Chronic gastric instability (CGI), potentially part of the gastric dilatation and volvulus (GDV) syndrome, was identified in four free-ranging Virginia opossums (Didelphis virginiana) treated at the Wildlife Rehabilitation Center of Minnesota in Roseville, Minnesota. These individuals displayed lack of expected weight gain, inappetence, gastric gas distension, and delayed gastric emptying time. One was diagnosed with GDV via diagnostic radiology, whereas the other three were diagnosed with suspected CGI using radiographs, ultrasound, and confirmed with exploratory surgery. Clinical signs fully resolved after surgical intervention and supportive management in all four cases. This case series illustrates the clinical signs, diagnostics, and treatment of CGI in Virginia opossums.