Outram Prison (Pearl’s Hill Prison)

Singapore Infopedia


One of Singapore’s earliest prisons was located at the foot of Pearl’s Hill in Outram.1 The original civil jail at the site was built in 1847 by Charles Edward Faber; in 1882, a new prison complex was built around the old civil jail by J. F. A. McNair.2 Originally known as Pearl’s Hill Prison, and Outram Prison in its later decades, it was demolished in 1963 to make way for redevelopment.3

Singapore’s first civil jail was built around 1823 between Macao Street (now Pickering Street) and South Bridge Road. It was subsequently rebuilt by Edward Lake between 1829 and 1830.4 However, due to the unsound structure of the building, as well as health-related problems suffered by the inmates as a result of frequent flooding, the site was converted into the Central Police Station while a new civil jail was constructed at the foot of Pearl’s Hill.5

The Bengal government approved the building of a jail at the foot of Pearl’s Hill in 1836.6 The site was chosen because of its proximity to Sepoy Lines – it was thought that the garrison troops quartered there could offer added protection should a mutiny occur at prison.7

On 6 February 1847, the foundation stone of the prison was laid by the architect and superintending engineer, Charles Edward Faber, in the presence of Governor William J. Butterworth and Resident Councillor Thomas Church. Buried at the base of the foundation stone were two time capsules: one containing a piece of parchment on which trade statistics and revenue figures were written, and another with specimens of various currencies. Copies of the local dailies, the year’s official directory and a brass plate with an inscription were also deposited beneath the stone. The inscription reads:8

This Foundation Stone
H. M. Jail, at Singapore,
was laid by Captain Faber, Madras Engineers,
Superintending Engineer, Straits Settlements,
On the 6th February, 1847–
The 27th Anniversary of the Formation
Of a British Settlement
On this Island.
The Hon’ble Colonel W. J. Butterworth, C.B.,
Being Governor of Prince of Wales’ Island,
Singapore, and Malacca,
The Hon’ble T. Church,
Resident Councillor at Singapore.

Queen of Great Britain and Ireland.

The Right Hon’ble Lord Hardinge, G.C.B.,
Governor-General of British India.
God Save the Queen.

Description of the original prison
It was envisaged in 1836 that the new civil jail would comprise a wall surrounding a quadrangle within which would be buildings made of kajang (also spelt cadjan; Malay term meaning “woven palm leaves”) and attap.9

The civil jail was built by Faber in 1847 based on the plan drawings of the government surveyor, John Turnbull Thomson.10 Convict labour was used to construct the two-storey, cross-shaped brick-and-mortar building with a pitched roof and enclosed by a wall. Each floor had 10 outward-facing rooms, with each of the ground-floor rooms linked to an adjacent yard. Each room and yard catered to a specific group of offenders, such as debtors, natives, Europeans and native capital criminals. There was also a yard and separate quarters for the warders. The jailer’s room was at the centre of the cross, allowing him a bird’s-eye view of all the prisoners.11

The Pearl’s Hill jail held both European and native offenders, and they were organised by race and type of conviction. European prisoners were accorded better treatment and living conditions – at least in the early decades of the prison’s existence.12

Following the prison riot at the Bras Basah convict jail on 13 February 1875, which resulted in the death of its prison superintendent, Digby Henry Dent, there were renewed calls for a new and more secure criminal prison. After some debate as to whether the new prison should be an extension of the Bras Basah jail or the Pearl’s Hill civil jail, it was decided that it would be constructed at the Pearl’s Hill site.13

The extension to the original civil jail was designed by the executive engineer and superintendent of convicts, J. F. A. McNair, between 1877 and 1878; by 1879, construction had begun.14 McNair’s plans for the extension showed how the prison philosophies of the day influenced his design. Building around the original prison, the space was more cellular and the focus of the prison philosophy was more punitive than before.15 The new complex was largely built by convicts from the Bras Basah jail, who were to be moved there upon its completion.16 The foundation stone for the new complex was laid by Governor William Cleaver Francis Robinson on 30 January 1879.17 Construction of the new complex was completed in 1882.18

