Windows 7 will use pop-ups to warn users of the operating system’s impending death

Pop-up ads have proven to be a PR nightmare before. Will they again?

Windows 7 support ends about nine months from now ( go.pcworld.com/ glry), on January 14, 2020— and if you’re a Windows 7 user, you’ll see more than this story reminding you of that date. In fact, according to Microsoft, you could see several pop-up reminders warning you to upgrade to Windows 10 before the year is out.

Microsoft says ( go.pcworld.com/says)

that Windows 7 users will see a notification appear on their PC “a handful of times” before the year is out. The company didn’t say what message it would contain, though, or when or where it would appear.

“By starting the reminders now, our hope is that you have time to plan and prepare for this transition,” Microsoft said in a blog post. “These notifications are designed to help provide information only and if you would prefer not to

receive them again, you’ll be able to select an option for ‘do not notify me again,’ and we will not send you any further reminders.”

Microsoft has previously experimented with pop-up notifications across Windows 10—tips to push users to Onedrive, for example. But nothing was worse than the infamous “click the X” pop-up that encouraged users to upgrade to Windows 10, and essentially tricked users into doing so ( go.pcworld.com/trik). Users were outraged. (Microsoft later eliminated the pop-up ( go.pcworld.com/elmn), but the damage had already been done.)

By now, Microsoft’s position should be clear: when Windows 7 officially exits support on Jan. 14, 2020, that PC will be at a greater risk of viruses and malware. (End of support means that Microsoft will no longer provide technical support for any issues at all, software updates, or security updates.) Microsoft’s attitude toward the transition has ranged from gentle reminders to starker, more fearsome warnings, and it’s not clear what language Microsoft will use in its popup reminders.

It’s a major concern (and opportunity) for Microsoft and the PC industry in general, as an estimated 40 percent of all PCS run Windows 7, according to Netmarketshare ( go.pcworld.com/ ntmk). If all of those PCS converted to a paid copy of Windows 10—or bought a new Pc—it would have a profound impact on the health of the PC market, and Microsoft’s bottom line.

Microsoft may be finally taking a kinder, gentler attitude toward the transition, though. What almost looks like a Microsoft ad is embedded on a dedicated Microsoft Windows 7 site ( go.pcworld.com/w7st) that attempts to help educate Windows 7 users on what they need to be concerned about. The video ( go. pcworld.com/w710) characterizes the transition from Windows 7 to Windows 10 like replacing a wallet, or upgrading from a beloved old clunker to a more modern SUV. In both cases, the owner is shown taking some personal (a picture, or a necklace) from one device to the other—just as files can be migrated from one PC to the next.

The story behind the story: Since the free transition from Windows 7 to Windows 10 has long since expired, Microsoft’s job now is to convince its most reluctant users to open their wallets for either a new OS or a new PC. To date, that hasn’t happened, at least where Windows 7 is concerned. As the deadline approaches, though, it will be critical to see how Microsoft responds: increasingly apocalyptic warnings? A gentle shrug?

A stubborn Windows 7 user doesn’t have much choice: they must choose between risking malware on an unsecured system, upgrading, or abandoning the platform for the Mac or Linux. But Microsoft would rather lock in users to buying a recurring subscription rather than a one-time fee: buying Windows 10 Home requires a one-time fee of about $129.99. Office 365 Home costs $99.99 per year. How Microsoft navigates the Windows 7 rapids could mean the difference between smooth sailing and users abandoning ship.