This paper explores the relationships between a number of different developments in higher education pedagogy, which are subsumed under the broad heading of progress files. The overall concern of the paper is to explore the ways in which personal reflection and learning is enhanced through dialogue. The paper explores the ways learners engage in dialogue in two environments that use different aspects of digital technologies to support the development of portfolios. The findings from the case studies point to the ways in which different technologies facilitated personal reflection mediated through sharing and dialogue. We develop the idea of affordances as a relationship whereby the learner is involved in a purposeful engagement with the possibilities created by their environment. The affordance of digitised technologies in supporting dialogue is, therefore, conceptualised in relation to the characteristics of the learner, not as a simple technology relation. (Contains 1 figure.)