Between 1995 and 2015, Ontario ushered in a new era of regulating the poor, whereby new welfare surveillance technology was mandated to disentitle recipients, reduce caseloads, and enforce workfare. A technologically infused welfare state automated eligibility and risk assessments to interact with welfare fraud hotlines, fraud enforcement officers, and other state surveillance practices. While the poor have always been monitored and surveilled by the state when seeking financial support, the methods, techniques, and capacity for surveillance within and across government jurisdictions has profoundly altered how recipients navigate social assistance. Welfare surveillance has exacerbated social inequality, especially among low income, Indigenous, and racialized single mothers. Krys Maki unpacks in-depth interviews with Ontario Works caseworkers, anti-poverty activists, and single mothers on assistance in Kingston, Peterborough, and Toronto, and employs intersectional feminist political economy and critical surveillance theory to contextualize the ways neoliberal welfare reforms have subjected low-income single mothers to intensive state surveillance. and centers their experiences to examine how their status as lone parents prompted fraud investigations, invasive questioning about their relationship status, and triggered investigations by other governing bodies such as child welfare agencies. This book also examines the moral and political implications of administering inadequate benefits alongside punitive surveillance measures. Despite significant restraints, anti-poverty activists, caseworkers, and recipients have discovered individual and collective ways to resist the neoliberal agenda.