The past two decades have witnessed an increase in scholarship devoted to political hostages in the Middle Ages. Under the broad heading of dispute settlement, scholarly attention has increasingly focused on the roles played by hostages in diverse forms of medieval diplomacy, especially their use in creating and cementing social and political bonds. However, almost without exception, the work on hostages has largely focused on males. The reason for this imbalance has little to do with sexism, at least not the modern variety. The medieval literary landscape suggests that male and female hostages were common throughout the period, used in connection with treaties, truces, legal agreements, financial arrangements and both formal and ad hoc dispute settlements. However, this routine use of hostages creates problems for modern researchers since medieval writers, taking the presence of hostages for granted, often provide only the barest details about them. Tracking female hostages can be particularly challenging as the detention of women was often disguised as betrothal or political marriage. This is especially true when the detainee was an heiress, regarded both before and after her detention as a conduit for the passage of land, power, or status from one man to another. One result of this is that sometimes women who were at the very center of significant political events are virtually invisible. Their stories, however, are worth the effort to uncover and tell, as they can provide us with a richer understanding of the aims and means of medieval diplomatic practice. Moreover, recovering the stories of female political hostages allows us not only to augment our knowledge about women in the Middle Ages, but provides an avenue for historians interested in hostages to examine questions such as whether or not gender was a significant factor in the reason particular hostages were taken, their treatment while being detained or the outcome of their hostage experiences. This article contributes to the process by looking at the stories of Eleanor of Brittany and Beatrice, the ‘Damsel of Cyprus’, two political hostages whose paths happened to cross in the twelfth century.