In 1230, Theodore was defeated and captured by Emperor Ivan Asen II of Bulgaria, after which Radoslav's position seems to have weakened; some of his nobility revolted in the autumn of 1233. Teodosije said that the nobility no longer supported Radoslav, and instead supported Vladislav. Radoslav and his wife fled to Dubrovnik in 1233. He was unable to regain the kingdom, but eventually returned as a monk. There are indications that Radoslav organized rebellions against Vladislav, and that he thought that he would regain the throne. This is evident from a document dated February 4, 1234, which promised Ragusa trading privileges once Radoslav had returned to Serbia and become king again. Because of this, Vladislav began threatening Ragusa, which then turned to Ban Matej Ninoslav of Bosnia for help. The revolt against Vladislav was unsuccessful, and Radoslav joined the court of Epirote ruler Manuel in Dyrrhachium.