Crack evolution is initiated by the occurrence of tensile wing cracks and is then further promoted due to the crack coalescence caused by the extension of a central tensile crack segment between two relatively adjacent flaws. To understand such progressive failures in rock, a parallelized peridynamics coupled with a finite element method is utilized. Through this method, the initiation position of tensile wing cracks is observed with respect to varying inclination angles of a flaw, and then its corresponding shifting mechanism is investigated. In addition, the phenomenon of the position shifting being sensitive to various flaw shapes is discussed. Moreover, it is observed that the inclination angle of a central flaw affects the initiation position of other flaws; therefore, the initiation positions of tensile wing crack emanating from other neighboring flaws are analyzed with their angles. Following tensile wing cracks, a central tensile crack segment occurs in the bridging region between a central flaw and other neighboring flaws; the developmental patterns caused by the crack segment are discussed as well. Finally, the role a central tensile crack segment plays in the formation of crack coalescence and specimen failure is investigated in detail. The numerical results in this paper demonstrate good fidelity with established physical test results and complement them, thereby expanding the understanding of fracturing morphology in rock specimens with various flaws.