A new form of conditional welfare through income management is being trialled in Australia, dubbed the “Cashless Debit Card”. It aims to reduce gambling, alcohol and illegal drug use to address social pathologies related to crime and welfare. Routinely collected data from government were used to assess if the targeted reductions arose. Store sales data were also used to evaluate impact on food purchases. No substantive impact on measures of gambling (p = .175), and intoxicant abuse (p = .662) were found. An increased spend on healthy foods (95%CI: 12.0% to 150.0%) was observed, but decreased as a proportion of all foods (95%CI: −6.3% to −13.1%). Impacts on crime and Emergency Department presentations were not substantively found. We conclude that targeting individual choices may not be as effective as policies targeting the historical social structures that serve as antecedents to such social pathologies.