This work will consider a range of encounters between Christian and Muslim leaders from late antiquity through to the middle ages. As explored through a lens of political and theological theory, this work will consider interfaith dialogues, encounters, and apologetics between different figures, in order to divine a means of understanding not just the results of these interactions, but their larger purpose as well. Four primary points of encounter between Christians and Muslims which will form the basis for this consideration. The first will be the encounter between Muhammad and the Christians of Najran in 628 AD., followed by the dialogue between Nestorian Patriarch Timothy I and the Abbasid caliph al-Mahdi in 781 AD. This work will then cover the work of Abu Bakr Muhammad al-Baqillani and Al-kindi, both of whose pivotal interactions took place during the latter centuries of the first millennium. These works will be considered from a perspective of their theological rhetoric as well as from the basis of their use as political documents and exhortations which were levied and extended for political purposes. Through a close analysis of these works through a range of modern theorists, and the concepts of implied and intended audience, debate, dialogue, discussion, monologue, and – in particular – the necessity of such dialogues and interfaith interactions, a range of findings will be shown. Of particular note among the findings to follow is the idea that these interactions were less openly theological in nature as they were political, and the idea that apologetics would find expression (in theology) of a range of power interactions between their debate partners. This work will show that the debates in which there was little (or no) power disparity between the figures debating Christian and Muslim theology could be far more openly contentious, while those where there was a considerable power disparity on display were often exercised primarily through diplomatic subtlety and implication.