The city is facing a multimillion-dollar budget hole. Utility rates are about to go up nearly 50 percent. And, in November, voters will weigh in on a list of ballot measures that add up to nearly $20 billion.

So it might seem like an inauspicious time for Mayor Greg Nickels to be asking for millions of dollars to upgrade the city's entire computer system, starting with its e-mail platform. Nonetheless, that's exactly what Nickels is doing; his budget, due later this month, will reportedly include nearly $5 million to "upgrade" the city's e-mail system from GroupWise, a system supported by the Massachusetts-based software firm Novell, to Outlook—the first step in transitioning the city's computer system over to Microsoft.

Sources at the city say the move to ditch Novell has been in the works for years. The official line, repeated by council staffers as well as officials at the city's Department of Information Technology (DOIT), is that Novell is on its way to obsolescence.

"In the long run, as Novell's market share continues to decrease, we expect it will become more difficult to support," says Erin DeVoto, DOIT's deputy director. Or, as another city employee put it, "We all hate Microsoft, but they've taken over the world. We've lost, therefore we must concede."

Nonetheless, some city employees are asking why Seattle's mayor is so eager to jump in bed with the software behemoth. The theories run the gamut from the mundane to the baroque. Generally, though, the most common theory is that Nickels is eager to ingratiate himself to the region's largest company—a company that, in the past, has reportedly been cool to Seattle city officials because the city has never invested heavily in Microsoft products.

Deputy Mayor Tim Ceis laughs at those rumors. "This has been one of the mayor's pet peeves ever since we got here seven years ago," Ceis says. "We are now the largest municipal user [of GroupWise] in the world; it's not going to be supported much longer." The Hague (population: 475,000), Toronto (population: 2.5 million), and many small U.S. cities use GroupWise; however, Microsoft is dominant among U.S. cities, and that trend seems unlikely to reverse.

On the other hand: Microsoft software is notoriously buggy. Dealing with the software's quirks, my tech friends tell me, is no problem for companies with massive, highly trained tech staffs—but it could bode poorly for DOIT, whose 200-odd employees include not just techies but cable technicians, Seattle Channel programmers, and telephone service workers. The last thing Nickels wants is a repeat of what happened at King County, which may soon spend $84 million to remedy a botched attempt to integrate the county's incompatible computer systems in the 1990s. That's a good reason for the city to move slowly—or think twice about spending tens of millions on a new computer system in the first place.

Comment on this story at www.thestranger.com