Upgrade: Windows 2008 to 2012 and 2019 (VMs)

Reference

https://techcommunity.microsoft.com/t5/itops-talk-blog/how-to-in-place-upgrade-windows-server-2008-r2-to-windows-server/ba-p/752330

https://www.nakivo.com/blog/hyper-v-generation-1-vs-2/

Pre-requisties

  • Need at least 20GB free space on VM
  • Make sure you have local username and password (not AD)
  • Use Shadow for good backup
  • Uninstall Shadow and anti-virus
  • Take Hyper-V Snapshot

Overview (2008 to 2012 Gen1)

  • Use 2012 ISO in 2008 VM
  • If DC: 'support' > 'adprep' > 'adprep.exe' - Drag to command prompt
    • /forestprep
    • /domainprep
  • Run setup/upgrade
  • Upgrade (3 reboots)

Notes

  • 2008 to 2012; (2012 Gen 1 to 2012 Gen2); 2012 to 2016/2019
  • 2008 VMs are Gen 1 - Ideally convert to Gen 2 (2 phase process)

Overview (2012 Gen 1 to 2012 Gen 2)

  • Backup using Shadow
  • Restore to VHDX
  • Create new VM using Gen 2, appropriate disk space
  • Boot VM into Storagecraft Recovery Edition (ISO)
  • Ensure Disk Map is GPT
  • Restore to GPT partitions
  • Use HIR
  • May need legacy NIC
  • ** IMPORTANT: If DC, first boot into Directory Services Recovery Mode'