This paper proposes the upscaling of conventional individual bridge health monitoring problems into urban regions and transportation networks via mobile and smart sensing techniques together with an innovative reconnaissance procedure. The paper associates structural failure probabilities with systemic features and proposes decision criteria to optimize postdisaster actions. Twenty bridges constituting transportation network infrastructure compose the testbed region and utilize smartphone accelerometers for dynamics characterization in a vibration-based framework. In this framework, reconnaissance output serves for model development, and mobile sensor data enable finite element model updating. Structural reliability analyses merged in a chain setting generate the systemic behavior of cascaded bridge performance. Combining systemic reliability with transportation and health services demand, one can optimize the response strategies of the bridge population and strategize disaster-related decisions in a postevent assessment setting. Based on a testbed region with remote access to nearby vicinities, 18 earthquake scenarios are conducted to visualize the optimal evacuation strategies on the network, taking systemic bridge performance into consideration. Cost-free mobile sensing support adds one more fundamental information source for reducing the uncertainty of the models and, therefore, improves associated mitigation actions.