On the 23rd May he wrote as a P.S.: "Since writing the above, I have made the big discovery that Franco himself gave special instructions some considerable time ago that, in this particular case of Frank Ryan, nothing should ever be done in the way of reducing his sentence without his personal consent. You can measure the difficulties we have had to overcome by knowledge of the fact that the obstacle to be overcome is Franco himself."  Kerney had at an earlier stage engaged the services of a Spanish lawyer, Baron de Champourcin, as legal adviser to the Legation. The latter had connections with both Spanish and German intelligence. At about this time Champourcin suggested that perhaps German influence could be brought to bear on Franco to bring about Ryan's release.  As all other avenues had failed, Kerney decided to try this approach as a last resort. Kerney reported that this would be done through the Gestapo but he may have been told this in order to mislead him as in fact it was the Abwehr, the German military intelligence, which was involved and they apparently laid down the condition that Kerney was to know nothing of their intervention. There was no communication, direct or indirect between him and the Germans. 
Through Champourcin various contacts were made between the Germans and the Spaniards and a direct approach made to Franco to obtain a pardon and release. It was reported that Franco had given his approval on the 3rd July and that the process had been set in operation; on the 6th July Kerney sent a telegram to Dublin to this effect, however on the 12th Champourcin was told that Franco had found it impossible to sign the order, but had instead given an order for an "escape" to be organised, this being in reality a hand-over of Ryan to the Germans with the express stipulation that he should leave Spanish territory and not return. This was possible to arrange as the Germans were now in possession of the Franco-Spanish border. This outcome was not what Kerney had hoped for, but in the circumstances there appeared to be little choice in the matter. The reason for Franco's reversal, within a week, of his earlier decision has never been explained  . What Kerney did not know at that time was that, independently, there was a move by German intelligence to get Ryan out of jail which had been instigated by the Clissmanns, then living in Denmark, who were friends of his from before the war. Kerney visited Ryan on the 12th July to inform him of what was going on, and the "escape" took place shortly after. Kerney reported that following some hitch on the 15th, he was finally informed that all was arranged for the night of the 24th. He had asked Champourcin to witness the event to make sure that nothing untoward happened, so after 2 am on that night, a small convoy from Burgos headed for the French frontier at Hendaye; there were two cars, one containing two Falangistas, the other the Germans and Frank Ryan; they were followed at a distance by Champourcin and behind that again at a discreet distance was Leopold Kerney who trusted neither the Spaniard nor the Germans. Champourcin had then gone ahead and reaching Irun, left his car in the town and made his way on foot to the international bridge between Irun and Hendaye. The other two cars arrived at about 8.30 am, the papers were quickly produced and the barrier lifted allowing through the car containing Ryan and the Germans. As they were passing, Champourcin saw Ryan in his car and the latter gave a quick glance showing he recognised Champourcin, but without betraying the fact to those beside him. Kerney was able to watch the proceedings from a distance. 
According to Kerney's report of 26th August 1940, his view was that decisions must have been taken at high level in Berlin and he surmised that "Irish elements in the U.S.A. or elsewhere" anxious to secure Ryan's liberty may have been in contact with Berlin. He concluded:
" It also has to be noted that Franco rejected all Irish appeals in favour of Ryan, even when precedents had been created by the release of others; if he had granted a pardon, Ryan would have remained under Irish control and supervision; he authorised and ordered a very unusual procedure, as a concession to Germany and not as a concession to Ireland; he authorised the placing of this alleged dangerous communist at Germany's disposal - a gesture which could conceivably have unpleasant consequences for the Irish Government, and therefore anything but a friendly gesture towards Ireland.
It is natural enough that relations between German and Spanish intelligence services should be very close; there are apparently certain services which the head of the State is ready to render to Germans even if this means exposing himself to reproaches by other friends.
If Frank Ryan is alive and at liberty today, we have no reason to thank the Spanish Government, and the result has been secured in spite of opposition from the highest quarter." 
Official notification was received from the Spanish Foreign Office on the 4th November that the War Office had informed them that Ryan had been transferred to Dueso Prison, Santander, on the 15th July and had escaped on the 20th July. They had no further information. This was the official explanation.  It should be borne in mind that the German operation to get Ryan out of the Spanish jail was carried out on the express condition that their involvement should not be made known.  This was also in the interest of the Spaniards who needed to lend credibility to the "escape" story and could not be seen to have acted under the influence of the Germans. Stories appear therefore to have been concocted to this end by both the Spaniards and the Germans. Champourcin reported that he had been told by his German friends that he could inform Kerney that Ryan had escaped with American help and that he had actually reached the U.S.A.  Ryan himself must have been primed to the same effect as he writes in his letter dated 20th August 1940 that on the occasion of his "recent unceremonious departure .... My American friends were in a hurry and could give me no time for leave-taking". 
