Background: The percutaneous transgluteal approach is a well-accepted method for drainage of deep pelvic abscesses. Recently, in 3 patients, transgluteal drainage was complicated by the development of large gluteal abscesses requiring multiple surgical interventions. Methods: This report describes these cases as well as a search of the literature. Results: Three patients with a complicated clinical course after colon resection are described. After CT-guided percutaneous transgluteal drainage of the pelvic abscess, large gluteal abscesses were diagnosed after 2–6 weeks. Subsequent surgical interventions were needed to adequately drain these abscesses. In the literature, transgluteal drainage of pelvic abscesses is well described as a safe and efficient method. However, until now the development of gluteal abscesses has not been mentioned as a complication in the literature. Conclusion: In our own experience, a transrectally (radiologically or surgically performed) drainage route is recommended in patients who develop a deep pelvic abscess after bowel resection and suspicion of an anastomotic leak.