Woman wins $10,000 judgment against Microsoft for forced Windows 10 upgrade

For months, we’ve cataloged continued user resistance to Microsoft’s Windows 10 upgrade policies, the company’s increasing attempts to shove users to adopt the OS, and its occasional backtrack when its own policies went too far. It seems that at least one customer took the fight to court and won a small judgment against the company for how it deployed its latest operating system.

The Seattle Times reports that Teri Goldstein, of Sausalito, California, sued Microsoft after a failed Windows 10 upgrade left her system performing poorly, prone to crashing, and reportedly unusable for multiple days. Given the general issues associated with performing in-place upgrades, even successful ones, it’s not surprising that some users would run into problems. Goldstein reached out to Microsoft customer service to attempt to resolve her issues, but filed suit against the company once it failed to resolve her problems. Her $10,000 figure reflected estimated lost compensation as well as the cost of a new system.

Microsoft had appealed the initial judgment but dropped that appeal last month. A spokesperson for the company told the Seattle Times that it denied any wrongdoing and had dropped the appeal to avoid the additional expense of further litigation.

One $10,000 judgment against Microsoft isn’t going to make a blip in the company’s financial earnings or its overall Windows 10 trajectory. But it neatly caps a year of self-inflicted damage regarding Windows 10 and Microsoft’s free upgrade. The repeated changes to Windows 10’s upgrade policy, mandatory telemetry collection, and decisions to kill off patch notes and make all updates mandatory (plus the issues with UWP and gaming) have collectively left a bad taste in many users’ mouths. None of these are fundamental reasons to stop using Windows 10, but they speak to the company’s profound trouble communicating what ought to be a winning strategy. The Windows 10 giveaway was a great concept, and the entire process could’ve been handled in a way that made people want to switch. Instead, Microsoft has been dragging people into upgrading in much the same way you might grab a cat and drag it off for a bath.

With just over a month to go until it officially stops offering free upgrades to Windows 10, Microsoft has yet to budge from its stance that once the one-year mark is done, the company will no longer offer a free upgrade to consumers. Currently, Windows 10 Home is $119, while Windows 10 Pro is $199. Prices are identical between the downloadable and USB versions of the operating system.

Microsoft hasn’t specified how it will price upgrades after the free offer has expired. In the past, upgrade-only versions of the OS typically sold for $50-$70 less than full versions, though this has varied depending on the OS in question. As for whether Microsoft’s recent actions have damaged the company’s long-term relationship with customers, it’s too soon to tell. At least some users claim to have sworn off Microsoft products or to have disabled Windows Update altogether to avoid the Windows 10 upgrade, but such remarks probably don’t reflect average user behavior (and we can’t recommend turning off all OS updates to avoid Windows 10 in any case). The bigger issue for Microsoft isn’t necessarily the loss of Windows users, but its failure to establish trust and a cooperative relationship at a time when the company is still trying to make major changes to its software distribution model. Microsoft needs enthusiastic buy-in for its various plans from both developers and customers — not a grudging acceptance of the new status quo.