Maps have legitimizing force. While typically perceived as accurately capturing objective reality, it has been well established that they are often manipulated to serve a pre-set agenda. Cartographers utilize boundary demarcations and toponyms, among other tools, to construct particular narratives. This paper studies how such critical cartographical tools have been used in political, conflict and geo-cultural maps of the Kurdish entity over the past forty years. It specifically focuses on the constitutionally recognized autonomous Kurdistan Regional Government in Iraq and the de facto self-governing experiment in Rojava in northern Syria. The purpose is to analyze maps produced by both sides of the conflict and those utilized by media outlets covering it to understand how maps are rendered to constructed texts through which to interpret the socio-political discourse of their respective creators and publishers. The study is based on maps procured from the Library of Congress, the Perry Castaneda Library Map Collection at the University of Texas, non-profit organizations like the Kurdish Institute (Institut Kurde de Paris), and various news media outlets. A longitudinal comparative analysis of the boundary demarcations and toponyms of the various types of maps is carried out. When applicable, maps are placed within the context and text of their sources and platforms. The study shows that platforms explicitly supportive of Kurdish initiatives for autonomy generally include thematic (both conflict and geo-cultural) and political maps that focus solely on the general area that Kurds inhabit, clear boundary demarcations for Kurdish administrations, and inclusion of Kurdish toponyms instead of Arabic ones where applicable. On the other hand, the Kurdish entity and its symbols were found mainly absent from neutral and pro-Iraqi or pro-Syrian platforms. While such findings are expected, it is in the analysis of the tools utilized and manipulated and the evolution over the years that the importance of this study lies. In a region prevalent with contentious borders, critical cartographic analyses are much needed in Middle Eastern studies. With the exception of the Israeli-Palestinian conflict, there is lack of in-depth cartographic comparative analysis across contending entities. Cartographic studies of the Kurdish case have mainly focused on geo-cultural maps and their shifting depictions over time on different platforms and how they are used to disseminate the concept of Greater Kurdistan and arouse Kurdish nationalism. Left unstudied are conflict maps, the tools used in constructing them, the narratives they covey, and their utilization by various sides of the conflict.