Examining 16th-century Kurdish politics, particularly in the frontier districts between the Ottoman and Safavid Empires, aptly serves as a starting point for understanding Kurdish regional semi-autonomy. This paper, dedicated to the activities of Kurdish individuals involved in information-gathering on behalf of both the Ottoman and the Safavid Empires, is the first of its kind. The findings presented here are the result of close exploration in the Ottoman archives as well as detailed reading of a number of materials from Ottoman and Safavid chronicles. The paper discusses three main subjects. The introductory section briefly explains the methods and potentials of Kurdish spying as well as some of the particulars of Ottoman–Safavid espionage. The second section provides an overview of two famous Kurdish intellectual historians and the role each played in information-gathering. The third section discusses cases of espionage throughout the political careers of several Kurdish frontier emirs.