This article discusses the challenges involved in Samoa’s teacher upgrade programme. The teacher upgrade initiative came about because of the Samoan Ministry of Education, Sports and Culture’s aim for all in-service primary and secondary teachers to hold a Bachelor of Education degree. However, challenges including time scheduling, teachers’ wider responsibilities, unsupportive school principals, and communication barriers with the National University of Samoa appear to have hindered the programme’s implementation. This study employed a qualitative research approach which incorporated talanoa (rich conversation) as appropriate to the Samoan context. The findings from the talanoa sessions with teachers, principals and Ministry officials, highlight the social, cultural, educational and economic challenges that the teachers encountered on their qualification upgrade journeys. We argue that the challenges between the upgrading teachers, the schools, the National University of Samoa’s Faculty of Education and the Ministry could be being resolved through the Samoan notion of va (relational space) in which stakeholders generate mutual solutions to the challenges they encounter. This article concludes with recommendations for each of the partners involved in the upgrade programme in order to move forward.