The main objective of this book is to introduce how to build a dynamic grouping maintenance strategy for a GDPS with consideration of dependencies between at both component and site level (economic, geographical dependencies) and impacts of dynamic contexts (i.e. varying deterioration rate of components, change of maintenance routes, maintenance opportunities, etc.). In this strategy, maintenance routing and scheduling are jointly considered in a global model. The model aims at finding an optimal maintenance and routing plan. For this purpose, a cost structure and a dependence model jointly considering economic and geographical dependence are formulated. They are used as a basis for the development of the global model of maintenance routing and scheduling. In addition, to find a joint optimal maintenance and routing plan, advanced algorithms using jointly Genetic Algorithm and Branch and Bound are proposed. Finally, a numerical study is investigated to evaluate the performance and the advantage as well as limits of the proposed maintenance strategy.