Medical residents in difficulty struggle to comply with educational requirements. They pose a liability to patient safety and they have problems to adapt to the professional role of a doctor. Consequently, being a resident in difficulty may cause identity crisis and have the potential to disrupt the resident’s professional identity as a doctor. Only few studies explore the tipping point between becoming a resident in difficulty or not, and these studies rarely reflect the surrounding sociocultural aspects of the residents’ difficulties such as organisational culture in the workplace. This article explores how medical residency training culture influence on residents’ risk of ending in difficulty. Our study was based on six focus-group interviews with residents (n=28) and in-depth interviews with residents in difficulty (n=10). The interpretation of data employed sociologist Pierre Bourdieu’s theoretical framework around dispositions. Across the data, we identified four themes: Conflicting games in the field of medical education, altruism, organisational hierarchy, and coping with stress. We found a (mis)match between legitimate rules in the field of medicine and the residents’ dispositions to appreciate those rules. These results can inform clinical supervisors and consultants in their decisions for supporting residents in difficulty and increasing educational achievement among struggling residents.