Variability in parental academic involvement and socialization practices could explain academic disparities among adolescents. Academic socialization during adolescence is likely to vary based on students' educational histories and ability levels. Thus, adolescents were purposively selected, from a larger longitudinal study, to vary in their "grade point average" (GPA) and "academic tracking" (e.g., Advanced Placement [AP]/honors, remedial). We examined 24 qualitative ecocultural family interviews with parents (n = 12) and their Mexican-origin high school-attending children (n = 12), conducted simultaneously but separately. Guided by the interpretative paradigmatic framework via thematic analysis, we examined practices in school, at home, and in the fostering of academic aspirations. Although families were met with low expectations from school personnel, we found variability in parents' abilities to overcome challenges. At home, parents of low-achieving students reacted to unmet expectations during academic emergencies (e.g., risk for failing a class), while parents of high-achieving students reacted on a daily basis by incorporating communication regarding academics into the family's routine. Although all parents aspired that their adolescents at least finish college, parents differed in their specific expectations of grades. Adolescents, in turn, differed in their own value of education. Understanding within-group differences in academic socialization practices may inform the way educators and interventionists work with families.