Purpose: A fundamental assumption of the apprenticeship model is that there are benefits to both employers and individual learners. This study offers a broad conceptual interrogation of this inherent assumption underpinning the apprenticeship model. Approach: This study combines analysis of literature and available data and draws upon apprenticeship systems and practices in ten nations: Australia, Brazil, Denmark, Egypt, England, Finland, Germany, India, Malaysia and South Africa. Results: For individuals, incentives to undertake apprenticeship may be linked to the process and outcomes of learning, such as the appeal of learning through doing; the opportunities for occupational socialization; the possibility of progression to employment or to additional education; and learning while earning. The analysis of incentives for employers shows a range of reasons related to their short-term interests and the needs of the production processes, technologies, and associated skills; longer-term benefits for the company's staffing strategy; and the opportunity to make a contribution to the wider education and economic systems. Despite all the potential incentives, many firms consider apprenticeships too costly, risky, and complex to justify the investment. However, firms that are making decisions as part of an umbrella associations are more likely to coordinate their skills investment strategies around collectively beneficial outcomes. Conclusions: The links to the labour market and specifically to employers are a key challenge for sustaining apprenticeship systems, as well as for the task of researching them. As such, policy maker (and researcher) consideration of apprenticeship should take account of the capacity and commitment of employers. Another key challenge for apprenticeship is related to the relative attractiveness of this pathway for individuals. What is clear from this study is that the development of a strong apprenticeship system requires the buy-in of both employers and individual learners, and as such the necessity to identify and implement incentives effectively cannot be underestimated. Governments can play a key role in realizing the potential incentives for both employers and learners, thereby yielding benefits for all parties engaged in apprenticeships.