For several months in 1575, Holy Roman Emperor Maximilian II's ambassador in Istanbul was engaged with reporting on, and attempting to prevent, an Ottoman spy mission entrusted to the recent convert to Islam Markus Penckner. The surviving sources afford valuable insights into the practicalities of Austrian-Habsburg intelligence against those they considered the 'hereditary enemy' and sheds light on the cooperation of the two branches of the House of Habsburg in such matters. At the same time, the episode provided an opportunity for the diplomat in question, David Ungnad, to demonstrate his competence as an information gatherer, his extensive network across the Habsburgs' realms, and thus his value for the dynasty. This chapter argues that such qualities were valuable resources for actors like Ungnad when pursuing their own goals.