In the 1980s, the United States first engaged the DPRK through the “Modest Initiative”, while simultaneously confronting North Korea over its nuclear development program. Since then, U.S.-DPRK relations have had their ups and downs and questions still remain regarding how best to manage North Korean nuclear, missile, and military provocations and which is the right approach to use to convince North Korea to denuclearize. In 2018, when the DPRK declared itself a de facto nuclear-armed state, the Trump Administration swiftly changed its approach from “Fire and Fury” to conducting summits. In 2019, summit diplomacy lost its magic and the COVID-19 pandemic brought everything to a halt. Both Kim Jong Un and Moon Jae-in mooted the idea of declaring an end to the Korean War in 2021. From an ethical, geostrategic, and non-major stakeholder’s perspective, this talk will highlight the major contentions surrounding the notion of “engaging North Korea.”