Windows 11 Upgrade Dilemma: Are You Ready for October 2025?

In a move that could have wide-reaching implications for nearly half a billion Windows users, Microsoft has laid bare its future roadmap for Windows operating systems—and it's not all sunshine and rainbows for many. If you're a Windows 10 user, especially one clinging to incompatible hardware, now may be the time to rethink your game plan. Here’s the scoop, dissected and explained, so you can prepare for the upcoming changes.

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The Big Picture: The Upgrade Push and What's Behind It​

Microsoft is ramping up its efforts to ensure users transition from the now-dated Windows 10 operating system to Windows 11. Why? Because Windows 10 is marching toward end-of-support in October 2025, with some extended support options rolling over until October 2026—for a price. Traditionally, an operating system nearing its expiration date sends most users scrambling to upgrade, but there’s been a surprising twist this time around.
Rather than seeing a steady migration, the curve has reversed—Windows 10’s market share has increased globally from 61% to 62%, while Windows 11 dipped slightly from 35.5% to under 35%. In the U.S., the numbers are even more pronounced, with Windows 10 jumping from 58% to 61%, and Windows 11 slipping under 37% after six months of momentum. So, what’s going on?
Let’s break it down.

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Why Aren’t People Upgrading to Windows 11?​

Here are four main reasons:

1. Hardware Incompatibility: Not all machines—400 million, to be precise—meet the hardware requirements for Windows 11, particularly the contentious need for TPM 2.0 (Trusted Platform Module 2.0). While users can sometimes bypass these restrictions, Microsoft has warned that doing so could have dire consequences, including no updates, invalidated warranties, and possible functionality issues.
   • What is TPM 2.0?
   Simply put, TPM 2.0 is a hardware-based security measure. It provides advanced encryption and key management capabilities crucial for features like Secure Boot, BitLocker, and Windows Hello. Without TPM 2.0, your PC is essentially more vulnerable to exploitation. For Windows 11, Microsoft insists that it’s non-negotiable as part of their broader Zero Trust security strategy.
   []Extended Support Option: Many users are opting to buy themselves more time. Microsoft announced that it will offer a 12-month extended support option for $30 per PC starting October 2025. This means users can stay comfortably on Windows 10 while still receiving crucial security updates.
   []AI-PC Fatigue: Microsoft has pitched Windows 11 as integral to the future of AI-powered computing, but as of now, many users don’t see enough value in upgrading to a higher-priced AI-ready PC when the features feel half-baked or underwhelming.
2. Windows "Nagging" Fatigue: Frequent pop-ups and reminders urging users to upgrade have started to annoy rather than motivate. In the tech world, less push often means users will eventually buy in organically—but Microsoft seems to have missed that memo.

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What Happens to the 400 Million Incompatible Machines?​

Here’s the sobering bit of news: It appears Microsoft isn’t budging on its minimum system requirements for Windows 11. Machines that don’t meet these requirements are being pushed toward obsolescence. Without an upgrade, these devices will lose security patch coverage and could end up as risky propositions for users continuing day-to-day operations.

Are You at Risk?​

If your PC doesn’t support Windows 11 natively, consider these options:

• Keep Windows 10 with Extended Support: Pay $30 annually per machine to stay protected until October 2026.
• Upgrade Your Hardware: Microsoft and its hardware partners will eagerly sell you a shiny new PC equipped with all the bells and whistles.

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The Recall Problem—Microsoft’s AI Jewel Is… Broken?​

Part of Microsoft’s Windows 11 value proposition is the integration of new AI-powered features, such as Copilot and Recall. For those unfamiliar, Recall is a hyped feature that captures and indexes screenshots automatically to help users search through their digital history using AI. Unfortunately, it's suffering from serious bugs even during its Insider Testing phase.
As reported:

• Recall Refusal to Save Snapshots: Insiders testing the feature have noted that the tool simply fails to save the snapshots it takes.
• KB5046740 Causing Mayhem: A preview update released in November conflicts with Recall, leading to the feature’s malfunction in some systems.

While Recall is not yet officially released, Microsoft’s struggles with it have exposed underlying issues. For a feature that doubles down on privacy concerns due to its deep system-level integration, bugs like these become glaring. It's a hard sell for users who would need to spend hundreds—or thousands—on hardware upgrades to enjoy such AI gimmicks.

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The Broader Implications for Microsoft (And You)​

For Microsoft, convincing more users to move to Windows 11, and by extension new hardware, isn’t just about updates—it’s about securing their foothold in the growing market for AI-integrated devices. Sluggish migration rates spell potential trouble for Microsoft’s long-term ambitions. After all, shiny new features like Recall and Copilot mean little if the majority of users stick to Windows 10.
But for you, the everyday user, it’s a balancing act:

1. Stay on Windows 10, pay the extended support fees, and take no risks.
2. Make the leap to Windows 11, either by upgrading your PC or slogging through unsupported workarounds.
3. Delay your decision until AI features like Recall actually ship, unbroken, and prove their worth.

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Conclusion: Your Next Steps as a Windows User​

The chaos surrounding Windows 10’s looming end-of-support deadline and the haphazard rollout of some Windows 11 features has exposed a bit of a weak spot in Microsoft’s strategy. More than anything, it’s rewriting the playbook for OS obsolescence: where upgrades are being dictated not by user adoption but by hardware limitations and AI ambitions.
So, what should you do today? First, check your system’s compatibility for Windows 11. You can use Microsoft’s built-in tool or check the TPM 2.0 status manually. Then, weigh your options around extended support, necessary upgrades, or simply biding your time.
October 2025 may seem far away now, but as the urgency grows, so too will the need to make a decision.
And for now, maybe disable those Windows 11 pop-ups before they drive you insane. Stay safe and happy computing!

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Source: Forbes Microsoft’s New Update—Bad News Confirmed For 400 Million Windows Users