Chronic sequelae of COVID-19 remain undetermined. We report a case of postinfection sequelae in a patient presenting with subacute obstruction 2 months after COVID-19 infection. A 34-year-old man with a prior prolonged hospital stay due to COVID-19 complicated by upper gastrointestinal (GI) bleed presented with subacute obstruction and failure to thrive. Upper GI push enteroscopy revealed residual ulcers and multiple proximal jejuno-jejunal fistulae. Midline laparotomy revealed strictures with dense intra-abdominal adhesions, a large jejuno-jejunal fistula, and evidence of prior jejunal perforation following severe COVID-19 infection. The patient recovered after small bowel resection with anastomoses and was discharged home. Histopathological examination of resected specimen confirmed transmural infarction with evidence of prior hemorrhage, diffuse ulcers, and multifocal inflammation. This is the first report of a chronic GI sequelae resulting from COVID-19. As the pandemic evolves, medical professionals must be vigilant to consider alternative GI diagnoses in the COVID-19 survivors.