The pivotal importance of workplace learning (WPL) within health professions education has elevated its understanding and improvement to a major research priority. From a sociocultural learning theory perspective, WPL is inherently situated and context-specific. This means that the health care settings in which (future) health care professionals are trained will impact how and what is learned. However, to what extent is the research performed thus far transferable across professional contexts, cultures and borders? To what extent has WPL research sufficiently addressed the contextual characteristics of WPL to enable the evaluation of its transferability? To what extent have methodological and theoretical approaches enabled the building of understanding across contexts? We propose that heightening the transferability of WPL research as well as opening up the conversation to more diverse WPL contexts, settings and cultures will require mapping context and theoretical engagement. To explore what theoretical engagement may afford to our understanding of the influence of context on WPL, we use two theories: Landscapes of Practice and Figured Worlds. These theories with sociocultural groundings provide concrete lenses to understand the interplay between the individual and the context. We conclude with implications for research and practice and advocate for more attention to research practices that may deepen our understanding and heighten the transferability of workplace learning research.