Studies have suggested that brittle fractures occur in steel because microcracks in the brittle layer at grain boundaries propagate as a result of the increase in piled-up dislocations. Therefore, prestraining can approach the limits of a material, which could lead to a decrease in fracture toughness. However, strains are tensors comprising multiple components, so the effect of prestrain on fracture toughness is not simple. Additionally, the mechanism of change in critical stress due to prestrain has not been thoroughly investigated. For the lifetime evaluation of steel structures with a complicated load history, it is important to generalize the effect of complicated prestrain on the decrease in fracture toughness. In this paper, a single prestrain was applied in a direction different from the crack opening direction. A general three-point bending test was employed for fracture evaluation. Numerical analyses using the strain gradient plasticity (SGP) theory, which is a method based on the finite element method (FEM) are carried out; conventional macroscopic material damage rules are considered as well. Using these FEM analyses, the critical stress is calculated. Finally, the change in critical stress can be expressed by the yield point increase and dislocation density and formulated based on the identified micromechanisms.