With Windows 10 end of support now past, enterprises must evaluate whether to upgrade to Windows 11 based on hardware readiness, application compatibility and lifecycle planning.
It has been more than three years since Windows 11 was first released, and following the October 2025 end of support for Windows 10, many organizations are now actively executing or finalizing their Windows 11 migration strategies.
Although many organizations still run Windows 10 in production environments for legacy applications or hardware constraints, it's worth considering whether a Windows 11 upgrade is worth the cost and effort.
Challenges of upgrading to Windows 11
Those who have never overseen an OS upgrade within a corporate environment might not fully appreciate just how challenging it is. There is far more to the upgrade process than just inserting installation media and running the setup or pushing a new Windows image to any managed endpoints. Although the purpose of this article is not to provide a migration guide, it's worth examining all the details involved in upgrading Windows desktop OSes.
One of the first things that an organization must do before updating its endpoints to a new version of Windows is to perform a comprehensive hardware inventory to ensure that the existing hardware is compatible with the new OS. For the most part, Windows 10 and Windows 11 have similar hardware requirements, but there are some key differences to consider.
Organizations must also test every application that users rely on for business workflows to verify that the application will run on the new OS. This testing process involves more than just making sure that admins can install the application and load it properly. Organizations must perform comprehensive testing to make sure that all the application's features still work properly.
To provide a more concrete example, I oversaw a recent migration of all my production systems to Windows 11 earlier this year. In doing so, I discovered that a particular computer-aided design (CAD) application initially seemed to work with Windows 11. However, I later discovered that the CAD software's 3D capabilities could no longer function because they were not compatible with high dynamic range video. I ultimately ended up switching to a different CAD package.
Although application compatibility testing is probably the biggest task that administrators must perform prior to an OS upgrade, it's far from being the only such task. Organizations should ensure they train users on how to use the new OS. Further, organizations must provide training to the help desk staff and to anyone in the IT department who will be responsible for supporting the new OS.
Comparison of Windows 10 and Windows 11 hardware requirements, including TPM 2.0, Secure Boot and memory minimums that affect enterprise upgrade planning.
What issues are common with a Windows migration?
It's extremely important for an organization to thoroughly test a new OS before it fully commits to an upgrade. OS upgrades sometimes need to be paused or even halted altogether as a result of issues found during the testing process.
When Windows 2000 was released, my former employer had planned to deploy it within one particular department. However, someone had put into the documentation that no device drivers existed for some of the special-purpose hardware that the department used. As such, the Windows 2000 adoption had to wait.
Similarly, when Windows Millenium Edition (ME) was released, the organization where I worked at the time planned to deploy it. However, testing revealed that Windows ME was incredibly unstable, crashing frequently. As such, the organization completely abandoned its plans for a Windows ME migration.
Going even further back, I once worked for an organization that was running Windows 95 and wanted to upgrade to Windows 98. Although its PCs were theoretically capable of running Windows 98, installing Windows 98 caused the machines to slow to a crawl because the PCs barely met the minimum hardware requirements. The organization postponed the upgrade until the next hardware refresh.
There are two important takeaways from these examples of OS issues:
Not every Windows upgrade is problematic. While there have been plenty of disastrous upgrade attempts, there have also been plenty that went smoothly.
When it comes to real-world OS migrations, things can -- and sometimes do -- go wrong. The best way to keep that from happening is by working through a comprehensive testing process, followed by a small-scale pilot deployment.
Is it worthwhile to migrate to Windows 11 now?
There are sometimes issues that occur as a part of an OS upgrade, so organizations must consider whether keeping pace with the latest OS to come out of Microsoft is worth dealing with any potential issues that might come with it.
Most of the issues that come with Windows 11 migrations have been hardware-related. Most notably, Windows 11 requires the presence of a Trusted Platform Module 2.0 chip and Secure Boot has to be enabled. However, these are not the only hardware-related differences. Unlike Windows 10, Windows 11 requires a 64-bit CPU. Additionally, Windows 11 requires 64 GB of storage, compared to the 20 GB needed by the 64-bit version of Windows 10. Windows 11 also requires twice as much memory -- 4 GB compared to 2 GB -- as the 64-bit version of Windows 10.
Although there are many people who prefer Windows 10, a migration away from Windows 10 seems all but inevitable.
In my environment, I rolled out Windows 11 as a part of a hardware refresh, so the hardware requirements were a nonissue. Even so, many people view the Windows 10 experience as superior. Windows 11 places greater emphasis on Microsoft account integration and cloud-connected features than previous versions. In some cases, this requirement is tough to avoid, even if the machine will eventually be joined to a domain.
Windows 11 is also a lot worse than Windows 10 about nagging you with constant notifications -- though, for the most part, you can disable these notifications. Windows 11 also seems to make it more difficult to protect your personal privacy. Administrators can lock down Windows 11 to prevent it from compromising user privacy, but doing so involves adjusting a lot of individual settings. Even after all that work, it's easy to accidentally undo your privacy efforts as the OS uses the local Microsoft account or Microsoft 365 account to log the user in to the Edge browser.
Is Windows 11 inevitable?
Although there are many people who prefer Windows 10, a migration away from Windows 10 seems all but inevitable.
After all, Microsoft is discontinuing official Windows 10 support on Oct. 14, 2025. While an organization could conceivably continue running Windows 10 beyond the end-of-support date, doing so might not be practical for a few different reasons.
The most obvious reason is because, at that point, Microsoft has shifted its focus to Windows 11 licensing for new devices, making Windows 10 licenses increasingly limited and harder to obtain through standard channels. This means that Windows 10 will become vulnerable to any new exploits that are discovered.
A second reason why it might not be practical to continue running Windows 10 past the end-of-support date is because, although Microsoft will likely offer extended support for Windows 10, it may be cost-prohibitive. This has happened in recent years, particularly with Windows Server OSes. Microsoft puts a high price tag on extended support as a way of pushing customers toward the adoption of a new OS.
Extended support for Windows 10 is now governed by Microsoft’s ESU licensing structure, and pricing and eligibility vary based on licensing agreements, device counts and deployment models. Organizations should confirm current ESU terms directly with Microsoft or their licensing provider, as costs and enrollment conditions may change over time.
A third reason why a transition away from Windows 10 may be inevitable is because Microsoft no longer sells Windows 10 licenses. It is still possible to purchase licenses from some third-party resellers, but Windows 10 licenses are becoming increasingly difficult to acquire. That means that an organization will most likely be stuck running Windows 11 on any newly acquired PCs.
Even though a transition away from Windows 10 might end up being inevitable, Windows 11 adoption might not be the only option. Some industry analysts have speculated about future Windows releases, but enterprise migration planning is still primarily centered on the Windows 10 end of support and the transition to Windows 11.
Brien Posey is a 22-time Microsoft MVP and a commercial astronaut candidate. In his over 30 years in IT, he has served as a lead network engineer for the U.S. Department of Defense and as a network administrator for some of the largest insurance companies in America.
