This chapter examines the case narratives in the second generation of negotiations between the Venezuelan government and the opposition in the period 2016–2018. This convulsed period is characterized by the consolidation of the regime, which eliminates any resemblance of independence and separation of powers by blocking a referendum recall attempt and actions to neutralize the opposition-led National Assembly, first through judicial ruling and then through the election of a National Constituent Assembly. In addition to the political turmoil, the dire socioeconomic situation and severe rise of criminality deepen an increasingly humanitarian crisis, leading to massive migration of Venezuelans across the hemisphere. In this context, the second generation of talks—one planned under the auspices of the Vatican (2016–2017) and another facilitated in the Dominican Republic (2017–2018)—featured a more structured approach compared to previous efforts, with defined negotiation agendas and greater international participation. The following chapter provides an account of these two negotiation processes and analyzes the conditions of deadlock through the lens of the HUSSS framework.