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Introduction The global obesity "pandemic" has resulted in an increase in bariatric surgeries, with laparoscopic sleeve gastrectomy (LSG) becoming the most commonly performed procedure. While rapid weight loss following LSG offers health benefits, it also raises the risk of gallstone formation. This retrospective study aimed to identify the prevalence of symptomatic gallstone disease after sleeve gastrectomy, determine the incidence of cholecystectomy, and evaluate the advantages of prophylactic cholecystectomy in a Qatari population. Methodology The study reviewed the charts of patients who underwent LSG at Hamad General Hospital, Doha, Qatar, between January and December 2021, with follow-up extending to May 2025. A total of 105 patients underwent LSG during this period. After excluding those with prior cholecystectomy and asymptomatic cases, 98 patients remained in the cohort. Results Among the patients in the cohort, 16 patients (16.3%) developed symptomatic gallstone disease. The cohort consisted of 64 female patients (61.0%) and 41 male patients (39.1%), with a mean age of 29.1±12.7 years. Female patients accounted for 81.2% of gallstone cases, while males accounted for 18.8%. Patients who developed gallstones were younger (median 21.5 years) than those who did not (median 26.0 years), though this difference was not statistically significant (p=0.237). The most compelling finding was the relationship between weight loss rate and the timing of gallstone diagnosis. A significant negative correlation was observed (r=-0.553, p=0.0262), indicating that faster weight loss was associated with earlier gallstone development. The Kruskal-Wallis H-test showed that patients with early diagnosis (≤6 months) had significantly higher weight loss rates (median 12.68 kg/month) compared to the intermediate (3.72 kg/month) and late diagnosis groups (2.21 kg/month) (p=0.0045). A Post-Hoc test was conducted among these groups, confirming that the early diagnosis (≤6 months) group had a significantly faster rate of weight loss compared to both the intermediate and late diagnosis groups. Linear regression analysis revealed that the weight loss rate explained approximately 30% of the variance in diagnosis timing. Conclusion One major postoperative complication after LSG is symptomatic gallstone disease. Its clinical relevance is highlighted by the study cohort's observed incidence rate of 16.3%. Our data suggest that a selective approach, based on individual risk factors for each patient, is warranted, with close follow-up of such patients. The most compelling finding is that the weight loss rate, rather than total weight, is a critical and statistically significant predictor of gallstone formation, especially for early onset, even though female sex remains a strong predisposing factor. This can serve as an important clinical marker for risk stratification and potential prophylactic intervention. A critical window for possible intervention is highlighted by the median time to gallstone diagnosis, which is approximately a year after surgery.