The Horn of Africa region has witnessed a protracted conflict and Somaliland has been a part of it. This article explores and seeks answers to questions related to the stumbling blocks to post-conflict peace-building in Somaliland, analysing and assessing the internal and external dynamics of stumbling blocks to peace, including but not limited to: constitutional gaps, individuals and interest groups, media and donor approaches. It also examines other challenges to peace-building, recognising that reaching a peace agreement or concluding a peace dialogue is often more important than its sustainability. Somaliland peace-building is a viable critique of all established peace-building and state[1]building models, including the liberal, republican NEPAD model. The study is exploratory in nature and seeks to identify and assess internal and external blockages - (including geopolitical implications) - to post-conflict peace-building. It used an in-depth review of existing literature as a method of data collection under the qualitative research approach. The study finds that Somaliland faces a number of internal challenges in its post-conflict peace-building, which include: constitutional gaps, individual and group interests, and the media, which could play a clear role in peace-building but could also exacerbate tensions and mistrust; external challenges include, but are not limited to, the failure of donors to invite the Somaliland government to participate in fundraising and sectoral allocation.