Poor sleep quality is associated with numerous physical and mental health problems. The purpose of this study is to analyze the occupational and demographic factors associated with sleep problems among a sample of urban transit operators. The sample consists of 676 workers (44% female, 67% African American) at a Northern California public transit agency who participated in a cross-sectional worksite tobacco survey. Approximately 27% of the sample reported that they often had trouble going to sleep or staying asleep in the past 12 months. Results of multivariate logistic regression analysis showed that frequency of job stressors (e.g., equipment problems, road or traffic problems, poor access to bathrooms) and amount of time needed to unwind and relax after work were significantly associated with often experiencing insomnia symptoms (odds ratio [OR] = 1.76 and 2.44, respectively). Younger workers, females, and nicotine-dependent smokers were more likely to report often experiencing sleep problems than older workers, males, and nonsmokers. Employment length and work shift were not associated with the outcome. The findings indicate that transit operators experience elevated prevalence of past-year sleep problems, and occupational factors play a role in their occurrence. Future research should explore if policies that help reduce frequency of job stressors can mitigate poor sleep quality among this occupational group.