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Is it worthwhile to upgrade to Windows 11 right now?

As Microsoft prods its customers toward Windows 11, organizations should be asking what their approach to the new OS will be and when is best for them to migrate.

It has been nearly three years since Windows 11 was first released, and organizations should be far along with the process of evaluating when and how they migrate to Windows 11.

Although many organizations continue to run Windows 10, it's worth considering whether a Windows 11 upgrade is worth the cost and effort. Further, the upcoming end of life for Windows 10 in 2025 looms for IT administrators, and they need a concrete plan for how they'll handle it.

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.

A chart showing the different requirements between Windows 10 and Windows 11

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.

These are far from isolated incidents. With Windows XP, for example, there were issues with the activation process.

There are two important takeaways from these examples of OS issues:

  1. Not every Windows upgrade is problematic. While there have been plenty of disastrous upgrade attempts, there have also been plenty that went smoothly.
  2. 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 is overzealous with trying to force you to use a Microsoft account. 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.

Overall, Windows 10 is better in many ways because it doesn't nag the user as much to integrate further into the expanding Microsoft account-reliant environment and because it feels a lot less intrusive than Windows 11. Of course, that's just my opinion.

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 will no longer provide security patches for the OS. 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.

For right now, though, there is no word on precisely how much extended support for Windows 10 will cost. Microsoft said: "Final pricing and enrollment conditions will be made available closer to the October 2025 date for end of support, approximately one year before the end of support for Windows 10." However, Microsoft has announced that extended support will be free for Windows 365 customers.

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. Many industry analysts -- myself included -- expect Microsoft to announce Windows 12 later this year. If Microsoft makes that announcement, then the new version of Windows might be available before Windows 10's end-of-support date.

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.

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