The perimeter of the prison is patrolled by the Los Santos County Sheriff and sometimes the Los Santos Police Department. 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
In the Heists Update, during The Prison Break, the crew must storm into the prison to release a Russian prisoner named Maxim Rashkovsky. Some missions and races also take place in the prison in 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 a The Lost MC member
- Jack Howitzer (Released)
- Harold "Stretch" Joseph (Released)
- Ralph Ostrowski (Determinant)
- Maxim Rashkovsky (Escaped)
- Karim Denz (Determinant)
- Norm Richards (Determinant)
- Trevor Phillips (Escaped or released)
- Many of the former students of class 2005 of Davis High School
- Glenn Scoville (Determinant)
- Larry Tupper (Determinant)
- Curtis Weaver (Determinant)
- Two people from random events (Determinant)
- Unnamed escapees (Escaped, can be killed).
- The airspace above the prison is a no-fly zone
- Shooting a firearm anywhere near the prison will cause an automatic three-star wanted level.
- 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 exterior of Bolingbroke resembles Texas state penitentiary in in Rocksprings, Texas.
- 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.
- When you play as Franklin or Michael, you will encounter a member of The Lost and he will tell you that a friend of his will be incarcerated in this prison for 5 years.
- It is said that many of the former students of class 2005 of Davis High School are incarcerated in this prison.
- 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. Since an achievement requires you to bring at least one of them alive, a gameplay trailer shows Trevor putting Ralph, in Maude's trailer, and bringing them will gut you $10,000 and killing them only gives you, $5,000, bringing all 4 of them alive are the canon choices. Also in the missions, if Trevor captures Ralph instead of killing him, he will describe his time in this prison and says that it was very freeing and that he even enjoyed himself there. Humorously, his tone leaves the impression that he had sexual relations with other prisoners in jail, though this could have been a joke on his part.
- 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 being 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.
- If Norm is chosen as the gunman for the smart or loud approach of The Jewel Store Job, his bike will apparently bust up before entering the sewer tunnels, causing him to lose control, fall off and be killed or badly wounded, if he is badly wounded, he will be arrested and be incarcerated at this prison.
- 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.
- Prison Guards in the towers are equipped with a default Sniper Rifle.
- In the subtle approach of The Big Score, if Karim Denz is chosen for the first time and is placed as the first driver, during the shootout between the crew and the Merryweather soldiers, he will drop some gold bars trying to load the Gauntlets, also, during the chase he will lose control of the car and be caught by the police. He will then be incarcerated in this prison if that happens.
- Many of the prisoners' face models are also used for models that spawn in south central Los Santos; face models extracted from default male pedestrians, and a few face models from the Original Covenant Ballas.
- A few prisoners also use the same voice and sound files as the Families gang members, as well as the Ballas gang members, referencing the notoreity both gangs hold in crime.