In 1998, seeing signs of freedom being threatened, Wenstrup accepted an officer’s commission with the U.S. Army Reserve, serving in the Medical Service Corps. In 2005, he deployed for a year of active duty in Iraq where he served as a Combat Surgeon and the Chief of Surgery with the 344th Combat Support Hospital. For his service and actions in Iraq, Wenstrup was awarded the Bronze Star and Combat Action Badge. Wenstrup continues his service in the U.S. Army Reserve as a Colonel and serves at Walter Reed National Military Medical Center in Bethesda, Maryland.