This paper explores how new regulatory technologies and front-line decision-makers reshape one another. Drawing on a recent qualitative study of caseworker decision-making in the Ontario Works program, it demonstrates the dialectical relationship between new case management software and caseworkers. While new technologies may attempt to deskill and decentre front-line decision-makers, transforming them into data entry clerks, caseworkers learn how to expertly translate and input client data to produce decisions that more closely match their interpretation of clients’ needs and welfare laws. The ways in which workers “manipulate the system” to produce a particular decision, though common knowledge among their colleagues, are black boxed to program managers, auditors, and benefits recipients.