Upper secondary vocational education in Denmark is based on the apprenticeship model, which is recognised as a valuable route to employment for young people who are not aiming for higher education. However, the apprenticeship model has a major weakness: it does not provide eligibility for higher education. The purpose of this article is to examine this problem for apprenticeship in a historical perspective by examining what has been done to solve it, and why the measures taken have not been very successful. The article builds on a combination of policy studies, an analysis of the linkages between apprenticeship and higher vocational education and interview studies. First, the article explores why progression from apprenticeship to higher education has become a major policy problem in Denmark. Secondly, it explores three political initiatives that have been taken to ‘build bridges’ to higher education. Thirdly, it examines the historical development of higher vocational education as an educational sub-system, which includes an analysis of the academisation of the applied engineering programme. Lastly, it examines the transition rates from apprenticeship to higher education during the last decades. This section build on a quantitative cohort study and two interviews studies on the transitions from apprenticeship to higher education.