The use of a well-chosen context for course assignments is widely regarded as motivating for students. However, it is challenging to study the utility of bringing a particular context to computing courses across different types of institutions and student demographics. This is especially true in introductory computing since courses vary widely, for example, in topic order and depth of coverage. In this experience report, we present our approach to, and lessons learned from, studying the efficacy of a specific context for introductory computing assignments across a variety of environments. We focus on the context of pencil puzzles (puzzles like Sudoku or crosswords, designed to be solved on paper using a pencil) and the deployment and fit of pencil-puzzle-based assignments across different institutions’ introductory curricula. We describe our overall process, including recruitment of instructors from a variety of institutions, development and deployment of assignments, and collection of student grade and survey data (including all necessary approvals). By design, we did not use the same assignment at each university, since we aimed to study the underlying context rather than a specific assignment, while also establishing the adoptability of the context to different circumstances. We discuss the heterogeneity of the resulting data set, how we chose to analyze it, and what conclusions can (and cannot) be drawn from such data. We conclude with lessons learned from this experience, with the hopes that they can help others who wish to propagate their innovations and study them in diverse situations.