Context: Transfer of learning refers to the process of applying knowledge learned in previous situations, usually the knowledge and methods acquired in school, to different contexts, such as in the workplace (Bransford & Schwartz, 1999; Marton, 2006). This process is especially relevant in vocational education and training, as learning occurs across different environments, from the educational context to the workplace. The objective of this research is to identify and analyze whether individual characteristics, motivational beliefs, and perceived training quality predict the transfer of learning among vocational apprentices in the Swiss educational context. Approach: A total of 840 dual VET apprentices participated in the study, representing four vocational fields: administration, retail, hairdressing and beauty, and construction. Participants completed a questionnaire assessing their learning transfer, their motivational beliefs (autonomous motivation, controlled motivation, default motivation, perceived academic competence, and workplace self-efficacy), and their perceived training quality. To address the research questions, multiple hierarchical regression analyses were conducted in three steps to predict learning transfer. Findings: Our result suggests that several factors relate to the transfer of learning in the workplace. Model 1 highlights that first-year apprentices experience a higher level of learning transfer compared to those from more advanced stages, while apprentices in administration and retail report lower transfer levels. Model 2 emphasizes the significant role of motivation (both autonomous and controlled), academic competence, and self-efficacy in predicting learning transfer. Notably, higher motivation and a stronger sense of competence and self-efficacy in the workplace are linked to greater learning transfer. Finally, Model 3 shows that a positive training context—characterized by treating apprentices as adults at school and demonstrating good teaching practices—further enhances learning transfer in the workplace. Conclusions: Our results support previous research that highlights the various elements involved in the transfer of learning. Therefore, our findings contribute with new data to the international literature by identifying several factors that significantly relate to the transfer of learning process for VET apprentices.