This chapter examines the first generation of negotiations between the Venezuelan government and the opposition between 2014 and 2016. This initial stage takes place in the midst of continuous economic deterioration, a new surge of protests, and an escalation of authoritarian repression. It also occurs as the opposition gains control of the National Assembly, opening a window for a long-awaited political transition that is rapidly threatened by the regime’s restructuring of the judicial branch, and pushes for a new referendum recall. Negotiation efforts include the intervention of Unasur and diverse mediations by former presidents, which mainly sought to encourage mere dialogue, not necessarily the goal of arriving at a negotiated solution through a well-structured process. This chapter provides an account of each negotiation process that took place during this first stage and discusses the conditions of deadlock present during this period through the lens of the HUSSS framework.