The United Nations’ (UN) engagement in post-war settings varies according to the level and dynamics of the conflict. In this regard, resolutions adopted by the UN Security Council, along with implementation reports, provide a frame of reference for the UN's objectives, priorities, and expectations in the given context. However, these objectives and the UN’s approach toward a solution may not adequately address the complexities of the problem nor the expectations of the domestic actors. Such cases hinder the implementation of UN objectives and highlight the issue of local ownership in these endeavours. This paper aims to reflect on what complexities and clash of perspectives have hampered the UN’s peacebuilding process in Lebanon. It will consider how the UN’s approach poses a dilemma regarding the realities and different political opinions in Lebanon, particularly when it comes to the security and sovereignty aspects. By analysing the implementation and follow-up process of the UN resolutions on Lebanon, particularly 1559 and 1701, and the conflicting views from the Lebanese side, the paper seeks to reveal the dilemmas of the UN’s peacebuilding objectives in Lebanon, pursuant to the critical literature highlighting ‘one-size-fits-all’ way of approach to conflicts. The paper suggests that ideational dilemmas between the UN and local actors, often overlooked, should be central to the UN's future refinements in its peace and political efforts. Such an attempt could facilitate local ownership of peacebuilding objectives and foster tangible progress.