This work addresses the Joint Maintenance and Routing (JMR) problem for geographically distributed assets in dynamic environments. We extend existing degradation-based models by incorporating sudden shocks, creating a dependent failure process where risk accumulates non-linearly. To solve this, we propose a Mixed-Integer Linear Programming (MILP) model that uses linearization to handle the stochastic nature of shocks. Numerical experiments validate the model's consistency and reveal a critical regime shift from preventive maintenance to risk avoidance as shock intensity increases.