This paper takes a critical look at the third party roles in conflict settlement processes by comparing Togolese mediation in the Lomé Peace Negotiations and Ugandan mediation in the Kampala Peace Dialogue. This study primarily aims to establish secondary party involvement in conflict settlement as a mediator can be one of the reasons why peace processes fail. More specifically, the paper argues that parties who provide financial and military support to insurgency should not serve as a mediator. In the two cases, the paper compares mediator characteristics such as bias, motivation and strategy. The findings indicate that Togolese mediation’s relative success over the Ugandan effort is mainly due to the former party’s sensitivity to answering demands of the conflicting parties, encouraging these parties to make concessions towards a comprehensive peace agreement.