Boyle joined the military in 1967, entering the Royal Military College of Canada as student #8790 and training under Brigadier General William Kirby Lye, whom he characterised as a "crusty old codger". He spent his first year at school in Fort Champlain, sharing a room with Brian D. Pashley, before moving on to spend his next three years living in the Stone Frigate; he participated in varsity football, handball and judo. He graduated with his Honours degree in Economics in 1971. He became Commanding Officer of 4 Fighter Wing and Base Commander of CFB Baden-Soellingen in 1988.