This report is intended to provide an analysis of when and under what conditions the Taliban might be willing to come to the negotiating table with the serious intention of reaching a peace agreement with the Government of the Islamic Republic of Afghanistan (GoIRA). Drawing upon the academic literature on the bargaining model of war and lessons learned from comparisons to other peace negotiations between state and non-state actors, it seeks to establish principles for evaluating if and when the Taliban could be incentivized to engage in serious negotiations. Noting the influential role of third parties, actors and interests this report examines both battlefield and off-the-battlefield considerations for the Taliban that may alter their interest in a negotiated settlement. In so doing, it provides insights for U.S. practitioners and policy-makers that balance the desire to further decrease the role of U.S. military forces in Afghanistan with the need for stability in Afghanistan.