Background: We sought to prospectively identify risk factors for biliary complications and 30-day readmission after cholecystectomy for choledocholithiasis and gallstone pancreatitis across multiple US hospitals. Methods: We performed a prospective, observational study of patients who underwent same admission cholecystectomy for choledocholithiasis and gallstone pancreatitis between 2016 and 2019 at 12 US centers. Patients with prior history of endoscopic retrograde cholangiopancreatography or diagnosis of cholangitis were excluded. We used logistic regression to determine associations between preoperative demographics, labs, and imaging on primary outcomes: postoperative biliary complications and 30-day readmission. Results: There were 989 patients in the cohort. There were 16 (1.6%) patients with postoperative biliary complications, including intra-abdominal abscesses, endoscopic retrograde cholangiopancreatography-induced pancreatitis, and biliary leaks. Increasing operative time (odds ratio 1.01, 95% confidence interval 1.00–1.01, P =.02), worsening leukocytosis (odds ratio 1.16, 95% confidence interval 1.07–1.25, P =.0002), and jaundice (odds ratio 3.25, 95% confidence interval 1.01–10.42, P =.04) were associated with postoperative biliary complications. There were 36 (3.6%) patients readmitted within 30 days owing to a surgical complication. A prior postoperative biliary complication (odds ratio 7.8, 95% confidence interval 1.63–37.27, P =.01), male sex (odds ratio 2.42, 95% confidence interval 1.2–4.87, P =.01), and index operative duration (odds ratio 1.01, 95% confidence interval 1.00–1.01, P =.03) were associated with 30-day readmission. Conclusion: Among patients undergoing cholecystectomy for common bile duct stones, jaundice, worsening leukocytosis, and longer operations are associated with postoperative biliary complications. A prior biliary complication is also predictive of a 30-day readmission. Surgeons should recognize these factors and avoid prematurely discharging at-risk patients given their propensity to develop complications and require readmission.