Employees working in residential treatment know from experience that holidays will be stressful and treacherous for the children and youth placed in their programs (and, consequently, for the staff themselves). Using a multiple systems approach, this article examines risk factors for holiday-related stress and crisis in residential settings treating children and youth. Holiday-related stress and crisis is conceptualized as arising from three distinct domains: child vulnerabilities, worker vulnerabilities, and contextual vulnerabilities; the accumulation of multiple vulnerabilities increases risk. The article concludes with practice recommendations to assist residential staff in minimizing the potential for holiday-related stress and acting-out. (Contains 1 figure.)