Organizations that use Windows for many desktops and VMs already understand how to work with Microsoft for volume licensing of OSes, applications and services, but migrating from Windows 10 to Windows 11 can create further licensing questions for IT teams.
Given the Oct. 14, 2025, end-of-life date for Windows 10, the plan for migrating to Windows 11 should already be in the works. In some instances, the migration to Windows 11 will be a simple process, but if organizations need to purchase new endpoints to run the OS or change their licensing plan, there will be more work for IT to do.
How to acquire Windows 11 licenses
Planning a Windows 10-to-11 transition requires an understanding of an organization's current or planned licensing arrangements with Microsoft. The good news is that, under existing licenses, organizations can switch over from Windows 10 to 11 without renegotiating those arrangements, so long as they want to keep the same licenses. Because it's already free to upgrade eligible hardware with a valid Windows 10 license to Windows 11, there are no added costs for making the transition from the older OS version to the new.
That said, it may be smart to take the opportunity to review current licensing terms and conditions to see if a change in OS could also warrant expanded licenses for added access to business software and services. Or, of course, organizations could opt for cheaper licenses, getting rid of unneeded features.
Microsoft's licensing arm operates a website that provides reams of information about licensing arrangements. Existing customers can investigate their current arrangements, associated costs, durations and renewal requirements by logging in to their Microsoft licensing accounts. New customers, or those who wish to investigate additional options, can use the Research Licensing feature from the site's homepage to determine the options available to them.
Organizations have at least five major programs through which they can license the Windows OS. Microsoft's subscription plans for Microsoft 365 are one of the more all-encompassing versions of that as most of them include a Windows OS license, all Office productivity apps, OneDrive cloud storage, and automatic updates and upgrades provided as a managed service. Customers that want licenses that can work on Mac desktops can even opt for a virtual Windows license or go with a more stripped-down version of the service that serves macOS directly.
In the Microsoft licensing world, users need licenses to run Microsoft 365 on up to five PCs and laptops, five tablets and five mobile devices. As long as each user has a license, they can share devices that run Microsoft 365 as well.
How much does it cost to license Windows 11?
Because of its great flexibility and built-in updates and management, Microsoft 365 is a compelling option for future-focused licensing arrangements. Simply put, Microsoft 365 lets users do what they've always done on PCs, but it also lets them use phones, Macs and tablets to perform work tasks. Microsoft documents its Windows 365 plans and pricing online and offers a wide range of virtual PC configurations at a range of per-user monthly subscription costs that range from $32 for two virtual CPUs, 4 GB RAM and 64 GB storage, to $158 for eight vCPUs, 32 GB RAM and 512 GB storage.
Compare this to the average licensing costs for Windows 10 or Windows 11 on a per-PC basis, which is typically an Enterprise, Enterprise E3 or Enterprise E5 license. Microsoft License Advisor is a good place to start estimating license costs of all kinds, including OS-only and OS plus applications selections.
OS-only licenses generally cost upward of $150 per user, and OS plus Microsoft Office tends to cost upward of $280 per user. Prices may decline somewhat as user counts increase. This would indicate an incremental cost of at least $110 per user, per year for a lowball virtual PC, up to $1,600 per user, per year for a high-end virtual PC based on the previously disclosed estimates.
The real issue, of course, is that organizations must negotiate volume licensing prices on a per-case basis. Organizations need to reach out to Microsoft or a Microsoft Partner to get real pricing information for their specific situation and needs.
One key element of total cost of ownership (TCO) is maintenance and support, and Microsoft takes over much of this burden depending on the specific plan when organizations subscribe.
Calculating TCO for Windows 11 migrations
Anybody who has been through prior Windows migrations -- especially those involving Windows 8.x -- already understands that planning for and performing a migration brings costs of its own into the picture as well. These costs include piloting Windows 11 deployments in a lab situation and compatibility and usability testing for all the applications and services that users need across devices and OSes.
There's a tremendous amount of work involved in ensuring that a transition does not disrupt normal workflows and activities. IT teams and data entry clerks have different profiles from software developers, IT support staff and executives, which all have slightly different needs.
Other factors that contribute to the cost of a Windows 11 migration are the following:
- Hardware refresh for systems that don't meet minimum Windows 11 requirements. According to various studies, somewhere between 40% and 50% of all PCs in the current business landscape do not meet these stipulations at the time this publishes. The primary culprit of the incompatibility is lack of Trusted Platform Module 2.0 and how modern the device's CPU is. The total cost of a refresh varies according to the needs of the targeted users but is seldom less than $1,000 per user.
- Training and familiarization costs for admins, support and users. Admins generally come first so they can work on migration planning and deployment. Support staff should come next so they're ready to help users when they make their individual transitions. Users come last as transitions are about to occur with access to materials and information thereafter. The numbers go up as the levels increase, but the amount of training and time needed goes down. That said, time and costs involved can be considerable but are best planned for and incurred to ease the transition process.