Radoslav was probably safe from domestic rebellion as long as his father-in-law Theodore remained strong. In 1230, however, Theodore was defeated and captured by Bulgarian Emperor Ivan Asen II, after which Radoslav's position seems to have weakened; some of his nobility revolted in autumn 1233. Serbian medieval biographers noted that the nobility had left the support of Radoslav and stood itself behind the younger Vladislav. Radoslav fled the country between 1 September 1233 and 4 February 1234, and was unable to regain the kingdom, but eventually returned as a monk. Radoslav fled to Dubrovnik (1233) with his wife, and there are indications that Radoslav had organized some actions against Vladislav and that he thought that he would manage to return to the throne - this is evident from an dated 4 February 1234, regarding a promise to Ragusan trading privileges once he had returned to Serbia. Because of this, Vladislav began threatening Ragusa, which then had to turn to Bosnian Ban Ninoslav for help, and as the action against Vladislav was unsuccessful, Radoslav found refuge with the Epirote ruler Michael II Komnenos Doukas in Dyrrhachium.