Abstract Acute large bowel obstruction secondary to complicated diverticulitis represents a high-risk surgical emergency with significant morbidity. The optimal operative strategy remains debated, with options including Hartmann’s procedure (HP) and primary anterior resection with or without diverting ileostomy (PAR). This study aimed to compare postoperative outcomes and complication rates between Hartmann’s procedure and anterior resection in patients undergoing emergency surgery for acute obstructing diverticulitis. Methodology Study Design and Setting A retrospective cohort study was conducted at a tertiary colorectal referral centre. Patients undergoing emergency surgery for acute large bowel obstruction due to diverticulitis between January 2015 and December 2024 were identified from institutional databases. Patient Selection Inclusion criteria were adult patients (≥18 years) with radiologically and/or intraoperatively confirmed acute diverticulitis causing large bowel obstruction who underwent resectional surgery. Patients were stratified into two groups: •Hartmann’s procedure (HP) •Primary anterior resection (PAR) with or without proximal diverting ileostomy Results A total of 168 patients met inclusion criteria. Hartmann’s procedure was performed in 96 patients (57.1%), while 72 patients (42.9%) underwent primary anterior resection. Baseline characteristics demonstrated higher physiological risk and disease severity in the HP group. Primary Outcome •Overall postoperative complication rate was 46.9% in the HP group compared with 33.3% in the PAR group (p = 0.04). Conclusion In patients presenting with acute large bowel obstruction secondary to diverticulitis, primary anterior resection is associated with lower postoperative complication rates and higher likelihood of stoma reversal when compared with Hartmann’s procedure. While Hartmann’s procedure remains appropriate in physiologically unstable patients or those with severe sepsis, primary resection with or without diversion appears safe and advantageous in carefully selected patients.