Data from the High School Longitudinal Study of 2009 were used to describe and compare postsecondary education enrollment patterns of first- and continuing-generation students. Social cognitive career theory was used to explain the processes of educational and career pursuit and attainment, as well as personal, behavioral, and contextual/environmental factors influencing these processes. Postsecondary educational self-efficacy (i.e., a belief or confidence in future educational success) had a significant positive influence on establishing higher postsecondary educational goals for all adolescents. Postsecondary educational self-efficacy and goals, together, also had a substantial positive influence on postsecondary enrollment patterns of both groups. Self-efficacy exerted a stronger total effect for first-generation students. Contextual supports and barriers directly influenced students' goals but played different roles depending on generational status.