We report the development of an extrinsic, self-healing coating system that shows no fluorescence from intact coating, yellowish fluorescence in cracked regions, and greenish fluorescence in healed regions, thus allowing separate monitoring of cracking and healing of coatings. This fluorescence-monitoring self-healing system consisted of a top coating and an epoxy matrix resin containing mixed dye loaded in a single microcapsule. The dye-loaded microcapsules consisted of a poly(urea-formaldehyde) shell encapsulating a healing agent containing methacryloxypropyl-terminated polydimethylsiloxane (MAT-PDMS), styrene, a photo-initiator, and a mixture of two dyes: one that fluoresced only in the solid state (DCM) and a second that fluoresced dramatically in the solid than in the solution state (4-TPAE). A mixture of the healing agent, photo-initiator, and the two dyes was yellow due to fluorescence from DCM. On UV curing of this mixture, however, the color changed from yellow to green, and the fluorescence intensity increased due to fluorescence from 4-TPAE in the solid state. When a self-healing coating embedded with microcapsules containing the DCM/4-TPAE dye mixture was scratched, the damaged region exhibited a yellowish color that changed to green after healing. Thus, the self-healing system reported here allows separate monitoring of cracking and healing based on changes in fluorescence color.