In this paper, the effectiveness of reinforcements for flexible pavements is evaluated through an analysis of reflective cracking. Different stiffness and thickness reinforcements are considered for the rehabilitation of an already cracked pavement. The effect of the reinforcement is assessed from two different perspectives: (i) the ability to reduce stresses in the rehabilitated pavement layers, and (ii) the capacity to mitigate the crack propagation from deeper layers. A finite element model (FEM) is adopted to study the stress and strain state of the pavement layers. The pavement model has been properly validated, transitioning from a simply supported beam scheme to an elastic multilayer model. In addition, to represent crack propagation, fracture evolution is analyzed using Linear Elastic Fracture Mechanics (LEFMs) and Paris’ law. The effect of different reinforcements on the pavement is then simulated. The results show that the reinforcement performance is strictly dependent on the interlayer thickness and stiffness. In particular, high stiffness reinforcements (geomembranes) show increasing effectiveness with stiffness, both in terms of reflective cracking and stress reduction. Conversely, low stiffness reinforcements (SAMIs) show a variable trend with the stiffness modulus. In fact, extremely low stiffness is effective in slowing down crack propagation but is detrimental to the wearing course’s stress condition. However, as the stiffness increases, the likelihood of cracking in the wearing course decreases, though only a small beneficial effect is registered for crack propagation in the base layer.