<p>Organizations are undergoing multiple transformations in which digital, sustainability-related, and cultural dynamics are profoundly changing the world of work. Since the COVID-19 pandemic, flexible working arrangements in terms of location and time have become established, particularly in knowledge-intensive professions, offering both opportunities and challenges. Against this backdrop, this study examines how employees who work in flexible forms of work perceive the aspects of workplace and working time autonomy discussed in the context of new ways of working in terms of their impact on health and productivity. The aim was to identify challenges for maintaining health and productivity and to derive requirements for occupational digital workplace health promotion. The study is based on twelve qualitative interviews that provide insights into the individual needs and perspectives of employees. The results show that new ways of working have both positive effects, such as time savings, flexibility, less stress, and more concentrated work, but also negative effects, such as lack of physical activity and lack of social interaction. Regarding digital health promotion, participants preferred features such as reminders and tips to support physical and mental health. This study thus contributes to understand the interactions between new ways of working, health, and productivity and offers implications not only for those responsible in organizations who design digital health promotion in the modern workplace.</p>