Historically, Dr. Maria Montessori doubted the value of young children’s play. Compared with how children became normalized through work, Montessori believed play was potentially harmful to children. Recent world events have challenged Montessori’s determination to “downplay” play. Children’s development of self-regulation and resilience, two necessary components of executive function, was severely disrupted when schools closed during the COVID-19 pandemic. Isolated at home, children did not experience normal social encounters. Months later, concentration and socializing are still difficult for children in Montessori classrooms. Research recommends play as a natural remedy, but classic Montessori education regards play as antithetical to work. During this session we will discuss challenges to children’s development, a resolution to the classic Montessori work/play dichotomy, and how children and their development can benefit from play practices at their Montessori school.