The Juba Peace Talks between the Lord’s Resistance Army/Movement (LRA/M) and the Government of Uganda were the most promising attempt to end one of Africa’s longest running wars, yet they ended without a peace agreement and are thus largely considered a failure. This chapter unpacks the lessons that the Juba Talks offer for contemporary peacemaking: The need to understand the importance of the developing dynamics and how individuals experienced the peace talks; the phenomenon that peace talks can entrench, rather than transform, violent conflicts; and the challenges in researching and documenting these dynamics and entrenchments. The chapter concludes that the LRA/M to a great extent maintained its reputation as an unreliable and violent negotiation partner torn apart by infighting. The Government of Uganda made few political concessions and instead relief on military intervention; international actors failed to establish themselves as principled with clear guidelines. These dynamics had been present in the conflict and continued during the Juba Talks and beyond, confirming the LRA/M’s perception of being trapped in a hostile and unchangeable system. Only with a holistic approach to managing the ebbs and flows of political conflict can interaction and systems in entrenched situations be changed over the long term.