We are decommissioning our ESXi hosts and plan to migrate several Windows Server 2019 Standard virtual machines to a new Proxmox environment. The licenses were obtained through TechSoup as retail or donated licenses. What licensing steps or restrictions should we be aware of when moving the VMs to different physical hardware? We are also planning to upgrade to Windows Server 2022 or 2025 next year.
3 Answers
Do not rely only on the product name in the TechSoup fulfillment email. Check the actual licensing agreement, the number of core licenses, the covered host hardware, and whether Software Assurance is attached. A VAR or managed service provider can usually validate the nonprofit purchase and help document the migration. Nonprofits can often buy Microsoft licenses through other authorized resellers as well, provided their nonprofit status is verified.
A Windows Server Standard license generally covers up to two virtual machines, but the license has to be assigned to and licensed for the physical host running those VMs. Make sure the host is properly licensed by its physical CPU core count, with a minimum of 16 cores per processor and 16 cores per server under the usual licensing rules. TechSoup purchases are sometimes made in core packs, so verify that you bought enough coverage for the new Proxmox host. Since this is a hardware move, it would also be wise to confirm reassignment rules and your specific agreement with a Microsoft licensing specialist or VAR.
If the licenses are perpetual licenses without active Software Assurance, they normally do not automatically grant rights to a newer release. You may need to purchase new 2025 licenses, although newer licenses can often run an older version through downgrade rights. Check whether Software Assurance was included and is still active before planning the 2022 or 2025 upgrade.

I am having trouble locating the agreement because the old licensing portal was moved into Microsoft 365. The fulfillment notice says automatic upgrades are available for two years for products covered by Software Assurance, so I am trying to confirm whether that applies to the seven Standard instances we received.