This study used structural equation modeling to evaluate whether a combination of social cognitive and self-determination theories [Bandura, A. (1986). "Social foundations of thought and action: A social cognitive theory." Englewood Cliffs, NJ: Prentice-Hall; Deci, E. L., & Ryan, R. M. (1987). The support of autonomy and the control of behavior. "Journal of Personality and Social Psychology, 53," 1024-1037] would effectively predict high school students' distress, achievement, and retention. Participants were 427 predominately Latino youth from an inner-city low-income high school. Results indicated that students who reported feeling connected to teachers and their school reported higher levels of autonomous motivation for attending school. Students reporting higher levels of autonomous motivation for attending school reported more confidence (i.e., self-efficacy) in their academic ability, and performed better academically. In addition, students who reported higher self-efficacy beliefs reported less physical and psychological distress and reported higher levels of achievement. Retention in school was predicted by a combination of achievement and the absence of physical/psychological distress. Implications for practice and further research on urban high school students' academic development are described.