Working conditions and the prevalence of perceived musculoskeletal symptoms (MSSs) among dairy farmers in 2013 were monitored by repeating a mail survey of dairy workers in Scania, southern Sweden, using the same method for collecting data on MSSs and working conditions employed in previous surveys conducted in 1988 and 2002. All dairy enterprises in Scania (total 419) were sent two copies of a questionnaire. One or more responses were received from 232 enterprises (55.4%), of which those from 247 dairy farmers (75% men and 25% women) in 199 enterprises are included in this study. The farmers had increased their weekly working hours in 2013 compared with 2002 (males [Formula: see text]; females [Formula: see text]). Each male milked on average 30 cows in 1988, 44 cows in 2002, and 86 cows in 2013. The corresponding numbers milked by female farmers were 29, 60, and 102, respectively. In 1988, almost all farmers used tethered systems, while in 2013, 54.4% of male and 66.1% of female farmers instead worked with loose-housing systems. Of the farmers who used loose-housing systems, 50.7% had a robotic milking system. In 2013, 79.0% of male and 88.5% of female farmers reported MSSs on some occasion, especially in the lower back, shoulders, and knees for men, and in the shoulders, lower back, and wrists/hands for women. However, there was no statistical change compared with the frequency of MSSs in 2002. In 2013, there was a tendency for younger dairy farmers (≤35 years) to report MSSs, especially in the shoulders, elbows, lower back, and feet, more frequently than younger farmers in 2002. The males who worked with robot milking systems in 2013 indicated less discomfort in the shoulders than men who worked with other systems. The corresponding females indicated fewer problems in the lower back in 2013. Various aspects of milking system design and technology have been improved to reduce the workload and prevent MSSs in dairy farmers. Nevertheless, more improvements are needed to make the milking process more attractive and reduce health problems, especially in younger farmers currently working with milking and in new recruits.