The purpose of this pilot study was to examine the impact of a 10-week psycho-educational group intervention entitled "Oppression to Opportunity Program" (OOP), which was designed to enhance the academic adjustment of vulnerable, first-generation college students. Participants in the pilot group also experienced multiplicative vulnerabilities as result of the intersecting identities of race, ethnicity, income, religious affiliation, disabilities, sexual orientation, and gender identity. The OOP intervention consisted of eight modules, plus an orientation and a closing session, designed to lessen key barriers (e.g., lack of knowledge of resources, lack of access to high quality mentorships, feelings of isolation) to academic success. The modules incorporated written worksheets and experiential exercises to foster group discussion, participant self-reflection, and community belongingness. Each group met once weekly for 1 h each session over 10 weeks, and was facilitated by an advanced graduate student in counseling. Participants completed the College Self-Efficacy Inventory and Student Adaptation to College Questionnaire as a pretest and post-test, and qualitative after session questionnaires. MANOVA results did not demonstrate a significant difference between OOP (n = 30) and comparison group (n = 33) undergraduates on efficacy and student adaptation. However, ANCOVA results show the impact of group (OOP vs. comparison) on post-tests of self-efficacy and adaptation, while controlling for pre-tests as covariates. Male participants rated the module pertaining to goal setting and establishing role models as most favorable, while the emotional management module was most preferred by female participants. African American participants rated the module pertaining to identity affirmation as most beneficial and the emotional management module was most preferable for Hispanic Americans. Lastly, Caucasian Americans rated the module on finding and sustaining supportive relationships as most favorable. Preliminary results were promising, however, the OOP program needs to be replicated in larger samples. Recommendations were offered including lessons learned regarding challenges associated with the implementation of a pre-post non-equivalent group design. Lastly, the significance of being flexible while building a sense of community, and the importance of providing food, supportive counseling, and peer mentoring were emphasized.