This is a unique case of a closed-loop bowel obstruction secondary to intra-abdominal drain insertion to illustrate a new complication of drain usage. A 47-year-old patient presents with bowel distention and obstruction. Laparotomy revealed obstructed small bowel looped around a fibrotic tract tracing back to a drain insertion point. This is a case report where a patient suffers rare long-term complications from routine drain insertion. Although beneficial in treating infection and abscess formation after anastomotic leaks, drain insertion as a prophylactic measure has not been proven to be beneficial. Surgeons who routinely use intra-abdominal drains should be aware of the complications of drain insertion and use with caution. Although not extensively documented, serious complications from drain insertion do occur. There is no role for prophylactic drain insertion in colonic anastomoses procedures.