The chapter discusses leaks following bariatric surgery, particularly from gastric sleeves, which can have severe consequences compared to complications of gastric bypass. Management strategies depend on factors like leak size and timing of diagnosis, ranging from conservative measures with antibiotics to more invasive interventions like laparoscopy with washout and drainage, endoscopic suturing, stenting, and even innovative techniques such as septotomy. The presented cases highlight the challenges in managing a leak from a gastric sleeve in a morbidly obese patient, necessitating multiple surgical interventions including laparotomy, thoracotomy, and eventual completion gastrectomy with oesophagostomy. Complications like fistula formation and subsequent lung infection underscore the complexity of treating such leaks and the importance of a multidisciplinary approach. Learning points emphasise the need for timely intervention and consideration of alternative surgical techniques in challenging cases to achieve successful outcomes.