The Montserrat Secondary School, often referred to for short as MSS, is the only pre-16 years of age secondary school on the island of Montserrat. The school's campus is currently located in Salem. Prior to 2004 it was responsible for Montserrat's sixth-form education (post-16); currently Montserrat Community College (MCC) now offers Caribbean Advanced Proficiency Examinations (CAPE) sixth-form classes.

It was established by the 1938 merger of a government boys' secondary school, Montserrat Boys Grammar School, and a private girls' secondary school.^[2] Originally not all Montserrat citizens had the right to a secondary education, and the school chose which students may be admitted. A May 2011 Montserrat government report stated that the school "produced excellent results and enjoyed national esteem" in that time.^[3] Wealthier families were the main clientele of MSS.^[2]

There were 64 students in 1941. In 1955 its senior/modern school opened. In 1971 its junior school opened. The May 2011 government report stated that these new divisions "did not substantially alter the elitist nature of the school."^[4] The school has multiple locations before settling in Salem.^[2]

In 1986 secondary education became universal in Montserrat, and the report stated this, as well as the 1997 Soufrière Hills volcanic eruption, which reduced the student population, altered the school's culture.^[4] As a result of the establishment of universal secondary education, MSS established three branch junior school campuses in Dagenham, Salem, and Thompson Field.^[2]

In the pre-1997 period it was the sole school with upper secondary education, with its senior secondary division being the Montserrat Senior Secondary School,^[5] and its junior secondary being a lower section.^[6] The campuses together had 1,043 students in 1988.^[7]

The volcanic eruption and population loss resulted in the dissolution of MSS's sixth-form college; Montserrat Community College took over sixth-form studies upon its opening in 2004.^[8] The school now has a single campus in Salem.

By 2011 the teacher population had a lack of stability, contrasting with local-origin teachers of previous generations. In addition, and multiple "behavioural problems" had occurred "for several years". In 2011 there were 300 students; some of the school's students had English as a second language as they were immigrants.^[4]

It occasionally closed during ash falls as it is in the volcano's ash shadow.^[9] A report from the UK Department for International Development (DFID) stated that the school is a long distance from the major settlements in northern Montserrat.^[10]

• H. G. Carrington (1928–1957)
• Vincent Bennett Browne (1957–1968)
• Mr Holden
• Mr Hoppy
• Charles T. John (1976–1979)
• Peter White (1979–1990)
• Oeslyn Jemmotte (1990–1993)
• Lucy Fenton (1993–1995)
• Camela Watts (1995–1998)
• Kathleen Greenaway (1998–2004)
• Glen Francis (2004–2006)
• Alric Taylor (2006–2009)
• Cherlyn Hogan (2009–2020)
• Tony Allen (2020-2023)
• Cherlyn Hogan (2023-present)

• Arrow, a calypsonian and soca musician named Alphonsus Celestine Edmund Cassell, who is regarded as the first superstar of soca from Montserrat.^[11]
• Donaldson Romeo, the second Premier of Montserrat.
• Sheree Jemmotte-Rodney, the current acting Attorney General of Montserrat.

• Education in Montserrat