Background/Context For the last 40 years, researchers have posited competing theories regarding the relative influence of social class background and racial-group membership on the school experiences, academic performance, behavior, and motivation of ethnic minority students. The general purpose of these competing theories has been to explain why ethnic minority students fail or succeed in schools. Many of these theories consider factors inside the school and the child's family, culture, racial/ethnic group affiliation, and responses to school. These theories are commonly situated into three categories of thought: cultural deprivation, cultural difference/discontinuity, and cultural ecology. Each theory juxtaposes dimensions of race as a significant variable, but each has omitted the meaning of race/ethnicity as internally and externally constructed, particularly among Latino groups. Focus of Study The study focused on discerning (1) how the students defined their own racial/ethnic identification and how they perceived that others defined them; (2) how they discussed the opportunities available for the social group with which they identified and the social group with which they believed others situated them; and (3) how the students’ academic orientation (which reflected their educational and occupational aspirations, participation in cocurricular activities, and accommodation to schooling norms) related to their experiences of racial and ethnic identification and their perceptions of opportunity. Population Interviews were conducted with 17 high school students. The students ranged from Grade 9 to Grade 12. In addition, students identified as Mexican or Puerto Rican. Research Design Qualitative interviews were conducted at three data points with participants. The interview protocol consisted of four main sections: (1) familial, socioeco-nomic, and migratory background of each student; (2) student's ethnic identification and construction; (3) student's academic orientation (i.e., educational and occupational aspirations, interpretation of school utility, school engagement, school experiences, and academic performance); and (4) students’ interpretation of constraint and opportunity. Conclusions/Recommendations This study represents an initial foray into a complex conversation on internal and external social identification, racial constructs, and interaction as part of the schooling experience of Latino students. Two significant findings from the larger study are reported in this article. First, the negotiation of identity among these Mexican and Puerto Rican students in predominantly African American schools demonstrates racial/ethnic boundary designations (i.e., who is in and who is out) as structured by skin color. Second, what is meant to be designated as White-looking, Hispanic/Mexican-looking, or Black/biracial-looking maintained differing meaning and latitude in the racial/ethnic boundary options across skin color groups. Both these findings posit further questioning as to what we know about identification among Latino students and, more important, how it gets played out in schools.