In this qualitative study, we explored the opportunities and difficulties experienced by cognitively high-ability students during the transition to higher education. Although high-ability individuals undoubtedly have the cognitive capacity to excel academically, research has demonstrated persistent underachievement among this group of students, and that they may face particular challenges within higher education compared to primary and secondary education. To better understand their experiences, 10 current and former highability students were selected by means of scores on standardized intelligence tests to participate in semi-structured interviews. Results revealed many similarities between the participants. The majority of the participants reported insufficient study skills and not knowing what was expected of them as obstacles during their transition to higher education. They also cited a lack of challenge in previous schooling as a source of transitional difficulties. On-time entry into higher education, good study skills, and clear expectations led to a more successful transition. Contextual factors, such as perceived support from the learning environment, seemed to have a facilitating effect on the students' transition experience but did not seem to determine the success of a student's transition on their own.