Musculoskeletal complaints comprise the majority of cases encountered by military physicians when evaluating young active duty Soldier-athletes. This is a case of reactive arthritis in a 19-year-old active duty Soldier-athlete whose failure to improve with conservative therapy initiated further investigation. When evaluating what appear to be routine overuse injuries, it is important to actively include other potential causes of musculoskeletal complaints in the differential diagnosis. Further investigation of disease in patients whose symptoms and complaints do not improve with routine conservative care is paramount. Reactive arthritis, though self-limiting in two-thirds of those affected, can become a chronic disabling disease affecting as many as 40 out of 100 patients. Current theories suggest the persistent presence of non-culturable bacteria and bacterial antigens residing in the joint synovia as the etiology of the disease state. There is no curative therapy for reactive arthritis and management is focused on the treatment of symptoms with non-steroidal anti-inflammatory drugs (NSAIDs), immunomodulator therapy, and antibiotics if an infectious source is suspected.