Objectives: Adapting to stress over time is a process involving various cognitive and emotional assessments; it also depends on the objective situation related to working conditions, as well as on individual factors. The aim of this paper is to outline the dynamic nature of stress experienced by workers employed on oil rigs over a period of 20 years. The presented research is part of a larger project and concerns subjective stress. Material and Methods: Longitudinal studies included the analysis of data regarding the period of 1993–2014. They concerned 167 Polish oil rig workers, all men; the average age at the beginning of the study was 29 years. Each employee was surveyed at least 4 times over a period of 20 years at intervals of 4–6 years in the workplace. The subjective level of stress at work (based on the Subjective Job Evaluation Questionnaire) and the level of declared stress (based on the Stress Survey) were examined. Results: Oil rig workers show different adaptations to stress over a long term, depending on their subjective perception of stress. Baseline stress levels can vary from person to person over the years. The first group was characterized by high initial stress, but the stress decreased systematically over 20 years (“stress resisting”). Employees from the second group were characterized by low initial stress, but declared a systematic increase in stress in the same period (“stress sensitizing”). Finally, employees from the third group adapted to stress in a flexible way, with subjective stress being most strongly associated with objective stress (“flexible group”). Conclusions: The presented prospective study showed differences between the subjective levels of stress depending on the distinguished groups over 20 years, i.e., between-group and intra-group variability. The method of prospective research shows that the perception of stress at work is a dynamic process and it changes over time. Int J Occup Med Environ Health. 2023;36(4):477–92