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Microsoft entered 2009, midnight PST to be exact, with egg on their faces over failure of the Zune Media player to account for the Leap Second which ended 2008.

According to Zune owners from across the globe, thousands of Microsoft’s 30GB iPod imitators suddenly gave up the ghost at exactly midnight Pacific time last night.

“We’ve got two Zune 30GBs,” says one poster to the Zune.net forums. “One was docked in the Zune Docking Station, the other wasn’t. At exactly 2am CDT (12am PDT), the docked Zune made the ‘unplugged from USB port’ bong-noise and went to the boot-up screen with the 100% loading bar…and froze.

It certainly was not a great start to what is to be a difficult year for the software company. The biggest challenge will be to deliver a successful launch of Windows 7, especially since it was announced today that according to Gartner, Enterprise adoption, the bread and butter of the Windows Monopoly is firmly stuck in single digits:

Just over two years since Microsoft launched Windows Vista, fewer than 10 per cent of PCs in the enterprise are running the successor to the company’s eight-year-old Windows XP.

That compares to last July when Forrester reportedly said Windows Vista adoption was at 8.8 per cent and Windows XP was at 87.1 per cent. In that report, Forrester said Windows Vista was like “new Coke”, which was killed by its corporate parent because nobody like it.

Shareholders are quite rightly disappointed in not only how long it took to deliver Vista, but how badly the launch of the product into the market and finally the adoption rate as we discuss below. Couple that with the news that Firefox continues to make significant ground in the browser wars, a key component of Microsoft’s online strategy.

Internet Explorer now has 67.55 percent of global browser market share, a drop of over seven percentage points in a year, according to figures from Web metrics company Net Applications, released Monday. Mozilla’s Firefox browser, meanwhile, has gained market share in the same time frame, climbing over three percentage points to 21.53 percent.

This continues to make Microsoft very uncomfortable because the Internet Explorer is and will be designed to work well with Windows Live, the partner and successor to the Microsoft Office Strategy. This is important because while other browsers have insignificant marketshare, Microsoft can safely ignore support for those browsers. But now Firefox has moved past 20% in North American market share (it has always been larger in Europe), it will come under greater scrutiny should they attempt to tie IE to Office Live Online.

The Windows Desktop, Windows Live and Windows Mobile are three interdependent legs, which are designed to strengthen and extend Microsoft’s franchises. They rely on each other to block competitions ability to attack Windows Desktop with a single point product.

Which brings use to Windows Mobile, another device that was designed to tie the Microsoft Enterprise Strategy to portable devices. Without a significant market share in mobile devices, it cannot use their strength in Office to nail the Live strategy and strengthen the desktop defense. They all rely on each other to work.

To top off January, Motorola has made sharp cutbacks it’s Windows mobile investment:

Now there are signs Motorola is shifting away from Windows as well. Its recent job cuts included a team of more than 70 employees working on the Windows Mobile platform at its facility in Plantation, Fla. Telecom analyst Ittai Kidron of Oppenheimer & Co. said delays in releasing a new version of the Windows platform may have caused Motorola to alter its plans in the short term.

With key partners HTC and Motorola dancing with Google’s Android platform, the iPhone and Blackberry blowing away records, makes the Microsoft tri-platform strategy look like it is taking on a lot of water. This is because each component is designed to support the others and without this approach, it makes it very difficult to build the network effect (read profits) that they have enjoyed with Windows and Office.

It is troubling to think that Microsoft, being a company with huge resources have executed poorly on the Windows Mobile strategy, are playing off the backfoot on the Online strategy and have failed to convince their customers to stay on the upgrade strategy that worked so well 8 or so years ago. If walking and chewing gum at the same time is so difficult thus far, can we expect them to be able to pick up the pieces in 2009?.

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