This study examines the root causes of student success and struggle in the first semester of a community college tuition-free promise program. The research is set within the context of the Gateway2NKU River Cities Promise Program (RCPP), a partnership between Gateway Community and Technical College (Gateway) and Northern Kentucky University (NKU) to provide a free tuition guarantee to students who are eligible for federal financial aid and graduate from one of six qualifying high schools. In the short existence of the program, first semester success has proven to be a concern, with the average GPA of participants in that semester below a 2.0. Thus, there is a glaring need to explore why these students are struggling and what recommendations can be developed from these findings to improve the RCPP for future students. The purpose of this study was to better understand the root causes of both student success and struggle and to consider solutions within the RCPP context to help more students succeed. Additionally, the importance of developing a college student identity and an academic mindset was specifically explored. To achieve these dual purposes, a qualitative design was utilized to identify root causes of first-semester student outcomes, including grade performance and retention. The collected data included semi-structured interviews with 8 former students and a current student focus group of 6, both of which were analyzed to find themes and commonalities. Primary findings included the significant influence of motivation on student success, seen most prominently through external relationships with friends and family. Half of the participants felt like they identified as a college student in their first semester, which was an indicator of success. The transition from high school to college, balancing work hours, developing good time management, and the influence of online classes were also prominently featured as impacting student success for this population. These findings implore community colleges to stress students to consider and develop their own motivation for attending and succeeding in college classes as well as creating an environment to promote engagement that instills a belief in students that they are a college student, even in a community college, and the understanding of commitments and responsibilities that go with that. Recommendations and implementations throughout the onboarding process and first semester are explored and considered for improved student success for this population. [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.]