Educators have a critical role in enhancing children's play interests within the classroom by determining the actions and context of their play. This study examined personal and professional characteristics associated with educators' self-reported play engagement preferences using a sample of Greek early childhood educators. One hundred participants self-reported their engagement preferences during children's free playtime. The Teacher Roles in Free Play questionnaire was used to assess participants' engagement preferences. This study's results showed the roles of "director," "leader," and "uninvolved" as the highest-ranked roles during free play. Multiple regression analysis showed that specific personal and professional factors could significantly predict the leader and uninvolved play roles. This study's findings offer evidence to help early childhood educators reflect upon their engagement practices and enhance their facilitative roles during free play, strengthening the benefits of these interactions.