In the following article, we share our findings from the comparative analyses of 54 lifelong learning policy measures implemented in nine European countries, with a particular focus on their orientations, objectives, and solutions devised. Informed by the theoretical framework of Interpretive Policy Analysis (IPA), we have further reasoned on the impacts and unintended effects on young adults’ life course transitions, especially those in vulnerable positions, as well as on the hidden ambivalences and incompatibilities in the objectives and orientations of lifelong learning policies. The article provides, first, a brief discussion of the conceptual and methodological choices made. Second, it gives an overview of the design and data basis of our research. In the third section, we present and discuss the central findings from our interpretive analyses, and we finally conclude with a discussion on current trends in lifelong learning policymaking and on their impact on young adults’ transitions.