Management of complex acute surgical pathology in austere environments necessitates rapid evaluation and resource appropriate management to avoid time-associated morbidity and potentially mortality. Obstructive upper gastrointestinal (UGI) pathologies can be particularly challenging and associated with significant morbidity. Herein, we present six patients with UGI obstructions encountered over the course of an 8-mo deployment onboard a US Navy Aircraft Carrier. Each patient presented to our medical department with signs and symptoms of obstructive UGI pathology including one gastric volvulus requiring operative management at sea, one with a new diagnosis of achalasia requiring transportation and continental United States outpatient evaluation, and four patients with food impaction requiring urgent endoscopic management. Although UGI pathology is seldom encountered at sea, definitive surgical interventions, including prompt evaluation and management of these acute pathologies, can be performed in an austere environment. We wish to call attention to these potential encounters in order that underway deployed medical units and supporting resources ashore are prepared and equipped to intervene on acute UGI obstructive pathology.