Background. Compared with other occupations, long-haul truck drivers (LHTD) engage in excessively unhealthy behaviors and experience disproportionately poor health outcomes. Health promotion efforts targeting LHTDs focus on improving individual-level behaviors; however, this occupation is replete with adverse work organization characteristics, high job stress, and compromised sleep health, which are hypothesized to cause poor health behaviors and outcomes among LHTDs. Therefore, the purpose of this study was to explore the connections between work characteristics, job stress, and sleep outcomes, and health behaviors and physical and mental health outcomes among LHTDs. Method. This was a cross-sectional study, using interviewer-administered surveys with LHTDs ( n = 260). Bivariate correlation analysis was used to explore the associations among work organization, job stress, sleep health, and health behaviors and outcomes. Logistic regression analyses were used to determine whether these work organization, job stress, and sleep factors predicted health behaviors and outcomes. Results. Long work hours of more than 11 hours daily (odds ratio [OR] = 2.34) resulted in increased odds of high caffeine consumption. High job stress (OR = 0.48) and poor sleep quality (OR = 0.42) led to decreased odds for spending at least 1 hour daily for cooking/eating. Low sleep duration, less than 7 hours daily (OR = 2.55), led to increased odds of a physical health diagnosis. Both high job stress (OR = 3.58) and poor sleep quality (OR = 2.22) resulted in increased odds of a mental health diagnosis. Conclusion. Health promotion efforts targeting LHTDs need to be coupled with upstream policy, environmental, and systems-level change, especially at the governmental and trucking industry levels.