Gregory then arrived to Marine Corps Base San Diego in June 1927 and served as post quartermaster until December 1928, when he sailed for his second tour of expeditionary duty in Nicaragua. He was attached to the Second Marine Brigade under Brigadier General Logan Feland and served as assistant to the brigade quartermaster until he was transferred as quartermaster to "Guardia Nacional de Nicaragua". While in this capacity, he aided in relief work in connection with the earthquake at Managua in March 1931 and was commended by the secretary of the Navy and the Red cross. He received Nicaraguan Presidential Order of Merit with Gold star and also Medal of Merit with silver star for his service in Nicaragua.