Postsecondary education is increasingly important to achieving a middle-class lifestyle, but many students are entering college unprepared and are not graduating. The role of parents in postsecondary preparation could make a difference in preparation. In this study, the author used surveys of parents and students in a Midwestern suburban high school to determine the relationships between parents' level of trust in the school, parents' own educational experiences, parents' knowledge of the postsecondary process, and students' perceptions of their postsecondary readiness skills. A significant correlation was found between parental trust of school and parental postsecondary knowledge (r (126) = .322, p< .05). In linear regression models, student gender and grades were found to be significant predictors of postsecondary readiness skills. The model functioned better for males and lower achievers than for females and higher achievers. Implications and directions for future research are discussed.