A former railway transportation officer, Wolff entered the military in 1912 and transferred to the German Air Force in July 1915. On his very first flight, Wolff survived a crash that dislocated his shoulder and killed the plane's pilot. On 5 November 1916, Wolff was posted to Jasta 11 but failed to score any victories until Manfred von Richthofen assumed command of the unit in January 1917. Scoring his 9th victory on 11 April 1917, Wolff downed a Bristol Fighter flown by Irish ace David Tidmarsh. On 6 May, having achieved 28 victories, Wolff was given command of Jasta 29. With this unit, he scored two more victories before returning to command Jasta 11 on 2 July 1917. Wounded nine days later, his left hand was injured in a dogfight with 10 Naval Squadron. When he returned to duty on 11 September 1917, he began flying one of the new Fokker Triplanes. Four days later, in another encounter with 10 Naval Squadron, Wolff was shot down by a Sopwith Camel flown by Norman McGregor. His Dreidecker, the first of its kind to be lost in aerial combat, went into a spin and crashed.