Despite widespread multisectoral efforts from a range of stakeholders, including parents, religious institutions, governmental bodies, and non-governmental organisations, to influence adolescent behaviours and decision-making, adolescents across cultures and generations will engage in sexual activity. Adolescents’ evolving capacities are marked by natural curiosity and experimentation in sexual matters, but these explorations also carry risks, especially if met with adult manipulation or exploitation. Adolescence is also a developmental stage characterised by increased vulnerability to sexual coercion and abuse. Adolescents’ capacity to consent to sexual acts is a multidimensional contention muddled by irrevocable evidence of their susceptibility to harm. At the core of policymaking around adolescent sexual and reproductive health (ASRH) is the notion of a duty to protect. The ultimate question is—from whom are we protecting adolescents? From themselves? From each other? From adults? From oppressive systems? In this chapter, we argue that policymaking around ASRH is a paradoxical dilemma because stakeholders across multiple sectors are at odds about the source of the harm from which adolescents need protection. We examine approaches to ASRH policy in the English-speaking Caribbean, focusing on the policy practice environments in Jamaica and Trinidad and Tobago. We discuss the significant divide between its aims and practical implementation in our contexts. We assert that adolescents are entitled to protection from all sources of harm that threaten their sexual and reproductive health (SRH) and argue that bridging policy gaps necessitate the formulation of policies that respect lived experiences and envisage adolescents, especially girls and queer youth, with autonomy to access services with dignity.