This paper examines the relationship between lone mothers’ repartnering trajectories and health in three distinct welfare contexts: the dual-earner, market-oriented, and general family policy model. Inspired by the resources and the crisis model, we apply mixture modelling for event-history analysis to the Harmonized Histories data. We uncover six distinct repartnering trajectories that vary with respect to the timing, type, and stability of higher-order unions for different cohorts of lone mothers. The few associations between repartnering trajectories and health differ systematically and significantly by welfare context. Lone mothers with some, yet unstable repartnering, reported better health in market-oriented contexts, compared to those living in general and dual-earner contexts. Market-oriented contexts were also those where unstable repartnering was more frequent. Overall, findings suggest that a less-generous welfare may encourage unstable, temporary repartnering out of economic need, while welfare contexts with more comprehensive family support allow for more stable repartnering choices.