INTRODUCTION: This study explores the impact of two major labor market phenomena—the aging workforce and digitalization, which have global significance. The COVID-19 pandemic accelerated the adoption of digital technologies, resulting in economic growth, improved business processes, and reduced social isolation. However, the study also addresses the challenges and threats associated with digitalization, with a specific focus on technostress. The research analyses the primary techno-stressors experienced by older employees and self-employed individuals in four EU countries. Investigating various demographic factors such as gender, age, education level, employment type, and country of origin, the study aims to identify stress levels related to techno-demands and techno-disruption. METHODS: This study utilized a quantitative research design with a cross-sectional survey approach. A Quota sampling method in combination with Computer Assisted Web Interviewing (CAWI) was used to collect data. The overall response rate was 42% (varied by country) in total data collected. A sample of 1306 workers (aged 50–64), representing diverse demographics, was recruited and interviewed. The techno-stressors were assessed using a 14-item scale encompassing major stress-creating conditions as already reported in earlier studies. RESULTS: The results reveal intriguing patterns, particularly notable gender-based differences in technostress experiences across age groups. Younger male seniors and female seniors reported higher levels of techno-disruption, while techno-demands were more problematic for female seniors. Additionally, respondents’ country of origin also influenced their experiences with technostress. DISCUSSION: Overall, the study sheds light on the challenges of digitalization for older workers in central European perspective and provides important missing information and data on variation in technostress based on nationality, age, and gender. The results prompt further research on longitudinal trends and discussions on geography, industry, and country specific impact of digitalization on the modern workforce.