Jejunoileal diverticulosis (JID) is a rare and nonspecific symptomatic disease. It is usually an acquired condition associated with false diverticula and integrated with colonic diverticulosis which can be diagnosed incidentally or later with complications. A sixty-nine-year-old male presented with sudden onset generalized abdominal pain. Computed tomography (CT) imaging was suggestive of ileal diverticulitis with localized perforation. The patient was treated conservatively with IV fluids and antibiotics and kept nil per orem for three days and discharged after symptoms subsided. The patient returned with a similar presentation but with a greater intensity. CT with oral contrast revealed evidence of distal ileal perforation. The terminal ileum was resected, and a double barrel ileostomy was created. Six months later, the stoma was reversed after resecting 50 cm of proximal terminal ileum which included all diverticula. The patient had a smooth postoperative recovery. Small bowel diverticulitis is generally managed conservatively unless the patient's clinical condition mandates urgent exploration. This report may add knowledge and lead to a change in clinical practice.