When installing vCenter update manager in a lab, I got this :
“Error 25005.Setup failed to generate the SSL keys”
It appears that since I have installed vCenter Server, vSphere client, and tried to install the update manager all in one sitting without rebooting, there has been some path confusion and it could not find openssl.exe (or the right version of it). Allowing it to roll back, rebooting, and trying again fixed the issue for me.
