In recent years, scholarship on borderlands, ransom slavery, and captivity in the pre-modern Middle East and Mediterranean has flourished, largely in Ottoman studies. This paper goes backward in time, looking at captivity and ransom in the Crusader period among Jewish communities in Egypt and Palestine. Although some published works have analyzed Jewish conceptions of charity, there has not been a study that has showed change over time in terms of Jewish ransom tactics. In this paper, I argue that Jewish leaders adopted different policies in order to accommodate the growth and variation in captives taken. Most of the documents utilized for this study are from the Cairo Geniza archive and are letters and petitions. Many are written either by or to Moses Maimonides, and a large number of them, particularly those dealing with piracy, are exchanged between Fustat and Alexandria. The documents I have chosen focus on the period right before the Crusades (i.e. the late 10th/early 11th century) and through about 1300, the period of major Crusader conflicts. This period experienced higher levels of piracy, as well, in large part because of the conflicts between the Fatimids and the Byzantines – this, in combination with the relatively high number of captives taken during the Crusades, sparked the change in their ransom tactics. While the infrastructure for ransom existed on the local level, in specific towns or cities, this period brought about changes in the way that ransoming was handled. From these letters and petitions, we can compare the more decentralized, urban nature of ransom before the Crusades to the changes that took place after. First, because Jewish lands and communities were being taken over by European Crusaders, they had to ransom not only their coreligionists but also the sacred Torah scrolls that had been captured. This increase in the number of captives (now people and texts) led to other changes, such as calling for funds from the countryside and small towns in addition to the urban centers. These communities were working together in ways that were not necessary before. Lastly, we see a move for centralization, for the funds to be collected in one place then disseminated to areas of greatest need. Under Moses Maimonides, one of the most influential Jewish rabbis and scholars of the Middle Ages, this project was realized.