I was just in a very odd situation. I was a Jailor. I chose to jail 8. The Kidnapper chose to jail me.
On my screen I saw: My name and 8's name both showed normally (unmasked). The kidnapper's name was masked as Jailor, as it should be. There were 3 of us in the chat.
On 8's screen: He could not see ANYTHING anyone typed. He was talking to himself, but he was jailed.
On the Kidnappers screen: He only saw me in his cell. He had no idea that 8 was 'in there with me'.
This can't be the intended mechanics...
I have attached the replay:
The hotkey for the Kidnapper is E
The hotkey for my screen (Jailor) is 5
The hotkey for 8's screen is CTRL+6
Edit: The event happened on Night 2.