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Background Anastomotic strictures represent a major source of morbidity in colorectal surgery with an incidence reported up to 30%. Despite this, the mechanism by which strictures develop remains unclear. This study aims to determine the incidence of colorectal anastomotic strictures and associated risk factors among a series of diverted patients. Materials and Methods A retrospective chart review was conducted of 142 patients over a 7-year period at a single institution after colorectal resection with anastomosis and diverting ileostomy creation re-examined with postoperative endoscopy. One patient was removed due to anastomotic tumor recurrence. Patient and technical factors were examined for significance using chi-square analysis. Logistic regression was used to perform multivariate analysis to estimate odds ratio (OR) and 95% confidence intervals (CI). Results Among 141 patients, 14.1% (20 patients) developed strictures detected on endoscopy. Strictures were observed in a greater percentage of women than men (21.2% vs 8%, P = .025). 30.6% of patients who underwent resections for diverticulitis developed strictures while those with neoplastic lesions and other indications had stricture rates of 6.8% and 17.6%, respectively ( P = .002). Anastomoses performed during a colostomy reversal were associated with a higher stricture rate (OR 4.23, 95% CI 1.37-13.40, P = .012). Anastomoses performed with a 28/29 mm EEA circular stapler demonstrated a significantly higher stricture rate versus a 31/33 mm stapler (OR 7.21, 95% CI 1.23-155.58, P = .045). Discussion Our data reveal that female sex, history of diverticulitis, anastomoses performed in the setting of colostomy reversal, and smaller stapler size are associated with a higher rate of anastomotic stricture.