Windows Server 2016 has been on the road to retirement for years. Mainstream support ended in January 2022. Extended support ends 12 January 2027. For organisations still running it — and there are more than the industry likes to admit — the migration runway is shorter than it feels.
The practical question for an SMB is rarely whether to migrate but where to migrate to. Windows Server 2022 is the safe upgrade. Azure Arc-managed instances and AVD-hosted application servers are increasingly the answer for workloads being modernised rather than lifted. For some line-of-business apps, the migration is a forcing function to evaluate whether the workload still belongs on a Windows server at all.
The wrong move is doing nothing and discovering, in late 2026, that the migration window is now a fire drill rather than a planned project. Inventory what's running, age it, plan the transition. Quiet work, but the kind of work that prevents loud problems.