This study investigates how perceptions of teacher support and achievement goal structures in the school environment correlate with school engagement, and whether depressive symptoms mediate or moderate this association, among 64 low-income teenage mothers. Controlling for prior grades, perceptions of teacher support correlate with higher levels of positive affect and lower levels of negative affect about school. Perceptions of an emphasis on mastery goals in the school environment correlate with higher levels of positive affect and lower levels of school alienation. In contrast, perceptions of an emphasis on performance goals in the school environment correlate with higher levels of negative affect and school alienation. Perceptions of performance goals are especially detrimental to teenage mothers with higher levels of depressive symptoms. (Contains 6 tables.)