Parental involvement in children’s education has benefits throughout a child’s academic career. Researchers and educators have developed parental involvement programs, the most effective being those that teach parents to understand open-ended mathematics problems, allowing time for children to think, share their mathematical understanding, and reflect on reasoning processes. The use of literacy strategies for mathematical understanding develops students’ communication skills. Having the same objective, we implemented a five-session intervention in our study with four parents and their children, during which we utilized literacy strategies to support parental involvement and children’s mathematical development. In each session, parent-child dyads were provided with a smart pen and smart notebook to record their interactions around the mathematical topics focused on during the session. Our findings showed improvements in parents’ level of assistance throughout our intervention. Additionally, our program contributed to students’ mathematical skills. We share implications for mathematics teacher educators and provide recommendations for further research.