At the outbreak of the Civil War, he enlisted as a private in Company H of the 2nd Ohio Infantry Regiment on April 17, 1861, for three months of service, during which time he participated in the First Battle of Bull Run. He soon re-enlisted in the Army for a three-year term, being mustered in on September 11, 1861, at Camp Dennison, Ohio, and days later joining the reconstituted 2nd Ohio Infantry as a corporal in Company G. Promoted to sergeant on March 13, 1862, Pittenger saw action in Andrews' Raid, also referred to as the Great Locomotive Chase. Captured on April 15, 1862, near Lafayette, Georgia, he escaped execution as a spy and was imprisoned until March 18, 1863, when he was paroled via City Point, Virginia. This is the story of the failed attempt, the escape, capture and execution of eight soldiers as spy's and Pittenger's eventual release by prisoner exchange.