This isn't constructive criticism. I can't do anything with this. I knew when I made the server it wasn't going to work as well as it does in Garry's Mod but I thought it may work to an extent and it does. The longer it is hosted the more people will understand how it is played. 
Let me be more specific.  I think that the essence of a jailbreak is there (if that makes sense) and the server is a well run one.  I was trying to point out some flaws, i was pretty general, i was trying to say that the communication between the Warden and the prisoners is flawed.  When i played, i had to constantly keep hitting page up just to see what the warden said.  To fix this, you could do what a lot of G-Mod servers do and have prisoners muted for a certain period of time.  Lastly, i think that the whole set-up for the warden is good with the huge spam name and the green text in the middle of the screen, but its really hard to understand a warden that:
talks
like
this
Hope this helps.