The ongoing dialogue between the US and the Taliban has generated lot of interest among strategic analysts in the region and beyond. There are indications that the Taliban are hardening their position as the US appears to be in a haste to pull off an agreement. This essay argues that given the extremely fractious nature of politics within Afghanistan and the prevailing culture of mis-governance, corruption, anarchy and violence, it is important to involve diverse ethnicities, regions and armed groups of all shades including dissenting groups within the Taliban to ensure that the post-Soviet withdrawal scenario of all-against-all does not emerge again, jeopardising prospects of peace and stability in future. At the regional level, countries having stakes in Afghanistan must be involved in a separate conversation to avert the possibility of any of them acting as spoiler. Managing the course of negotiations would involve mature bargaining, efficient and firm signalling from the US, and reinforcing the values that promote human dignity, individual liberty and inclusive democracy through effective advocacy of liberally mediated/interpreted religious and cultural principles that enjoy a greater degree of acceptability in Afghan society.