This work addresses the events involved in the fracture of tool steels, aiming to understand the effect of primary carbides, inclusions, and the metallic matrix on their effective fracture toughness and strength. Microstructurally different steels were investigated. It is found that cracks nucleate on carbides or inclusions at stress values lower than the fracture resistance. It is experimentally evidenced that such cracks exhibit an increasing growth resistance as they progressively extend, i.e., R-curve behavior. Ingot cast steels present a rising R-curve, which implies that the effective toughness developed by small cracks is lower than that determined with long artificial cracks. On the other hand, cracks grow steadily in the powder metallurgy tool steel, yielding as a result a flat R-curve. Accordingly, effective toughness for this material is mostly independent of the crack size. Thus, differences in fracture toughness values measured using short and long cracks must be considered when assessing fracture resistance of tool steels, especially when tool performance is controlled by short cracks. Hence, material selection for tools or development of new steel grades should take into consideration R-curve concepts, in order to avoid unexpected tool failures or to optimize microstructural design of tool steels, respectively.