This chapter analyses apprenticeship as a hybrid legal institution at the intersection of education and employment, highlighting the structural tensions that arise when training becomes an integral component of the employment relationship. After reconstructing its historical evolution from the guild system to contemporary labour markets, the study examines the heterogeneity of apprenticeship models in Europe, outlining common risks such as exploitation, fragmented protections, skills mismatch, and unequal access. Particular attention is devoted to the European Union’s regulatory role, constrained by the division of competences between labour law and education policy. The 2018 Council Recommendation on a European Framework for Quality and Effective Apprenticeships, despite introducing common quality criteria, has proven insufficient to overcome regulatory fragmentation and disparities across Member-States. Against this backdrop, the 2024 Proposal for a Directive on improving working conditions in traineeships—although formally centred on internships—emerges as a potentially more impactful instrument for apprenticeships, due to its focus on contractual transparency, remuneration, and equal treatment. The analysis demonstrates how EU intervention risks reinforcing the labour-oriented dimension of apprenticeships at the expense of their educational function, while neglecting the role of collective actors historically central to their governance. By assessing national models, EU competences, and recent policy developments, the paper argues that apprenticeship represents an emblematic case of the challenges posed by the intersection of labour law and lifelong learning policies and calls for stronger, binding European regulation capable of balancing protection, training quality, and labour market integration.