Get ready for Windows 11 with these tips

The Microsoft Windows 11 release date of October 5 is looming, which means serious deployment planning is underway at many organizations, and there’s a lot to think about before diving into any new operating system.

Here are a few things to consider:

Will the hardware even run Windows 11?

First thing first – will your computers even run Windows 11? If not, the discussion may have to segue to whether you can afford to replace incompatible machines now, or whether it’s time to start budgeting for new machines next year. For those with a large stable of incompatible hardware, or who prefer not to upgrade, never fear – Windows 10 support continues until October 14, 2025.

Microsoft provides several ways to determine if computers are compatible. The PC Health Check app that checks PC compatibility with the new OS is finally available again, after having been pulled in June over complaints about its poor reporting of PC status. If you use Microsoft Endpoint Manager, the September release includes a compatibility assessment tool. Failing those, you can rely on the published specs to determine whether your machines can cope.

But even if they pass the test, there are many other factors to take into account before allowing even compatible systems to update.

And you will have a choice; when KB5005101 (now in preview) is final, it will add an update to Group Policy settings that allow you to select the OS and version you want to keep. Choose Windows 10, and the Windows 11 upgrade will be blocked. Note, however, that since Windows 10 Home does not support Group Policy, if you have any Home versions in your stable, each machine will need a Registry tweak to accomplish the block.

What to look at

Now that you know the hardware supports the OS, it’s time to consider whether the software you run can cope. Microsoft has released testing guidelines for applications to help you determine if there will be issues.

  • Check your security software. If Microsoft Defender is your default, you’re likely fine, but make sure any other vendors you use have vetted their products on Windows 11 and support the new OS.
  • Check your productivity software, be it Microsoft Office or Google Workspace, or something else. Does each component run properly, and do functions work as expected?
    If you run Microsoft Office, be aware that as of November 1, only Office 2013 service pack 1 and above will be able to connect to Microsoft 365 services, regardless of the operating system.
  • How about your accounting, ERP, CRM, and so forth. Most cloud-based products will likely work (but test them anyhow); look harder at the older on-prem systems that may have been quietly running on a machine in the corner.
  • The daily use stuff is easy(ish) – you usually know what it is; now identify and check that intermittently-used products such as tax software will support Windows 11. If not, you may have to keep at least one machine on your current operating system for the time being.
  • Microsoft says its management tools will manage both Windows 10 and Windows 11. What about your third-party tools?
  • Are you running anything in virtual machines (VMs)? Windows 11 running in VMs has the same hardware requirements as bare-metal installations. Microsoft originally said it would not enforce hardware compliance for VMs but has since reversed its stand. Additionally, Microsoft Hyper-V VMs need to be Generation 2 VMs, and some hypervisors, such as Oracle’s VirtualBox, which doesn’t provide trusted platform module (TPM) tech, just plain won’t work. Have a chat with vendors and do some testing to prevent nasty surprises.

Do you really need to buy a TPM for Windows 11?

Windows 11 release date announced; no Android app support at launch

  • If you find application incompatibilities, take advantage of Microsoft’s App Assure with FastTrack. It’s free for eligible companies with 150 or more licenses. With enrollment in the App Assure service, any app compatibility issues that you find with Windows 11 can be resolved; Microsoft will help you remedy them at no cost.
  • For software publishers, systems integrators, and IT administrators, Test Base for Microsoft 365 (currently in private preview) is a service that allows you to validate your apps across a variety of Windows feature and quality updates and environments in a Microsoft-managed Azure environment.

Don’t forget the people

Although Windows 11 looks a lot like Windows 10, there are enough differences that you’ll need some user training with. To assist you, Microsoft’s Help and Learning site will provide instruction on Windows 11. Currently, the Windows 11 page just says “Coming soon”; check out the Windows 10 page to see what’s on its way.

It also helps to upgrade a few power users or eager volunteers first, assuming the application software they use is compatible. Once they’re comfortable with the OS, they can encourage and assist colleagues.

Don’t forget your service desk techs – they’ll be the ones fielding questions about everything from the upgrade experience to where on earth one can now find – well, pretty much anything. Windows 11 is just different enough to confuse users who aren’t comfortable with new things.

Don’t panic

Windows 11’s rollout will be phased. It will begin with newer machines, and slowly proceed over the next months, ending in mid-2022. You have time to do a proper evaluation (and Microsoft has time to fix initial hiccups); you can block the upgrade now and allow it once you’re confident nothing will break. And for new computers that come with unwanted Windows 11, enterprise customers will have downgrade rights to Windows 10.


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Jim Love, Chief Content Officer, IT World Canada

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Lynn Greiner
Lynn Greiner
Lynn Greiner has been interpreting tech for businesses for over 20 years and has worked in the industry as well as writing about it, giving her a unique perspective into the issues companies face. She has both IT credentials and a business degree

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