Students who enrol in a Bachelor of Education (Early Childhood Education) at the Institute of Early Childhood, Macquarie University, with a Diploma in Children's Services attained from a Technical and Further Education (TAFE) institution or a Registered Training Organisation (RTO) often experience challenges in their first professional experience unit. Utilising a phenomenological approach to understand the students' previous knowledge and experiences as they navigated through their first professional experience unit, this qualitative study identified factors including institutional structures and course content as challenging to the diploma student. To ensure diploma students can successfully transition to and participate in their first professional experience unit at university, all stakeholders including the university, the academics teaching the students, and the students themselves need to commit to a multilevel support programme. Key findings from this study support the previous research on this student cohort.