Jail Break

Jail Break (also known as Pirate Prison Break) is a challenge that originated in as a tribal Immunity Challenge. It would also be used as a Redemption Island duel.

Rules
When used as a tribal Immunity Challenge, players are locked in a makeshift jail cell and shackled. To escape, players must use the resources provided to create a long pole to retrieve three keys. These keys are to be used to unlock their shackles and then they must dig out of the cell. The first tribe out of the cell would win.

In the individual Redemption Island version of the challenge, players are no longer shackled. Because of this, the keys are now used to unlock the cell door. The first person to open their cell door would "stay alive" in the game, eliminating the last place finisher.

History
This challenge debuted in. Shackled by locks, each tribe would be placed in a jail cell. Using the resources on the ground, they had to escape the cell by reaching for the keys that hung on posts outside of the cell. They would then unlock their shackles and dig out of the jail. The Chuay Gahn tribe beat Sook Jai for immunity.

In, in order to escape of the cage, the tribe members had to untie a series of ropes in order to release a machete. Then the tribes had to use their machete to cut through a rope, undo another series of knots in order to release a plank, which will in turn release a pole. Then they used the pole to retrieve a set of keys on the outside of the cage. Once the keys were collected, they unlocked their chains and released their escape hatch. Jaburu won their second Immunity Challenge.

In it was used as The Outcasts Immunity Challenge. If The Outcasts beat one tribe they would vote one member back into the game and the losing tribe would vote somebody out, if they beat both tribes they would vote two members back into the game and both tribes would vote somebody out. The Outcasts tribe infamously won this challenge, sending both Drake and Morgan to Tribal Council.

In the challenge was used as the first Redemption Island duel. The castaways had to build a long pole out of sticks and rope. They would then use the pole to retrieve three keys hanging outside their cells. once all the keys were retrieved they had to unlock three padlocks on their cell doors, open the door and walk through. Matthew Elrod defeated Francesca Hogi in this challenge, eliminating her for good.

In the concept of the challenge was the same as in the season before it. This time it was used as the final pre-merge Redemption Island duel. Ozzy Lusth defeated Redemption Island champion, Christine Shields Markoski, re-entering the game and eliminating Christine.

In, the challenge was be used as the duel between Katie Collins, Laura Morett and Katie's mother Tina Wesson. Tina gave advice to Katie in hopes of having her and Katie advance together. Unfortunately for the mother & daughter, Laura was able to continue her Redemption Island dominance and come in first. Katie initially had the lead, but when she dropped the second key in the sand, she was unable to get it out. This enabled Tina to catch and beat her daughter, before opening the door and walking through, Tina asked Katie if she was alright with her doing it. Katie said she was alright with her mother advancing, which meant Katie was eliminated for good. Victory was bittersweet for Tina as Katie was permanently out of the game while she stayed on Redemption Island.

Trivia

 * This challenge was used in all seasons to feature the Redemption Island twist:, and.
 * It is one of three challenges to have this achievement. The other two are Snag, Drag & Bag and House of Cards.
 * It and Snag, Drag & Bag are the only ones to appear as a duel in all three seasons.
 * In Pearl Islands, The Outcasts did not sit anyone out despite having an extra member. Despite having to rescue one extra person, they still won the challenge.
 * The majority of the times this challenge has been used, it was fought by players trying to return into the game.
 * It has been used as a Redemption Island duel in three of its uses and once as an Outcast's challenge.