Gastrointestinal complications in critically ill patients during the COVID-19 pandemic pose a diagnostic and treatment dilemma. We present a case of a 74-year-old male who was brought to our emergency department with worsening shortness of breath, fever, and dry cough and was found to have COVID-19 pneumonia. Early in his hospital course, he was admitted to the intensive care unit, and was found to have significant abdominal distension with large amounts of simple fluid on bedside ultrasound. Bedside paracentesis returned succus and enteric feeds, and a methylene blue test confirmed a likely gastrointestinal perforation. The patients' family refused surgical intervention and the patient underwent bedside drainage. This case represents several critical dilemmas clinicians faced during the recent surge of the COVID-19 pandemic.