The complex had five prison blocks for male criminals: four for natives and one for Europeans. Other buildings and amenities included the women’s criminal and civil prisons, hospitals, employees’ quarters, work sheds, a photography department, punishment cell, execution room and dead house. The new structures were erected around the old civil jail, which retained its former function.19

The Pearl’s Hill prison underwent a host of changes over the years. In January 1937, its long-term prisoners were transferred to the new convict prison in Changi. The Pearl’s Hill jail subsequently held offenders serving short sentences.20

By 1949, the jail complex had 988 cells, spread among the criminal, remand and female prisons, 944 of which were in the criminal section. The hospital was equipped with 94 beds.21

In 1951, the block for European convicts was converted into a new female prison.22 Four years later, in April 1955, one of the halls in the complex was used to house 220 one-man cells for incarcerating convicts who intimidated others in the shared cells.23

On 1 July 1957, a reformative training centre for youths opened at the Outram complex, replacing the remand prison.24

Prior to World War II, the prison superintendent headed the staff of warders. Complaints, requests and breaches in prison rules were brought to the superintendent. Second in rank was the gaoler (jailer), then the deputy gaoler, followed by the warders and sub-warders. Those in the positions of warders and above were typically Europeans and provided with accommodation. The starting salary of a warder was around $200 a month in the 1930s.25

After the war, the headquarters of the newly formed Prisons Department was housed in the administrative block within the complex. The Prisons Department, as well as the Pearl’s Hill jail, was administered by the commissioner of prisons, who was assisted by three gaolers (known as chief officers from 1950).26

Prison labour and industries
The prison generated income through a range of crafts and skills provided by the prisoners. These included husk-beating, carpentry, tinsmithing, weaving, tailoring, rattan work and shoemaking.27

Almost all the mailbags used by the postal and telegraph services in the 1920s were made by the inmates. Uniforms, shoes, blankets and towels that were used in the jail were woven and produced by the prisoners. They also maintained a photography studio, bakery and laundry, among other services. One of the highest-earning industries was the press that printed government publications.28

Despite these vocational duties, no training system was in place to seriously cultivate the prisoners’ skills with a view to preparing them for life after the prison.29

Punishment and executions
Prisoners who flouted rules were punished using the rotan (Malay for “rattan”), before which a hearing with the prison superintendent was conducted. The caning process was observed by the superintendent and a medical officer.30

From its earliest days, execution by hanging were carried out at Pearl’s Hill jail.31 Between February and April 1915, 47 men from the Indian 5th Light Infantry Regiment who were involved in a deadly mutiny on 15 February that year were executed by a firing squad at Pearl’s Hill. Most of the condemned were publicly executed outside the prison gates as a form of deterrence, with crowds numbering in the thousands for some of the executions.32

Japanese Occupation
During the Japanese Occupation, half of the prison was used to hold military prisoners or prisoners-of-war, while the other half was for civilian prisoners.33 A total of 1,470 prisoners, mostly Chinese, died at the Outram Prison during the war – 141 were executed while the rest died of torture, starvation or diseases. Only 400 survived upon liberation in September 1945.34 Forty-three Japanese military men were tried for war crimes committed while they were in charge of the Outram Road jail.35

After the war, British forces returned and continued to use the Outram Prison for detaining common criminals,36 which was overcrowded in the immediate postwar years. The problem was eased when the British military, which had been using Changi Prison to hold Japanese war criminals, handed it back to the Prisons Department in 1947.37

The Japanese removed the foundation stone of the Outram Prison during the Occupation.38

Political detentions
After World War II, the Outram Prison was also used as a detention and interrogation centre for political detainees such as the Middle Road trade unionists who were imprisoned during the 1956 riots.39 In 1963, most of the left-wing political activists and unionists arrested during a series of security crackdowns known as Operation Coldstore – numbering over a hundred including Barisan Sosialis leader Lim Chin Siong – were held at the Outram premises for several months before being relocated to Changi Prison and St John’s Island.40


As early as the late 1920s, the land on which the prison sat was deemed too valuable for carceral purposes, and calls were made to relocate it.41 Additionally, the prison was unable to support an entrenched system of segregation and classification, and overcrowding was an issue. As a result, hardened criminals were incarcerated together with vagrants and juveniles, and recalcitrant civilian prisoners were also held together with first-time offenders. The prison was also perceived to be at risk of collective unrest.42

