Apprenticeship in academic prose is a transformative experience (Hayot, 2014); this paper investigates the development of self-regulation (SR) in three bachelor (BA) literature essay writers using the theoretical lens of participatory appropriation by Rogoff (1990), explaining how individuals’ cognitive development stems from social interaction. Research on writing instruction shows that students who learn to self-regulate towards concrete goals achieve better text quality (Rogers & Graham, 2008; Graham & Perin, 2007). Furthermore, research with learners of academic writing suggests that metacognitive skills are integral to the development of genre knowledge and rhetorical effectiveness (author). In this study, we investigate how interaction with a supervisor supports students’ development of self-regulatory and metacognitive skills towards alignment with the stakeholders’ (the examiners) evaluation of the quality of writing. Data was collected through in-depth qualitative interviews at three points in the term; interview data was also collected from the examiners. Data was analyzed in NVivo, using Pintrich’s (2000) SR framework to code the comments by the students. The coded data shows their individual development in SR over the course of the essay writing term. Results show a strong role of the interaction with their supervisor in planning and monitoring their writing. Participatory appropriation thus seemed to help the students plan towards genre-relevant aspects such as what the essay should aim for (genre goals) and what would be the expectations to meet (genre criteria), or monitor some key aspects of essay writing that they would otherwise have not paid attention to. Overall, this investigation responds to calls for context-sensitive inquiries of self-regulation and metacognition, where individual development is highlighted against the backdrop of the social context in which it is embedded (Pieschl, 2009).