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College students in the U.S. are experiencing rising levels of anxiety, depression, and psychological distress, yet often face barriers to accessing care. This study evaluates YOU, a university-provided wellbeing platform, through a task-based usability test with five students navigating mental health challenges. Using UX methods such as think-aloud protocols, the System Usability Scale (SUS), and Single Ease Questionnaire (SEQ), the study identified key usability barriers related to navigation, content relevance, and emotional accessibility. Findings highlight the importance of institutional trust, intuitive design, and personalized wellbeing features. This research offers practical design implications for researchers and designers building empathetic digital mental health tools that support student wellbeing, academic success, and a sense of belonging in higher education contexts.