In April 2015, just a few months before the public launch of Windows 10, Microsoft announced its ambition to have one billion machines running Windows 10 within two to three years. To achieve this milestone, Microsoft began an aggressive push to get Windows users to upgrade to the new OS, first through the “Get Windows 10” program which automatically installed on all eligible machines, then by setting Windows 10 as a “Recommended Update” in Windows Update, a move which could lead to an automatic installation if you have not been careful with your update settings.

While the free upgrade to Windows 10 will now end on July 29, we reported last month that Windows 10 was now running on 300 million devices, though the road towards 1 billion devices has been bumpy so far, to say the least. Indeed, according to a new report from The Seattle Times, Teri Goldstein, the head of a Sausalito, California travel-agency, has sued Microsoft over a failed Windows 10 update which she says she didn’t authorize and that made her business PC unusable. She won the trial, and Microsoft dropped an appeal and agreed to pay $10,000 in damages.

Sadly, Goldstein’s bad experience with Windows 10 is not a first. Early after the public release of Windows 10 on July 29, 2015, we reported that the update was giving users some headaches as some who wanted to update could not, and some who didn’t want to upgrade had still received the update without their consent. In the worst case, some users who were not aware of the update and did not explicitly agreed to install it had still to deal with it after their PC launched the upgrade process automatically. According to the report, that’s what happened to Goldstein who claimed that “I had never heard of Windows 10, nobody ever asked me if I wanted to update.”

After the Windows 10 update failed to install on the PC that she used to run her business, Goldstein explained that her PC began to be slow and to crash randomly, which hit her productivity pretty badly. As Microsoft’s customer support couldn’t help her with her issues, she chose to took the company to court asking or compensation for lost wages and her unusable computer. The Redmond giant didn’t appeal to avoid the litigation to continue, and a company’s spokesperson told in a statement that “we’re continuing to listen to customer feedback and evolve the upgrade experience based on their feedback.”

Wes Miller, an analyst with Directions on Microsoft and also a previous Microsoft worker familiar with the team responsible for the Windows Update tool explained to the Seattle Times that Microsoft’s push to get user to upgrade could challenge the trust of its users:

My worry with this is that they are fundamentally manipulating the trust Windows consumers will have in Windows Update from this point going forward. You can’t perform an action for a user without their explicit permission, it’s just not acceptable.

Windows 10 is a great operating system, and Microsoft deserves credit for allowing Windows 7 and Windows 8 users to install it for free for a year, though the company poorly managed this free upgrade offer during all these months. The confusing and eventually annoying “Get Windows 10” program led some developers to create software to disable it, and in the end Microsoft should really have given eligible users the choice to refuse the update once and for all.

If you definitely don’t want to upgrade your PC to Windows 10 before the free update ends on July 29, Microsoft previously explained last month that the “Get Windows 10” app will be removed from all Windows 7/8.1 PCs after the end of the free upgrade. Do you think Microsoft could have avoided to get sued because of this mis-managed free upgrade offer to Windows 10? Let us know what you think in the comments below.

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