Cortical bone is a tough biological material composed of tube‐like osteons embedded in the organic matrix surrounded by weak interfaces known as cement lines. The cement lines provide a microstructurally preferable crack path, hence triggering in‐plane crack deflection around osteons due to cement line‐crack interaction. Inspired by this toughening mechanism and facilitated by a hybrid (3D‐printing/casting) process, the study engineers architected tubular cement‐based materials with the stepwise cracking toughening mechanism, that enables a non‐brittle fracture. Using experimental and theoretical approaches, the study demonstrates the competition between tube size and shape on stress intensity factor from which engineering stepwise cracking can emerge. Two competing mechanisms, both positively and negatively affected by the growing tube size, arise to significantly enhance the overall fracture toughness by up to 5.6‐fold compared to the monolithic brittle counterpart without sacrificing the specific strength. This is enabled by crack‐tube interaction and engineering the tube size, shape, and orientation, which promotes rising resistance‐curves (R‐curve). “Disorder” curves and statistical mechanics parameters are proposed for the first time to quantitatively characterize the degree of disorder for describing the representation of the architected arrangement of materials in lieu of otherwise inadequate “periodicity” classification and misperceived disorder parameters (perturbation and Voronoi tessellation methods).