In the light of many changes taking place in higher education, it is often problematic to align the theoretical pronouncements with their application on the ground. This article is based on a study that tracked steps taken by educators to introduce portfolio assessment in an institution of higher learning. A phenomenographic research method was used to capture data from the documents the educators had produced over a two-year period. The focus of the research was on the manner in which three factors revealed the experiences of the research participants, namely the past of the participants and the institutional culture, the educational beliefs of the participants, and their educational understanding of portfolio assessment. Analysis of documents on programme design, implementation and evaluation revealed how the participants struggled to implement the use of a portfolio for assessment. After persistence and reflection, they improved on their practical interpretation of the theory.