Thanks Andrew -- after further investigation, I was able to replicate what you're experiencing. That is a bug -- you should remain connected while the guest is rebooted and reconnected, and be able to see the login screen after reboot and reconnect. We'll have to look into this. 

I'll update here as we figure out what's going on!

- Caitlin 

Hi Andrew, 

Are you attempting to execute this during a support session or through unattended access? I've just tested this on my Mac with FileVault 2 enabled during an unattended access session. I was able to reconnect to the session as both host and guest after executing restart and reconnect. In my experience, the host remains connected. 

- Caitlin 

Hi -- sounds like your request can be handled by Auto Consent. If you're on a cloud instance, you can download the Advanced Configuration Editor and allow auto consent to your endpoints. Auto consent allows consent to control the machine if no user process is running on the guest machine. 

Hope this helps!