Tire rubber particles (NaOH-treated and untreated) were investigated as possible crack stabilizer and toughness enhancer when added to cement paste through in situ crack propagation measurements using two different types of cement, type I/II and an Interground polypropylene Fiber Cement (IFC). Crack deflection and crack bridging were observed in specimens with untreated rubber in cement type I/II. Crack tip mechanisms associated with crack pinning and acrack arrest were present in type I/II cement and IFC with treated rubber particles. Crack tip mechanisms in IFC with treated rubber lead to the increase in CMOD at the ultimate load level. Crack wake mechanisms in IFC with untreated or treated rubber lead to strain hardening and strain softening behavior. Crack wake bridging mechanisms were replaced by multiple cracking mechanisms in the IFC specimens with treated rubber. The IFC specimens with untreated rubber inclusions provided the best results with respect to toughness enhancement.