This chapter shows that, as a national compliance and enforcement actor, the Dutch labour inspectorate faces many challenges. It utilizes a detailed assessment study of the Dutch case to illustrate the complex processes of institutional changes set in motion by the phenomenon of cross-border posting. The chapter outlines a variety of company practices used to engage with–and circumvent–the existing regulation regarding posted workers. The bulk of the involved workforce, both Dutch and foreign, was engaged through one form or another of posted or outsourced recruitment in hiring or subcontracting chains. The chapter focuses on the Dutch experience and argues that problems persist despite reforms. The Dutch case thus gives grounds for discussing the need for enhanced cross-border institutional cooperation and for a thorough social revision of the internal market principles that constitute the foundation of labour mobility across the European Union. The Dutch labour inspectorate has slowly changed to a mixed ‘generalist’ model.