Over the last few months, concerns regarding the slow transition of home users, business customers and IT support teams from the decade-old Windows 10 to Windows 11 have mounted significantly over the past few months.
Even though the older operating system reached its End of Support (EoS) date on 14th October 2025, this means that people outside of extended support will no longer receive upgraded features or security updates.
What makes this concerning is that there were an estimated half a billion users who were still using Windows 10. What makes this much worse is that computer giant Dell believes that the actual figure is more than double that, according to a recent earnings call published by The Motley Fool.
Whilst some of these may have subscribed to the Windows 10 Extended Security Updates programme, many others are left insecure, putting them at greater risk of viruses, hacking and other cyberattacks, which still leaves hundreds of millions of users with newly-unsafe systems.
There are a lot of reasons why this is the case, and IT support teams have had to navigate several pain points to find the ideal set-up for the customers they work for. After all, given that upgrading is as little as three clicks away, not using Windows 11 is often a deliberate choice.
What are the biggest pain points? Why have they been such dealbreakers? And what can Windows and tech support teams do to win this gigantic group over?
Would Lowering System Requirements Help?
The Dell earnings call noted that there was a roughly equal split between people who had chosen not to upgrade and those who could not upgrade.
The latter category highlights a problem that has stopped people from upgrading from the very start: the much higher system requirements.
In particular, the requirement for a Trusted Platform Module (TPM 2.0) and Secure Boot means that a lot of computers that are very capable of running Windows 11 will not pass the PC Health Check and thus cannot install it.
In practice, this has limited installations to computers that are less than six years old, and whilst many people and many organisations have three-to-five-year upgrade cycles, this does leave a lot of people who have a computer that works fine but cannot upgrade to a secure system.
Many companies prefer to upgrade in phases, but the requirement to replace hardware in one go can strain cash flow and cause further frustrations.
If your computer system is working for you and changing will cost both money and time to adjust, the EoS date seems less about major improvements to security and more about planned obsolescence, which reduces the willingness to do so.
What Are The Benefits Of Upgrading To Windows 11?
Some people cannot upgrade right now, some are unwilling to upgrade their hardware, and others still have a capable enough PC but still choose not to upgrade.
Why are people choosing not to upgrade to Windows 11?
To answer this, flip the question around: what reasons do the vast majority of users have to upgrade?
Many end users prioritise functionality over security, if they are forced to choose between one and the other, and many users are confused about why they need to change.
This situation mirrors to no small degree the problems surrounding Windows Vista’s launch in 2007.
Users did not initially appreciate the Aero desktop, the significant improvements to security and user access control led to nagging “Cancel or Allow?” requests, and the optimistic minimum system requirements led to many people complaining about lagging systems.
History has managed to repeat itself somewhat; PC Gamer reported that File Explorer was slow, users are somewhat lukewarm about Copilot and its potential for causing security exploits, and the interface has typically been regarded as a step backwards in both aesthetics and functionality.
It also does not help that Microsoft admitted, again, according to PC Gamer, that the chatbot-based system is vulnerable to prompt injection attacks, including PDFs with hidden instructions, malicious content in the UI of software and hiding prompts in poetry.
Does Windows 11 Need A Service Pack?
Microsoft has gone full steam ahead with its AI plans, perhaps in part because of its huge investments in AI and the fears of a potential financial bubble popping, as reported by Bloomberg.
However, this has led to a lot of fundamental functionalities breaking through updates whilst others are left to wither on the vine, frustrating users who just want their computers to work.
According to Dave Plummer, a former software engineer at Microsoft, Windows needs what he described as an “XP Service Pack 2 moment”.
Windows uses a more incremental approach of regular software updates rather than significant installable packages of upgrades, but what Mr Plummer means is that Windows 11 needs to pivot away from AI and add new features that executives believe users want.
Instead, they should focus on what users need: improved reliability, better performance, huge bugfixing efforts and prioritising fixing broken eements of the OS rather than adding new features.
This approach was remarkably successful with XP SP2, adding the Security Centre, a built-in pop-up blocker, activating Windows Firewall by default and laying the groundwork for the huge security updates in Vista such as Windows Defender.
In order to win back some of the billion users who have yet to upgrade, Microsoft needs to win back their trust.