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While socioeconomic inequality in postsecondary outcomes is well documented, limited research explores the extent to which seeing a high school counselor can help to reduce inequality in college destinations. In particular, previous research rarely considers the context in which counselors work. Using the Educational Longitudinal Study (ELS: 2002), we find that previous research has overestimated the role of seeing counselors by not considering the broader cultural context in which students consult multiple sources of information in the college-search process. Moreover, the relationship between seeing a high school counselor and whether and where students apply to college varies across high school contexts, with counselors being most relevant in mid habitus schools. Results also indicate that on average. Seeing counselors does not mediate the relationship between social class background and whether and where students apply to college. However, seeing a counselor helps to compensate for the disadvantages associated with lower socioeconomic status in low habitus schools. These findings provide important insights into reproduction of social inequality.