In recent weeks we had a couple of discussions with customers planning to upgrade from SharePoint Server 2016 to SharePoint Server 2019.
What was interesting to hear was that some customers were not aware that SharePoint Server 2016 and 2019 will both reach end of support on the same day: July 14th, 2026
As SharePoint Server 2016 can be directly upgraded to SharePoint Server Subscription Editon (unlike earlier versions where it was unsupported to skip an intermediate product version) upgrading from SharePoint Server 2016 to SharePoint Server Subscription Edition is not more complex as upgrading to SharePoint Server 2019.
Also keep in mind that SharePoint Server 2019 will reach end of mainstream support next year in January – just 6 months from now. After this date only security related fixes will be released.
Planning a migration from SharePoint Server 2016 to 2019 would require a very good reasoning which would not include the support lifecycle.
The general recommendation is to plan upgrades for SharePoint Server 2016 to Subscription Edition rather than SharePoint Server 2019.