Social work is a gendered activity, in terms of both its workforce and client group and it is well documented that more women than men enter this area of work. Recruitment campaigns have had some success in attracting underrepresented groups to apply for social work training. However, achievement and retention data maintained and monitored by the General Social Care Council (GSCC) revealed that certain students did not progress as well as others. The GSCC commissioned research to consider students’ progression and success rates on courses of study in England. Although the majority of students and qualified social workers are female, there have been higher relative numbers of men who fail social work training courses. This article will examine the literature and draw on material gathered from interviews with six experienced practice educators about their observations of assessing both male and female students in order to identify any factors or themes that contribute to men being overrepresented amongst those failing.