On 24 July 1861, 3 days following the First Battle of Bull Run (Manassas), Roller enlisted as a private in the Confederate States military forces at Fairfax Court House. He joined General J. E. B. Stuart’s 1st Virginia Calvary Regiment which fought in that first major conflict of the war. For 4 years he served with Company E which had been organized in Waynesboro and was composed almost exclusively of men from Augusta County. The company was known as the Valley Rangers, or the Augusta Rangers.
The Valley Rangers participated in skirmishes and battles throughout the war, suffering casualties at Port Republic, Chancellorsville, Gettysburg, Spottsylvania, Cedar Creek and many other places. The Regiment’s first casualty of the war was a soldier in Company E.
On 8 April 1865, Roller was riding as a courier for General Fitzhugh Lee’s command near Appomattox Court House. He was injured slightly when thrown by his horse, and he was captured and made a prisoner of war. The following day Lee surrendered to Grant ending the war in Virginia and prompting Roller’s release.