Since 2015, Al-Shabaab and the Federal Government of Somalia (FGS) have been locked in a violent, protracted stalemate. There is little momentum to pursue a political settlement, with Al-Shabaab rejecting any overtures of dialogue. Drawing on theoretical perspectives from peace and conflict literature and key interviews with clan elders and Al-Shabaab defectors, this article explores two interconnected themes. First, Al-Shabaab’s dynamic attitudes towards dialogue since the group’s establishment; and second, how clan elders play diverse peace-seeking roles, negotiating between Al-Shabaab and FGS at the microlevel. The article highlights two important findings. First, Al-Shabaab was initially inclined toward dialogue but, following the death and defection of senior members, increasingly adopted an anti-negotiation stance. Second, whilst Al-Shabaab is obstinately refusing any dialogue on the macrolevel, at the microlevel, the group indirectly negotiates with the FGS and other actors using clan elders as interlocutors and facilitators. Finally, the article explores the idea that, instead of relying on foreign third-party mediators to resolve Somalia’s protracted stalemate at the macrolevel, clan elders, as credible insider-partial mediators possessing locally sourced legitimacy and perceived integrity, have the capacity to help overcome the stalemate between Al-Shabaab and the FGS.