Discussion of Key Leader Engagements (KLE) as a nonlethal option for countering insurgent organizations. Outreach to insurgent organizations through KLE can be both an economy of force measure and, in some circumstances, could be more effective than engaging insurgent organizations with lethal force. The challenge with insurgent outreach to KLE, though, is that it must be tied to a legitimate host-nation government effort towards reconciliation or, at a minimum, accommodation with the insurgent organizations in question. Through the lens of the Multi-National Forces-Iraq Force Strategic Engagement Cell (FSEC), the author illustrates how KLEs can be incorporated as targets in the U.S. military’s targeting process. FSEC’s mission to reach out to Iraq-based insurgent organizations who sought reconciliation with the Iraqi government was entirely based in KLE-related targeting. FSECs activities, therefore, present a suitable case to study how including KLE as “targets” within the targeting process can maximize the utility of the relationships commanders and diplomats alike establish during counterinsurgency and nation-building operations. The operations of this strategic engagement cell also demonstrate the employment of KLE as a part of Information Operations, and the challenges associated with developing and refining intelligence to support KLE targeting. The other challenges FSEC personnel dealt with highlight some additional difficulties commanders and diplomats face with respect to KLE operations with emphasis on managing expectations, continuity, capability, and synchronization of effort. Finally, FSEC’s endeavors in Iraq underscore the utility of outreach to both local leaders and insurgent populations in counterinsurgency operations.