Introduction: Many operative strategies are used to assess anastomotic integrity such as an air leak test or intraoperative flexible sigmoidoscopy, however an objective anastomotic checklist is yet to be developed and studied. This study aims to develop an anastomotic specific checklist and determine its feasibility for implementation. Methodology: Patients undergoing left sided colorectal resections with primary anastomosis without a de-functioning ileostomy were prospectively included between May 2021 and December 2022. A photographic checklist assessing anastomotic perfusion, integrity via either air test or endoscopic image, evidence of complete operative donut specimens and the assessment of tension was implemented. The feasibility of an anastomotic checklist was externally validated by four independent colorectal surgeons from Australia, New Zealand and United States of America. Results: The anastomotic checklist were completed in 44 patients. Mean age was 62 years, with 43% male and mean BMI 28. Operations included high anterior resection (45%), low anterior resection (18%), ultra-low anterior resection (20%), reversal of Hartmann’s (11%). Median length of stay was 4 days. Complications post operatively were documented in six patients with anastomotic leak in 2% and wound infection in 6.8%. There was poor inter-reviewer agreeance in the assessment of perfusion, tension, air leak test, doughnut integrity and the need for a diverting stoma. Conclusion: The introduction of an anastomotic checklist was a feasible tool to systematically assess and document anastomotic integrity. However, there was substantial disagreement in the subjective evaluation of the checklist.