Conditional Cash Transfers (CCTs) provide mothers of school-age children in extreme poverty with a cash subsidy conditional on their children’s attendance at school and health clinics. This paper builds on the author’s earlier gender analysis and critique of these programmes by examining evaluations of CCTs in order to assess the evidence for their claim to empower women. It analyses the assumptions underlying the definitions of empowerment used in the evaluations, questions their adequacy, and advances alternative measures of empowerment. In so doing it hopes to stimulate debate about theory, methodology and policy. It advances four main propositions: (1) claims that CCTs empower women are questionable and are weakly supported by the evidence; (2) in reinforcing a maternal model of care, CCTs reinforce asymmetrical gender roles and risk establishing a trade-off between children’s and women’s needs for long-term security; (3) given the inequalities in gender relations at household level, programme design needs to encourage a more dynamic model of gender and generational cooperation, which has the potential to generate more positive outcomes for all household members, including fathers who are otherwise marginalised from the responsibilities of care.