Students who are engaged in their high school environment have higher graduation rates, fewer discipline problems, and lower delinquency rates. In addition, students who are connected to teachers and involved in extracurricular activities consistently experience positive outcomes. However, although the benefits of school resources such as extra-curricular activities and connections to supportive individuals during high school have been well documented, the factors influencing utilization of these resources have not yet been established. Given the known benefits of activity participation and connection to supportive individuals in school settings, and the voluntary nature of their utilization, it is important to investigate factors influencing students' decision to use these resources. The current study investigated potential barriers and facilitating factors for high school students' activity involvement and support seeking from school personnel. Survey data were collected from 1522, 9-12th grade students in four Pinellas County high schools. Questions regarding students' school, family, and social relationships were assessed via psychometrically valid scales, district records, and items created collaboratively with school district administrators for this specific project. Results were analyzed using bivariate correlations and hierarchical multiple regression. Race, free/reduced lunch status, parent involvement and psychological distress were among the strongest correlates with the support seeking outcomes whereas gender, race, free/reduced lunch status, global self worth, self esteem, antisocial peer group, and perceived school support were among the variables most strongly correlated with the activity involvement outcomes. All significant relationships found were in the predicted direction with barrier variables leading to lower levels of school engagement and facilitating factors leading to higher levels of school engagement. Contrary to the hypotheses, the selected barriers and facilitating factors did not contribute to a significant amount of variance above that accounted for by gender, race, and free/reduced lunch status. In general, males, students receiving free/reduced lunch, and black students had the lowest rates of school engagement. The current results add to existing literature by showing that students who would benefit most from positive assets such as support seeking from adults at school and activity involvement are least likely to engage in the behaviors.