In 1947, the security of the prison complex came under public scrutiny following a spate of escapes.43 Three years later, the prisons commissioner labelled the facility as “antiquated and wasteful in manpower” in the 1950 Prisons Department annual report.44

In March 1963, then Prime Minister Lee Kuan Yew announced that the Outram Prison would be demolished and a Housing and Development Board estate built in its place. The land on which the prison complex sat was part of a large area slated for redevelopment.45 Demolition of certain sections of Outram facility began shortly after.46

The Outram Prison was replaced by the Queenstown Remand Prison, which opened in September 1966.47 The latter was built at a cost of S$2 million and continued to uphold the policy of rehabilitating and re-educating prisoners.48

By October 1966, piling work for the housing project had begun on the site of the former jail.49 The resulting Outram Park estate featured some 1,240 flats and 464 shops. By 1970, the Outram Park Complex was almost entirely opened, although business in the residential-cum-shopping complex was dismal.50

Variant names
H. M. Prison (colonial times) (His or Her Majesty’s Prison, depending on the gender of the ruling British monarch at the time)51

Singapore Prison52
Criminal Prison53

Bonny Tan, Vernon Cornelius-Takahama, Faizah bte Zakaria and Fiona Lim


1. Norman Edwards and Peter Keys, Singapore: A Guide to Buildings, Streets, Places (Singapore: Times Books International, 1988), 102 (Call no. RSING 915.957 EDW-[TRA]); Anoma Pieris, Hidden Hands and Divided Landscapes: A Penal History of Singapore’s Plural Society (Honolulu: University of Hawaii Press, 2009), 79. (Call no. RSING 365.95957 PIE)
2. Survey Department, Singapore, Street Directory and Guide to Singapore with Sectional Maps (Singapore: Survey Department, 1954), 16 (Call no. RCLOS 959.57 SIN); Pieris, Hidden Hands and Divided Landscapes, 206–7; Walter Makepeace, Gilbert E. Brooke and Roland St. J. Braddell, One Hundred Years of Singapore, vol. 1 (Singapore: Oxford University Press, 1991), 282. (Call no. RSING 959.57 ONE-[HIS])
3. “Lee Launches Spearhead to Remodel ‘Old S’pore’Straits Times, 16 March 1963, 6 (From NewspaperSG); Legislative Assembly, Singapore, Yang di-Pertuan Negara’s Speech (Debate on the Address), vol. 20 of Debates: Official Report, 8 April 1963, col. 170 (Call no. RCLOS 328.5957 SIN); “These Men Are Happy They Went to Gaol,” Singapore Free Press, 19 December 1952, 5. (From NewspaperSG)
4. Pieris, Hidden Hands and Divided Landscapes, 79; Victor R. Savage and Brenda S. A. Yeoh, Singapore Street Names: A Study of Toponymics (Singapore: Marshall Cavendish Editions, 2013), 296 (Call no. RSING 915.9570014 SAV-[TRA]); Survey Department, Singapore, Street Directory and Guide to Singapore with Sectional Maps, 10.
5. Makepeace, Brooke and Braddell, One Hundred Years of Singapore, 282; Survey Department, Singapore, Street Directory and Guide to Singapore with Sectional Maps, 10.
6. “Untitled,” Singapore Free Press and Mercantile Advertiser (1835–1869), 28 July 1836, 2. (From NewspaperSG)
7. “Prison Reflections,” Singapore Free Press and Mercantile Advertiser (1884–1942), 26 March 1929, 8. (From NewspaperSG)
8. “Untitled,” Singapore Free Press and Mercantile Advertiser (1835–1869), 11 February 1847, 2. (From NewspaperSG)
9. “Untitled”; Anoma Pieris, Architecture and Nationalism in Sri Lanka: The Trouser under the Cloth (New York: Routledge, 2013), 221; Pieris, Hidden Hands and Divided Landscapes, 260.
