Microsoft is officially in the blackmail business now

The company puts further pressure on consumers to leave Windows 10 for Windows 11 by setting vague deadlines and leveraging Office


Microsoft Windows 11
Microsoft made headlines again recently because of its plans regarding Office 365 support on Windows 10, but the truth is that the company has been handling the Windows 11 transition badly from the get go. (Image: Sunrise King, Unsplash)


It’s no secret that Windows 11 has not exactly been popular with consumers – in fact, given that Microsoft’s latest OS has been offered to hundreds of millions of Windows 10 users as a free upgrade, it’s fair to say that it’s been a resounding failure on several fronts. Windows 10, released almost 9 years ago, still commands more than 60% of the global Windows install base while Windows 11 has not even reached 35% yet, despite the fact that every new Windows PC sold since early 2022 is shipping with Windows 11.

This has been one of the roughest transitions in Windows history and one that could cost Microsoft precious market share in the years to come, even if Windows 12 turns out to be a great OS. The company knows this, which is why it’s been trying to have Windows 10 users upgrade to Windows 11, in various ways, over the past 18 months or so. Based on what most of them choose to do – that is, remain on Windows 10 – Microsoft has been largely unsuccessful in its efforts thus far, leading its management to extreme measures.

It’s latest tactic? Blackmail, pure and simple – on a scale never before seen in the tech industry. Here’s what this means and what choices consumers are left with in 2025.

What does Office have to do with anything?

It all started with a blog post published (since removed) in the Microsoft Community Hub, mentioning that when official support for Windows 10 ends – that’s October 14th of this year – support for the locally installed versions of all Office 365 applications will also end for this particular operating system (but obviously not for Windows 11). This means that Office apps running on Windows 10 will continue to work, but they will no longer receive feature updates or security updates, the latter clearly being the more important of the two.

There is no obvious technical reason why Office 365 applications cannot receive security updates on an older version of Windows.

While that blog post is not available anymore, Microsoft is stating the exact same thing in an official Office 365 support document recently updated. The company claims that “using Microsoft 365 on older, unsupported operating systems may cause performance and reliability issues over time”, which is conveniently vague.

People using MS Office for many years can attest to the fact that newer versions of this popular software suite have always worked fine on the previous Windows version at minimum. There’s no obvious technical reason why locally-installed applications cannot, at the very least, receive security updates (even if certain new features may indeed depend on the latest Windows core or components in order to work as intended).

Office 365
There’s no technical reason why Office 365 apps cannot receive security updates on Windows 10 even after October 14th, but it seems that Microsoft has no qualms about leveraging the vast customer base of its productivity suite in order to make another Windows 11 push. (Image: Ed Hardie, Unsplash)


It will certainly be interesting to see whether the company will enforce the same Office 365 limitation – it not being updated at all on Windows 10 after October 14th – upon customers who choose to be part of the ESU program. This program will allow individuals and companies to remain on Windows 10 and receive Extended Security Updates after October 10th in exchange for an annual subscription. These paying customers will probably expect proper Office 365 support on Windows 10, especially small businesses likely using Windows-based PCs so as to have access to the latest Office 365 applications.

If Microsoft does offer Office 365 security updates to consumers or businesses as part of the ESU program, it would mean that there’s no technical reason keeping those updates away from non-paying Windows 10 users. That limitation would be just another way to put pressure on consumers who want to use Office 365 without migrating to Windows 11 or an obvious way to literally blackmail those people into paying in order to keep using Office 365 while remaining on Windows 10. For, if a company is giving consumers a “choice” that isn’t really a choice if they are to use its products safely, how else would one call this tactic but “blackmail”?

Upgrading to Windows 11 for free also in doubt

In the same blog post that has been taken down Microsoft also noted, prominently, that the free Windows 11 upgrade is now offered to Windows 10 users “for a limited time only”, so the company is seemingly planning to deprive consumers of that option in the near future. This has never happened so soon before: every free upgrade period, from Windows 7 to Windows 8 to Windows 10, lasted – officially or not – for five, six, seven years or longer. It was in late 2023 (!), for instance, that Windows 7/8 keys ceased to legally activate Windows 10 installations.

