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Student success programs aim to bridge the achievement gap among different student populations in their pursuit of a college education (Acevedo-Gil & Zerquera, 2016; Ganss, 2016; Trautwein & Bosse, 2016). This study conducted semi-structured interviews with five conditionally admitted students participating in a student success program, catering to a significant number of first-generation, non-traditional students, those from low socioeconomic backgrounds, and various marginalized communities. The interviews revealed that students' perceptions often differed from the services offered, leading to three core themes of barriers faced during their college journey: lack of personal investment, self-doubt, and confusion. These themes, along with their respective sub-themes, provide valuable insights for student success programs to assess their initiatives and practices, ultimately fostering academic excellence.