Harold was born in 1913 in Johannesburg, South Africa to Abraham and Bertha nee Grün and had three siblings, Morris, Jeanette and Frances. Their father died in 1923 when Harold was ten years old.

Harold was educated at King Edward school, Johannesburg and was a member of the school Cadet Corps. He travelled to England and on 9 August 1937 he was granted a short service commission as Acting Pilot Officer. He was posted to No. 8 Flying school at Montrose and afterwards to 9 Squadron at Stradishall in June 1938 after completing a navigation course.

Harold was the first South African to be killed in the war and the first Jewish casualty. He originally was buried with a cross on his headstone and this was changed in 2012.

Harold was the pilot of Wellington L4320 which departed RAF Honington for air firing practice over Berners Heath. The aircraft flew into trees and crashed near Elveden, Suffolk.

All five crew killed:
Pilot Officer Harold Rosofsky, aged 26.
Pilot Officer Bruce Innes Clifford-Jones, born New Zealand, aged 22.
AC.1 Hugh McGreevy, aged 23
AC.1 Thomas Purdie, aged 24
AC.2 William Charles Hilsdon, aged 20