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As autonomous systems and robots are applied to more real world situations, they must reason about uncertainty when planning actions. Mission success oftentimes cannot be guaranteed and the planner must reason about the probability of failure. Unfortunately, computing a trajectory that satisfies mission goals while constraining the probability of failure is difficult because of the need to reason about complex, multidimensional probability distributions. Recent methods have seen success using chance-constrained, model-based planning. However, the majority of these methods can only handle simple environment and agent models. We argue that there are two main drawbacks of current approaches to goal-directed motion planning under uncertainty. First, current methods suffer from an inability to deal with expressive environment models such as 3D non-convex obstacles. Second, most planners rely on considerable simplifications when computing trajectory risk including approximating the agent’s dynamics, geometry, and uncertainty. In this article, we apply hybrid search to the risk-bound, goal-directed planning problem. The hybrid search consists of a region planner and a trajectory planner. The region planner makes discrete choices by reasoning about geometric regions that the autonomous agent should visit in order to accomplish its mission. In formulating the region planner, we propose landmark regions that help produce obstacle-free paths. The region planner passes paths through the environment to a trajectory planner; the task of the trajectory planner is to optimize trajectories that respect the agent’s dynamics and the user’s desired risk of mission failure. We discuss three approaches to modeling trajectory risk: a CDF-based approach, a sampling-based collocation method, and an algorithm named Shooting Method Monte Carlo. These models allow computation of trajectory risk with more complex environments, agent dynamics, geometries, and models of uncertainty than past approaches. A variety of 2D and 3D test cases are presented including a linear case, a Dubins car model, and an underwater autonomous vehicle. The method is shown to outperform other methods in terms of speed and utility of the solution. Additionally, the models of trajectory risk are shown to better approximate risk in simulation.