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Currently, tertiary education student retention is an important concern for universities. Prior research suggests that course completion depends on a number of factors, many of which relate to previous educational histories and life experiences. This paper focuses on the experiences of first-year mature-age adult and vocational education students in terms of their readiness for academic study, individual engagement and institutional affordances, particularly in relation to online learning. Data resulting from an initial survey of incoming students, and follow-up interviews, regarding educational background, motivation for becoming educators, and preparedness for university will be presented in order to highlight factors associated with the students’ experiences at university. The latter is of particular importance in the light of one finding that initial levels of enthusiasm are not matched by similar levels of preparedness or knowledge of academic discourses.