10. Survey Department, Singapore, Street Directory and Guide to Singapore with Sectional Maps, 16;The Prison Story,” Singapore Prison Service, accessed 27 May 2011.
11. Pieris, Hidden Hands and Divided Landscapes, 79–80.
12. Pieris, Hidden Hands and Divided Landscapes, 79, 109–10.
13. “Papers Laid before Council,” Straits Times, 16 November 1878, 2; “Legislative Council,” Straits Times Overland Journal, 17 January 1879, 4. (From NewspaperSG)
14. Survey Department, Singapore, Street Directory and Guide to Singapore with Sectional Maps, 16; Prisons Department, Singapore, Annual Report 1950 (Singapore: Govt. Print. Off., 1950), 3 (Call no. RCLOS 365.95957 SIN); Ray Tyers and Siow Jin Hua, Ray Tyers’ Singapore: Then & Now (Singapore: Landmark Books, 1993), 184. (Call no. RSING 959.57 TYE-[HIS])
15. Pieris, Hidden Hands and Divided Landscapes, 202, 206.
16. “Monday, 10th March,” Straits Times Overland Journal, 15 March 1879, 6. (From NewspaperSG)
17. “Summary of the Week,” Straits Times Overland Journal, 1 February 1879, 1. (From NewspaperSG)
18. Makepeace, Brooke and Braddell, One Hundred Years of Singapore, 282.
19. Pieris, Hidden Hands and Divided Landscapes, 202–7.
20. “New Changi Gaol Opens Its Doors,” Straits Times, 31 January 1937, 14; “Singapore’s $2,000,000 Convict Prison,” Straits Times, 13 December 1936, 41 (From NewspaperSG); Prisons Department, Singapore, Annual Report 1955 (Singapore: Govt. Print. Off., 1956), 1 (Call no. RCLOS 365.95957 SIN); Prisons Department, Singapore, Annual Report 1959 (Singapore: Govt. Print. Off., 1961), 1. (Call no. RCLOS 365.95957 SIN)
21. Prisons Department, Singapore, Annual Report 1949 (Singapore: Govt. Print. Off., 1950), 4. (Call no. RCLOS 365.95957 SIN)
22. Prisons Department, Singapore, Annual Report 1951 (Singapore: Govt. Print. Off., 1952), 3 (Call no. RCLOS 365.95957 SIN); “He Wanted Gaol Without Bars,” Straits Times, 18 June 1952, 6. (From NewspaperSG)
23. “To Each a Cell in This Gaol Soon,” Straits Times, 12 October 1954, 5 (From NewspaperSG); Prisons Department, Singapore, Annual Report 1955, 2.
24. Prisons Department, Singapore, Annual Report 1957 (Singapore: Govt. Print. Off., 1958), 2 (Call no. RCLOS 365.95957 SIN); “Borstal instead of Jail Now – Bid to ‘Reclaim’ Youths,” Straits Times, 6 December 1956, 7. (From NewspaperSG)
25. “Life in the Singapore Prison,” Straits Times, 12 May 1935, 7. (From NewspaperSG)
26. Prisons Department, Singapore, Annual Report 1947 (Singapore: Govt. Print. Off., 1958), 1 (Call no. RCLOS 365.95957 SIN); Prisons Department, Singapore, Annual Report 1948 (Singapore: Govt. Print. Off., 1949), 1 (Call no. RCLOS 365.95957 SIN); Prisons Department, Singapore, Annual Report 1949, 1; Prisons Department, Singapore, Annual Report 1950, 1; Singapore Prison Service, “The Prison Story.”
27. “Singapore Prison Life,” Straits Times, 3 July 1925, 9; “Inside the Singapore Prison,” Straits Times, 21 April 1935, 7. (From NewspaperSG)
29. “Life in the Singapore Prison,” Straits Times, 12 May 1935, 7. (From NewspaperSG)
30. “Life in the Singapore Prison.”
31. “Executions of Saffer Ally and Others for Murder,” Straits Times, 4 March 1851, 4; “Mutiny Execution,” Singapore Free Press and Mercantile Advertiser (1884–1942), 22 April 1915, 10; Alison Mayhew, “Hangman’s House,” Straits Times, 10 June 1948, 8. (From NewspaperSG)
