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Students who demonstrate aligned educational and occupational expectations have higher educational attainment and improved employment outcomes. Despite extensive research on the development of educational expectations, little is known about how social intuitions shape the alignment of expectations. Using the High School Longitudinal Study (HSLS:09) this paper investigates how social background contributes to the alignment of expectations, and whether school-based planning initiatives are able to mitigate socioeconomic inequalities. Using mixed-effects multinomial regression models, I find large SES differences in the alignment of expectations as early as 9th grade. I further identify academic achievement, early college and career planning, and high parental expectations as key mechanisms to expectational alignment. However, although school-based college and career planning appears to reduce uncertainty relative to high and aligned expectations, it does not appear to have a greater benefit for low-SES students. My findings identify an untapped opportunity for schools to assist low-SES students with achieving the higher expectational alignment expressed by their more advantaged peers.