On his arrival in Berlin, Ryan was introduced to SS Colonel Dr. Edmund Veesenmayer. Veesenmayer, as part of his roving SS and German Foreign Ministry brief, was intimately involved in the planning of all Abwehr operations in Ireland during 1940 – 1943, particularly those involving Russell and Ryan. The day after arriving, Ryan was asked by Russell to accompany him to Ireland as part of Operation Dove (""Unternehmen Taube"" in German). Although Ryan had not been involved in the training or preparation for Dove, both he and Russell departed aboard U-65 on 8 August 1940. When Russell became ill and died during the journey (of a perforated ulcer), Ryan asked the Captain of U-65, Hans-Gerrit von Stockhausen, to cable Germany and ask for fresh instructions before proceeding. The mission was subsequently aborted and Ryan returned to Germany via Bordeaux.