Numerous studies have shown that mathematical knowledge is situational, meaning that students' abilities to transfer and apply skills depends on the conditions in which they were learned (Barab 1999; Boaler 2002, 2016). Given that the real world seldom presents problems that are confined to a single discipline (Barab 1999), it is imperative that teachers use instructional models that allow for the development of holistic understandings of mathematical concepts that are transferable beyond the classroom. This is especially crucial with foundational concepts that permeate higher-level-mathematics courses, such as function identification. In this article, the authors examine how cryptology-based investigations can help students develop conceptual understandings.