Hackers are causing trouble for Microsoft (NASDAQ:MSFT) again. Only this time, their aim isn't so much to create mischief as to protect Windows XP users who won't upgrade to newer software. According to trade magazine Computerworld, the hack tricks Microsoft's Windows Update into thinking that an XP PC is actually running "Windows Embedded POSReady 2009," which is due to continue receiving security updates till at least 2019.

There's genius in the trickery. Embedded POSReady 2009 closely resembles XP in terms of functionality. Patches aimed at one OS should work for the other. So while it's technically an exploit, it's also one that fills a gap for a huge number of PC users around the globe.

After all, save for an emergency patch issued earlier this month, Microsoft ended support of XP in April in hopes users would upgrade to Windows 8. They've been slow to do so, leaving XP as the governing OS for nearly 30% of the world's computers. (This report at Beta News shows just how bad it's been for Windows 8.)

Welcome to the Kobayashi Maru, Mr. Nadella
From an investor's perspective, the hack places Microsoft in an unwinnable scenario. Support a hack that helps at least some intractable XP users -- forfeiting revenue in the process -- or deny it, and run the risk of an even worse exploit running rampant through a huge number of Internet-connected Windows computers.

Lose, or lose huge. Or, if you're a Star Trek fan like me, you might call it Microsoft's own personal Kobayashi Maru.

For now, Microsoft CEO Satya Nadella is standing firm. Computerworld quotes a spokesperson who says that customers who run the hacked updates run "a significant risk of functionality issues." While that's no doubt true, it also comes as a platitude wrapped in a sales pitch. What about customers in the developing world who find XP to be serviceable for most tasks? Would they really spend at least $200 for an upgrade? I'm not buying it, and neither are they.

Is free the only strategy left?
For me, it's easy to see why. Windows XP was, and still is, "good enough" in so many ways. For everyone else, free options abound. From Linux to Google's free Chrome OS, computing power has never been cheaper.

Consumers like the model. NPD recently found that 25% of all low-cost laptops sold in the U.S. are now Chromebooks. A staggering number when you consider it was only 2011 when Google partnered with Acer and Samsung to introduce its first Chrome OS machines.

Now think about how hard it's been for Microsoft to get users to upgrade to Windows 8. I can't be the only one wondering if it's time for Mr. Softy to start thinking about free OS upgrades, right?

Tim Beyers is a member of the Motley Fool Rule Breakers stock-picking team and the Motley Fool Supernova Odyssey I mission. He owned shares of Google (A and C class) at the time of publication. Check out Tim's web home and portfolio holdings or connect with him on Google+Tumblr, or Twitter, where he goes by @milehighfool. You can also get his insights delivered directly to your RSS reader.

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