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    TLS Error upon connnecting in PFsense server with openvpn client

    Scheduled Pinned Locked Moved OpenVPN
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    • johnpozJ
      johnpoz LAYER 8 Global Moderator
      last edited by

      openvpn openvpn version: 1.2.16 ???

      Huh?? Are you talking about the openvpn export package version?  That is not openvpn client.. or the server..  What is the version of the client you are running on your machine?  Are you downloading the client that is in the export link??  Looks like that is 2.3.6-Ix03 which should be updated since 2.3.7 has been out for couple of months.

      Yes you use the wizard to create a CA, Cert and then using Cert Manager in Pfsense using that CA create a user cert.  Then using the client export package you can download the config that has the info needed for the client to install.

      I just went over the instructions here
      https://doc.pfsense.org/index.php/OpenVPN_Remote_Access_Server

      And from a quick read over they look to be spot on.

      An intelligent man is sometimes forced to be drunk to spend time with his fools
      If you get confused: Listen to the Music Play
      Please don't Chat/PM me for help, unless mod related
      SG-4860 24.11 | Lab VMs 2.8, 24.11

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      • S
        secad000
        last edited by

        I see..the problem is in the pfsense version isn't compatible with openvpn client version. pfsense 2.2.3 is compatible with openvpn 2.3.6..when I update pfsense to 2.2.4., openvpn client didn't work.

        As you said their is new version of openvpn client 2.3.7, so how to update openvpn export package since it gives me 2.3.6 of openvpn client?

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        • johnpozJ
          johnpoz LAYER 8 Global Moderator
          last edited by

          There is nothing saying you have to use the bundled client - just download openvpn from openvpn https://openvpn.net/index.php/open-source/downloads.html

          Grab your config from the export client, but I don't buy that client 2.3.6 is not compatible with 2.2.4.. That doesn't make any sense at all..  I could always just run 2.3.6 and test it.. Will do from work.

          From your error
          error=unsupported certificate purpose

          points to using the wrong certs

          edit:  As I thought I uninstalled my openvpn client (2.3.8 is out btw) and installed the bundled exe from export client, and connected without any issues

          Wed Aug 05 07:42:22 2015 OpenVPN 2.3.6 i686-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [IPv6] built on Mar 19 2015
          Wed Aug 05 07:42:22 2015 library versions: OpenSSL 1.0.1m 19 Mar 2015, LZO 2.08
          Wed Aug 05 07:42:24 2015 Control Channel Authentication: using 'pfSense-TCP-443-johnpoz-tls.key' as a OpenVPN static key file

          Your issue is not with the client version.

          An intelligent man is sometimes forced to be drunk to spend time with his fools
          If you get confused: Listen to the Music Play
          Please don't Chat/PM me for help, unless mod related
          SG-4860 24.11 | Lab VMs 2.8, 24.11

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          • V
            viragomann
            last edited by

            @johnpoz:

            Grab your config from the export client, but I don't buy that client 2.3.6 is not compatible with 2.2.4.. That doesn't make any sense at all..  I could always just run 2.3.6 and test it.. Will do from work.

            Confirm that.
            As I had the same issue with an older OpenSSL version and pfSense 2.2.4, I installed 2.3.6 from the Clien Export utility and it work flawlessly.

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            • S
              secad000
              last edited by

              I have 10 openvpn client with same openvpn installer that exported from pfsense and one of them encountered the error stated above (subject) and the rest works fine. I have disable the windows firewall and antivirus but got same error.

              Any idea?

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              • johnpozJ
                johnpoz LAYER 8 Global Moderator
                last edited by

                And validate your using the correct certs.. What part of about "error=unsupported certificate purpose" is not clear??

                Are you trying to use a cert marked as server for user?

                An intelligent man is sometimes forced to be drunk to spend time with his fools
                If you get confused: Listen to the Music Play
                Please don't Chat/PM me for help, unless mod related
                SG-4860 24.11 | Lab VMs 2.8, 24.11

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                • K
                  kcmichaelm
                  last edited by

                  I had the exact same error, using the wizard exactly as I thought I was supposed to. The "invalid purpose" message is really the key here, but it took a while to sink in for me.

                  Making this worse was the fact that my VPN was working through the iOS OpenVPN app but refused to work through Viscosity or Tunnelblick on Mac.

                  Make certain that your OpenVPN server is using a "Server cert", and that your user is using a "User Cert".

                  After I finished the Wizard, my OpenVPN server had been assigned the user cert and it took me like 4 days to catch it. Going into the Cert Manager and creating a fresh server-only cert, and then assigning it to the OpenVPN Server instance fixed this perfectly and Viscosity connected.

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                  • johnpozJ
                    johnpoz LAYER 8 Global Moderator
                    last edited by

                    Not sure what to tell you other than the openvpn wizard doesn't create user certs..  You have to create that in the CA manager after you setup the server..  So not sure what you think you did with the wizard but it doesn't create user certs.

                    It will create your CA, and then it will create your server cert..

                    An intelligent man is sometimes forced to be drunk to spend time with his fools
                    If you get confused: Listen to the Music Play
                    Please don't Chat/PM me for help, unless mod related
                    SG-4860 24.11 | Lab VMs 2.8, 24.11

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                    • K
                      kcmichaelm
                      last edited by

                      In the few times I've posted here, with a question or trying to be helpful (to the other newbs like me) - every single time "experts" come along and make me feel stupid.

                      This is such an unwelcome forum to be new.

                      I had created a user cert (yes I know it wasn't done through the wizard) - and I finally figured out that I broke the setup myself by accidentally assigning it to the server. "Invalid purpose" wasn't as clear an error message as people here seem to think it is.

                      I have no grudge against pfSense and I'm not asking anyone to make any changes based on my experience - just posting a specific fix in a forum against a specific error message.

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                      • johnpozJ
                        johnpoz LAYER 8 Global Moderator
                        last edited by

                        "After I finished the Wizard, my OpenVPN server had been assigned the user cert"

                        Again dude the Wizard does NOT do that, can not do that!!  So if you did that that is on you not the wizard.. Not sure how that could ever happen other than just pure stupidity??

                        If english is not your native language ""Invalid purpose"" might be a bit confusing, but if you actually speak english how is that not clear??

                        An intelligent man is sometimes forced to be drunk to spend time with his fools
                        If you get confused: Listen to the Music Play
                        Please don't Chat/PM me for help, unless mod related
                        SG-4860 24.11 | Lab VMs 2.8, 24.11

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