In the context of a programming course taught to college freshmen, we give an account of the switch from a classical, Moodle-based discussion forum to MIT’s NotaBene (NB) platform. One of the defining features of NB is to anchor each discussion thread to a given rectangular zone freely highlightable in any of the course’s PDF documents. In doing so, it forces a precise contextualization of every post–be it to a slide from the lectures, to a sentence from the instructions in the exercises, or to lines of code in the given exercise keys. We hypothesize that this feature lowers the contextualization effort needed to ask a question, thus strengthening students’ engagement and, ultimately, understanding of the matter. Using historical data on three years of giving the same course, we first examine and classify the students’ interventions with both the traditional and the NB-based approach to see if the questions significantly differ qualitatively or quantitatively. We also quantify the contextualization effort needed in both approaches. Finally, we discuss our teacher experience with both platforms and make recommendations on the choice such a discussion forum in a programming course.