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Assignments based on meaningful real-world contexts have been shown to be valuable in introductory computing education. However, it can be difficult to distinguish the value of a broad context from the value of a particular instantiation of that context. In this work in progress, we report on our initial findings gathered from deployments of different pencil-puzzle-based assignments. Specifically, we have investigated the use of pencil puzzles as a contextual domain, working with instructors at eight institutions to deliver assignments appropriate to their situation and aligning with their existing materials. We then evaluate the assignments using student grades and survey responses regarding student perceptions of the assignments including self-assessed learning, given a wide array of demographic variables. Our initial results show that while there was some dependency of student responses on their prior programming experience, and female students’ feedback were more positive about one aspect, overall these types of assignments do not appear to put particular groups of students at a strong (dis)advantage.