Background <p>The management of gallstones in patients undergoing bariatric surgery remains a topic of debate. This study assesses the management of gallstone disease (GSD) and the development of postoperative gallstones in patients undergoing laparoscopic sleeve gastrectomy (LSG).</p> Methods <p>This study included all patients who underwent LSG at our institution between October 2020 and November 2023. Data on patient demographics, gallbladder status, operative details, complications, and outcomes were collected. Simultaneous cholecystectomy (SCC) was performed in patients with symptomatic GSD and in asymptomatic patients who agreed to undergo the procedure.</p> Results <p>Among 2930 LSG patients, 391 (13.34%) had GSD, including 243 (8.29%) with gallstones and 148 (5.05%) with a history of cholecystectomy. SCC was performed in 142 (4.84%) patients, while 101 asymptomatic patients declined cholecystectomy. SCC increased operative time by 35 ± 11 min without an increase in the complications rate compared with LSG alone. Postoperative gallstones developed in 160 (6.3%) of primary gallstone-free patients and in five (4.95%) of the asymptomatic GSD patients who declined SCC. Postoperative cholecystectomy was performed after a mean of 6.11 ± 2.6 and 5.2 ± 2.4 months, respectively. Mean %EWL at cholecystectomy was 57.89 ± 14.83% and 49.81 ± 15.64%. Weight loss outcomes and improvements in obesity-related diseases were satisfactory.</p> Conclusion <p>SCC is safe but results in a longer operative time with no increase in complication rates. Postoperative gallstone formation remains a concern, with more acute symptoms and earlier cholecystectomy at a lower %EWL in asymptomatic GS patients, compared to gallstone-free patients. Our findings showed that postoperative gallstones developed in only 4.95% of the asymptomatic GSD patients who declined SCC. Preoperative counseling is recommended to inform patients of the potential need for cholecystectomy following LSG.</p>