This article examines how the introduction of western European crusaders and settlers to northern Syria from 490/1097 onwards impacted upon two important mechanisms of regional diplomacy; the ransom of prominent political prisoners and tributary relationships. Discussion begins with a comparison of the capture and ransom of high-ranking captives in northern Syria between 442-522/1050-1128, where it is argued that the establishment of the crusader states led to an increase in both the rate at which prisoners of elite status were ransomed and the financial sums involved in these interactions. This is followed by a reassessment of the various peace treaties, tributary arrangements and condominia or munāṣafa agreements concluded between the rulers of Antioch and Aleppo during the late fifth/eleventh and early sixth/twelfth centuries. Ultimately, this article seeks to place key features of northern Syrian diplomacy from the early crusading period within the context of regional norms in the decades preceding the crusaders’ arrival.