The purpose of this study was to investigate the perceptions Latino eighth grade students have of school and schooling factors as they transition to high school and the factors that may influence their self-perceived likelihood of graduating from high school. Middle schools are poised to help Latino students prepare themselves for a smoother adjustment to high school academic life and reinforce the enthusiasm with which they anticipate the transition. Adopting the additive model of acculturation as its theoretical framework--with the belief that acculturation is a more inclusive approach than classic assimilation for linguistic minority students--this study investigated what factors may best predict eighth graders' confidence regarding high school completion. Data were collected from 74 Latino eighth grade public school students in a state in the southeastern region of the United States. Findings from the study showed that eighth grade Latino students, particularly female students, are eager and excited to transition to high school, but they perceive challenges from the school social and cultural environment and a disconnect between their home and school lives. Multiple regression analysis indicated the strongest predictors of a student's self-perceived possibility of completing high school include: (a) gender, (b) a home language other than English, (c) a sibling who had dropped out of school, and (d) after school employment. Ideas for supporting the aspirations of Latino students transitioning to high school are presented.