The UK government has called for employers to make work adaptations in response to changes in health individuals may experience as they age. However, government assumptions place too much emphasis on the voluntary actions of employers and managers, without placing the management of health in a wider context. Drawing on insights from Thompson’s disconnected capitalism thesis, we explore whether financial/competitive pressures facing many private and public sector organisations today, alongside other factors, contribute to organisations not considering or implementing work adaptations. In this context, it is suggested that older workers may also hide health issues because of anxiety, or ‘ontological precarity’, regarding working longer. Qualitative case studies compare the delivery of work adaptations in three organisations: ‘Local Government’, ‘Hospitality’, and ‘Trains’. Work adaptations were only widely available in Trains; this was for a range of reasons, including the fact that Trains was relatively insulated from financial pressures and able to deliver job and financial security for older workers. As many older workers will continue to be employed by organisations similar to Local Government and Hospitality, we argue that policy makers cannot rely solely on employers to make adaptations.