exposed its issues in the rollout and development, it also provided the space for firms like Winternals—where he went after leaving Microsoft in 2004—to innovate.

“I’m not sure the right lessons were learned, I would say [from] my perspective, looking in from the outside, was that it was kind of depressing,” Miller said. “But at the same time, it created an opportunity, because at Winternals, we created software that could make XP last longer.”

Gutmann was more succinct.

“It was an example of what not to do,” he told IT Brew.

Reached for comment, Microsoft, through a PR company, asked IT Brew for a detailed list of questions about Vista. They then declined to comment.