The number of first-generation students entering higher education has increased over the years. Unfortunately, their retention rates are lower than their peers (Cahalan & Perna, 2015; Robb et al., 2012). The Portuguese comprise the largest immigrant population in southern New England, many of whom are first-generation students (MAPS, 2016). Researchers have suggested various student engagement programs that help improve student retention (Astin,1999; Stephens et al., 2014), yet there is a lack of research showing persistence rates for first-generation Portuguese students. This study was guided by the following research questions: 1. Is there a significant difference in self-reported involvement for first-generation Portuguese compared to continuing-generation and first-generation students? 2. Is there a significant difference in identified obstacles to involvement for first-generation Portuguese compared to continuing-generation and first-generation students? 3. How do first-generation Portuguese students perceive academic and extra-curricular involvement? 4. How do first-generation Portuguese students describe their college experience and challenges on their journey to graduation? This explanatory sequential mixed methods study began with a survey of undergraduate students (N = 389) to investigate if there were differences in student involvement and challenges among the three groups. This was followed by interviews with seven (n = 7) first-generation Portuguese students to further explore their perceptions of involvement and challenges. Major findings included significant differences in obstacles such as family financial support (F = 5.95, p = 0.003, n[superscript 2] = 0.03sm) and the level of parent loans (F = 6.77, p = 0.001, n[superscript 2] = 0.03sm) among continuing-generation (M = 3.56; M = 4.53), first-generation (M = 3.00; M = 4.24), and first-generation Portuguese (M = 3.09; M = 4.95) students. First-generation Portuguese students had the lowest number living on campus (9.1%), the highest number living with their parents (63.6%); and the highest number working over 25 hours per week (54.5%) compared with continuing-generation (32.2%; 37.7%; 26.1%) and first-generation students (42.5%; 36.2%; 16.3%). There were no significant differences in many areas such as academic engagement outside the classroom, emotional support, encouragement, and objection to education received from family. The study also revealed the following themes: Cultural differences, indebtedness to family; financial burden and time management; and, college involvement, experience, and mentors. The results and recommendations of this study may assist institutional leaders in enhancing and implementing programs to improve persistence rates, especially for Portuguese students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]