Researchers in the UK and Ireland have noted declining levels of mathematical preparedness amongst students entering universities over the last twenty years. Third level institutions already invest significant resources in the provision of mathematics tuition to first year students and in response to this decline in standards have further invested in the provision of mathematics supports. Research has shown that a significant minority of students at risk of failing do not engage with these resources appropriately. The central research question of this thesis is to explore the reasons for this non-engagement. This thesis presents the findings from a study of two groups of students at the National University of Ireland Maynooth. The 1st group consisted of seven students who had failed their first year of mathematics. They all had very low levels of engagement with available supports. The 2nd group consisted of nine students with similar mathematical backgrounds to the 1st group who had passed their first year of mathematics and had engaged to a significant extent. It emerged that students’ levels of reaction to a number of critical events in their mathematical education were key to their engagement levels and their subsequent progression. The 2nd group were, in general, able to approach their difficulties with mathematics while the 1st group avoided facing up to their difficulties with mathematics. We supply evidence that the students’ behaviour was influenced by fear, social interactions, and motivation.