This two-year study was part of a larger project on parental involvement in children’s mathematics learning conducted in Taiwan from kindergarten to grade six. The aim was to study parental roles and to document exemplars for use in subsequent projects. Data sources were from a bi-weekly workshop (family math camps): Teacher educator journals, diaries, focus group interviews, worksheets, and videos. Results indicated that research-based tasks enabled parents to be involved and they assumed multiple roles over time. Parents’ roles were learners, teachers/observers, facilitators, and, partners/opponents. Such roles created bonds among parent groups and contributed potential to motivate children’s mathematics learning in school and at home. The chapter included exemplars of parental involvement and roles using problem posing and problem solving, with math contents from grades five and six.