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Mechanophores (MPs) undergo chemical reactions to become fluorescent in response to a mechanical stimulus that reflects the magnitude and distribution of applied stress. MPs are an emerging technology for self‐reporting damage sensing applications in polymeric materials in the aeronautical, energy generation, and automotive industries. However, quantitative calibration of the MP response to local stresses remains an outstanding challenge. Herein, a method to calibrate the intensity of the MP fluorescent activation (I) with local hydrostatic stresses (σ_h) is presented. Uniaxial tension is applied to a simple composite comprised of a rigid sphere (silica) embedded in a MP‐functionalized elastomeric matrix (spiropyran (SPN) functionalized polydimethylsiloxane (PDMS)). By monitoring the fluorescence intensity with a confocal microscope while a quasi‐static deformation is applied, in situ observations of MP activation as a function of applied uniaxial strain are obtained. To calculate the associated stress fields, a finite element analysis (FEA) with cohesive zone elements is employed. By comparingσ_h, calculated through FEA with theIof the PDMS/SPN system, a linear relationship betweenIandσ_his directly determined. The technique presented can be employed for many MP‐containing materials systems to calibrateItoσ_h.