Init2Winit, a gamified mobile application designed to increase students' alignment knowledge between college, career, and salary expectations has been beta-tested in midwestern urban and rural U.S. high schools (age 14-18). Students earn different points in the game when their educational expectations and expected annual income are matched with their desired careers. Propensity score matching was used with 481 high school students to compare the changes in 4-year college plans, college-going aspirations, and educational expectations between players and non-players. Results show that Init2Winit players significantly increased their 4-year college plans and educational aspirations from fall 2018 to spring 2019 compared to those students who did not play the game.