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Montessori attendance as a child predicts higher adulthood wellbeing. Here we ask if there are more optimal times to attend Montessori, and more optimal times to transition to conventional schools. Using data from almost 2000 adults (Mage 37, range 18-81 years) who responded to a series of standard measures of wellbeing, we examined whether adult wellbeing was higher if one had attended Montessori during specific childhood periods (e.g., 3 to 6). The strongest effects were found for preschool but all periods were significant. On transition, leaving at the end of Montessori’s 3-year classroom cycles (age 6, 9, 12, and 15) was associated with higher adult wellbeing than was leaving in the middle of those cycles (e.g., ages 3, 4, 7).