Students with aligned educational and occupational expectations have improved college and labor market outcomes. Despite extensive knowledge about the ways social background and school context contribute to educational expectations, less is known about the role of social intuitions in shaping expectational alignment. Drawing on data from the 2009 High School Longitudinal Study, I estimate the magnitude of socioeconomic inequality in alignment. I examine how differences in observed student characteristics contribute to, and whether school-based postsecondary planning initiatives mitigate, that inequality. Results from multinomial regression models show large socioeconomic differences in ninth-grade alignment, and I identify achievement, attitudes about college and careers, and relationships with significant others as contributors to those differences. Participation in postsecondary planning is associated with reduced uncertainty and increased alignment, but this relationship does not differ by social background, indicating that the examined college and career planning policies do little to address inequality in alignment.