The qualitative study explored the opinions and perceptions of freshman, sophomores, and freshman students that dropped out of the university to understand the obstacles and enablers that millennial freshmen faced transitioning into a college environment. To understand these factors the study posed the question, how do the participants (i.e., freshmen, sophomores, and non-returning freshmen students) describe and reflect on their freshman college year at the institution? Describing and reflecting on the experience uncovered college initiatives that were more effective in supporting the transitions, obstacles freshmen encountered, and factors that enabled a seamless transition into the college environment. The study results revealed four core themes that served as either an obstacles and/or enabler that millennial freshman college students encountered that influenced the transition into the college environment. The themes were organized in order by priority: freshmen focused activities, developing effective study skills, instructor-student relationship, and academic advisements-support. The themes functioned as both independent and interdependent factors that influenced the social and academic transition. No one theme dominated the freshman or first-year transition. A combination and orchestrated interaction of all of the themes framed and shaped the experience. Spady (1970) postulated that the first year transition and academic persistence is directly influenced by the level of social and academic integration of the student into the institutional environment. An atmosphere conductive to a successful integration is formed when the institutions have constructed programs, policies, and activities that provide a balance between the social and academic experience. When there is improper balance or an imbalance the student commits "academic suicide" or chooses not to persist academically (Spady). The students possessed positive opinions and attitudes toward the institution. Four of the freshman students that dropped out of the institution are considering returning. A recommendation is that efforts be made to continually engage and follow-up with non-returning freshman so the students are motivated to return to the university. Some areas of improvements were identified in the academic environment. Millennial freshman students required ongoing academic guidance, a collaborative and interactive learning environment, and skill development training during the first-year to create a seamless social and academic transition into the college environment. The institution could benefit greatly from constructing aggressive academic advisement-support mechanisms or conducting an extensive re-evaluation of already existing programs to create a balanced academic and social experience. Hopefully the students' voices and suggested recommendations can serve as tools in the further exploration and development of effective freshman programs and initiatives.