Microsoft’s Latest Windows 10 Ultimatum: ‘Upgrade Now’ or ‘Upgrade Tonight’

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Windows 10 is available as a free upgrade to valid Windows 7 and Windows 8 license holders, and predictably, Windows users like it when the word “free” is tossed around for a brand new product. As a result, Microsoft has seen a pretty impressive launch for its latest operating system, will well over 100 million installs today. In fact, Gartner claims that Windows 10 is set to become the most used version of Windows… ever.

Some people have taken issue with how Microsoft is “persuading” stubborn users to upgrade to Windows 10. For starters, the company silently began downloading the Windows 10 ISO in the background, much to the ire of many users. More recently, Microsoft “accidentally” checked the box to install Windows 10 via Windows Update, when the download is supposed to be marked as “Optional.” Even though users had to click through and approve the installation of the operating system, it was still an unneeded annoyance. Microsoft later apologized for its mistake.

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It now looks as though Microsoft is trying new ways to persuade Windows 7 and Windows 8 users to upgrade to Windows 10. Microsoft has introduced a new upgrade dialog box that seemingly gives users an ultimatum on upgrading to Windows 10: either “Upgrade Now” and be done with it, or “Upgrade Tonight.” There are no other readily visible options for the user to choose from, so unsuspecting users will likely just choose one of the two options to initiate the installation.

Of course, you can always hit the red “X” and close the dialog box, but Microsoft is quite persuasive with its insistence that Windows 10 will “[Leave] your files right where you left them” and that it is “Fast, familiar, and more secure.” The bottom line is, Microsoft is likely to reel in quite a few stragglers with this latest upgrade scheme, especially if they’re apt to just “click and run” when dialog boxes are presented to them.

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The latest nag screens started popping up over weekend, right in the middle of the holiday shopping rush. So don’t be surprised if your Aunt Jackie or Uncle Jimmy starts grilling you (as the family’s resident PC guru) about why their computer looks different while you chow down on turkey and ham at the dinner table next week.

Starting next year, Windows 10 will be “upgraded” from an Optional update to a Recommended update. That change means that a whole new wave of Windows 7 and Windows 8 machines will begin downloading the installation files for Windows 10 automatically and will initiate the install process for the operating system.

“Our aspiration is for customers to choose Windows, and to love Windows,” said Windows chief Terry Myerson back in late October. “We would encourage everyone to upgrade because Windows 10 is the best Windows ever – familiar, safer, faster, and full of innovations.”