While coaching contracts might seem straightforward with predefined clauses, some contractual situations and items can generate complexity for the coach. This chapter highlights some of the issues and complexities that result from contracting in coaching. By reflecting on two cases, we examine the issue of contracting from different perspectives (philosophical, performative, legal), putting emphasis on different types of contracts in coaching (administrative, psychological, relational). Some recommendations are offered for coaches on how to deal with the complexity of contracting.