Chapter 5 examines the evolving legal context and the practical effectiveness of CoE interactions with the central case study, Kosovo. Kosovo is a sui generis case, distinct from all others, but it is an appropriate case study as it has faced and, in several cases, overcome similar engagement challenges. Over more than two decades, the CoE has innovated and adapted its relationship with Kosovo, and so this chapter seeks to illustrate the pragmatism and creativity which can be employed when the political will to do so is in place. The chapter elaborates the principle of engagement on the basis of ‘functional capacity’ and the practice of monitoring substitution.