Family stressors predict negative psychological outcomes for immigrant adolescents, yet little is known about how such stressors interact to predict school outcomes. The purpose of this study was to explore the interactive role of family stressors on school outcomes for newcomer adolescent immigrants. Using a convergent parallel mixed-methods design, we used quantitative methods to explore interactions between family separation, acculturative family conflict, and family life events to predict 2 school outcomes, academic achievement (via grade point average [GPA]), and externalizing problems (student- and teacher-reported). The sample included 189 newcomer immigrant public high school students from 34 countries of origin. Quantitative measures included the Multicultural Events Scale for Adolescents, Family Conflicts Scale, and the Achenbach System of Empirically Based Assessment (ASEBA). Qualitative data were collected through a semi-structured interview. Quantitative results found that more family life events were associated with lower GPA, but this association was weaker for participants who had been separated from their parents. More family conflict was associated with more externalizing symptoms (both youth- and teacher-reported). However, the association between family conflict and teacher-reported externalizing symptoms was found only among participants reporting a greater than average number of life events. Qualitative results show that separation from extended family networks was among the most stressful of experiences, and demonstrate the highly complex nature of each family stressor domain. At a time when immigration is rapidly changing our school system, a better understanding of early risk factors for new immigrants can help teachers, administrators, and mental health practitioners to identify students with greatest need to foster behavioral, academic, and emotional well-being.