The term (re-) entrenchment can be used to uncover the contingency of the clashes, alignments and re-alignments during negotiations among the warring parties in Libya. Entrenchment does not necessarily describe a solidity and rigidity, but reveal fortification and transgression simultaneously. This paper surveys the United Nations Support Mission in Libya’s ongoing negotiations and resolutions in Libya to identify the shifting positions of the domestic and international parties involved in the process, identify mechanisms that can trigger democratization or de/democratization and develop a critical perspective about the opportunities of democratic governance in the country. (Re) entrenchments of parties in Libya are contingent on the larger developments in the region as much as the rival governments’ competition regarding the control of vital resources, international support and legitimacy. More specifically, consolidation of ISIS in Libya is a regional issue that may undermine the efforts of UNSMIL that has been so far bracketing the impact of such presence in the country.