 Rolle joined the United States Army Reserve in September 2001, receiving a direct commission in the Judge Advocate General's Corps.In 2006, Rolle was defense counsel in the court-martial of Sergeant Michael Smith, a dog handler at Abu Ghraib prison, and is credited for the light sentence Smith received based on his arguments to the military jury at sentencing.In January 2008, he was called to active duty and mobilized for a thirteen-month tour at Fort Meade, Maryland, and was responsible for most cases arising from the Walter Reed Army Medical Center in Washington, DC.