Background: Predicting the difficulty of laparoscopic cholecystectomy (LC) preoperatively is pivotal in reducing complications and improving patient outcomes. This study examines clinical, biochemical, and imaging factors contributing to challenging LC cases, aiming to develop a predictive model for better surgical planning. Methods: A prospective study involving 60 patients with symptomatic gallstone disease was conducted at Krishna Mohan Medical College, Mathura. Preoperative parameters such as demographic data, laboratory findings, and ultrasonographic features were analyzed in relation to intraoperative outcomes, including conversion rates and complications. Results: Gallbladder wall thickness, pericholecystic fluid, and WES (wall-echo-shadow) sign were significantly associated with difficult surgeries (p<0.05). Male gender was also correlated with higher conversion rates. Thirteen percent of cases required conversion to open cholecystectomy. Conclusion: Identifying high-risk factors like gallbladder wall thickness, pericholecystic fluid, and WES sign preoperatively can enhance surgical planning and mitigate complications. Tailored strategies are recommended for better management of challenging cases.