The current emphasis in European welfare states on ‘activation’ increases the relevance of insight into social assistance dynamics and work–welfare/welfare–work transitions. This article reports on a study that explored the employment, unemployment and social assistance careers of a large group of people who managed to become independent from social assistance by finding a job. Using the databases of social security agencies in the Dutch city of Rotterdam, it investigates the sustainability of social assistance independence and labour market inclusion, and identifies groups that are more or less likely to be confronted with spells of renewed social assistance dependency or unemployment.