Citizen trust is a prerequisite for the success of service provision. However, working relations are typically shaped by power asymmetries and one-sided dependencies, contributing to cautiousness towards or distrust of caseworkers (Dumbrill, 2006; de Boer and Coady, 2007). This article sheds light on the conditions and mechanisms that lead (some) citizens nevertheless to trust their caseworker. Based on thematic coding of semi-structured interviews with twenty-five German and sixteen Danish welfare users, our findings elucidate how shared problem perceptions and positive experiences in direct working relationships with committed, citizens-oriented caseworkers mitigate structural asymmetries and allow trust-building. In particular, they underscore the importance of personal bonding and positive emotions, including feelings of sympathy, or even friendship, and of being seen, understood and respected. Our article strengthens the interpersonal, micro-level perspective on trust-building in welfare service provision and provides new empirical insights into the role of personal relations in trust-adverse institutionalised contexts.