While Crutchfield never enlisted, he frequently provided information on Confederate troop movements to Union forces operating in Chattanooga and the vicinity. During the Union bombardment of Chattanooga in August 1863, he was again pursued by Confederate authorities, but eluded them by swimming across the Tennessee River and reaching Union lines. He provided the leaders of the Army of the Cumberland with invaluable information regarding Confederate troop positions, and would subsequently serve as an honorary captain and local guide to Union generals throughout the Chickamauga Campaign. He assisted William B. Hazen and John B. Turchin at the Battle of Brown's Ferry in October 1863, and Ulysses S. Grant and George H. Thomas at the Battle of Missionary Ridge in November 1863. After the Union Army solidified its control of Chattanooga, Crutchfield provided assistance to General James B. Steedman and other post commanders until the close of the war. In his memoirs, General Philip H. Sheridan wrote that Crutchfield's "devotion to the Union cause knew no bounds," and described the information he provided as critical to the Union Army's success in the Chickamauga Campaign.