Against the background of an increasingly individualising welfare‐to‐work regime, sociological studies of incapacity and health‐related worklessness have called for an appreciation of the role of history and context in patterning individual experience. This article responds to that call by exploring the work experiences of long‐term sick people in East London, a post‐industrial, multi‐ethnic locality. It demonstrates how the individual experiences of long‐term sickness and work are embedded in social relations of class, generation, ethnicity and gender, which shape people's formal and informal routes to work protection, work‐seeking practices and responses to worklessness. We argue that this social embeddedness requires greater attention in welfare‐to‐work policy.