Philosophiae Doctor - PhD / This research project explored the learning experiences of two groups of first-year students in the Faculty of Economic and Management Sciences, University of the Western Cape during the course of 2009/2010. The aim was to obtain insight into the learning challenges that these students encountered and the reasons why some of them were less successful in the learning process, while others were successful. The perspective of this study was therefore student centred. The project was undertaken against the backdrop of a higher education institution that caters mainly for so-called 'disadvantaged' and 'underprepared' students. Such students come predominantly from marginalised and poorly resourced education environments and socio-economic backgrounds, which suggests that they would find higher learning challenging and, as a result, would most likely experience failure in the learning process. The objective of the research project was two-fold: firstly, to identify and determine which factors have an impact on failure or successful completion of the first year of study in this faculty; and secondly, to derive from the data a socially situated, supportive and holistic learning approach that could assist more students to be successful in the learning process. The argument in the study was that learning is socially situated and constructed. To realise the objective, Vygotsky's social cultural theory and Bandura's social cognitive theory were used as theoretical orientation of the study. This qualitative, interpretive inquiry was characterised by multiple data collection methods. Qualitative data concerning the perceptions of the participants were generated via written reflective pieces, a questionnaire and individual interviews and content analysis. In addition, quantitative data were collected and this further contributed to the triangulation of rich, in-depth data. An 'open coding' strategy for the content analysis was used, but the approach for the analysis was not purely inductive. A student-centred analytical framework based in part on theories and findings of five studies conducted on student learning, failures and dropouts, and the context of UWC as HSU served as a framework for the analysis but new subthemes also emerged from the data collected The results of these two Case studies revealed that some of the students experienced multiple learning challenges simultaneously which increased in severity during the course of the academic year, and that, in Case 1, these challenges became too overwhelming and severe for the students and that was why they were less successful; while in Case 2, the students managed to overcome and deal with these challenges successfully. The findings of this project, while specific to the context in which it was undertaken, contribute to the growing body of knowledge in the field of higher education and in the identification of enabling factors that could assist more students to be successful in their first year of study at a higher education institution. The findings provide guidelines for a socially situated, supportive and holistic learning approach that could help higher education institutions to mitigate the cumulative effects of learning on students' personal, academic and social lives.