An investigation of the stress distribution patterns in post– core restored teeth and the behavior of dentin material to fracture propagation was conducted using experimental techniques such as digital photoelasticity (on photoelastic models), mechanical testing and scanning electron microscopy (SEM) (on extracted teeth). Digital photoelastic experiments showed that endodontic post–core restoration resulted in regions of high tensile stress and of stress concentrations in the remaining dentin structure. It was observed from mechanical testing that the fracture resistance in post–core restored teeth is significantly lower (p<0.0001) than that in intact tooth. There was a significant correspondence between the plane of stress concentrations identified in the photoelastic models and in those of the plane of fracture exhibited by the rehabilitated tooth specimens. While the fracture of post–core rehabilitated teeth was consistent, that of control teeth was not as distinct. The SEM highlighted varying dentin response to fracture propagation at the inner core and the outer regions. The fractographs showed brittle and ductile response to fracture propagation in the outer and inner core dentin, respectively. These photomechanical studies highlighted that the stress concentrations, high tensile stress and loss of inner ductile dentin associated with post endodontic rehabilitation diminished their resistance to fracture.