Cruikshank was later transferred to a Methodist church in New Haven, Connecticut, where he continued his social work. Cruikshank worked closely with local labor unions, eventually splitting his time between pastoral work and union organizing. He became close friends with Frank Fenton, who later became the director of organizing for the American Federation of Labor (AFL). Working with the Connecticut AFL-CIO, he organized unions at a number of local businesses—even serving briefly as the business agent for a local of the UE at the Whitney Blake Company. He also became tangentially involved in the Workers' Education Bureau of America. But Cruikshank was dissatisfied with pastoral work. He saw his career as a pastor taking him away from felt that people's needs were so great that in 1936, Cruikshank moved to Washington, D.C. and took a series of government jobs. He first worked for the Farm Security Administration (FSA) as a labor relations officer. He later transferred to the FSA's Migratory Farm Labor Program, where he worked to establish several hundred camps for farm workers migrating out of the Dust Bowl—a program later made famous in John Steinbeck's novel "The Grapes of Wrath".