Negotiating with insurgents to end a counterinsurgency (COIN) conflict is an undervalued and largely unaddressed topic in US Army COIN doctrine. Historically speaking, however, insurgencies end in negotiated settlements more than any other form of war termination. In fact, the current US strategy to end the war in Afghanistan is to seek a negotiated political settlement with the Taliban. Given these realities, US Army leaders and planners must have a better understanding of the military and government roles in successful strategic negotiations with insurgent groups. This monograph addresses how current US Army COIN doctrine does not adequately address how to establish ripe moments for successful negotiated settlements in COIN conflicts. The paper is divided into four sections beginning with an overview of what current US Army COIN doctrine says about negotiations and negotiated settlements. The second section presents ripeness theory as a framework to consider the conditions that are necessary for negotiations to occur. The third section includes the case study of Colombia's three negotiations conducted with the Revolutionary Armed Forces of Colombia (FARC) between 1982 and 2016. The conclusion section will discuss the implications for US Army COIN doctrine. Contents: 1. Introduction * 2. Doctrine Review * 3. Ripeness Theory: Support to an Operational Approach * 4. Case Study: Negotiations between Colombia and the FARC - Historical Background of the Colombian Conflict * 5 Conditions of Failure: The Betancur and Pastrana Years * 6. Establishing Conditions of Success: The Uribe and Santos Years * 7. Conclusion and Implications Colombia and the Revolutionary Armed Forces of Colombia (FARC) signed a peace agreement in November 2016 that ended the longest running war in the Western Hemisphere. The war tore the country apart for fifty-three years, killed over 220,000, and displaced as many as eight million Colombians from their homes. The negotiation that produced the peace agreement overcame numerous challenges: a history of failed negotiations, organized opposition, decades of bitterness, and irreconcilable ideologies to name just a few. Colombia's "forever war," as it was known, only came to an end after its government and military learned, adapted, and accepted an approach to counterinsurgency (COIN) that focused on the ends rather than the ways and means. An acceptable negotiated peace replaced decisive military actions as the definition of victory. This is an important lesson for the US Army to heed. As the threats of near-peer conventional conflict rise in areas of the world like the South China Sea, Eastern Europe, and the Korean Peninsula, the focus on counterinsurgency in the Army has waned. Unfortunately, insurgency is not expected to disappear as a threat to regional and international stability, and it is unclear if current COIN doctrine conclusively addresses these potential threats. The last two decades of US and coalition COIN operations exposed how difficult it is to defeat insurgencies outright. Colombia's experience is a useful reminder that victory does not always require an enemy's defeat. In some cases, negotiated settlement may be the best approach to victory.