Contextualization refers to "a diverse family of instructional strategies designed to more seamlessly link the learning of foundational skills and academic or occupational content by focusing teaching and learning squarely on concrete applications in a specific context that is of interest to the student" (Mazzeo, 2008, p. 3). In practice, contextualization has been operationalized through several formats of instruction, such as embedding basic skills instruction within subject matter courses, offering a companion course that contextualizes a basic skills course, or simply teaching knowledge and skills with immediate reference to real-life examples. Contextualization has significant implications for improving remedial math instruction at community colleges. This study capitalizes on a researcher-practitioner partnership aimed at improving the success of students underprepared in math through contextualization at an urban community college. Based on data collected from interviews, classroom observations, and surveys involving students enrolled in several contextualized remedial math courses within manufacturing and engineering technology programs, the authors examine the following research questions: (1) how do students' experiences within contextualized remedial math courses influence their learning experiences and motivational beliefs about their math abilities and future success? and (2) based on the voices of students and instructors, what are the lessons learned regarding the potential promises and pitfalls of adopting a contextualized approach to teaching remedial math in occupational programs at community colleges? Through the first question, they examine the contextualized remedial math classroom and how students experience and make sense of it. Through the second question, they tap into both student and instructor perspectives to carefully consider the benefits and challenges of implementing a contextualized approach to remedial math instruction in specific community college programs.