The majority of the photographs relate to the early stages of Sheppard’s career with the Malayan Civil Service. They illustrate his accommodation; varied range of work in Kuala Lumpur, Pahang, Perak and Terengganu; Malay and European colleagues; official events, military service, travel and recreation. A number of prints are uncaptioned and have been provided with tentative titles in square brackets and approximate dates.

The images begin with Sheppard's arrival in Jan. 1928 via the ‘Ismailia’. They document his first posting to Temerloh, including his work as head of a field rent collection team. In Sept. 1928, he was promoted to Private Secretary to the Chief Secretary, and moved to Kuala Lumpur, where he was based in the Carcosa Residence. In July 1932, Sheppard was transferred to Taiping as Assistant Secretary to the Resident and became commander of the Taiping Platoon of the Perak battalion of the Malay Volunteer Infantry. During that year, Sheppard received eight months’ leave, spending time in England and Ireland. Following his return, in 1933 Sheppard was posted to Kuala Terengganu and then to Kemaman, from which period the remainder of the images date, including a few from the 1940s and 1950s.