My dissertation is a study of imperial dynamics and borderlands of the Hittite Empire. The Hittite Empire dominated parts of what is now modern Turkey and northern Syria between the 17th and 12th centuries BCE. To investigate the Hittite imperial system, I look across the larger Anatolian peninsula and northern Syria through a diachronic perspective throughout the second millennium BCE to contextualize imperialism and responses to it in the local diachronic histories of these regions. I explore what the Hittite Empire looked like on the ground in its borderlands – how its power was projected by the central administration and how it was received by the inhabitants of the border regions. Succinctly, the questions driving my dissertation are: How did Hittite imperialism operate in the different border regions over which the Hittites claim to have dominated? How did these borderlands respond to Hittite rule? I respond to these questions through three case studies using original texts and archaeological material collected through fieldwork. I explore imperial dynamics and responses in the Ilgın Plain in inner southwestern Turkey, in the city of Emar in northern Syria, and in the Cilician Plain in southern Turkey. In each case, I argue that the manifestations of the Hittite Empire were mainly conditioned by the pre-Hittite trajectories of these regions. The strategies that the administration chose to use in different borderlands sought to identify what was important locally. The Hittite Empire aimed to integrate itself into networks that were already established as manifestations of power, instead of replacing them with new ones. Last, I suggest that while the varied borderlands created their own manifestations of the Hittite Empire by overlaying its imperial strategies onto their local, long-term networks of power, the center of the empire did not remain static. The different Hittite Empires in the borderlands got transposed onto the capital city of the empire and its environs, invading its urban, rural and mental landscapes with different incarnations of the empire, making the narratives of supremacy and control of the center unsustainable. The borderlands transformed, stretched, and eventually dissolved the center of the empire.