There has been little research investigating parenting strategies and child outcomes in British Caribbean populations. This study examined the relations of parental control, structure, and autonomy support and children’s motivation and symptomatology in the Caribbean country of Barbados. Results indicated that parental structure was related to higher levels of child academic engagement, perceived competence, perceived control, and intrinsic and identified self-regulation. Parental control was negatively related to engagement, perceived competence, perceived control, and identified self-regulation, and positively related to depression. Autonomy support was, in general, positively related to these same outcomes, and negatively related to depression; however, autonomy support items tapping parents’ acknowledgment of the child and allowance of opinion exchange were related more strongly to positive outcomes than items tapping allowance of choice and independent decision making. Implications for understanding parenting in Caribbean families, and for future cross-cultural parenting research, are discussed.