I played Jailbreak gamemode a shit ton on various servers and games (GMOD/GO) and I've come to a conclusion
Your server can be improved
The Jailbreak server is a little bit broken and lacks a little rules to make it more enjoyable.
First up, orders are completely incomprehensible. The server needs a warden system or something that looks like it. Even if it might have few advantages to run the server without any, imo, with is better. Orders are usually clear and understood by the majority of players. Some Gmod servers feature a Warden voting system, which let guards vote for the next warden. It's voted everyround so if a Warden goes nazi, it can be replaced.
Next, it also needs clearer server rules, especially concerning warning shots. CT's need to read these carefully, I rarely see a whole guard squad to handle prisonners correcly using warnings.
You guys also need a max ct number. The best Guard/Prisonner ratio is approx. 1:4. When the server is full, there should be a maximum of 6 guards able to play at once. Gmod also features a cool guard queue, whenever a guard leaves, it automatically switches the first one in the queue to the CT side.
I would also recommend to add more maps. I was disappointed on the numbers of good old CS:S or Gmod maps in the map pool. There isn't many jb_ maps on the workshops, but it is possible to get gmod maps ported to GO.
I know this is a shit ton of suggestions and it is a lot of work to do, but the more I put in here, the more you'll maybe accept.
Thank you very much for reading! Give feedback!