Many People Refuse the Free Windows 10 Upgrade, Here’s Why

Have you ever noticed how people’s behavior suddenly changes, when free samples are being given out? You may have observed it at Costco. People who have never walked through the fish aisle in their life become preoccupied with getting a small polystyrene cup of whitebait or crayfish. Those who habitually avoid the produce aisle are prepared to reenact a scene from Grand Theft Auto over a taster of Soybeans. People like free stuff.

Except, it seems, when it comes to operating systems. Linux has been around since 1995-ish, and it only just passed two percent market share. Meanwhile, millions insist they would never upgrade (nay, pollute) their machines with a complimentary install of Windows 10.

To them, the idea of upgrading from Windows 7 is a bit like swallowing poison, or bathing in the Hudson River – completely unthinkable. I found some of these Windows 10 holdouts, and asked to speak to them. I wanted to know what made them tick, and why they were refusing to upgrade to Windows 10.

“I Am Not a Product”

For the longest time, Microsoft has earned its billions by selling software. It’s a pretty straightforward business model. If someone was on Windows XP and they wanted to get Windows 7, they would have to buy a license key and an install medium. Then, voilà. They’ve upgraded.

It’s interesting, but that kind of transaction begets trust. People know where all parties stand. They know that they’re exchanging money for a product. Windows 10 threw away that social contract, and replaced it with one that was foreign, and unlike anything Microsoft had done in the previous 25 years.


Instead of actually buying it, people could upgrade for free. It was monetized with a combination of advertising, analytics, and subscription services. This alone made many people reticent to upgrade. David Jason – a senior software developer and freelance project management consultant from New England – strongly echoed this sentiment.

I deal with a lot of sensitive information. With Windows 10, I just don’t know if I can guarantee its security. I don’t know if Microsoft are going to screw me over.

During our interview, Jason described Windows 10 in a variety of unfavorable terms. He said it was a “keylogger“, a “botnet“, and an “abomination“. Some of the language he used was even biblical. He said it was “Lucifer incarnate“. I’m not sure if he was joking.

A Fundamental Lack of Trust

Such extreme language illustrates the dearth of trust many people have for Windows 10. Microsoft’s relationship pivot with its customers, coupled with a deluge of bad press, hasn’t helped. But privacy isn’t the only reason why many are reluctant to upgrade.

Sara is 22. She only recently finished her teacher training at a university on the outskirts of Liverpool, England. Sara claims that Windows 10 almost stole her degree.

I went to bed with Windows 7. When I woke up, Windows 10 had installed itself, and nothing worked.

The approach Microsoft has taken to recruiting new installs to Windows 10 has been controversial to say the least. Some have accused the company of employing subterfuge and deception to get people to upgrade.

In the case of Sara, it seems likely she clicked a pop-up without realizing. This started the install process. As more pop-ups emerged (an unavoidable component of the Windows 10 install experience), she pressed the affirmative.

Alert messages and notifications are an inevitable part of 21st century Internet life, and many of us have developed a muscle-memory to dismiss them without actually reading them. Unfortunately, this commenced the irreversible Windows 10 installation process.


When she woke up, she noticed her computer had changed. Not just in appearance. It was slower. Things didn’t work, and she was constantly being bombarded with error messages. Her screen was, as she said, “smaller yet bigger“. Her graphics drivers had stopped working.

Stability problems started to creep in. She’d be working, and suddenly the Windows 10 “frowny face of death” would make an appearance.


Unable to afford a new laptop and lacking the technical know-how to roll back her install, she had to copy her files onto a USB flash drive, and work on her coursework during the limited opening hours of the university library.

My friends are really hesitant to upgrade” she said. Some of her more technically minded friends are waiting until the last minute, hoping that the initial kinks might be worked out. Others aren’t willing to risk it. “It’s not worth it”, interjected Sara’s friend Hanna, who was sitting on the corner of her bed.

The Sticks in the Mud

Last year, I interviewed a number of people who were desperately clinging to Windows XP, despite Microsoft having retired it in 2014. One person I spoke to echoed many of the sentiments of those who were reluctant to upgrade to Windows 7, or beyond.

Mary Tomaszewski is retired, and lives in Northern Illinois. She owns a Compaq Presario she estimates is “at least 10 years old”. It’s ancient, and when she turns it on it sounds like the jet engines on a Boeing 747 are warming up in her living room. Despite it still works fine, so she’s never felt the need to upgrade it. Although many things don’t work (I remember trying to interview her over, and failing miserably), it’s more than adequate for her needs.


Almost ten months since our initial interview, she’s still using Windows XP. I asked her, over instant messenger, if she had heard of Windows 10. She said that she had, but she didn’t know much about it. Her veterinarian daughter had bought a new laptop which came with it, but she didn’t know what made it different.

She didn’t know why she was supposed to upgrade.

She has never seen an advert on TV for Windows 10 – at least not one she recalls. Her friends haven’t brought it up in conversation (although that might have something to do with her friends being retired, and not especially interested in tech). She doesn’t know what Windows 10 offers over her current setup. As a pensioner, she doesn’t want the expense of buying a new computer.

On the other side, her Windows XP machine works just fine. It’s old, but it plays her favorite online Sudoku games. She can use it to download recipes. Why would she upgrade?

A Question of Confidence and Purpose

As I put the finishing pieces to the article, it’s the morning of July 9. In twenty days’ time, Microsoft will cease its free Windows 10 upgrade promotion. After that point, anyone hoping to make the switch from Windows 7 or 8.1 will be forced to pay for an upgrade.

Windows 10 has undoubtedly been a rousing success for Microsoft. It’s a great product, and one I use every day. Literally hundreds of millions of people have been convinced to make the switch. But I worry that Microsoft has failed to communicate the benefits of it to a great many people.

Despite the billions Microsoft has to throw into marketing and communications, it hasn’t been able to address many concerns people have about the business model of Windows 10. The surreptitious way in which it has been foisted upon users has made some even more suspicious. Rather than being seen as a gift, many regard it as a curse.

The damage is done, I fear. For that small group of people, they’ll always see Windows 10 as toxic. What do you think?

Photo Credits: plugging ears with fingers by pathdoc via Shutterstock, Compaq SR1130NX Desktop PC (Kevin Jarett)

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