Once Frank Ryan was out of Spain Kerney had no further say or control over him, but a certain amount of correspondence was maintained mainly through the Clissmanns. The first question raised by everyone, friends and foes alike, was where was Frank Ryan? The Germans, for their own reasons, wanted to keep this secret, to the extent that they changed his identity and called him Frank Richard. His first letter, dated 20th August, posted from Estoril, near Lisbon, in September and received in Madrid shortly after confirms that he is "safe and sound" but that it is impossible for him to get home until the war is over. This letter was possibly written and posted to give the impression that he was on his way to the U.S. though the statement that he cannot get home until the end of the war seems to give the lie to this.  Indeed at one stage Kerney, as noted above, was told categorically by Champourcin that Ryan was in the U.S.  He had earlier expected this to be the outcome as he knew that Ryan had friends in the U.S., in particular Gerald O'Reilly. As we now know, by the 20th August Ryan was probably on the way back to Germany following an aborted submarine trip to Ireland, Sean Russell having died on board. 
The connection with the Clissmanns dates back to around 1934 when Budge (Elizabeth) Mulcahy, as she was then, came to Paris to study at the Sorbonne. Leopold Kerney, who was then Commercial Secretary at the Legation in Paris, having started as Irish Consul in 1919, looked after her as he often did with Irish people passing through Paris. In fact, she was treated as a member of the family. When they were next in Ireland in 1935 the Kerney family visited the Mulcahy family in Sligo; and when, in due course, Budge met and married Helmut Clissmann, he was also accepted as a friend. Clissmann had studied for a while at Trinity College, Dublin, and was then appointed by the German Academic Exchange Service to arrange cultural exchanges. As the Mulcahys were a republican family, they were friendly with Frank Ryan and while on a visit to Budge Mulcahy which she had arranged, probably in May 1935, Kerney was introduced to Ryan but they did not meet again until Ryan's imprisonment in Spain in 1938.  Although Kerney was a lifelong republican, he fully supported de Valera's policy as set out when the latter founded Fianna Fáil in 1926 and disapproved of the use of force to achieve Ireland's final goals.
After September 1939, the Clissmanns returned to Germany and Helmut Clissmann was then appointed to Denmark by the Exchange Service but, other than personal letters from Budge Clissmann, there doesn't appear to have been any special contact until December 1940 when she visited Madrid, bringing news of Frank Ryan. There was never any correspondence between Kerney and Helmut Clissmann. Prior to this, she had mentioned in a letter dated 21st November that she had seen "someone who has many, many reasons to be thankful to you. He has asked me to be remembered to you."  The Germans were anxious that Kerney should think that Ryan had escaped with the help of American friends and Budge Clissmann had apparently been sent with the covert mission of ensuring that Germany would not be implicated. They appear to have been satisfied.  Budge had brought a letter from Frank Ryan dated 11th December 1940, in which he confirms that Clissmann (to whom he refers as Mr. Mulcahy(Jr.)) and his friends had originated his "trip" (i.e. his "escape") and were able to link their efforts with those originated by Kerney. He said that they had insisted that there would be no conditions as far as he was concerned and that he enjoyed the status of a "gentleman at large". He talks of having had hopes of reaching home, but they were short-lived; then of arrangements to go to "Gerald's" (U.S.), which he seems to link to his first letter of 20th August, but having had to come back due to an "unforeseen circumstance"; and now there was talk of making the journey a longer way.