We explored the associations of collective self-esteem and parent educational practices with school engagement in a sample of 128 Samoan middle and high school students in an urban school district. Simultaneous regression analysis revealed that each of these independent variables contributed to significant variance in school engagement. Specifically, the overall regression model accounted for 22% of the variance in school engagement. Collective self-esteem was the most significant association, followed by parent educational practices. Implications discuss how we must consider Samoan and other marginalized youths’ cultural worth and perceptions of parental practices as critical factors influencing their school connections.