For those of you who don’t know this game mode, Jailbreak is a psychological experiment disguised as a TF2 game. There are no respawns, and it requires custom specialized maps designed for the mode. Most of the server plays as RED, and begins the round drained of all ammo and clip. The BLU team consists of a few guards and a Warden, who have allcrits. The Warden must order the prisoners around, using his guards’ superior firepower to enforce control, and get them to participate in mini-games, where the players who lose the mini-games often die. When a single RED player is left, they are considered to have won the round, and are granted a “last request”, which carries over to the next round (for example, “next round we play the Soccer mini-game,” “next round I want the freedom to run around and ignore this song and dance,” or “right now I want all the guards to play Nine Square until they’re dead.” That’s it, there’s not much to the game.

UNLESS the prisoners decide to rebel. If anyone can survive long enough to reach the armory, they can refill their ammunition and get working weapons again. If the rebelling RED players can kill all the BLU players, they win in a much more satisfying way.

After a decent amount of playing this mode a few months ago, I’ve found some strategies that work pretty well.

If your goal is:

Living to the end: Stop being a pansy, this gamemode isn’t called “jailbabies I hope the nice warden gives me a baba.” Seriously, I’ve never understood why anyone would follow the rules. If you do, I have no strategy for you, keep your head down and every blue moon you’ll win and get a short-lived request. Wuss.

These prisoners have the right idea.
These prisoners have the right idea.

Escaping alone: Go scout, drink Bonk! a second before the doors open, (after the doors open, your Bonk wont recharge) run to the hills. Equip Atomizer and beeline for the closest death trap maze/bottomless pit jumping puzzle/little ledges up into the sky puzzle etc. The point is it’ll be very hard for the guards to follow you, and people who play guards suck at TF2 so they probably can’t navigate the thing and catch you.

Some Jailbreak servers remove all non-damaging weapons like Bonk and shields. This makes Mediguns your best bet, but requires teammates. See below.

Starting a riot: go Medic, spam over and over “Repeat instructions” while the cells are still closed (otherwise they’ll open the doors before you can get Uber), find a competent teammate once they let you out (I’ve had the most success with fellow medics, especially when they have an Uber too). While invincible, slay the warden in front of everyone and make for the weapons. This has a ridiculous success rate. If your teammates proves to be particularly intelligent, use the Vaccinator because it will negate the BLU team’s crits.

Suicide picking the Warden: If the server allows shields, any demoknight will do. If not, then caber. Either way, warden is always the first guard through any door, so after all the prisoners walk through a door, wait patiently and explode the Warden’s ♥♥♥ once he comes through. Lower success rate than the above medic strategy and almost always results in your death but doesn’t require a competent teammate. There’s also a chance the RED team won’t take the opportunity to rebel because they are cowardly people who bring shame and disgrace to their family name.

All in all, definitely something you should try at least once. It’s not like any other game mode in TF2, but the thrill of starting a successful prisoner riot that leads to victory is awesome.