Ssgt. Cunningham enlisted in the US Army in Jackson, MS, on August 24, 1967. Following enlistment, he completed basic training at Ft. Jackson, SC, on September 11, 1967. He stood out so much to his superiors, that this, combined with his prior ROTC experience, granted him officer candidacy. As a result, he was enrolled in the Leaders Preparation Course (LPC) on November 3, 1967. This was followed by further advanced training on November 20. He was noted as being jump school certified and mobile qualified, allowing him to be classified among the most elite army units to serve in Vietnam. His combined experience also qualified him as a Student NCO Candidate, enabling him to receive non-combat leadership training first at Fort Benning, Georgia, then later at Ft. Jackson, SC. Following the completion of his training, he was promptly promoted to Staff Sergeant (designation E-6) on June 12, 1968.