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We aimed to embed silica optical fibers in composites (epoxy vinyl ester matrix reinforced with E-glass unidirectional fibers in mass fraction of 60%) in order to further monitor the robustness of civil engineering structures (such as bridges). A simple system was implemented using two different silica optical fibers (F1—double coating of 172 µm diameter and F2—single coating of 101.8 µm diameter respectively). The optical fibers were dynamically tensile tested and Weibull plots were traced. Interfacial adhesion stress was determined using pull-out test and stress values were correlated to fracture mechanisms based on SEM observations. In the case of the optical fiber (OF) (F1)/resin system and OF (F1)/composite system, poor adhesion was reported that may be correlated to interface fracture at silica core level. Relevant applicable results were determined for OF (F2)/composite system.