Objective To determine whether four consecutive extended work shifts are associated with an increased risk of subjective pain complaints, sleep duration, and sleep disturbances. Methods Forty-three healthcare workers, 41 cabin crewmembers, and 18 airline pilots working 4 consecutive extended workdays reported subjective pain complaints and sleep after the 1st and 4th workday. Results The risk of headache (odds ratio [OR] 21.4, 95% confidence interval [CI] 1.85 to 246.5) and pain in the hands, arms, or wrists (OR 3.78, 95% CI 1.84 to 7.76) increased after workday 4 versus workday 1 in cabin crewmembers. Sleep duration was longer (0.6 to 1.1 hours), and sleep disturbances fewer, the night before the fourth extended workday, compared with before the first workday, in all occupations. Conclusions We found no general support for an association between extended work shifts and subjective pain, whereas sleep duration was improved, and sleep disturbances reduced after 4 consecutive extended workdays.