32. R. W. E. Harper and Harry Miller, Singapore Mutiny (Singapore: Oxford University Press, 1984), 195, 201–3 (Call no. RSING 355.1334095957 HAR); Jackie Sam, “Outram Park,” Singapore Monitor, 30 September 1984, 6 (From NewspaperSG); Nicholas Tarling, “‘The Merest Pustule’: The Singapore Mutiny of 1915,” Journal of the Malaysian Branch of the Royal Asiatic Society 55, no. 2 (243) (1982): 50. (From JSTOR via NLB’s eResources website)
33. Sam, “Outram Park.” 
34. L. C. Hoffman, “Memories of Outram Road,” Straits Times, 5 September 1946, 4; “Jap Generals Hanged,” Straits Times, 18 April 1947, 5; “Outram Gaol Trial,” Straits Times, 16 August 1946, 3; “Deaths in Outram Road Gaol during Japanese Occupation,” Straits Times, 25 February 1946, 4; “Chinese Who Died in Outram Road Gaol,” Straits Times, 23 February 1946, 4. (From NewspaperSG)
35. “Outram Rd Japs on Trial Soon,” Straits Times, 15 July 1946, 5; “Jap Executioners Awaiting Trail in Singapore,” Straits Times, 15 November 1945, 3. (From NewspaperSG)
36. Sam, “Outram Park.” 
37. Prisons Department, Singapore, Annual Report 1947, 1, 5; Sam, “Outram Park.” 
38. “Foundation Stone Back,” Straits Times, 9 October 1948, 5. (From NewspaperSG)
39. “Another Year’s Jail for 19 Detainees from Middle Road,” Straits Times, 9 November 1958, 3; “Four Women Detainees Released,” Straits Times, 2 October 1959, 1. (From NewspaperSG)
40. Tommy Koh et al., eds., Singapore: The Encyclopedia (Singapore: Editions Didier Millet and National Heritage Board, 2006), 224 (Call no. RSING 959.57003 SIN-[HIS]); Jackie Sam, Abul Fazil and Philip Khoo, “40 Held in 4-hr Swoop,” Straits Times, 12 September 1964, 1; “Shocking, Says Barisan Leader,” Straits Times, 30 March 1963, 20; “Detainees Sent to Changi - Jail,” Straits Times, 1 May 1963,  9. (From NewspaperSG)
41. “Prison Reflections.”
42. “A Potential Prison Danger,” Straits Times, 23 January 1933, 12; “Singapore’s New $2,000,000 Prison,” Straits Times, 13 December 1936, 9. (From NewspaperSG)
43. “Outram Gaol ‘Old and Insecure’,” Straits Times, 25 June 1947, 5; “What Is the Use of Outram Road?Straits Times, 25 June 1947, 4; “Prison Escape: $500 Reward,” Straits Times, 17 June 1947, 1. (From NewspaperSG)
44. Prisons Department, Singapore, Annual Report 1950, 3.
45. “Spearhead to Remodel ‘Old S’pore’”; “Start to Be Made on S’pore Slum Clearance,” Straits Times, 22 March 1963, 18; “Outram Jail Is to Be Demolished, Straits Times, 21 March 1963, 9. (From NewspaperSG)
46. Legislative Assembly, Singapore, Yang di-Pertuan Negara’s Speech, col. 170.
47. “Wok Opens $2 Mil Prison in Queenstown,” Straits Times, 24 September 1966, 8. (From NewspaperSG)
48. “New Prison in Queenstown Planned,” Straits Times, 14 August 1964, 6 (From NewspaperSG); “Wok Opens $2 Mil Prison in Queenstown.” 
49. “A Prison Makes Way for 1,000 Flats,” Straits Times, 5 October 1966, 5. (From NewspaperSG)
50. “New Homes for 12,500 at the Old Jail for 760,” Straits Times, 12 May 1970, 4; Mathew Yap, “Woes of Outram Park,” Straits Times, 16 November 1984, 1; “Move to Draw More Shoppers to Outram,” Straits Times, 12 February 1971, 8; “HDB’s ‘Take It or Leave It’ Attitude,” Straits Times, 14 May 1971, 24. (From NewspaperSG)
51. “Problem of the Ex-Prisoner,” Straits Times, 19 April 1934, 13 (From NewspaperSG); Tyers and Siow, Ray Tyers’ Singapore, 184.
52. “Report on the Prisons of the Colony,” Straits Times, 2 May 1903, 2. (From NewspaperSG)
53. “Report on the Singapore Criminal Prison,” Straits Times, 19 May 1877, 9. (From NewspaperSG)

