Although Western nations have long placed conditions on access to social security payments, many of the more recent conditions utilising technological tools have intensified surveillance and control of the poor and imposed weighty administrative burdens on social security recipients as they attempt to navigate these systems. The Cashless Debit Card (CDC) imposes additional administrative burdens – learning costs, compliance costs, and psychological costs – on people in receipt of social security as part of an overall welfare conditionality project that structures in disincentives to claim government income support. Cardholders experience heavy administrative burdens in securing essentials and managing their social security income via the CDC, seeking a reduction of their restricted payment portion, and seeking a well-being exemption or a financial responsibility exit to regain their budgetary autonomy. Evidence suggests that numerous people in need of social security who have been forced on to the CDC could do with a reduction in burdensome processes – which would be facilitated by designing systems that are autonomy enhancing, respectful of the human dignity of claimants, and fairly easy to navigate.