Residence hall and house employees (resident assistants) at postsecondary institutions in Canada are an important part of the social and rules-based structure that allows these facilities to operate. These employees are challenged with varied situations that require the application of mediation, authoritarian, recognition, and referral skills. To date, studies have ignored the ways in which the experiences of RAs may be gender-specific. This study, conducted with Canadian university residence employees, used an online survey of scale and open-ended questions to establish if the experience of female RAs matched the available information on the resident assistant position. Survey responses indicated a distinct difference between what female RAs believed was expected of them and the actual experiences they had while working within residence halls. It was also clear that some female RAs felt that they were treated as surrogate mothers in the residence setting. Current literature on resident assistants may not accurately reflect their experience; the resident assistant position appears to be a gendered space in which biological sex and gender play important roles in employee experience. The training literature for RAs could be revised to prepare female students for these specific challenges.