Further resources
100 Years Ago,” Straits Times, 20 March 1993, 18. (From NewspaperSG)

Life in the Singapore Prison,” Straits Times, 19 May 1935, 6. (From NewspaperSG)

Revelations of Life in Singapore Prison,” Straits Times, 28 April 1935, 9. (From NewspaperSG)

Revelations of Life in Singapore Prison,” Straits Times, 5 May 1935, 6. (From NewspaperSG)

The Criminal Prison Report 1877,” Straits Times, 13 July 1878, 1. (From NewspaperSG)

The Singapore Jail in 1892,” Straits Times Weekly, 22 March 1893, 7. (From NewspaperSG)

The information in this article is valid as of 10 June 2015 and correct as far as we are able to ascertain from our sources. It is not intended to be an exhaustive or complete history of the subject. Please contact the Library for further reading materials on the topic. 




Rights Statement

The information on this page and any images that appear here may be used for private research and study purposes only. They may not be copied, altered or amended in any way without first gaining the permission of the copyright holder.

More to Explore

Finlayson Green


Finlayson Green is the name of both a traffic island (a small raised area on a road which provides a safe place for pedestrians to stand, and acts as a divider that channels traffic flow) and a street in the Central Business District. The green lung served as a road...

Kallang Gasworks


Constructed in 1862 by the Singapore Gas Company, Kallang Gasworks was the first site dedicated to the manufacture of gas from coal for street lighting. In 1901, this function was taken over by the Municipal Commissioners, and gas production was expanded for industrial and home use. Kallang Gasworks was decommissioned...

Bukit Brown Municipal Cemetery


The Bukit Brown Municipal Cemetery was established to serve the burial needs of the Chinese community. Officially opened on 1 January 1922, it operated for more than half a century before its closure in 1973. The cemetery was previously a section of a 211-acre plot of land, belonging to the...

Macpherson Road


MacPherson is one of the five sub-zones in the Geylang Planning Area. MacPherson Road lies between Woodsville Flyover and MacPherson Lane. ...

Fort Road


Fort Road, in the eastern part of Singapore connects Mountbatten Road to the East Coast Parkway, and connects to this expressway at the Tanjong Rhu Flyover. The road was named in the 1920s after the now demolished Fort Tanjong Katong. On the grounds of the fort presently stands Katong Park,...

Earth tremors in Singapore


There are no records of earthquakes occurring in Singapore, as the island is located outside earthquake zones. However, Singapore does periodically experience low-level earth tremors caused by earthquakes in Sumatra, Indonesia. Occasionally, these tremors may cause buildings to sway, but they are not serious enough to affect the structural integrity...

Major floods in Singapore


Floods are a common occurrence in Singapore usually caused by a combination of heavy rainfall, high tides and drainage problems, especially in low-lying areas. Most floods in Singapore are flash floods that subside within a few hours. Although most floods cause only minor inconveniences, Singapore has also experienced several major...

Adelphi Hotel


Some of the earliest mentions of Adelphi Hotel can be found in newspaper advertisements published in 1850. The proprietor of the hotel, C. Goymour, announced in the 7 May 1850 issue of The Straits Times newspaper that the hotel had moved to High Street. Subsequently, Adelphi Hotel moved to Coleman...

McAlister & Co. Ltd


McAlister & Co. was founded in 1857 by two Scots: Alexander McAlister and James Parker Niven, who saw the opportunity to set up a trading partnership in Singapore. During its initial years, the partnership was involved in general trade and Australian pearling. It was incorporated as a limited liability company...

Stamford House


Stamford House, located at the junction of Stamford Road and Hill Street, is an ornate building designed in the Venetian Renaissance style favoured during the Victorian era. Built in 1904, it was designed by Swan and Maclaren architect R. A. J. Bidwell as a commercial entity. The building was better...