The period for free Windows 10 upgrades ends July 29, 2016 for users with valid Windows 7 and Windows 8/8.1 licenses. After that, Microsoft will make you pay for it—$120 for Windows 10 Home, and $199 for Windows 10 Pro. This alone makes upgrading to the latest Windows a sensible thing for those who have not yet done so.

As always, there are a vocal group of holdouts and naysayers happy to stay put on their Windows of choice. They even have their own Twitter hash tag!

I have identified seven different types of Windows 10 Holdouts and their unique approaches to Windows 10 abstinence. All in good fun, of course.

Pavlov’s Administrator

Reason for holding out: After months of clicking away constant Microsoft Update notification popups in the system tray, the Pavlov Admin’s brain became hardwired to deny Windows 10 updates without any conscious thought. He was finally able to relax after finding the Never10 blocker app, but the damage has been done.



Course of action: Seek professional help to break the cycle before Windows 7 end of support in 2020 and worse problems start to set in.

Traumatized Early Adopter

Reason for holding out: Taking a gung-ho approach to installing the latest Windows operating system after its release last July resulted in driver issues and hours of troubleshooting. It prompted a rollback to an earlier version of Windows where this former early adopter has stayed ever since.



Course of action: Irrationally put off the upgrade until the purchase of a new PC with Windows 10 pre-installed.

The Shaky Legacy Software Admin

Reason for holding out: This IT pro isn’t sure whether the company’s legacy software will or will not work with Windows 10. Considering that the last Internet Explorer update resulted in weeks of Frankenstein patch-ups for its proper operation, confidence is low for putting legacy apps onto a whole new operating system.



Course of action: Find a different job before Windows 7 end of support rolls around.

The Privacy Freak

Reason for holding out: That’s none of Microsoft’s damn business, nor is it yours for that matter.

Course of action: Installing a Tor Router to read up on how to disable Windows 10 telemetry before making the final decision to move to a new operating system.

The Windows XP Straggler

Reason for holding out: More people use Windows XP than Windows 8 and 8.1 combined, a statistical fact the XP Straggler loves to point out every month. The XP Straggler doesn’t buy into all those vulnerability “scare tactics,” and out-of-support doesn’t mean broken. Windows XP is a timeless classic, like the ’67 Ford Mustang of operating systems.



Course of action: Until IE7 fails to load Hotmail, or WinAmp stops playing Limewire-downloaded MP3s, Windows XP Straggler will keep it rockin’.

The Anti-Authoritarian

Reason for holding out: Nobody dictates how or when this user updates the operating system. Just wait until he learns Linux; that will show those fascists in Redmond what’s what. In the process, Anti-Authoritarian signs a petition for the Electric Frontier Foundation to investigate Microsoft’s coercive conduct for system upgrades.

Course of action: “What, this game needs DX12 support?” User then conducts furious Google searches on how to obtain free Windows 10 after July 29.

The Stubborn Old Dad

Reason for holding out: Stubborn Old Dad is busy, and doesn’t have time to relearn a whole new operating system. He tried Windows 8 once a few years ago. He developed a migraine and blew out his back looking for the Start Menu.



Course of action: His daughter comes home from college for the summer and upgrades his Windows 7 PC to Windows 10. Dad complains about her changing the wallpaper, but otherwise carries on without noticing it’s a different operating system.

Final thoughts

Considering a Windows 10 upgrade before the free period is over? Find out more how Windows 10 Pro can increase productivity and collaboration in the workplace.

Learn how to deploy Windows 10 Pro in a small- to medium-sized workplace with this step-by-step Windows 10 installation guide.

Prefer to talk to a specialist about Windows 10 licensing for your business? NeweggBusiness Account Executives are happy to provide their expertise – get in touch by calling (888) 482-6678 from 6 a.m. to 5:30 p.m. Monday thru Friday.