Pittard served as a Military Aide to President Bill Clinton from November 1996 until January 1999. In June 1999, he assumed command of 1-32 Armor/1-14 Cavalry at Fort Lewis, Washington as a part of the army's first Stryker Brigade until June 2001. Pittard took command of 3rd Brigade, 1st Infantry Division (3/1 ID) in July 2002 and led the unit on deployments to Kosovo (2002–2003) and to combat in Iraq (2004–2005). (Pittard observed that he and Captain Humayun Khan, who was killed in Iraq, both led the same platoon of 3/1 ID, for which Pittard was later brigade commander.) In July 2005, Pittard was assigned as the Assistant Division Commander for Maneuver, 24th Infantry Division later to transition to the 1st Infantry Division. In July 2006, he deployed on Operation Iraqi Freedom where he assumed command of the Iraq Assistance Group, while still serving as the Assistant Division Commander for Maneuver of the 1st Infantry Division. He was the commander of the Iraq Assistance Group in combat in Iraq from June 2006 through June 30, 2007, and transferred command to Brigadier General James C. Yarbrough. On August 8, 2007, he assumed command of Fort Irwin. On December 18, 2008, Pittard announced his plans to leave Fort Irwin sometime in March 2009. He became the Deputy Chief of Staff for Operations and Training at TRADOC in March 2009.