Interest has recently developed in the purposeful retention of root fragments with their periodontal apparatus to support bone and soft tissue at immediate implant sites in the esthetic zone. This methodology is designed to avoid bone grafting, connective tissue grafts, and the use of membranes and may have short-term benefits in terms of tissue preservation. However, it is not completely without long-term risks. At times, implants may be unintentionally placed into edentulous sites where root fragments remain. This report presents two cases of long-term failure postloading associated with unintentionally retained root fragments. Histologic evaluation evidenced retained root fragments in close association with dental implants and the surrounding bone. Scanning electron microscopic evaluation revealed that the failed implant surfaces were infiltrated by bacterial deposits and calculus. Clinicians should exercise caution when placing dental implants in sites with retained root fragments, as long-term risks may be associated with this therapy.