Background/Objectives: Population ageing and rapid digitalisation are reshaping the healthcare workforce, raising new challenges for occupational health, inclusion and well-being. Older healthcare workers are often assumed to be less digitally adaptable, yet empirical evidence remains limited in public health services. This study aimed to assess digital skills, institutional support, perceived digital inequality and health-related impacts of digitalisation among healthcare professionals aged 50 years and over in a large Portuguese Local Health Unit (ULS São João).

Methods: A cross-sectional mixed-methods study was conducted in February 2025 among professionals aged ≥ 50 years at ULS São João. Of 1,855 eligible workers, 368 completed a structured online questionnaire (95% confidence level; 5% margin of error). The survey assessed digital competence, training, technical support, usability of systems, perceived digital inequality and well-being. Ninety-four open-ended responses were analysed using content analysis. Quantitative data were analysed with descriptive statistics and Pearson’s Chi-square tests (p < 0.05).

Results: Most participants perceived digitalisation as beneficial to their work (81%) and indispensable for the institution’s future (93.5%). Self-perceived digital competence was high (61.7%) and 96.5% reported being motivated to adapt, contradicting age-based stereotypes. However, important institutional gaps were identified: 57.6% reported inadequate digital training and only 28.8% considered technical support to be fast and effective. System usability was problematic for 46.5% of respondents. While only 16.6% perceived digital inequality, nearly half recognised that employers play a key role in reducing it. Digitalisation was associated with increased workload in 17.9% of participants and poorer work-life balance, although reported mental health impacts were lower (7.6%). Non-medical staff reported significantly higher satisfaction with institutional support, technical equipment and overall job position than medical staff (p < 0.05).

Conclusions/Recommendations: Older healthcare workers show strong adaptive capacity and positive attitudes towards digitalisation, but institutional barriers in training, system design and technical support create avoidable occupational health risks. Strengthening continuous digital training, improving usability and ensuring accessible technical support are essential to reduce inequalities and promote healthy and sustainable working lives in an ageing healthcare workforce.

Funding: FCT - Fundação para a Ciência e a Tecnologia, I.P. (RISE - LA/P/0053/2020).