This study discusses the dilemma facing low-income and first-generation potential college students, and how the College Reach-Out Program (CROP) can help. The problem to be addressed in this study was how low-income and first-generation potential college students perceived their lived experiences in CROP on their college readiness, academically, socially, and financially. The purpose of this qualitative case study was to examine how the seven low-income and first-generation college-bound middle school students, enrolled in CROP, and their four tutors/proctors perceived their lived experiences in the program, and the influence the program had on the students' college readiness, academically, socially, and financially. Constructivism theory was the theoretical framework utilized. The research study was directed by three questions, and a qualitative methodology was utilized. A case study design was used to examine student participants and tutors/proctors' perceptions of CROP influence, academically, socially, and its tutoring and financial assistance. Seven student participants from a middle school in Florida enrolled in CROP, along with four tutors/proctors were selected for the study. The data were obtained using questionnaires, semi-structured interviews, CROP artifacts, and a focus group. Inductive analysis was applied resulting in Microsoft Excel coding. Seven themes emerged based on the research questions and theoretical framework: (a) getting better improved grades build confidence; (b) CROP helps with SAT/ACT preparation; (c) CROP offering preparation improves schoolwork; (d) CROP helps meet goals and improves speaking and social skills; (e) receiving tutoring helps to encourage students; (f) CROP utilizes tutors to help with SAT/ACT preparation; and (g) CROP helps with financial aid and scholarship preparation. After applying inductive analyses and the coding method seven themes emerged. The implications were that CROP influenced low-income and first-generation potential college students academically, with tutor assistance, scholarship assistance, and financial counseling. For future practice the study revealed additional promotion needed, influencing social and speaking skills, and additional tutors be implemented. Future research recommendations include increasing sample size, utilizing the narrative model design, and utilizing the program for reducing barriers facing low-income 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 (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]