In place OS upgrade

Microsoft has made In-place upgrades much more reliable than the days of Windows 95/98. I've seen them become a more popular option for physical servers in need of an OS update to remain in compliance, but otherwise no significant changes. 

If this is a VM, you may want to consider a zero-downtime migration as another option. https://thwack.solarwinds.com/resources/b/product-blog/posts/how-to-migrate-orion-to-a-new-server-with-zero-downtime

I do need to ask though, why 2012? Given that its end of mainstream support ended nearly three years ago and even the limited extended support window is quickly approaching, wouldn't Server 2016 or 2019 be a better choice? 

In place upgrade failed. Dependent services won't start at all. And then we had a good opportunity - got Win 2016 approved with MS SQL 2017 and we are up and running with brand new Orion 2020.2.5 platform. I have taken note on the THWACK article you shared previously, thanks much.

In place upgrade failed. Dependent services won't start at all. And then we had a good opportunity - got Win 2016 approved with MS SQL 2017 and we are up and running with brand new Orion 2020.2.5 platform. I have taken note on the THWACK article you shared previously, thanks much.