Balancing demands between work and family domains can strain even the most resourceful employee. When the tipping point of conflict between the two is reached, a negative impact on employee well-being can result. Within correctional environments, the psychosocial well-being of officers is critical given the potentially significant impact of having a “bad day on the job.” This study examines work–family conflict as it relates to job stress and job satisfaction within a diverse sample of correctional officers (N = 441) employed at 13 public, adult correctional facilities in a Southern state. Findings indicate strain and behavior-based work–family conflict and family–work conflict were significantly related to both job stress and job satisfaction. Family and supervisory support were uniquely related to job stress, whereas supervisory support, education, and ethnicity were uniquely related to job satisfaction. Implications for correctional organizations are discussed.