Activated on 1 April 1941 as the 5th Reconnaissance Squadron, its personnel and equipment being drawn from the inactivated 27th Reconnaissance Squadron at Borinquen Field, Puerto Rico. The squadron had actually been constituted as early as 22 November 1940 to augment the reconnaissance forces available to the Puerto Rican Department. The squadron consisted of three Douglas B-18As, and these constituted the sole strength of the unit at Borinquen Field until the unit was redesignated as the 395th Bombardment Squadron (Medium) on 22 April 1942.