Despite serving as the Philippines’ main social protection strategy, debate continues surrounding the ability of the Pantawid Pamilyang Pilipino Program (4Ps) to meet its long-term goal of breaking cycles of intergenerational poverty. To engage with this debate, this study brings together the constructs of entitlement and agency to analyse how different actors associated with 4Ps understand and experience the program. Drawing on forty-three semi-structured interviews with 4Ps beneficiaries, non-beneficiaries, and implementers, we provide a provisional explanation as to why a disconnect exists between the long-term goals of 4Ps and the experiences with the program among these different actors. In addition, this study highlights how challenges associated with the design and implementation of 4Ps, including limited transparency and communication of the program’s eligibility requirements, rigid monitoring of beneficiary compliance, and delays in receiving cash transfers, may constrain the transformational potential of this social protection strategy.