The article examines how technological change and organisational restructuring interacts with population ageing and policies that extend working life, and how older workers understand these trends. Using organisational and contextual approaches and qualitative research on nurses and bankers in Czechia, we investigate older workers' experiences with digitalisation. The age disadvantage older workers experience in digitalising workplaces is produced by three processes: responsibilisation, production of insecurity and ontological precarisation. The responsibilisation of employees for their own digital training is disadvantageous for older workers both in banking and nursing. Digitalisation and restructuring make older bankers feel insecure. To decrease their insecurity, nurses construct a boundary between technology and personal care. The sectoral labour market context is important, as exemplified by a shortage of nurses decreasing insecurity. The precarisation of older workers is further shaped by how the organisational context in which digitalisation occurs intersects with individuals' household situation and welfare state provisions.