Autonomic self-healing of interfacial damage in a model single-fiber composite is achieved through sequestration of ca. 1.5 μm diameter dicyclopentadiene (DCPD) healing-agent-filled capsules and recrystallized Grubbs’ catalyst to the fiber/matrix interface. When damage initiates at the fiber/matrix interface, the capsules on the fiber surface rupture, and healing agent is released into the crack plane where it contacts the catalyst, initiating polymerization. A protocol for characterizing the efficiency of interfacial healing for the single-fiber system is established. Interfacial shear strength (IFSS), a measure of the bond strength between the fiber and matrix, is evaluated for microbond specimens consisting of a single self-healing functionalized fiber embedded in a microdroplet of epoxy. The initial (virgin) IFSS is equivalent or enhanced by the addition of capsules and catalyst to the interface and up to 44% average recovery of IFSS is achieved in self-healing samples after full interfacial debonding. Examination of the fracture interfaces by scanning electron microscopy reveals further evidence of a polyDCPD film in self-healing samples. Recovery of IFSS is dictated by the bond strength of polyDCPD to the surrounding epoxy matrix.