College and university remain the dominant academic pathways for graduating Canadian high school students. However, apprenticeships can provide alternative education pathways for a significant proportion of the population. Despite the push to undergraduate programming, some students end up in fields that don't suit their interests. To pursue academic programming that better suits personal interests and academic aptitudes, students have the option of transferring schools. However, no study to-date has explored the transfer reasons and process of students moving between university and apprenticeships in Canada. To address this knowledge gap, we collected qualitative interview data from post-secondary administrators who work directly with transfer students. We also collected interview data from Ontario-based students who transferred to apprenticeships from university. Analysis of our interview data identifies mechanisms that influenced participants' education pathway choices.