The 1517 Ottoman Conquest of Egypt, especially the conditions of the political transition from Mamluk to Ottoman rule, has been studied in modern scholarship primarily through certain well-established and canonical Ottoman Turkish and Arabic speaking commentators. The perspectives of these commentators on the Ottomans and the conquest's ramifications for the region helped shape a varied understanding of the Ottoman enterprise, including its glory, success, failure, bloodshed, and violence, as well as the chaos that ensued during and its aftermath. However, the predominant historical narrative is lacking and limited in its incorporation and analysis of dissenting and critical voices of the imperial project, as well as certain political agendas that provoked rebellions against the Ottoman government between 1517 and late 1520s. This was a very complex historical period for all of Egypt's inhabitants, including its conquerors and governing elites. Issues such as the political and ideological dimensions of the conquest, Selim's position vis-v-vis the religious implications of warfare against fellow Muslims, and Ottoman interpretations of the idea of holy war have yet to be evaluated in order to achieve a balanced perspective on the Ottoman imperial enterprise in the East. In my paper, I will revisit these issues and challenge the limits of the imperial enterprise in Egypt, as well as the overall success attributed to it. I will do so by textually analyzing narrative texts that depict the interactions and dialogues of three protagonists: Gilteni, Diyarbekri, and Sultan Selim. As their paths converge, I will investigate these men who reflected on the Ottoman presence before its reign, lead the conquest, lived under Ottoman sovereignty, served them, and voiced frustrations with their government and legitimacy. By focusing on 1517-1520, I will challenge perspectives that see this period as part of the ascendant Ottoman imperial narrative and as reflective of the larger success story of integrating Egypt into the larger Ottoman polity. I will pay special attention to Gtloeni, whose Ottoman Cairo years are regarded as valuable by modern-day scholars only to the extent that his experiences reinforced the argument that he was a prominent supporter of the Ottoman conquest and helped transform Egypt into an Ottoman province.