Student academic progress has been at the centre of concern to all higher education institutions in South Africa. It is understood that student progress emanates from a range of dynamics that gives students different educational experiences. The student cohort at University of Pretoria (Abdulghani et al., 2014) come from diverse cultural backgrounds in South Africa, aptly called the rainbow-nation, and subsequently bring different levels of proficiency and world experiences to the higher education sector. The student population is like a tapestry interwoven from different cultures and includes students from all �walks of life�, rich and poor, alternative lifestyle and background, as well as students who are disabled, and students who have diverse sexual orientations. The transition from school to university is regarded as a time of extreme stress for students arriving at the university door for the first time. The expectations of students are mostly unknown, but educators know that students entering university come from positions of extreme inequality, not only in terms of schooling, but also of financial and other resources. It is well-documented that in addition to all the other changes, a large number of students arrive at the university lacking the necessary knowledge and skills that will help them cope at university. These are largely students that come from underprivileged schools that still bear the ravages of apartheid education. To assist students in overcoming the lack of these skills and bridging the educational gap, higher education has to address these needs. Hence, it is the intention of this research to �explore the undergraduate Information Technology experience of an extended programme1�. The research is a four-year longitudinal study of IT students in the extended (four-year) IT degrees at UP, and has analysed interviews conducted with IT graduates in a range of professional settings. Taken together, these components have been designed to expand the researcher�s understanding of undergraduate IT experience (extended programmes) and the transition from university to the workplace. Furthermore, it focuses on how students in Information Technology experience their education, how they gain knowledge of what Information Technology is, and what their post-graduation plans are. Based mainly on the theoretical framework of Vincent Tinto (1975), this study provides an analysis of research regarding student experiences, retention and withdrawal in the extended four-year programme (E4YP) in IT. The research methodology used to conduct this study includes a mixed methods approach undertaken from more than one point of view. The researcher used a combination of qualitative and quantitative research features. The data was generated by surveys (online questionnaires and mini-questionnaires), mini-essays and the results of statistical analysis using academic results and Students� Academic Readiness Survey (STARS) scores. The findings of this study paint a portrait of typical first-year students irrespective of study direction. Their experiences and journey during the first-year are fraught with issues such as finance, accommodation, transport, gender inequality, institutional hiccups, loneliness and exhaustion, and difficulty in finding their way around campus. However, many expressed experiencing the euphoria of freedom from school/parental rules, meeting new friends and socialising, and enjoying the general feeling of being a university student.