This study explores whether randomly assigning group membership enhances the student learning experience. The paper starts with a critical analysis of the approaches to student learning within higher education and how these approaches conflict with findings from applied psychology on group behaviour. The study adopts a serendipitous qualitative methodology to explore how changes to assessment requirements can result in a more holistic learning experience. The findings suggest that students perceive the adoption of randomly allocated groups as an unnecessary risk to their performance within assessment as opposed to an opportunity to enhance their learning. This raises questions regarding the conflict that can exist within education between assessment and learning. The results suggest students operate in a ‘comfort zone’, which can be detrimental to their overall learning experience. Getting students to leave the comfort zone is a particularly stressful situation for both student and educator. Once students leave the comfort zone, competencies that have been dormant surface and they are able to utilise and acquire a wider range of skills. Leaving the comfort zone also results in the creation of a critical incident, which can assist the student in developing their reflective capabilities. The results suggest that randomly allocated groups enhance both an individual’s task capabilities and their teamwork capabilities. The paper concludes that the findings have significant implications for those involved in the design of assessment. The paper also provides an interesting commentary on the issues educators face when undertaking education research within a higher educational context.