SYDNEY, 13 OCTOBER 2008 - They say money can't buy you love, which might be why Microsoft is preparing to unleash yet another version of Windows next year even as US comedian Jerry Seinfeld attempts to win customers over to its spurned Vista software in a $US300 million ($440 million) ad campaign.
The plan is seen by many as a tacit admission from the company that Vista was nothing short of an abject failure despite the sale of more than 150 million copies since it was launched early last year.
That's a number that Microsoft is clinging to as a sign of its success, but critics equally argue that few businesses would stump up several hundred million dollars for an advertising campaign if everything was going swimmingly.
The ads themselves acknowledge that the Redmond, Washington, headquartered technology heavyweight has taken more than a few hits to its image in recent years courtesy of antitrust woes, dodgy software launches and the rise of uber cool Google and Apple.
Depicting Bill Gates shopping in a cut-price shoe store while Seinfeld helps one of the world's richest men try on a new pair of boots, the advertisement is more about recasting the notorious monopolist as a kinder, gentler software maker than promoting a particular product.
A second ad in the campaign that riffs on Apple's popular Mac vs PC campaign deals more directly with the company's software.
But Microsoft's costly campaign is unlikely to wipe away the tarnish of Vista, which has led personal computer makers to offer special downgrade packages to the previous and more popular version of Windows, XP.
It also isn't stopping some of the company's great allies, including Hewlett-Packard, from mounting their own attempts to fix Vista as they grow more and more concerned that broad disdain for the computer operating system (OS) could drag down PC sales.
All in all it's a major embarrassment for Microsoft, which was already grappling with widespread perceptions that its software had grown bloated and painful to use.
It has also increased the pressure on the company to deliver something better with Windows 7, which is tipped to replace Vista in the second half of next year. So far the specifics of 7 are a little unclear and much of the attention that the software has garnered has focused on what is likely to be just a 21/2 year break between operating system launches.
Critics say that's a clear sign Microsoft has accelerated production of the platform so it can pull Vista off store shelves. But in the software developer's defence, it also has a widely touted goal of releasing new versions of Windows at least every 36 months and has been working on this new flavour going on eight years.
Sign up for CIO Asia eNewsletters.