Background: Anastomotic leaks are inevitable complications of gastrointestinal surgery. Early hospital discharge protocols have increased concern regarding outpatient presentation with anastomotic leaks. Methods: One hundred anastomotic leaks in 5,387 intestinal operations performed at a single institution from 2002 to 2007 were identified from a prospectively maintained database. Statistical analysis was conducted by the unpaired t test, Chi-square test, and analysis of variance. Results: Overall anastomotic leak with a rate of 2.6% for colonic and 0.53% for small bowel anastomoses. Mean time to anastomotic leak diagnosis was 7 days after operation. Twenty-six patients presented after discharge, with mean time to diagnosis 12 days versus 6 days for inpatients (P < .05). Patients presenting after hospital discharge were younger, had lesser American Society of Anesthesiologists (ASA) scores, and were more likely to have colon cancer and less likely to have Crohn's disease. Ninety-two patients required operative management, of whom 81 (90%) underwent diversion. No difference in management, intensive care unit (ICU) requirement, duration of stay, or mortality between inpatient versus outpatient diagnosis was demonstrated. Follow-up at mean of 36 months demonstrated no difference in readmission, reoperation, or mortality rate between outpatient and inpatient diagnosis. Restoration of gastrointestinal continuity was achieved in 61-67% in the outpatient and 59% in the inpatient group (P = NS). Conclusion: Outpatient presentation delays diagnosis but does not alter management or clinical outcome, or decrease the probability of ostomy reversal. Prolonging hospital stay to capture patients who develop anastomotic leak seems to be unwarranted. For patients requiring operative management, we recommend diversion as the safest option with a subsequent 61% reversal rate.