With nearly 25% of bridge infrastructure deemed deficient, repair of concrete structures is a critical need. FRP materials as thin laminates or fabrics are appearing to be an ideal alternative to traditional repair technology, because of their high strength to weight ratios and stiffness to weight ratios. In addition, FRP materials offer significant potential for lightweight, high strength, cost-effective and durable retrofit. One drawback of using CFRP retrofitting is its brittle-type failure; caused by its nearly linear elastic nature of the stress-strain behavior. This causes a strength reduction of the retrofitted member, thus the health of the retrofit applied on the structure becomes equally important to sustain the serviceability of the structure. This paper provides a system to monitor damage on the CFRP retrofits through optical fiber sensors which are woven into the structure to provide damage sensing. Precracked reinforced concrete beams were retrofitted using CFRP laminates with the most commonly used FRP application technique. The beams were tested under constant stress to allow the retrofitting to fail while evaluating the performance of the sensing system. Debonding failure modes at a stress of 9 MPa were successfully detected by TL optical fiber sensors in addition to detection during flexural failure. Real-time failure detection of FRP strengthened beams was successfully achieved and the retrofit damage-monitoring scheme aims at providing a tool to reduce the response time and decision making involved in maintenance of deficient structures.