Context Students who engage in self-regulated learning (SRL) are more likely to achieve academic success compared with students who have deficits in SRL and tend to struggle with academic performance. Understanding how poor SRL affects the response to failure at assessment will inform the development of better remediation. Methods Semi-structured interviews were conducted with 55 students who had failed the final re-sit assessment at two medical schools in the UK to explore their use of SRL processes. A thematic analysis approach was used to identify the factors, from an SRL perspective, that prevented students from appropriately and adaptively overcoming failure, and confined them to a cycle of recurrent failure. Results Struggling students did not utilise key SRL processes, which caused them to make inappropriate choices of learning strategies for written and clinical formats of assessment, and to use maladaptive strategies for coping with failure. Their normalisation of the experience and external attribution of failure represented barriers to their taking up of formal support and seeking informal help from peers. Conclusions This study identified that struggling students had problems with SRL, which caused them to enter a cycle of failure as a result of their limited attempts to access formal and informal support. Implications for how medical schools can create a culture that supports the seeking of help and the development of SRL, and improves remediation for struggling students, are discussed.