There has been widespread concern about widening disparities in parental investments that may be associated with widening gaps in educational attainment. Using data from the National Education Longitudinal Study of 1988 and the Education Longitudinal Study of 2002, this study examines parents' investments and engagement in the college-going process for two cohorts of high school students, focusing on adolescents from low- and high-income families. Between the high school classes of 1992 and 2004, income gaps widened in financial preparation for postsecondary education expenses and student college-admissions test-preparation. In contrast, the income gap in parents-child conversations about the college-going process narrowed, due to a larger increase among low-income parents. I examined potential explanations for growing gaps and found evidence supporting both rising income inequality and changing associations between income and college-going activities. Implications for educational attainment gaps are discussed.