Structure and dynamics of complex systems are often described using weighted networks in which the position, weight and direction of links quantify how activity propagates between system elements, or nodes. Nodes with only few outgoing links of low weight have low out-strength and thus form bottlenecks that hinder propagation. It is currently not well understood how systems can overcome limits imposed by such bottlenecks. Here, we simulate activity cascades on weighted networks and show that, for any cascade length, activity initially propagates towards high out-strength nodes before terminating in low out-strength bottlenecks. Increasing the weights of links that are active early in the cascade further enhances already strong pathways, but worsens the bottlenecks thereby limiting accessibility to other pathways in the network. In contrast, strengthening only links that propagated the activity just prior to cascade termination, i.e. links that point into bottlenecks, eventually removes these bottlenecks and increases the accessibility of all paths on the network. This local adaptation rule simply relies on the relative timing to a global failure signal and allows systems to overcome engrained structure to adapt to new challenges.