I'll try that when it happens again. Thanks

The OS runs Windows 2008 R2 , on a Oracle's Virtualbox, so I wouldn't consider this being a headless Windows installation, why? When you first create your keypairs it goes pretty fast usually under 5 mins. But if you recreate or try an create a new keypair it never completes, takes 20+ minutes or longer. But if you shut down the OS, or restart the OS, and try it again then it completes in under 5 mins.