The role of generational status (first-generation vs. continuing-generation college students) as a moderator of the relationship between psychological factors and college outcomes was tested to determine whether generational status acts as a risk factor or as a sensitizing factor. The sample consisted of 322 undergraduate students who completed online measures of self-esteem, locus of control, and academic adjustment and provided self-reports of GPA. Generational status significantly moderated the relationship between psychological factors and academic outcomes. Generally, it was found that the relationship between psychological factors and academic outcomes were strongest among first-generation students. Further, it was found that for the majority of the interactions with locus of control, first-generation status acted as a sensitizing factor that amplified both the positive and negative effects of locus of control. In contrast, for self-esteem, first generation status acted as a risk factor that only exacerbated the negative effects of low self-esteem. These results are interpreted as reflecting motivational differences between first- and continuing-generation students and are discussed with respect to the social/cultural capital hypothesis that is most frequently presented in the existing literature.