Windows 10: Six years on, still a free upgrade
There are reasons why - just not necessarily the ones Microsoft would like people to think about

Windows 10, Microsoft's latest operating system for PCs and the most used globally right now, is fast approaching its 6th birthday in a world that's quite different from the one it was born in. There was so much talk regarding "the future of computing" back in 2015, whether that was still involving traditional PCs or whether other form factors, such as tablets or even smartphones with a handful of accessories, would take over. The COVID-19 pandemic, of course, and the millions of people who suddenly had to stay at home changed that tune - at least for the time being - as it became clear that the personal computer is still the device one turns to when almost everything has to be done through that one device, be it work, communication or entertainment.
With PC sales being revitalized Windows 10 finally achieved market share dominance - but there's still an anomaly in the transition to Microsoft's latest operating system and that is none other than Windows 7. Despite the fact that the Redmond giant has offered a free Windows 10 upgrade path to all Windows 7, Windows 8 and Windows 8.1 users since day one, hundreds of millions of those consumers opted not to follow it. Microsoft set a theoretical time limit to that offer - even used some rather questionable tactics in order to persuade enough of those users to migrate - but many of those consumers simply resisted.

In the end, it took a literal threat to move the needle of Windows 10 upgrades: it was not until the final months leading to Windows 7's end-of-life support in January 2020 that many consumers (and businesses) using it finally chose to upgrade rather than be left unprotected to all sorts of security vulnerabilities. Even then a not insignificant percentage of Windows 7 users chose not to upgrade to Windows 10: as of February 2021, 16.5% of all Windows-based PCs in the world still run Windows 7. All these millions of people (more than 175 million consumers!) prefer being exposed to malware, botnets, DDoS attacks and other network-related threats to installing Windows 10 on their PCs.
Now that is a message that any tech company would hate to receive.
One would have thought that, since Windows 10 has now ascended to the operating system throne, Microsoft would have blocked that upgrade path from Windows 7/8/8.1 to its newest operating system (as it was supposed to do five years ago). Not so. Yours truly had to reconfigure a desktop PC and fix a laptop a few days back and opted to install Windows 10 on new SSDs, thinking that he'd have to buy new product keys in order to activate fresh copies of Microsoft's latest operating system. To his surprise, both a Windows 7 key and a Windows 8.1 key that was lying around, unused from God knows when, activated these new installations with no trouble at all. A quick Google search revealed that other people found out the same thing as recently as last week. So one has to assume that Microsoft's "offer" is still standing, almost six years after it was first made.

It would be nice to think that Microsoft is doing this out of the kindness of its executives' hearts. It would be nice to think that they are doing it for the greater good of the Windows ecosystem, as all Windows 7 PCs are now weak links to a global chain: possible points of entry to malicious software that can hop from one networked PC to another with ease. It would even be easy to think of it in "why not" terms since it does not actually cost Microsoft a penny to offer that Windows 10 digital entitlement (the legal activation code attached to any PC being upgraded from an earlier Windows version).
The truth of the matter, though, is that the Redmond giant still offers that free Windows 10 upgrade path because it's in his best interest to do so. More Windows 10 PCs mean more telemetry data gathered, which in turn means more accurate troubleshooting on hardware and software. It means a larger userbase on which Microsoft can promote its own products and services, such as Edge or Office or Game Pass. It also means more user information gathered, which was one of the main reasons so many dozens of millions of people were reluctant to upgrade to Windows 10 in the first place. Even if one takes Microsoft on their word that it is not gathering personal data anymore - and that is a very, very big "if" - anonymous usage information is still extremely valuable.

The only relevant question that matters is obvious: should any of this deter 175 million consumers from upgrading to Windows 10? It is, after all, the best overall version of Windows available, despite its numerous issues. It's certainly the safest and most well-protected, which is more important than ever in this day and age. An affirmative answer would be an easy one under different circumstances, but Microsoft has burned through a lot of goodwill over the last five years and done too many mistakes for that to be as clear-cut as it should. Here's hope that now, amidst a global pandemic that's radically changing the computing landscape of the next decade, the Redmond giant can finally bear the responsibility for what it means to offer and support humanity's most popular operating system - and act accordingly.