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To do a rolling upgrade of an Availability Group from Windows 2012R2, SQL 2012 to Windows 2019, SQL 2019 do I have to have an intermediary set of servers on Windows 2016? Based on the documentation it sounds like you can only go up one version (verbiage: "You can upgrade to the next version"). The only clustering component is for the Availability Group, no other roles and no services are clustered. I know SQL can go directly to 2019, it is the clustering component of the AG I am unsure about.

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You are correct. For a Windows Cluster, you can only upgrade to the next version. Even though the Availability Group is the only resource, it is still built on Windows Clustering and must follow those upgrade rules. SQL Server can be upgraded anytime before or after upgrading the cluster.

So if you need to get from Win2012R2 to Win2019, then you would follow these basic steps.

  1. Upgrade all cluster nodes to Win2016
  2. Update the cluster function level to 2016
  3. Upgrade all cluster nodes to Win2019
  4. Update the cluster function level to 2019.

https://learn.microsoft.com/en-us/windows-server/failover-clustering/cluster-operating-system-rolling-upgrade

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