Though the notion of the "problem" is central to self-directed and research-like problem-oriented learning approaches in universities, few studies have focused on how students themselves conceptualize it. The purpose of this study is to investigate how university students communicatively frame "the problem-oriented problem" in their own problem-oriented writing, and how such frames develop over time. The corpus of analysis consists of a total of 30 student reports each presenting a self-generated problem-oriented project within the humanities, performed and written collaboratively. Thirteen of the reports were produced after one semester and 17 after four semesters of academic studies. The results show that while one half of the students can be said to articulate heuristic problems, the other half only manage to present subjects without problems. It is suggested that in order to challenge and develop students' conceptualizations of a problem-oriented "problem" in the study of the humanities, the genres of their writing might benefit from being redesigned. A more experimental and situated writing-, genre- and literacy approach may be useful to promote, visualize and qualify students' work and provide scaffolding in order to enable students to recognize, understand and challenge academic framings of problems, academic practices and knowledge.