Over a decade now, Distance Education (DE) has become ubiquitous in the Ghanaian educational system. Four public universities in Ghana are currently running DE programmes in addition to a few private universities. Effective DE programme demands that strategic planning be made at all times. Such planning could be done well if challenges confronting learners on the programme are identified and addressed. This paper sets out to explore and provide an up-to-date picture of the challenges faced by DE students in their quest to study at the university level. Specifically, the study focused on students of the University of Education, Winneba (UEW) as a case study. UEW is one of the nine public universities in Ghana which has been involved in distance education for teachers at the pre-tertiary level. The study adopted both qualitative and quantitative research designs with interviews and questionnaire as the data collection techniques. One hundred and fifty-six students comprising sixty-eight males and eighty-eight females responses out of initial three hundred were received which is equivalent to a response rate of 52%. This constitutes the sample size for the study. Among the challenges identified were - institutional, instructional, social, psychological, and financial. The findings of the study, it is expected, will be utilized instrumentally and conceptually in informing policy directives by public universities presently involved in DE programmes. Further, private and potential providers of DE programme in the country stand to gain a lot from the findings and recommendations of the study.