Are high school students ready for college mathematics? This qualitative case study examined how fifteen former high school students from a small, rural high school in central Vermont perceived their preparedness for college level mathematics and identified recommendations for improvement. Student interviews and math assessment data for each participant were analyzed to respond to the research question. The interview protocol consisted of one-on-one semi-structured phone interviews that were recorded for transcription. Thirteen open-ended questions were developed to answer the research question and sub-questions grounded in the research literature and specific concerns identified by the math teachers defined in the case study. The conceptual framework for this research study included six areas that influenced student success in preparation for college mathematics: improving communication and aligning standards between high school and college; expectations, confidence, and belief in capabilities; transition programs; assessing readiness; interventions and recommendations for high school programming; and student perception and voice.