In 1561 Barbary corsairs took captive two men from Sicily, Visconte Cicala and his son Scipione. To students of the Ottoman Empire the latter is probably better known by the name assumed at his conversion to Islam, Cigalazade Yusuf Sinan. Some contemporary Christian European observers claimed that Cigalazade had been lured into becoming a Muslim with the promise that his father would be released immediately. Although this story is probably false, an experience of captivity played an undeniable role in the Italian's conversion. And while captivity and an attempt to overcome the numerous disadvantages and limitations associated with the status of a captive/slave can hardly be sufficient explanations for conversion, a sample of roughly 150 renegades active in the Ottoman Empire during the late sixteenth and early seventeenth century indicates that, for the majority of them, experiences of captivity influenced their decisions to accept Islam. These did not always mean captivity at the hands of the Ottomans however. In the case of the Heidelberg theologian Adam Neuser, for example, imprisonment for heresy and treason in the Holy Roman Empire eventually led to his flight to the sultan's domains, where he was imprisoned once more before "turning Turk". On the basis of case studies drawn from the above-mentioned sample undertaken as part of my doctoral research, the paper will examine the relationship between captivity and conversion from Christianity to Islam and, as far as possible, vice versa in the context of the Ottoman-Habsburg frontier. While this relationship has been dealt with frequently in the context of the Mediterranean by scholars such as Bartolome and Lucille Bennassar, the model developed in this context is not easily transferable to the land frontier in South Eastern Europe where a largely artificial - and never fully stable - line separated communities with shared customs, languages, and ethnicities. It will be argued that captivity, if anything, provided individuals with an occasion and at best an added incentive for conversion. Whether or not taking this step acted as means of "career advancement" very much depended on the talents, skills, knowledge and, not least of all, the contacts -- both within and without the Ottoman Empire -- of the individual in question.