The authors used observational job analysis as a conceptually based technique to measure stress factors unbiased by worker appraisal with 81 transit driving tasks on 27 transit lines. Stressor dimensions included work barriers that interfere with task performance due to poor technical–organizational design, time pressure, time binding (autonomy over time management), and monotonous conditions. Line-specific average stressor values were assigned to 308 transit operators who mainly worked the particular line. Logistic regression analyses showed associations for high work barriers and sickness absences (odds ratio [OR] = 3.8, p = .05). There were elevated risks for work accidents for high time pressure operators (OR = 4.0, p = .04) and for the medium time-binding group (OR = 3.3, p = .04) and significant (α = .20) unadjusted interaction terms for barriers and time pressure in predicting accidents and absences, and barriers and time binding in predicting absences. Findings suggest guaranteed rest breaks and flexible timing for accident prevention and removal of work barriers for reducing absenteeism.