How often do you actually need to upgrade Windows Server?

Ask what the next upgrade is supposed to accomplish. If there is a feature you need, a compatibility requirement, or a support deadline you are planning around, that gives you something concrete to weigh against the work and downtime.

Being on the newest release is not much of a reason by itself. A multi-year plan with a mix of supported versions can spread the migrations out instead of turning them into a permanent project.

Separate new builds from existing servers. It can make sense to test 2025 and use it for suitable new deployments, while leaving working 2022 servers alone. For the remaining 2019 systems, consider whether moving directly to 2025 fits the application and migration requirements.

That does not mean changing the plan halfway through without testing. Check the supported upgrade paths and application compatibility first, and factor in the cost of revising work already underway.

Be especially careful with domain controllers and authentication. There have been reports of trouble with 2025 domain controllers in mixed environments, particularly where older Kerberos or NTLM configurations are involved. That is not the same as saying every 2025 deployment is broken.

Test the domain controller role and the applications that authenticate against it in a representative environment. A successful test of a basic member server does not tell you much about those dependencies.

If there is no pressing need, sticking with 2022 for now is a reasonable choice. Start evaluating 2025 on less critical workloads and give the team time to find compatibility or performance problems before making it the default everywhere.