Research on older workers and retirement has yet to adjust fully to an environment influenced by a combination of demographic change, technological developments and economic recession. A key dimension to the changing relationship between ageing and work is the tension between policies to extend working life and the increasingly fragmented nature of late working life, with the emergence of varied transitions, including: bridge employment, second/third careers, part-time working, early retirement and other variations. These developments indicate both the challenge of conceptualising new forms of work-ending, and – in policy terms – the extent to which these can successfully accommodate longer working lives. The paper provides a critical perspective to the policy of extending working life and the narrative which underpins this approach. The paper argues that retirement has become a ‘contested’ institution in the 21st century, fragmented across different pathways and transitions affecting people in their fifties and sixties. The paper argues the case for improving work quality and security as a precondition for supporting policies for encouraging working in later life. An essential requirement for this will include linking debates on extending working life with technological developments and changes affecting the workplace, creating differentiated paths to retirement and labour force exit, enhancing the provision of training and continuing education, and re-thinking the idea of the ‘older worker’.