Microsoft depriving consumers of the free upgrade from Windows 10 to Windows 11 in the future is another way of putting pressure on them today.

It seems, though, that Microsoft is so determined to put extra pressure on Windows users this time around – it’s no accident that it wants 2025 to be “the year of the Windows 11 PC refresh” – that it may actually stop offering that free upgrade path to Windows 11 on October 14th or even earlier. It would be an unpopular move, but not much is beneath this company’s management nowadays in terms of marketing tactics, so…

If history is any indication, then Microsoft may just announce the end of its “free upgrade offer” and then turn a blind eye to any Windows 10 user’s attempt at migrating to Windows 11 after October 14th. By suggesting, though, that it will officially deprive consumers of this option, the company is essentially trying to – again – blackmail hundreds of millions of computer users worldwide into installing Windows 11 within the time frame Microsoft needs, whether they want to do that or not.

Microsoft Windows 11
People have not been all than keen on upgrading to Windows 11 from Windows 10 – even for free – up until now, but they might change their minds when the latter stops being supported. That is, if Microsoft is still offering that upgrade after October 14th. (Image: Microsoft)


What Microsoft and its partners would prefer is for every single Windows 10 user to just go out and buy a new, Windows 11-based PC. But shouldn’t consumers be able to decide for themselves whether they actually need one of those without being pushed around? Since when do software companies get to determine when it’s time for consumers to purchase new hardware? It sounds ridiculous to even entertain that notion, yet here we are.

What are the choices available to Windows 10 users going forward?

Microsoft’s stance leaves little choice to Windows 10 users who need to keep using Office 365 safely and securely: they will have to either upgrade to Windows 11 or continue working with a version of MS Office that may be exposed to malicious software in the future. The MS Office user base is vast and the Windows 10 user base even more so. It’s really, really not hard to imagine hackers targeting any Office application vulnerability they discover and actually succeeding because so many people will almost certainly choose to remain on Windows 10 using Office binaries nor properly updated.

Windows 10 users will have no choice but to migrate to Windows 11 in due course, especially if they need to keep using Office 365 safely.

The company’s apparent plan to not allow upgrading from Windows 10 to Windows 11 at some point could have even more dire consequences. This approach will most probably lead to what happened during the transition from Windows 7 to Windows 10: when the older OS stops getting security updates it will be swiftly targeted by malware, viruses and other forms of hacker attacks, becoming a weak link in the Windows ecosystem as a whole.

Windows 10 users will then have no choice but to either migrate to Windows 11 or leave Windows behind for macOS or any one of several user-friendly Linux distributions widely available. The cost of the yearly subscription to Microsoft’s ESU program for Windows 10 is low ($30), but consumers will only be able to take advantage of it for one year. Businesses can do so for three years but – as Microsoft very well knows – it will eventually make sense for them to just upgrade to new, Windows 11-based PCs for easier deployment and management.

Microsoft Windows 11
Microsoft’s consumer-hostile tactics have been more and more aggressive over the last decade, so frustration online regarding many of is choices is palpable nowadays. This is something the company should not take lightly ahead of a future Windows 12 release. (Image: Microsoft)


If the company actually goes through with its plans – to weaponize the Office security updates and the free upgrade path from Windows 10 to Windows 11 so as to put pressure on hundreds of millions of consumers – it may find out that there’s a price to pay for that. The migration of its Windows 10 install base to Windows 11 has already been problematic due to the strict hardware requirements the company set from the start (a situation that’s an OS security ticking bomb all on its own). But Microsoft practically trying to blackmail consumers into adopting a version of Windows they don’t like really feels like a step too far – even by this company’s standards.

Here’s hope that Microsoft’s management will take a long, hard look at these plans soon and reconsider. If for nothing else, then for Windows 12’s sake… maybe?

ABOUT THE AUTHOR


Kostas Farkonas

Veteran reporter and business consultant with over 30 years of industry experience in various media and roles, focusing on consumer tech, modern entertainment and digital culture.

Veteran reporter and business consultant with over 30 years of industry experience in various media and roles, focusing on consumer tech, modern entertainment and digital culture.