Abstract Chronic microleak following laparoscopic sleeve gastrectomy (LSG) represents a complex and morbid complication that can persist despite prolonged conservative and endoscopic management. Ongoing leakage is associated with sepsis risk, malnutrition, prolonged hospitalisation, and reduced quality of life. Conversion to Roux-en-Y gastric bypass (RYGB) has been proposed as a definitive surgical strategy by diverting enteric flow away from the leak site. This study aimed to evaluate the clinical outcomes, safety, and effectiveness of conversion to RYGB for the management of chronic microleak following LSG. Methodology Study Design and Setting A retrospective observational study was conducted at a tertiary upper gastrointestinal and bariatric surgery centre. Patients managed between January 2016 and December 2024 were identified from a prospectively maintained bariatric database. Patient Selection Inclusion criteria comprised adult patients (≥18 years) with a diagnosis of chronic microleak following LSG, defined as a contained gastric leak persisting beyond six weeks despite non-operative management. Outcome Measures Primary outcome: •Successful resolution of the gastric microleak following conversion to RYGB Results A total of 34 patients met the inclusion criteria. The median interval from index sleeve gastrectomy to conversion surgery was 6.1 months (IQR 4.5–10.2). Primary Outcome •Complete leak resolution was achieved in 32 patients (94.1%) following conversion to RYGB. •Two patients required prolonged drainage but achieved eventual resolution without further operative intervention. Conclusion Conversion to Roux-en-Y gastric bypass is a safe and effective definitive treatment for chronic microleak following laparoscopic sleeve gastrectomy when conservative and endoscopic strategies fail. The procedure reliably achieves leak resolution by excluding the leak site and diverting gastric contents, with acceptable morbidity and favourable nutritional outcomes.