© The Author(s) 2017. Background: During the school years, a cleft of the lip and/or palate (CL/P) may pose a risk to educational achievement. To further understand this multifaceted association, and to offer suggestions as to how young people’s educational experiences might be improved, qualitative investigation is warranted. Design: Semi-structured telephone interviews were conducted with young people born with CL/P (n = 10; aged 10-16 years) and their parents (n = 10). The resulting data were subjected to inductive thematic analysis. Results: Negative social interactions, cleft-related treatment, the presence of an additional condition, and a lack of appropriate support from teachers was found to influence young people’s educational experience. Methods for promoting diversity, support from clinical teams, facilitation of positive school transitions, implementation of training for teachers, and a holistic approach to the measurement of “success” were suggested by participants as potential ways of improving this experience. Conclusions: The findings of this study point to a need for a range of school-focused interventions, as well as the inclusion of a number of potentially impactful variables within future quantitative research.