This article discusses factors shaping street-level caseworkers' role in the ‘personalization’ of activation for people with employability and health-related barriers to work. Rice's (2013) micro-institutionalist framework understands street-level bureaucracy as being defined across three levels: interactions between caseworkers and clients; the environment of the implementing organization that shapes, and is shaped by, these interactions; and the relationship between these two levels of interaction and the wider economic, policy and social context. While building on the foundations laid by previous scholars, we use Rice's framework as the starting point for a preliminary study of street-level bureaucrats' role in compulsory activation. We analyse in-depth interviews with caseworkers and clients involved in the UK government's main activation programme – ‘The Work Programme’. Our findings support other studies and add to the literature by suggesting that a number of organizational and high-level policy factors have contributed to an increasing standardization of street-level practice.