Issues with Inplace Upgrades from 2012R2 to 2019

  1. 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
  2. Breaks AD Connect
  3. Breaks NPS Azure Radius  ( needs to run repair on installer ) 
  4. Document the firewall status before upgrade ( whats enabled on what profile ) 
  5. TS Upgrades ( works with 2019 as well )  -> Upgrading your Remote Desktop Services deployments to Windows Server 2016 | Microsoft Docs
  6. Your SMTP Virtual services configuration will be wiped out during an in-place upgrade.
  7. When upgrading fileserver server with DFS , I had to manually start the DFS Server
  8. Need to fix WDS Service 
  9. WSUS needs to be rerun after upgrade ( Settings are kept )
  10. Rerun Veeam Agent Config if you have it installed

  11. If stuck on “91%” , Just wait! 
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