Which screen are you seeing when you finish the second room (and when you get looped back)?
Viewing post in The Greatest Escape(room)! comments
It just says "Bad End: Last Shift", and gives the option to try the room again or go to main menu. I've attempted both options, retry room doesn't seem to be any different and going to the main menu/restarting the game is the same as always. I did follow the guide for the room and am quite sure I finished it... I didn't get looped back anywhere, if I was supposed to then that's probably where I went wrong.