Instead, Crutchfield served as Stonewall Jackson’s chief of artillery in the Valley Campaign, beginning on April 21, 1862. On May 23, he hurried guns to the front in the Battle of Front Royal, but they were able to do little with the available ordnance. Crutchfield saw service at the First Battle of Winchester on May 25, 1862, including carrying orders to Maj. Gen. Richard S. Ewell. He and his assistant, Edward Willis, were briefly captured on June 8, when a Federal raiding party got into the rear of the Confederate position at Port Republic. Lt. Col. Crutchfield was back on duty the next day at the Battle of Port Republic, directing the guns, having escaped during a melee between his captors and troops from the 37th Virginia Infantry.