By the outbreak of the First World War Sherriff had left school and begun working as a clerk at the Sun Fire Insurance Office, the same company as his father. Correspondence suggests that his employers preferred for Sherriff not to enlist due to staff shortages, but he nevertheless joined up on 20 November 1915 with the Artists Rifles. By early January 1916 he had begun his training at Hare Hall Camp at Gidea Park, Romford, Essex.
Sherriff now began to write the wartime letters to his mother and father which form one of the most significant components of his surviving papers. At this stage the letters show he was battling acute homesickness, although he gradually became used to the camp routine. The letters also suggest that he was one of the more restrained soldiers in the camp, as he wrote in disapproving tones of other men’s drunkenness, as well as the amorous attentions of the local girls. His training revolved around lectures, sentry duty and physical activities such as trench digging, bayonet practice, bomb throwing and route
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