Best practices for an in-place upgrade from Server 2008r2 to 2016/2019?

Solution 1:

If you must stay with the same hardware/machines, then a two-step upgrade is your only option:

2008 to 2012, then 2012 to 2016.

But, if you have a virtual infrastructure or can use additional hardware, you can treat this as a migration rather than an upgrade.

Build new SQL servers and new IIS hosts, and then migrate the applications rather than upgrade the OSes.

Solution 2:

I'm afraid not as there is no in-place upgrade path from 2008 to 2016. At least not from Microsoft. Not sure if there're 3rd party utilities out there to achieve this.