Microsoft's product support timelines have always ticked away quietly in the background—but as 2026 approaches, those ticking clocks are starting to matter a lot more. A growing list of Windows editions, Office releases, and enterprise tools are heading toward end-of-life, and for many users, the impact goes far beyond simple version numbers.

Even though millions of PCs are still running older software comfortably, Microsoft's support policies are steadily pushing users forward. And with several widely used products set to lose security updates in 2026, the questions around safety, upgrade costs, and long-term viability are becoming harder to ignore.

What "End of Support" Really Means

When a Microsoft product reaches end of support, it doesn't suddenly stop working. You can still boot your PC, open documents, and run applications just as before. The real issue lies under the surface.

Once support ends, security updates stop arriving. That means newly discovered vulnerabilities remain unpatched, leaving systems increasingly exposed over time. For personal users, this raises security risks. For businesses, especially those in regulated industries, it can quickly become a compliance problem.

Windows 11 24H2 Is on the Countdown

One of the biggest upcoming milestones is the end of support for Windows 11 version 24H2, scheduled for October 2026. That's roughly a year after standard support for Windows 10 ended, continuing Microsoft's push toward faster OS turnover.

Microsoft has already begun nudging some systems toward Windows 11 version 25H2, and before long, upgrading will no longer be optional for users still on 24H2. That transition may feel underwhelming for some, as the newer release introduces mostly incremental changes rather than major new features.

The Quiet End of Windows 11 SE

The end of Windows 11 24H2 also marks the final chapter for Windows 11 SE. This edition was introduced in 2021 as Microsoft's answer to ChromeOS—a lightweight, cloud-first operating system aimed at low-cost education laptops.

Because 24H2 is the last Windows version compatible with SE, its retirement effectively ends the platform altogether. Schools and institutions that adopted Windows 11 SE will need to plan migrations sooner rather than later, especially if device refresh cycles haven't caught up yet.

Enterprise and Education Editions Aren't Exempt

It's not just consumer editions feeling the pressure. The 23H2 releases of Windows 11 Enterprise, Education, and IoT Enterprise are scheduled to stop receiving updates in November 2026.

On the server side, several editions of Windows Server 2022 will shift from "Mainstream Support" to "Extended Support" on October 13. While this still includes free security updates, it signals the beginning of the long tail toward eventual retirement—something IT teams usually factor into multi-year infrastructure planning.

Office 2021 Reaches the End of the Line

October 13, 2026 also marks the end of the five-year support window for Office 2021. That includes both the standard standalone version and Office LTSC 2021 for Windows and Mac.

For users who deliberately avoided subscriptions, this is a key turning point. To continue receiving security updates and feature improvements without moving to Microsoft 365, the only path forward will be upgrading to Office 2024.

Office 2024: More Expensive, Modest Improvements

Office 2021 has often been heavily discounted, sometimes selling for as little as $35. Office 2024, by contrast, comes with a much steeper price tag. A lifetime license typically costs around $150, though current pricing sits closer to $120—with far fewer deep discounts so far.

Feature-wise, Office 2024 brings practical but not revolutionary upgrades. Word gains support for ODF 1.4, improved collaboration tools, and better document recovery. Excel introduces new array functions designed for complex data handling, while PowerPoint leans further into multimedia with voice recording, ink annotations, captions, and enhanced video tools.

For some users, these additions justify the upgrade. For others, the higher price raises questions about how long standalone Office will remain attractive compared to subscriptions.

Other Microsoft Products Ending Support in 2026

Beyond Windows and Office, several long-standing Microsoft products are also set to reach end-of-life in 2026:

For organisations still relying on these platforms, the coming year is less about upgrades and more about migration strategy.

Planning Ahead Matters More Than Ever

Microsoft's 2026 roadmap makes one thing clear: holding on to familiar software is becoming increasingly costly in the long run. Whether it's upgrading Windows versions, moving to newer Office releases, or replacing deprecated enterprise tools, the transition workload is stacking up.

For individuals, this might mean budgeting for a new Office license or accepting automatic Windows upgrades. For businesses and institutions, it's a reminder that lifecycle planning isn't optional—it's essential.

As 2026 approaches, the safest move isn't waiting to see what breaks, but deciding early which upgrades make sense and which legacy systems finally need to be left behind.