This paper explores how Problem-oriented Project Learning (PPL) can be organized in a context that meets the pedagogical needs of first year students. Under the assumption that, while PPL provides a fruitful context for learning, it is also challenging for early stage learners, the article formulates the theoretical considerations underlying a strategy for entry-level PPL. On that foundation, this paper discusses a case study where a set of scaffolding structures has been put in place to support the transformative development of first year students acquiring the study habits of PPL. This paper finds that a highly structured approach to entry level PPL promotes the students' academic achievements as well as their sense of meaning in the PPL programme.