Context-based assignments have been shown as effective and popular for introductory-level computing courses. We study the use of one such context, pencil puzzles (puzzles typically found in newspapers), in upper-level core computing courses. These puzzles are designed to inspire computational thinking, making them a great choice for introductory-level computing assignments, but their fit for upper-level courses is less clear. We collaborated with several instructors of upper-level courses at four institutions, who delivered a pencil-puzzle-based assignment in their course and allowed us to survey their students about their experience. Overall, the students indicated positive perceptions of the assignments. The most varied answers related to implementation aspects of the assignments. To analyze correlations between students’ sentiments and their demographic and experiential background, we used mixed-effects regression modeling to analyze this heterogeneous data set. The survey responses were characterized by two dimensions, one roughly corresponding to students’ sentiment about the assignment and the other to their technical assessment of the assignment. For the first dimension, we found that the students’ self-reported level of preparedness from earlier courses positively correlated with their enjoyment of and satisfaction with the pencil puzzle assignment. The second dimension was correlated with both the level of preparedness as well as the students’ self-reported problem solving type: Clarifier, Implementor, Ideator, and Developer. Somewhat surprisingly, the analysis indicated Ideator as being the most positively correlated with the technical aspects of the assignment. Notably, the analysis did not indicate any correlation with students’ race or gender in either dimension.