The persistent presence of armed groups in local communities is largely due to ineffective community security management, weak rule of law, and the constant shift in peace and security policy guidelines. Compounding the problem is the limited capacity of local government units and the lack of strong political will of officials to address security issues. Irregular forces offering private security services thrive in this environment. Armed groups gain legitimacy since they fill security service gaps in communities and because they assist government security forces in their counterinsurgency operations. Gray zone activities are activities by armed groups that happen in-between the space of nonviolent and violent actions, legal and illegal policy environment, and legitimate and illicit engagements. The tenuous policy environment creates the political opportunity for these groups, and the dysfunctional rule of law and ineffective management of security provide the context for irregular forces to mobilize and operate. The paper looks at the threat landscape and the contemporary security problems that make it difficult to clearly distinguish what is legal, legitimate, and appropriate in appraising irregular forces. It likewise highlights the problematic nature of politically sanctioned groups or groups created based on peace agreements and how vulnerable they are to cross over to criminal groups, if not terror groups.