Purpose: Insufficient coronal tooth structure may require restoration of endodontically treated (ET) teeth with cast posts and cores (CPCs). The prognosis for these teeth is a matter of scientific debate, especially if they serve as distal abutments in cantilever fixed dental prostheses (FDPs). The purpose of this study was to study stress field development in distal abutments in two types of FDPs with different pulp cavity conditions. Materials and Methods: The methodology involved the development of four digital models in which the right mandibular premolars were splinted via an FDP with: (1) no cantilever and a vital distal abutment, (2) no cantilever and an ET CPC distal abutment, (3) a single-unit cantilever and a vital distal abutment, and (4) a single-unit cantilever with an ET CPC distal abutment. The models were analyzed using a three-dimensional finite element program, and von Mises stress values and patterns were evaluated. Results: The results revealed that although the stress distribution patterns in dentin were dissimilar, the von Mises stress values registered for the vital and ET CPC distal abutment were not considerably different. However, higher stress values were detected in the dentin area surrounding the post-gutta-percha interface after CPC placement. The addition of the cantilever resulted in a considerable increase in stress on the dental tissue structures. Conclusions: CPCs appear to create a risk of potential fracture that is initiated in the dentin at the apex of the post. The type of restoration appears to have a much more serious impact on the stress pattern developed in the distal abutment, and the addition of a cantilever appears to biomechanically compromise both biologic and restorative structures.