Informed by institutional theories of microfoundations, this study elucidates how employment service caseworkers negotiated the configuration of welfare conditionality based on age, thereby establishing a microfoundation for policies aimed at extending job-seeking lives. Through conducting in-depth interviews with twenty-four frontline social workers and a context-mechanism-outcome analysis, the findings uncover how service providers incorporated age-specific considerations and redefined the meanings of work in later life. While organisational adjustments extended the service goals and mobilised extra resources, structural constraints forced caseworkers to adopt pragmatic attitudes towards workfare measures. Consequently, a ‘more-than-employment’ approach to older jobseekers was formulated concerned with age, relationship, and health. This research contributes to social policy studies by theorising welfare conditionality as a product of negotiated configuration that crafts the microfoundation of activation policies. Empirically, this study enriches the literature by linking extending job-seeking lives and older claimants to welfare conditionality within Hong Kong’s work-first model.