Bolingbroke Penitentiary is a prison located in Blaine County, San Andreas and to the north of Los Santos. The prison can be accessed off Route 68. Entering the prison, which is necessary to complete a stunt jump, will result in the player gaining a two-star wanted level. Prison guards will also attack the player if they go near the prison while wanted by the police. Prison guards are armed with Assault Rifles and Assault Shotguns with snipers in the guard towers. The Los Santos County Sheriff control the prison although LSPD police cars can be found driving around inside the prisons gates.
In 2013 a prisoner has his jaw broken by Harold "Stretch" Joseph after snitching on a fellow inmate, which lands Stretch in isolation for five days, which he completes. Stretch also gets a tattoo, which later starts '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, which he unsuccessfully attempts on three occasions.
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.
- Merle Abrahams (serial killer, imprisoned between 1999 and December 2004 when he died)
- Demarcus Bradley (transferred to Bolingbroke in 2013)
- Jack Howitzer (1992 - 2007) and (2010 - 2013)
- Harold "Stretch" Joseph (released in 2013)
- A wall inside Bolingbroke Penitentiary has the message: "Where water meets land and fire once spewed forth, there the infinite 8 shall stay until I return". The message is left by Abrahams, who was obsessed with the number eight and had killed eight people in 1999.