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    Upgraded pfSense from 2.4.5 to 2.5.2 or 2.6.0 and OpenVPN no longer works

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    • J
      jhdeval
      last edited by

      I appreciate the information and I am also using ssl/tls + auth settings but using either the new or old config I am unable to connect to any OpenVPN server that was created in 2.4.x. As I said in my original post I can see the connection going through the firewall and I can see it "attempt" to connect to the OpenVPN server but it seems like it half connects then just drops the connection and tried again. There is no meaningful data in the logs to indicate what the failure is.

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      • K
        kitdavis @jhdeval
        last edited by

        @jhdeval Try modifying the server to just use ssl/tls and I think it will work - at least for me the problem is only with the ssl/tls + authentication and is related to the private key error. This isn't a solution, since you have to re-export the client config but I think it narrows the problem.

        bingo600B 1 Reply Last reply Reply Quote 0
        • bingo600B
          bingo600 @kitdavis
          last edited by

          @kitdavis

          Could this be a match ?
          https://redmine.pfsense.org/issues/12475

          If you find my answer useful - Please give the post a šŸ‘ - "thumbs up"

          pfSense+ 23.05.1 (ZFS)

          QOTOM-Q355G4 Quad Lan.
          CPUĀ  : Core i5 5250U, Ram : 8GB Kingston DDR3LV 1600
          LANĀ  : 4 x Intel 211, DiskĀ  : 240G SAMSUNG MZ7L3240HCHQ SSD

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          • V
            viragomann @jhdeval
            last edited by

            @jhdeval said in Upgraded pfSense from 2.4.5 to 2.5.2 or 2.6.0 and OpenVPN no longer works:

            There is no meaningful data in the logs to indicate what the failure is.

            May we see it anyway?

            If the packets are reaching the server, there must be log entries, telling you what's going on on the server.

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            • K
              kitdavis @viragomann
              last edited by

              @viragomann I took a working 2.4.4 installation (i.e. I could connect to it via OPENVPN) and upgraded it to 2.5.2 - after the upgrade the openvpn connection cannot be established and the error in the log is:

              May 3 05:03:21 openvpn 24521 TLS Error: cannot locate HMAC in incoming packet from [AF_INET]167.94.138.105:64805
              May 3 00:16:50 openvpn 24521 TLS Error: cannot locate HMAC in incoming packet from [AF_INET]146.88.240.4:46211

              running openvpn from the client terminal I see:

              2022-05-03 10:59:43 OpenSSL: error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed
              2022-05-03 10:59:43 TLS_ERROR: BIO read tls_read_plaintext error
              2022-05-03 10:59:43 TLS Error: TLS object -> incoming plaintext read error
              2022-05-03 10:59:43 TLS Error: TLS handshake failed
              2022-05-03 10:59:43 SIGUSR1[soft,tls-error] received, process restarting

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              • V
                viragomann @kitdavis
                last edited by

                @kitdavis
                Seems the server log lines have nothing to do with the error on the client.

                Obviously there is something wrong with the server cert from the point of the client. Normally you can see details one line above of that one you've posted.

                But your error differs totally from the above.

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                • J
                  jhdeval @viragomann
                  last edited by

                  @viragomann I am working on the logs. Since this is a production server I had to restore from backup to bring users live again. I will need to clone this server and use it in a closed environment to get the logs.

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                  • K
                    kitdavis @viragomann
                    last edited by

                    @viragomann I agree there is something wrong with the certificate. As per my other thread, once the upgrade occurs - if I try to use the client export took, I get the private key missing error which I think it referenced in: https://redmine.pfsense.org/issues/12475

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                    • S Stewart referenced this topic on
                    • S
                      Stewart @kitdavis
                      last edited by

                      @kitdavis @jhdeval @viragomann

                      I know this post is a few months old but I ran into the same thing with the same update path and the same errors. I can't find that you were able to resolve your problem but I wanted to post my experience here as it was one of the first threads that popped up while searching. I found in my case that the issue was the new version of OpenVPN restricts the age limit of the certificates to about 13 months whereas before the default was 10 years. If the certificates extend beyond the time threshold then the client considers it to be invalid. I had to regenerate my certificates with shorter times and reissue them to the workstations for it to work.

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                      • K
                        khodorb @Stewart
                        last edited by

                        @stewart
                        https://forum.netgate.com/topic/172870/crl-has-expired/24
                        https://blog.nuvotex.de/pfsense-crl-has-expired/

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                        • S
                          Stewart @khodorb
                          last edited by

                          @khodorb said in Upgraded pfSense from 2.4.5 to 2.5.2 or 2.6.0 and OpenVPN no longer works:

                          https://blog.nuvotex.de/pfsense-crl-has-expired/

                          Thanks. I tried that patch and it was unsuccessful in fixing the issue. This was my post.

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