A epoxy resin with the capability of detecting damage has been created by incorporating a mechanophore probe crosslink at 0.2 % by mass. This probe crosslink responds to the strain of fiber fracture with a chemical transformation into a fluorescent configuration. We demonstrate the activation of the mechanophore probe with the single fiber fragmentation test. Compared to older optical strain measurements, the damage probe illuminates regions changed by fiber breaks, even at large distances immediate failure sites. We use Fluorescence lifetime imaging to analyze these changes and provide an indication of degree of damage localized to the nanometer. By observing this damage sensing resin we may gain new insights into the fatigue and failure mechanisms of glass fiber reinforced composite interphase and other material systems that involve localized energy release events.