After the plan comes together, collecting the needed information, resources and assistance from multiple sources, Bishop informs TK that they're ready for the "big job". He lets him know that the prison transport is waiting outside Ray's Autos in La Guardia, where the player arrives. He tells him the plan is to get inside the prison with the van, use the dozers in the construction yard of the south wall to smash through the jail wall, and gain access to the prison doors. From there, he says that he'll need to locate Candy, use the escape van as a means of transport to get out of the prison, and get him to the hideout in Queens.
Once TK arrives at the main gatehouse for the prison, after the primary gates open, the guard that was used to gain information in prior events tells TK that he will tell the other prison guards that "you waved a gun in my face and tore out the phone". After letting him know, the second gates are opened, and TK makes his way across the bridge to the island itself. From there, prison members on the watch towers begin to shoot at TK in the prison van. TK reaches the construction yard and makes his way down to a dozer located in the yard, which he uses to make his way around a maze of hills of sand and containers. Prison guards continue to shoot him within the yard, before he reaches the main wall, and uses the digger to smash it down. After exiting the dozer at the other side of the gate, he makes his way through the jail cells which have raised alarms, using a small door on the end of a jail house.
After breaking inside, the alarms are alerted throughout the island, and TK fights off all the prison guards within the jails, making his way through the canteen and kitchen, before reaching the drier and food room, where Candy is taking cover behind a meat table. Candy asks "who are you? My fucking fairy godmother?", before TK explains that Bishop sent him here to get him out. After Candy gives the all clear, they exit the main prison, reaching a food delivery truck out back.
They make their way out onto the main roads of the prison, with watchtower guards continuously shooting the player. Reaching the gates, they plow through, with a continuation of more gatehouse guards firing at the player. The main gates reopen and the pair escape in the van, with numerous police units in patrol cars attempting to tail the player. Candy will repeatedly criticize TK for his driving, that he "doesn't want to go back inside", and that it's "good to be out of that shit hole."
Subsequent to escaping most of the tailing police, they arrive at the hideout in Queens.
Succeeding the heist, the crew are found in a strip club post-mission, celebrating their success. However, shortly after getting him out, TK gathers doubt for Candy, after Candy suspiciously states numerous things relating to what he believes to be "upcoming plans" for himself and the team, which TK speculates to scare the girls he's "seducing". TK builds up the celebrations, claiming they're living the life with drugs, drink and girls, but it's shortly stopped after Corrigan turns up to their little "party". After Corrigan turns up, the guys are seen back at TK's safehouse, where Corrigan explains the plan; committing a ransom against the Columbians who are competing them in the drug trade, where Corrigan defines the expertise of each of the guys in front of him, and also claiming that he's out to look out for them, to pull off the ransom.
- Get in the transport. [Back to top]
- Once the mission is started via Ray's Autos in La Guardia, the player is told to get in the prison transport. The prison van is located at the side of the garage.
- Take this transport to Riker's. [Back to top]
- Once entered, they're told to take it to Riker's Island. Riker's Island will be marked on the map, in Queens. No police attention should be gained on the way. The player must also not wreck the vehicle.
- Wait for the prison gates to open. [Back to top]
- After the player reaches the island, the gates will slowly open. The guard interacted with in Turning The Screw opens the gate for TK. After getting in, the player is stopped to talk to the guard, who explains the plans to get himself out of trouble.
- Get across the bridge. [Back to top]
- After the second gates are opened, the player is told to cross the bridge connecting the main land with the prison island. At the other end, security guards will shoot at the player. The player has to smash the second set of gates down with the truck.
- Ditch the transport. [Back to top]
- Subsequent to arriving at the construction yard to the left of the access bridge, the player is told to exit the vehicle after reaching the checkpoint.
- Get to the dozer. [Back to top]
- Then, the player must reach the dozer marked on the map. It is located just to the left of the checkpoint reached, down inside the construction yard.
- Get inside the jail. [Back to top]
- Following entering the dozer, the player has to make their way around a maze of containers and sand walls. They have to choose the correct route around the zone, crossing a bridge and cornering around several walls before reaching the main wall.
- Smash through the wall! [Back to top]
- Once they reach the wall, they must smash it down, by accelerating towards it. The wall will collapse on-top of the dozer. After reaching the other side, they must exit the truck and head to the checkpoint outside a jailhouse door.
- Find Candy and get him out. [Back to top]
- After reaching the door, and entering the jailhouse, the player is told to find Candy. Firstly, the player must be equipped to tackle the numerous prison guards within the prison. Numerous health packages are found around the jailhouse. Inside the canteen and kitchen are many officers, with weapons such as the Shotgun, Revolver, 44H and even the LI-15. It is advised to pick up these weapons after killing each officer.
- Candy is found in the kitchen drier room, where meat is prepared. He is hiding behind a meat table.
- Get off Riker's Island! [Back to top]
- The two get into a food van outside the jailhouse and kitchen, where they are told to get off the island once entered. The player must drive out of the prison, making there way across the bridge and through the main gates. From here, they must lose the police, without killing themselves or Candy. The hideout location will be marked on the map, where they must reach without a tail. After, the player is put into a cutscene, which follows with the player being rewarded the LI-15 weapon at the safehouse in which they spawn in.
- Collect the prison transport.
- Get onto Riker's Island.
- Find Candy inside the prison.
- Get candy to the hideout.
- This is the only time the player can access the prison, without glitches.
- Despite the second gates are smashed down on the way in, they have to be smashed down again on the way out.
- TK will continuously complain at how slow the Prison Van is, regardless of how fast he goes in it.
- Players have reported a bug where a Zartex will spawn on the corner of the road next to the hideout which will not move, rendering the mission impossible to complete, as the police will spot the player regardless of how they far they keep away from the police car as they enter the hideout, and the players have to kill the cops inside to lose them and complete the mission.
- Rarely, driving quick enough into the hideout sometimes results in completing the mission, immediately followed by a police chatter message stating they've seen the suspect and are in chase.
- Oddly, the cutscene following the mission will not play after this mission if the player hasn't already completed Circuit Breaker - if they haven't, the cutscene will player after Circuit Breaker instead.
- ↑ Because the mission which unlocks "Circuit Breaker" also lies alongside the mission "Jail Break" (see next reference), if the player decides to complete Rosalita Racer before Jail Break, Circuit Breaker will be unlocked and be alongside Jail Break.
- ↑ Because the missions which unlocks "Jail Break" ("Paddy Wagon" and "Turning The Screw") also lies alongside the mission "Rosalita Racer", Jail Break can become inline with this mission if the player decides to complete "Turning The Screw" and "Paddy Wagon" beforehand. In other words, Jail Break is not inline with this missions until "Paddy Wagon" and "Turning The Screw" are completed.