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A secure attachment provides a child a base from which to explore, facilitating motivational development in school. With a sample of 3,268 preschool children (ages 36-71 months), this study sought to establish “secure exploration” as a homogenous construct and used structural equation modeling to examine a mediation model of environmental factors (i.e., socioeconomic status [SES], parental depression, neighborhood support) predicting children’s exploratory behavior, mediated by parenting practices. This model explained 36% of the total variance in secure exploration, with parenting practices partially mediating the relationship between secure exploration and both neighborhood support and parental depression. The relationship between SES and secure exploration was fully mediated through parenting practices. Implications for theory and practice in supporting children and caregivers are discussed.