Terry Hilderbrand graduated from West Point in 2001 and commissioned as an Infantry Officer. He served as a Platoon Leader in the 1st Battalion, 30th Infantry Regiment in the 3rd Infantry Division during OIF (Operation Iraqi Freedom) I in 2002. He returned to Iraq with 3rd Brigade of the 101st Airborne Division in 2005-2006 for OIF IV, and again after taking command of A Company, 3rd Battalion, 187th Infantry in 3rd Brigade of the 101st Airborne Division in 2008-2009 for OIF VII. In 2012, he deployed to Afghanistan as the Executive Officer for 2nd Battalion, 503rd Parachute Infantry Regiment in the 173rd Airborne Brigade for OEF (Operation Enduring Freedom) XIII. An assignment as an Observer Controller at Fort Polk’s Joint Readiness Training Center (JRTC) followed. After that assignment, he returned to West Point, where he served as the Aide de Camp for the 59th Superintendent, LTG Bob Caslen, before assuming the duties of Deputy Director for the Simon Center for the Professional Military Ethic. LTC Hilderbrand then took command of 2nd Battalion, 508th Parachute Infantry Regiment, in the 82nd Airborne Division from June 2018 to May 2020. He is currently the Deputy Director for the Department of Military Instruction at the United States Military Academy. In this interview he talks about counter insurgency operations. He describes his experiences at different levels, including his company’s efforts to find two missing 10th Mountain Soldiers in Iraq. He discusses various techniques he employed at different times and locations. He highlights the importance of understanding local cultures. Near the end of the interview he reflects on how he developed his command philosophy, including how it evolved as he grew as a leader.