AbstractWhile there is a growing body of literature on the lived experiences of people in poverty, their interaction with the welfare delivery system at different levels is still under‐theorised. This article presents a multi‐level institutional framework to qualitatively study the low‐income families' experiences in claiming in‐work benefits (IWBs). Considering the Low‐income Working Family Allowance (LIFA) in Hong Kong as an extreme case of IWB's residualism and productivism, the findings suggest that LIFA claimants faced cycles of counter‐productive re‐assessment in their everyday frontline practices, and underwent organisational barriers in workplaces and families in collecting the proofs required by the means‐testing and work‐testing procedures. These experiences were linked to Hong Kong's macro‐systemic contexts that prioritised long working hours and strict targeting of low‐wage breadwinners. This study contributes to the literature by linking social policy implementation and welfare delivery to claiming experiences, and empirically reveals the complexities of IWBs using means‐tests and work‐tests.