Increasingly, contemporary work means graduates will operate in multiple workplace settings during their careers, catalysing the need for successful transfer of capabilities across diverse contexts. The transfer of skills and knowledge, however, is a complex area of learning theory which is often assumed and lacks empirical analysis. Facilitating transfer is critical for preparing students for effective transition to the workplace. Work Integrated Learning (WIL) provides an opportunity for tertiary education students to â€˜practice’ transfer across classroom and work settings. Building on existing scholarship and using a mixed-methods design, this study aimed to explore the nature of transfer across these contexts during WIL, influencing factors and WIL design principles that optimise transfer. Survey data were collected from WIL students (N = 151) and interview data from WIL industry supervisors (N = 24) across different disciplines/professions in three universities (Australia and New Zealand). Findings indicate that students practice transfer during WIL, yet it is often during less complex tasks that relate to discipline-specific skills, rather than generic ones. WIL thus augments transfer, yet certain program and workplace characteristics enhance student confidence and capabilities in this process, highlighting the need for careful curricula design. Findings also highlighted the important role of paid work and volunteering and emphasise the importance of educators taking a holistic approach to developing students’ transfer ability, drawing on practical and authentic learning in curricular, co-curricular and extra-curricular activities, particularly those that engage industry. Implications for stakeholders are discussed, and strategies identified to enhance skills and knowledge transfer from classrooms to the workplace.