Length of stay (LOS) is an important issue for many healthcare organizations. In-patients with extreme LOS account for a disproportionately large percentage of hospital costs. Our analysis of over 15,000 pediatric hospital discharges at The Hospital for Sick Children (Toronto, Canada) between 2015 and 2016 revealed that the vast majority of patients with extreme LOS were discharged directly home, with only a minority receiving home-based services. Patients with the greatest LOS were accounted for by primarily four subspecialty services. Although this report outlines an analysis of pediatric in-patients, our findings and implications are relevant for all jurisdictions and populations as many acute care hospitals often "hold" patients with complex, chronic illness as in-patients for extended periods because alternate appropriate services may not exist or be available. Our case study highlights three key areas to improve quality of care for patients with extreme LOS: alternate levels of care, system resources and transitions to home.