Background/Context: Policies featuring individualized learning plans (ILPs) have become increasingly popular among states seeking to improve college and career readiness through early postsecondary planning. Although ILPs are featured in legislation for more than 35 states, limited work has been done on measuring their effectiveness to ensure that students are better prepared for college and career. Purpose: In this study, we fill this gap in the literature by exploring the effects of completing an ILP and potential spillover effects in schools that require the use of this tool. We also explore whether these effects vary by parental income status. Using a quasi-experimental design, we offer nationally generalizable evidence of the ILP on individual student's transition from secondary to postsecondary education Research Design: We use data from the High School Longitudinal Survey of 2009 (HSLS:09), a nationally representative survey of students in 944 public and private high schools who are surveyed at multiple points during their time in high school. Using these data, we employ the quasi-experimental propensity score matching approach to generate balance between treated and untreated groups on observed covariates. Findings: The findings from this study suggest that students who completed ILPs were more likely to identify a career of interest and make informed college choices with respect to institutional fit as compared with peers who did not use this tool. In particular, low-income students who completed an ILP were more likely to apply for financial aid and submit applications to multiple institutions when compared with economically similar students who did not use ILPs. Also, schools offering ILPs were more likely to help students enroll in moderately selective four-year colleges and to complete some advanced credits in English. Conclusions: This study's findings offer evidence that schools can use ILPs to help students prepare for college through the college search and selection process. Although ILPs seem to be most effective in helping students plan for the process of applying to college, greater emphasis may be needed to ensure that ILPs also support students in the effort of academic course planning.