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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.

The Seven Types of Windows 10 Holdouts
Article Name
The Seven Types of Windows 10 Holdouts
Free Windows 10 upgrades end July 29, 2016. As always, there are a vocal group of naysayers for the new OS. I have identified seven different types Windows 10 Holdouts.
Adam Lovinus

Author Adam Lovinus

A tech writer and Raspberry Pi enthusiast from Orange County, California.

More posts by Adam Lovinus

Join the discussion 13 Comments

  • Kevin says:

    Did you consider there are people holding out because they CAN’T upgrade. Literally the Win10 drivers for some critical parts of a setup don’t exists

    • Adam Lovinus says:

      I’m not surprised by that. Is this affecting your particular setup? Which hardware / driver isn’t supported?

  • Kevin says:

    Yeah, I have two older Dell laptops in my house that can’t upgrade. Drivers for the harddrives don’t work until Win10. Dell has indicated there will not be drivers for Win10 for this model. I worked with the MS Techs for several days to try to make it happen, they eventually told me my only option was to fall back if my manufacturer couldn’t provide any suitable drivers.

    Upgraded the other PCs in my house, but those two laptops remain on Win7 and will until they brick.

  • Phat Jeebus says:

    I don’t have an OS to play with the OS. I have an OS to run the programs with which I make money. If my OS is working, secure and not having any issues, I have nothing to gain by changing the OS. If fact, changing the OS will inevitably cost me time and lost earnings.

    Free operating systems are like free kittens. They inevitably cost you a lot of money and time.

    • Adam Lovinus says:

      I hear that, Jeebus. Productivity comes first. Just know that free kitten will run you $199 in about six weeks.

  • Windows Media Centre, There are still quite a few of us with HTPC’s running Windows 7 or 8. Microsoft’s decision to drop Windows Media Centre is easily enough to keep Windows 10 off your system.

  • JKG says:

    Meet the Shaky Legacy Software Admin Windows XP Straggler Stubborn Old Dad.

  • Robert B. Marks says:

    I’m sorry, but as a small business owner and contract writer, I actually found this article offensive. You’re presenting Windows 10 as the “future,” with everybody who doesn’t upgrade having hangups that leave them damaged. So, rebuttal time:

    Pavlov’s Administrator: There is a difference between a product and a service. For a product, you are placing your faith in the product. For a service, you are placing your faith in the company providing the service. When the company providing the service is taking a number of actions without the user’s consent and acting in a deceptive fashion, it becomes impossible to have faith in that service. And that’s not even counting the fact that Microsoft does not bring out a good OS every time, but instead alternates between good and bad versions of Windows – so, if you’re signed onto the service, you no longer get to skip the bad.

    Traumatized Early Adopter: An operating system is a tool, and one of its purposes is to run programs on the user’s hardware. If it fails to do so, then it is not a useful tool. Getting a new operating system with a new computer that WILL run it instead of trying to shoehorn it onto a computer that won’t is not irrational – it’s common sense.

    The Shaky Legacy Software Admin: As mentioned above, an operating system is a tool, and most of its usefulness is based on whether it runs the programs the user or business requires. If it will not do this, then it is not useful. It is not the program or administrator’s failure – it is the operating system’s. And, by the way, the correct course of action for a system administrator isn’t to “find a different job before Windows 7 end of support rolls around” when Windows 10 fails to support the business’ critical applications – it’s to maintain the current operating system, and if necessary, find and implement a new operating system that WILL run those applications.

    The Privacy Freak: Privacy matters. Speaking personally, I own and operate a small publishing company, and I have done contract work for a number of clients, including Canada’s Department of National Defence. Microsoft’s EULA and privacy policy allowing it to copy files and emails is a complete dealbreaker for somebody like me, and here’s why:

    1. All of the files pertaining to my business are governed by intellectual property contracts to which Microsoft is NOT a party, and therefore has no right to copy, or even to transfer onto one of their servers.

    2. Even though the Department of National Defence work I did was sensitive instead of classified, the files on my computer for that project required a security clearance. Not only is Microsoft not entitled to those files, I do not have the authority to share them – that can only be granted by the Department of National Defence.

    3. The communications and files for my clients are often governed by Non-Disclosure Agreements, and I cannot allow Microsoft to copy these files or communications without breaching these NDAs. So, again, even if I had the inclination to let Microsoft copy the files, I am not empowered to let them.

    The Windows XP Straggler: There’s this thing called “legacy software” – I suggest you look it up. It’s one of the reasons that a number of large corporations are still using Unix systems from the 1960s and 1970s.

    The Anti-Authoritarian, and The Stubborn Old Dad: Here’s a concept for you – somebody’s personal computer belongs to THEM. THEY decides what software goes onto it, and if it gets upgraded to a new operating system. Any upgrade program that uses deceptive practices to circumvent basic consent represents a massive breach of trust involving serious issues, both moral and legal, that can NOT be hand-waved away.

    MY final thoughts: Windows 10 has a LOT of issues right now, and if somebody has a system that currently works for them there isn’t much reason to upgrade unless you ARE buying a computer with the latest and greatest hardware. The cycle where everybody had to upgrade every three years or be left behind hasn’t existed in over a decade. These days, unless you’re in a field like video editing or a hobby like hardcore gaming, your hardware will fail before it becomes obsolete.

    Windows 7 support lasts until 2020 – another four years, which is the rough expected lifespan of a new consumer grade laptop.

    Windows 8.1 support lasts until 2023 – another seven years, which is around the rough expected lifespan of a desktop or a business-grade laptop (and, if you buy business-grade, you often get the install media for both the operating system of your choice, and Windows 10 Professional).

    As of October, all new PCs, business and consumer, come with Windows 10 pre-installed – meaning that you get it anyway as part of the price of that PC. So the argument that if you don’t get the free upgrade now, it will cost you an extra $120 or so later does not hold a drop of water – if you upgrade when it’s time to buy a new computer, you will not spend an extra cent outside of what you would have paid for that computer anyway.

    So, all this taken into consideration, shame on you for using this article to belittle people who have very legitimate concerns, and who don’t actually need to upgrade right now in the first place.

    • Adam Lovinus says:

      Robert, these are all valid points about Windows 10. My goal here was to incite a discussion about the issues confronting Windows users, and you do a great job summarizing all these issues and more in your commentary. For that I thank you. Please understand the “Windows 10 Holdouts” here are caricatures, nothing more. They’re certainly not meant to offend or belittle you or anyone else.

  • Many of my friends has refused to switch to Windows 10 because many games does not work correctly under Windows 10.

    I have hundreds of games on my Steam account, and I’m unsure what should I do! I have dual boot system (Win7/10), but it seems that I always return to Win7 after restart (all my programs are installed on it). 🙂

  • sam says:

    Windows 7 and Windows 8.1 are the most reliable and safest OS for home and business’s. even though windows 8.1 is ordinary, both OS are more efficient faster and secure than Windows 10. windows 10 is not the most secure OS ever made by Microsoft and was over hyped beyond stupidity yet was supposed to be the tool MS foolishly believed would pull them out of the huge hole they currently occupy. Simply another Failure.

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