Apprenticeship training in Sweden and many other European countries goes back to the middle ages. Yet, this special model of vocational education still attracts significant interest due to the challenges young people face in preparing to enter the current labour market. This is obvious both in Sweden and in other comparable countries. The apprenticeship model is primarily promoted as achieving two important goals: first, as a tool to achieve a better match between young people’s qualifications of employer demands for skills; and second, as an education pathway that can make the transition from school to work easier and therefore contribute to social inclusion. Many initiatives to spread information and provide support have been rolled out in the European Union, with the intention to strengthen apprenticeships in EU Member States.This chapter discusses recent relevant experiences linked with vocational education (VET) and apprenticeship training in Sweden. The main issue relates to basic requirements that have to be in place for establishing an apprenticeship training model, and the challenges a country like Sweden – with its mainly school-based VET – will face when aiming to initiate more of a classical apprenticeship training approach within vocational programmes at upper secondary level.