Get your Windows 11 upgrade budget priorities in order now
Even if Microsoft’s newest OS doesn’t cost you a penny, you still need to have a solid plan in place

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We understand – moving to a new operating system is a seismic change. Once your organization is ready to migrate to Windows 11, your IT team will have a checklist that rivals your last receipt from your favorite chain pharmacy in length.

And as you draft your Windows 11 upgrade budget, you’ll need to:

  • Determine staffing costs for the migration itself.
  • Understand how the introduction of a new version of Windows into your environment will impact hardware maintenance and acquisition plans.
  • Build and schedule end-user employee training.
  • Figure out how you’ll pay for it all.

Here’s some key considerations as you allocate funds for Windows 11:

You can probably get Windows 11 for free

Depending on your licensing program, you can upgrade to Windows 11 as part of the licensing you already own. However, not all devices running Windows 10 are capable of receiving the Windows 11 upgrade.

Not sure which version of Windows your organization is using?

Windows 10 was released in July 2015, so if you’ve purchased new end-user hardware in the past eight years, your organization is probably ready to make the move to Windows 11 right now. If you’re still relying on an older version of Windows, it’s likely time for a hardware upgrade, too.

Do you rely on volume licensing on Windows Enterprise?

Additional upgrade licensing will be necessary. But if you have active Software Assurance on your Windows Desktop OS licensing – that is, an active Windows E3/E5 subscription or an M365 suite bundle that includes Windows Desktop OS – you will be entitled to Windows 11 Enterprise.

Adjacent costs to keep in mind

Once you’re ready to migrate to Windows 11, keep in mind that there may be some additional costs. Even if the actual operating system upgrade doesn’t show up as a line item on your budget, you’ll need to account for the following potential expenditures:

Outdated hardware

Now is a good time to take stock of your refresh timelines. How old are your laptops and PCs? Does it make sense to invest in new hardware instead of updating the OS on machines that are slated to be retired within the next twelve months?

Incompatible software

You may find that some of the mission-critical applications your end users rely on to conduct business are not compatible with Windows 11. Or if they are, you’ll need the most current version. We recommend that you compile a list of all the software your employees use, and research where each title stands with regard to Microsoft’s new OS. While this may be a small number of niche or legacy apps, as Microsoft claims a 99.7% app compatibility rate with Windows 11, it’s still best to check compatibility to avoid unwanted surprises.

Migration technicians

Who will perform the migration to Windows 11? Your own technicians? Contractors? A service provider? If you have a sizable end-user fleet, your migration services may come with a hefty price tag.

End-user training

We recommend investing in end-user training once Windows 11 is installed on everyone’s machine. End users must relearn how to perform certain functions each time a new operating system rolls out. Consider offering a virtual tutorial, rather than leaving your employees to flounder while they get used to the new look and feel of their computers.

It can’t wait

Even if you’re not ready to switch yet, keep in mind that Windows 10 will reach end of support on October 14, 2025. It’s never too early to prepare your Windows 11 upgrade budget or to figure out how it will influence your hardware, software, and training spend.

Our experts are here to help you plan, purchase, deploy, train, and manage your way through this significant update. Contact us today or reach out to your SHI Account Executive for guidance and support as your organization maps out a route to Windows 11.