Issues with Inplace Upgrades from 2012R2 to 2019

HPE Insight Management Agent needs upgrading , latest here : Software Details – HPE Insight Management Agents for Microsoft Windows Server x64 Editions | HPE Support ,does not support 2019 so you have to extract and install MSI manually
Breaks AD Connect
Breaks NPS Azure Radius ( needs to run repair on installer )
Document the firewall status before upgrade ( whats enabled on what profile )
TS Upgrades ( works with 2019 as well ) -> Upgrading your Remote Desktop Services deployments to Windows Server 2016 | Microsoft Docs
Your SMTP Virtual services configuration will be wiped out during an in-place upgrade.
When upgrading fileserver server with DFS , I had to manually start the DFS Server
Need to fix WDS Service
WSUS needs to be rerun after upgrade ( Settings are kept )
Rerun Veeam Agent Config if you have it installed
If stuck on “91%” , Just wait!

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