Whereas typical Crohn's disease is confined to the terminal ileum and presents with abdominal pain and diarrhea, gastroduodenal manifestations of Crohn's disease are rare, with often asymptomatic patient presentations and inconclusive diagnostic testing. It is, however, a more severe form of Crohn's disease and thus warrants treatment with steroids and biologics much earlier than its ileocolonic counterpart. We present the case of a young, otherwise healthy, male with newly diagnosed ileocolonic Crohn's disease with concurrent gastroduodenal involvement that initially failed management with biologic agents. We discuss the clinical manifestations and often obscure pathology of gastroduodenal Crohn's disease and highlight the necessity of performing a concurrent esophagogastroduodenoscopic evaluation on newly diagnosed ileocolonic Crohn's disease to assess the presence of upper gastrointestinal involvement.