A significant number of studies have been conducted with the specific aim of formulating generic strategies to enhance student transition and retention [1, 2]. Far fewer studies have been carried out into the causality of transition and retention failure within computer science based courses. This work aims to explore the reasons why students specifically studying computing based courses may find transition into higher education difficult and ultimately highlight the causes of retention failure within the field. The work attempts to evaluate the benefit of the traditionally proposed transition and retention guidelines when applied to computing courses and where appropriate makes subject specific recommendations to enhance transition and retention within the field