Background/Objectives: Anastomotic leakage (AL) is among the most serious complications after colorectal resection with primary anastomosis. Emergency surgery has been identified as a procedural risk factor, but data from mid-volume, non-specialized centers in Central and Eastern Europe remain scarce. This study aimed to evaluate the association between emergency surgery and AL in a sample of unprotected colorectal anastomoses, while adjusting for selected clinical factors. Methods: We conducted a single-center retrospective observational study of consecutive adult patients undergoing left-sided or segmental colorectal resection with primary anastomosis and without protective diversion at a hospital in Gyula, Hungary, between January 2018 and December 2024, irrespective of whether the underlying indication was benign or malignant. Right colectomies, abdominoperineal resections, transanal total mesorectal excisions, Hartmann’s procedures, and diverted anastomoses were excluded. After further exclusion of patients with undocumented operative urgency, 268 patients were analyzed. AL was defined according to International Study Group of Rectal Cancer (ISREC) criteria (grade B or C). The association between emergency surgery and AL was assessed using univariable tests and an age-adjusted logistic regression model. Surgical approach was not included as a covariate because of its strong collinearity with operative urgency. Results: Of 268 patients, 61 (22.8%) underwent emergency surgery. AL occurred in 23 patients (8.6%). The leak rate was higher after emergency than elective surgery (19.7% vs. 5.3%; p = 0.001), although the confidence interval for the adjusted association was wide. Emergency surgery remained independently associated with AL after age-adjustment (adjusted odds ratio (OR) 4.35; 95% confidence interval (CI) 1.81–10.46; p = 0.001). No other variable was significantly associated with leakage. Conclusions: Emergency surgery was independently associated with an increased risk of AL in unprotected colorectal anastomoses. Operative urgency should be considered a relevant element of anastomotic risk stratification, warranting heightened vigilance and individualized protective strategies.