Since the very beginning of query processing in database systems, cost-based query optimization has been the essential strategy for effectively answering complex queries on large documents. XML documents can be efficiently stored and processed using native XML database management systems. Even though such systems can choose from a huge repertoire of join operators (e. g., Structural Joins and Holistic Twig Joins) and various index access operators to efficiently evaluate queries on XML documents, the development of full-fledged XML query optimizers is still in its infancy. Especially the evaluation of complex XQuery expressions using these operators is not well understood and needs further research. The extensible, rule-based, and cost-based XML query optimization framework proposed in this chapter, serves as a testbed for exploring how and whether well-known concepts from relational query optimization (e. g., join reordering) can be reused and which new techniques can make a significant contribution to speed-up query execution. Using the best practices and an appropriate cost model that will be developed using this framework, it can be turned into a robust cost-based XML query optimizer in the future.