The recruitment of overseas trained teachers (OTTs) in England is a matter that has received as much attention inside the United Kingdom as outside. Education systems in small island and developing states, especially, were believed to have been placed ‘at risk’ following the departure of experienced and qualified teachers. Correspondingly, the presence of OTTs in England has contributed to, inter alia, workforce stability, behavioural management solutions and curriculum enhancement. Despite these contributions, however, very little is known about the career progression of OTTs in England. Through a tracer study of OTTs recruited between 2001 and 2008, in the first phase of teacher migration to the UK, this qualitative study explored the perceived factors that facilitate and/or hinder the progression of Caribbean OTTs in England. Drawing on postmodernism, critical and social identity theories, this paper examines how institutional racism and discrimination play a part in restricting the promotion and career progression of OTTs.