Radical left and right parties are increasingly successful – particularly among the less well-off. We assess the extent to which this negative effect of wellbeing on radical voting is moderated by contextual factors. Our study suggests that less well-off citizens vote for radical parties mainly under favorable aggregate-level circumstances. We distinguish two possible mechanisms underlying this effect – relative deprivation and risk aversion – and find support for relative deprivation only among radical right voters and for risk aversion for both types of radical voters, yet with predictable differences between the radical left and right supporter bases. Economic hardship leads to radical right voting when the socioeconomic circumstances are favorable, and to radical left voting when net migration is modest. Our findings suggest a genuine paradox of radicalism: individual economic suffering might foster left and right radicalism, but mainly when that suffering takes place amidst favorable conditions at the aggregate level.