So, this has been baffling me for a bit. Trying to run some prep tasks to package a machine automatically, the last step is to sysprep. On a high level, I run a script on the "orchestration" server ...

I create the image, then run c windows\system32\sysprep\sysprep.exe. I choose OOBE, Generalize, and shutdown. Once the computer syspreps and shuts down, I capture the image using Acronis - you could ...