Single fiber pullout experiments were conducted to determine the adhesion quality, debond behavior and subsequent matrix fracture behavior for a variety of end-modified copper fibers. The matrices were: two different epoxy resins, polyester and polyurethane; the end-modified copper fibers were: straight, flat end-impacted, flat end-impacted with release agent applied and straight end-oxidized. The goal was to determine how the bonding and debonding behavior as well as the pullout behavior of the various fiber-matrix combinations affected the composite fracture toughness increment (DeltaG). Results indicate that the greatest improvement in the calculated DeltaG occurred with a fiber-matrix combination that had a moderate interface bond strength with an interfacial bond failure, minor matrix damage during fiber pullout and moderate post-debond interface friction. Selective oxidation of the fiber end was performed to determine if chemical anchoring of the fiber end could be as effective as mechanical (end-shaping) anchoring of the fiber into the matrix. Improvement in the adhesion bond strength as a result of the chemical anchoring resulted in a significantly lower DeltaG compared to the end-impacted fibers because interfacial failure was not possible. This indicates that for the materials tested, mechanical anchoring of the fiber was better than chemical anchoring in improving DeltaG. To decrease the adhesion bond strength and allow the fibers to debond, a release agent was applied to the flat end-impacted fiber prior to embedment into the matrix. This resulted in a significantly lower DeltaG compared to straight and flat end-impacted fibers for all matrices tested, because the resulting debonding force and friction were significantly reduced. Pullout curves showed that with release agent applied, the end-shape did not effectively anchor the fiber into the matrix. The reduction in the pullout work indicates that the friction at the fiber-matrix interface plays a crucial role in actively anchoring the end-shaped fiber into the matrix after debonding.