After the failure of Operation Dove, Ryan remained in Berlin. Between Autumn 1940 and January 1943 he lived in a "large gloomy flat" in Berlin with an acquaintance from Ireland, Helmut Clissmann, and Hans Ritter, both of whom were Abwehr assets. Clissmann was married to Elizabeth "Budge" Mulcahy of Sligo, a friend of both Ryan and Leopold Kerney. As an exchange student in Dublin in the 1930s Clissmann had known Ryan and other republicans and socialists well; before Hitler came to power, he had been a member of a left-wing student organisation. Ryan was not in good health as a result of his wound and treatment in the Spanish prison, and at one stage he had a stroke, but he remained convivial and drew around him a small circle of friends. He had to remain incognito and in general did not discuss politics. He grew increasingly deaf (though his friends suggested that he sometimes feigned deafness to avoid uncomfortable conversations with the German authorities) so that he could not be left alone at night – he could not hear the anti-aircraft sirens. He later had to spend his days outdoors or in cafés (where he became friendly with Francis Stuart, whom he had known from Dublin) so that people could see him if the sirens sounded. He took Irish newspapers to Stuart and, being in a position to get extra rations, shared them generously with his friends. In return, Stuart took Ryan, who had a lot of time on his hands, on trips to the countryside and on outings with his students. Stephen Hayes, Chief of Staff of the IRA, claimed that Ryan and Stuart were carrying out propaganda work among Irish prisoners of war. This was untrue. They visited a camp for Irish prisoners, who signified their intent of joining an "Irish Guard". Ryan and Clissmann also visited a camp containing some men who intended setting up this Guard. Ryan had nothing to do with this and the scheme came to nothing. Ryan regretted visiting the camp and told Stuart that the whole scheme disheartened him – he only had sympathy with men who were, like he and his comrades had been, in prison camps.