This study uses mixed methods to identify the factors linked to varying levels of academic performance among Latina/o students enrolled in an alternative high school. Results from the quantitative analyses suggest students who had highly educated fathers and who reported high levels of English literacy are very likely to be classified as academic high achievers. In addition, students who received school suspensions were more likely to get lower grades than their never suspended counterparts. A majority of the students reported lack of authentic caring student-teacher relationships and a culture of low academic expectations prevailing at the school. Academic achievement was also impeded by accelerated role taking among the students, such as becoming parents and working long hours. Implications for urban small school education are discussed.