Examining the role of humanities graduate preparation programs in facilitating underrepresented undergraduate students' socialization to the field (social context) of graduate education, this critical multisite case study finds that these programs are crucial to bidirectional anticipatory socialization for graduate education, where one gains new ideas but does not abandon one's background. Additionally, these programs helped in the acquisition of the type of cultural and social capital that are likely to be relevant to disciplinary knowledge, skills, and competencies in graduate education.