This study used comparative case study methodology to investigate student perceptions of different programmes that prepare them for a challenging high school education programme: the International Baccalaureate Diploma Programme (IBDP). Given the benefits and challenges of the programme, educators and stakeholders want to ensure students feel ready to participate. In the literature, studies support that programmes such as the International General Certificate of Secondary Education and the International Baccalaureate Organisation’s Middle Years Programme prepare students for the IBDP; however, there is a need for students’ voices on how they perceive they are prepared through these programmes. This study investigated three different approaches to IBDP preparation by gaining student insights through a scaled-item questionnaire and interviews. Students identified experiences that gave them skills to monitor their learning and resources that motivated them to participate in an advanced upper-high school programme.