Parental involvement was emphasized in the latest Taiwan mathematics curriculum standards. The investigator conducted two case studies on having parents do math problem posing (MPP) with children while completing homework on Mensuration and Numbers. Data collection included parent–child problem-posing worksheets, students’ “math diaries”, measures of math attitude, and, interviews of parents and students. For case one, results showed that most parent–child pairs posed solvable mathematical problems on Numbers, even for worksheets on Mensuration. On parent–child interactions, parents and children were primarily positive in using real-life examples, they expressed interests through MPP, and, appreciated each other. For case two, students learned MPP in school and then showed parents how at home. Parent–child dyads posed different categories of math problems and children’s math attitudes increased over time. The report included parent–child interactions and their views on math problem posing.