Many students pursuing post-secondary education will experience the imposter phenomenon at some point in their academic career. The imposter phenomenon can lead to anxiety, self-doubt, and self-handicapping strategies that can impair academic success for students. Self-presentation strategies can be adaptive in the competitive and evaluative environment that is education in the U.S., but not all students use these strategies in the same way. To understand the differences, this study looked at how attachment style relates to the imposter phenomenon from an interpersonal perspective. Due to the evaluative and social nature of education, we also looked at how social comparison changes how students portray themselves to others or how they view themselves. We studied 946 university students and found an indirect effect from the imposter phenomenon and self-handicapping via avoidant attachment. Further, social comparison moderated the indirect relation between avoidant attachment and self-handicapping. Specifically, the indirect effect from avoidant attachment and self-handicapping was weaker with higher levels of social comparison. Results highlight the importance of tailoring counseling and career development interventions to the student and emphasize how educators can address social comparison in the classroom.