The perimeter of the prison is patrolled by the Los Santos County Sheriff. There are armed San Andreas State Prison Authority officers standing near the entrances, making sure that no one attempts to break in or out.
Events of GTA Online
Events of GTA V
In 2013, a prisoner has his jaw broken by "Stretch" after snitching on a fellow inmate, which lands Stretch in isolation for five days, which he completes. Stretch also gets tattoos, one of them starts with leakin' real nasty according to Stretch on his Lifeinvader page. It is during his time in Bolingbroke that Stretch forms an alliance with the Ballas and plans to sell out Franklin Clinton and Lamar Davis.
A random encounter can occur around the prison where a prisoner pulls the protagonist over and then points a gun at them, and forces them to get out of their vehicle.
Demarcus Bradley, another inmate, states on his Lifeinvader page that a number of Davis High School students in the 2005 graduating class are in the prison and that he had received a friend request from the guard on his wing. He later goes blind, although it may only be temporary, after drinking prison made wine, watches his cellmate using a toothbrush he had used for other purposes and visited the prisons 'total psycho' dentist. Prison food, judging by Demarcus' comments, is of poor quality in Bolingbroke.
- GTA Online
- Vapid Interceptor
- Sheriff's Cruiser
- Park Ranger
- Police Maverick/Air Ambulance (sometimes flying around the prison)
- Prison Bus (Center courtyard of the prison. Extremely hard to reach and even harder to drive out)
- Warning: Cameras operate in this area
- Authorized personnel only
- Notice: This area is protected by electronic surveillance
- Danger: Guard dog on duty
- Merle Abrahams (Deceased)
- Demarcus Bradley
- Franklin Clinton (Released)
- Unknown friend of Lost MC member
- Jack Howitzer (Released)
- Harold "Stretch" Joseph (Released)
- Ralph Ostrowski (Determinant)
- Maxim Rashkovsky (Escaped)
- Glenn Scoville (Determinant)
- Larry Tupper (Determinant)
- Curtis Weaver (Determinant)
- 2 people from random events (Determinant)
- Un-named escapee(s) (Escaped, can be killed).
- If the player is near the penitentiary while being wanted, the prison alarm will go off and guards will be warned of the player's presence, causing them to attack. This can be remedied by using the "Cops Turn Blind Eye" feature from Lester as to safely gain access inside the prison for a limited time.
- LSPD patrol cars can be found patrolling inside the prison, despite being city police. They can also be seen patrolling outside of its borders alongside San Andreas Park Ranger.
- Shooting a guard with a sniper rifle from the front or back will give the player a two star wanted level. If approached from the back with two stars and goes up the prison's west side they will receive four stars, which is also received for punching the guard who occasionally spawns next to the barriers.
- Inside the recreation yard, there is writing on a wall that reads, "Where water meets land and fire once spewed forth, there the infinite 8 shall stay until I return." The message is left by Merle Abrahams, who was obsessed with the number eight and had killed eight people in 1999.
- The prison is mentioned many times during the storyline - Trevor thinks that Brad is incarcerated there, until he discovers that he is actually buried in Michael's place in Ludendorff.
- If the player manages to get in without a wanted level (such as entering the prison in a mission where wanted levels are disabled) and get close to building 9A, they can hear blood-curdling screams coming from it.
- In Maude's Bail Bond missions, if Trevor captures any of the targets Ralph Ostrowski, Larry Tupper, Glenn Scoville or Curtis Weaver, they will be incarcerated in this prison.
- Inside the guard booth at the entrance to the prison is a Burger Shot bag and cup.
- In 2 Random Events, someone will be running from a cop, the player can either kill him, help the cop catch him, or the cop can catch him by himself. If they are caught instead of killed, they will be incarcerated in this prison.
- Inside the top of the guard tower are pictures of strippers, an emergency procedure guide, a fire hydrant, a security camera and more.
- Sometimes an Air Ambulance can be seen flying around the prison. This is most likely a glitch as the Air Ambulance is actually a re-skinned Police Maverick. Though it might be reference to prison and the fact that Air Ambulances are often used to lift wounded or seriously injured inmates to hospitals which might be a distance away.