The release of Ryan into the custody of German military intelligence has been described as having taken place "with the connivance of the Irish minister in Madrid, Leopold Kerney"  Apart from being a loaded word, the use of the word "connivance" is irrelevant and at best indicates a lack of comprehension of the situation which is accurately described in the documents mentioned above. The fact is that the handover of Ryan to the Germans was on the direct orders of Franco and was not approved by the Irish minister who could only confine himself to ensuring the safety of Ryan while on Spanish soil, as was his duty. The order given by Franco concerning Ryan's release apparently countermanded an earlier undertaking to have him pardoned and released in the usual way, which was the outcome Kerney was trying to obtain. Although himself a republican, Kerney was a follower of de Valera and did not suppport Ryan's political views and methods. His brief was to get Ryan out of jail. Once out, he had expected Ryan to make his way to the U.S.
A recent publication  gives an account of the circumstances of Frank Ryan's release which is somewhat tendentious and sometimes incorrect. Kerney's decision to seek the help of German influence was taken not merely after the rejection of his proposal for a trade agreement, but after every other means had been exhausted.
The legation's legal adviser's connections with the intelligence world are referred to as 'dubious'. This is a curious interpretation of the fact that such connections would not be openly discussed. It is stated that Franco agreed to permit an escape. It is not made clear that this agreement was with the Germans and not with the Irish Minister. Ryan is referred to as a political prisoner, whereas in fact he was a prisoner of war.
There is a quotation from a G2 report that he (Kerney) 'had no means of getting a decision on that matter from the Dept. of External Affairs, so took upon himself the responsibility' of agreeing to Ryan's release. This is incorrect. The full quotation is 'took upon himself the responsibility of telling his Spanish friend to go ahead, but instructed him to keep the name of the Irish Minister to Spain out of it'.
It is incorrectly stated that the Irish government executed Republicans 'due to the danger of IRA collaboration with Germany'. It is also stated that it is 'unlikely' that de Valera would approve of Ryan's release. This is also incorrect. As stated in note 7 of the previous page, all the Minister's efforts on Ryan's behalf had the full approval and authority of the Irish Government, and therefore had de Valera's support and approval.
It is implied that there was cooperation between Kerney, Clissmann and Abwehr in arranging Ryan's 'escape'. The fact is, at no time was Kerney in touch with Helmut Clissmann, except when the latter made personal visits to Madrid after Ryan was taken to Germany. While Kerney had been in sporadic correspondence with Budge (Elizabeth) Clissmann over a period, largely in connection with conveying news to and from her Sligo home, the first mention of Frank Ryan occurs in a letter from Budge Clissmann on 21st November 1940 when Ryan was already in Germany. Kerney was unaware of any link between Helmut Clissmann and Abwehr and in fact, believed it that it was the Gestapo are not Abwehr who were dealing with the matter. The suggestion that Kerney cooperated with Helmut Clissmann in securing the release of Frank Ryan does not stand up to reason. Apart from a total lack of evidence to support this view, if that had been the case, there would have been no need to involve Champourcin in the matter. An intriguing possibility would be that the Germans may have put it to Champourcin to suggest using their influence, however, this would seem to be unlikely, given that the Germans apparently insisted on keeping their involvement secret and not even divulging it to the Irish Minister. In December 1940, according to the German War Diary, Abwehr arranged for Budge Clissmann to travel to Madrid to visit the Irish Minister with the covert instruction 'to ensure that no connection between Ryan and German authorities will be suspected. The plan seems to have been successful ...'  .
If Kerney had met Frank Ryan on one occasion at Budge Clissmann's flat in Dublin he obviously must have forgotten about this event and there was certainly no further contact between them until Ryan's imprisonment in Spain.
The question is sometimes raised as to whether Kerney had got prior approval from Dublin for his course of action.
When considering these matters, it is necessary to remember that they occurred over 70 years ago, when the world was vastly different to what it is now. It was a world where transatlantic air travel had just become a commercial possibility. Jet engines had not yet been invented. Long-distance phone calls had to be booked in advance and were invariably connected through an operator. The cost was quite high and could be as much as £3 a minute, which today would probably be the equivalent of about €70. These days of instant communication and travel we are accustomed to high-ranking officials picking up the phone and talking directly to their counterparts in other countries or taking a plane and making a personal visit. In former times communications were much more difficult and it was customary to appoint heads of diplomatic missions as Minister Plenipotentiary representing their government in negotiations with the host nation, any representations made or agreements reached being recognised by their government. This was particularly true in wartime Spain when communications were slow and insecure. So the answer to the question as to whether prior approval was obtained to seek German influence on the Spanish government to obtain the release of Frank Ryan is of course "no" for the above reason. In fact, in Leopold Kerney's minute of the 23rd May 1940 he informed the Department that he had begun to use "another channel" without giving further details which would have been dangerous at that stage if that information had been intercepted by the British, the Germans or the Spaniards. His report of 26th August 1940 sets out the details of the sequence of events which culminated in Ryan's release into custody of the Germans insofar as it was known to him. At that stage he was told that Ryan had actually reached America. As noted above Kerney knew nothing at this stage about Clissmann's involvement in Frank Ryan's release, in fact the first contact with Helmut Clissmann since before the war was on the occasion of Clissmann's visit to Madrid during Kerney's absence in November 1941.