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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

      So did this ever work and it just started happening, or you trying to setup openvpn server?  Are you using the wizard?  What version of pfsense what version of the openvpn client?

      I just set this up for another user here that couldn't figure it out.. It takes all of 30 seconds to get openvpn up and running with the wizard.

      I would guess from this
      "error=unsupported certificate purpose: C=test, ST=test, L=test, O=test, emailAddress=test@test.com, CN=test"

      That your just trying to set this up and using the web gui cert vs creating a new cert.. You really should go through the wizard, create a new CA for openvpn, create your cert for openvpn with that CA and then create a user cert using that CA.

      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 tried to set up new open vpn server. Yes Im using wizard to setup.

        pfsense version: 2.2.4
        openvpn version: 1.2.16

        So you mean that I will use the wizard to create CA and user Cert together with openvpn server?

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        • S
          secad000
          last edited by

          I got this error after  using wizard to setup openvpn server.

          Tue Aug 04 12:17:47 2015 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
          Tue Aug 04 12:17:47 2015 TLS Error: TLS handshake failed
          Tue Aug 04 12:17:47 2015 SIGUSR1[soft,tls-error] received, process restarting
          Tue Aug 04 12:17:49 2015 UDPv4 link local (bound): [undef]
          Tue Aug 04 12:17:49 2015 UDPv4 link remote: [AF_INET]122.55.12.162:3880
          Tue Aug 04 12:17:53 2015 SIGTERM[hard,] received, process exiting

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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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