This research focuses on fleet management in freight transportation systems. Effective management requires effective planning and control decisions. Plans are often generated using estimates of how the system will evolve in the future; during execution, control decisions need to be made to account for differences between actual realizations and estimates. The benefits of minimum cost plans can be negated by performing costly adjustments during the operational phase. A planning approach that permits effective control during execution is proposed in this dissertation. This approach is inspired by recent work in robust optimization, and is applied to (i) dynamic asset management and (ii) vehicle routing problems.In practice, the fleet management planning is usually decomposed in two parts; the problem of repositioning empty, and the problem of allocating units to customer demands. An alternative integrated dynamic model for asset management problems is proposed. A computational study provides evidence that operating costs and fleet sizes may be significantly reduced with the integrated approach. However, results also illustrate that not considering inherent demand uncertainty generates fragile plans with potential costly control decisions. A planning approach for the empty repositioning problem is proposed that incorporates demand and supply uncertainty using interval around nominal forecasted parameters. The intervals define the uncertainty space for which buffers need to be built into the plan in order to make it a robust plan. Computational evidence suggests that this approach is tractable.The traditional approach to address the Vehicle Routing Problem with Stochastic Demands (VRPSD) is through cost expectation minimization. Although this approach is useful for building routes with low expected cost, it does not directly consider the maximum potential cost that a vehicle might incur when traversing the tour. Our approach aims at minimizing the maximum cost. Computational experiments show that our robust optimization approach generates solutions with expected costs that compare favorably to those obtained with the traditional approach, but also that perform better in worst-case scenarios. We also show how the techniques developed for this problem can be used to address the VRPSD with duration constraints.