From kindergarten through high school, it is a widely accepted belief that students need to complete mathematics homework in order to become fully proficient with the subject. Throughout the years, however, there have been concerns raised regarding not only the amount of homework that teachers assign to students, but also the potential harm to students’ well-being that mathematics homework may evoke. This study limited the research to mathematics homework practices in the middle grades. This study sought to learn how well the homework practices of middle school math teachers aligns with the best practices associated with mathematics homework (as determined from current research), to gain insight into the perceptions middle school students and parents of middle school parents have concerning homework in mathematics classes, and lastly, how time spent on homework affects students' well-being and the well-being of students’ families. Findings included that overall, teachers did not align their homework assignments and policies with best practices. A majority of students and parents do not feel that the math homework they are assigned helps them to understand math better. The findings from the study have determined there is a disconnect between teachers’ perceptions and students’ perceptions (and also between teachers’ and parents’ perceptions) concerning middle school math homework. Furthermore, findings show that math homework induces stress in students and their parents that in turn affects the family’s well-being. The results from this research will help educate school leaders with information on the effects math homework has on student well-being.