This paper examines the relationship between Track I Diplomacy and Civil Society in Cyprus. Cyprus has been a divided island for over 45 years despite numerous attempts at reconciliation on the societal level and ongoing negotiations on the diplomatic level. It was the aim of this study to examine the ways in which both civil societies and their leaders do or have worked together, if at all, to negotiate a political solution or reconciliation between the two communities. Interviews were conducted on both sides of the cultural divide and within both political and civil society sectors. Those interviews were coded, categorized, and then thematically analyzed. Findings explicate three themes that challenge the relationship and cooperation between Track I and Track II; Structural Elements, Nationalism, and International Support. Furthermore, it is proposed that the leaders must lead and support their citizens in reconciliation and peacebuilding efforts while continuing to negotiate a solution to the Cyprus problem as civil society organizations continue to support negotiation efforts.