Dear helpful people, The problem is now solved by a workaround based on a new CAPF certificate. That is that. Concerning the discussion here, i (representing my supervisor) would like to pinpoint 2 facts that arouse: First and foremost the attached cacert.capf.pem is based on a Cisco __System generated__ CSR and results in a certificate with the attributes: X509v3 Key Usage: critical Digital Signature, Certificate Sign, CRL Sign X509v3 Extended Key Usage: critical TLS Web Server Authentication This very certificate is than used by the Cisco __system__ to issue telephone/end-entity certificates in the likes of the attached SEPxxxxxxx-L1.pem. These end-entity certificates have the following attributes: X509v3 Key Usage Digital Signature, Key Encipherment X509v3 Extended Key Usage TLS Web Server Authentication, TLS Web Client Authentication, IPSec End System This is just wrong and we know that. But the Cisco System does it anyway. Despite being wrong it is also absolutely irrelevant, because FreeRADIUS retrieves the OpenSSL rejection of the cacert.capf.pem before any end-entity certifcate is ever seen. We now have a very plain cacert.capf.pem. It only shows the following attributes: X509v3 Key Usage: critical Certificate Sign, CRL Sign and things work. So to sum up: there is a mistake, that we know of, but really it is not in our hands to change it. And we do not need to change it, because it is of no concern to the problem at hand. Secondly the presented cacert.capf.pem is (by itself) a valid certificate. It does not present a mistake. We should also not need to change it - but we do. Why? Having read all the discussion i do not know why. It is a CA certificate and Cisco somehow restricts this CA certificate to a certain chosen purpose. It is also ok to issue an intermediate CA certificate with pathlen=5 and then issue right beneath it a intermediate CA certificate with pathlen=0 instead of 4 to further restrict. Restriction is a tool to reach more secure environments. The keyUsage attributes are a way to use the tool of restriction. OpenSSL should not interfere at this point. This is my take on this topic. I do thank you very much for your help and effort. Even if some of you see the topic different, i like the fact that we discussed this really vividly. Robert
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