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TLS Error: TLS handshake failed

Scheduled Pinned Locked Moved OpenVPN
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  • T
    thetallkid
    last edited by Sep 9, 2015, 2:01 AM

    Had a client order a SG-2440, set it up with static ip, alls good.

    Setup self signed CA and cert. Added users, added the cert to the user. Used the wizard to setup OpenVPN, making sure that I checked the boxes to add the rules  to the firewall. Installed the OpenVPN Client Export Utility and exported the Viscosity bundle.

    Transferred the viscosity bundle to the client machine, installed it and tried to connect. No go. On the client side it said: TLS Error: TLS handshake failed.
    I checked the OpenVPN logs and saw the following errors: VERIFY ERROR: depth=0, error=unsupported certificate purpose
    TLS_ERROR: BIO read tls_read_plaintext error: error:140890B2:SSL routines:SSL3_GET_CLIENT_CERTIFICATE:no certificate returned
    TLS Error: TLS object -> incoming plaintext read error
    TLS Error: TLS handshake failed

    I also tried using the OpenVPN wizard to create the CA and certificates but that didn't work either.

    I checked the forums, found a few other reports of this issue but no definitive solutions. Is there a solution to this problem?

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    • J
      johnpoz LAYER 8 Global Moderator
      last edited by Sep 9, 2015, 2:58 AM

      " error=unsupported certificate purpose"

      You have the wrong certs selected..  I would delete what you did and walk through the wizard!!  It walks you through creating a CA, Server cert and then you create a client 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 2.7.2, 24.11

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      • T
        thetallkid
        last edited by Sep 10, 2015, 4:53 AM

        I did use the wizard as stated above. Never had any trouble before.

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        • J
          johnpoz LAYER 8 Global Moderator
          last edited by Sep 10, 2015, 3:23 PM

          well you created a wrong cert from that error or picked the wrong one in the dropdown box on the openvpn setup.. You need to create a SERVER cert.. Please post up the certs your using.

          So see attached.  My CA I created for openvpn use, then the server cert that was created and a user account cert.

          openvpncerts.png
          openvpncerts.png_thumb

          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 2.7.2, 24.11

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          • J
            jimp Rebel Alliance Developer Netgate
            last edited by Sep 10, 2015, 4:42 PM

            When making the cert, you need to pick "Server Certificate" – it's very easy to overlook. When setting up test VMs I'd say I forget it on the first try about 2/3 of the time :-)

            Remember: Upvote with the 👍 button for any user/post you find to be helpful, informative, or deserving of recognition!

            Need help fast? Netgate Global Support!

            Do not Chat/PM for help!

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            • J
              johnpoz LAYER 8 Global Moderator
              last edited by Sep 10, 2015, 7:50 PM

              which is why I asked if he went through the wizard - the wizard creates SERVER cert.. Just ran through it again as test..  Never asks you - it auto creates the correct one.. So if you create a new CA, and next step create the cert its going to be a server cert.

              If he ran through the wizard after trying to create his own certs then yeah he could of messed it up with your example.

              wizardcert.png
              wizardcert.png_thumb

              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 2.7.2, 24.11

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              • T
                thetallkid
                last edited by Sep 11, 2015, 3:31 AM

                See attached screenshots. I am making the correct certificates but no matter which method I use, the end results are the same.

                ![Screen Shot 2015-09-10 at 8.52.11 PM.jpg](/public/imported_attachments/1/Screen Shot 2015-09-10 at 8.52.11 PM.jpg)
                ![Screen Shot 2015-09-10 at 8.52.11 PM.jpg_thumb](/public/imported_attachments/1/Screen Shot 2015-09-10 at 8.52.11 PM.jpg_thumb)
                ![Screen Shot 2015-09-10 at 9.01.40 PM.jpg](/public/imported_attachments/1/Screen Shot 2015-09-10 at 9.01.40 PM.jpg)
                ![Screen Shot 2015-09-10 at 9.01.40 PM.jpg_thumb](/public/imported_attachments/1/Screen Shot 2015-09-10 at 9.01.40 PM.jpg_thumb)

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                • D
                  divsys
                  last edited by Sep 11, 2015, 6:44 AM

                  One other odd gotcha I've run into:  make sure the time is correct on both client and server.

                  Perhaps try with a Windows export just to see if it my be a Viscosity prob?

                  No other good suggestions other than try to build OpenVPN clean from scratch?

                  -jfp

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                  • J
                    johnpoz LAYER 8 Global Moderator
                    last edited by Sep 11, 2015, 12:35 PM

                    why does it say user cert on that - are you trying to use the server cert as your user cert as well?  You have to create a specific user cert, you can not use the same server cert for your user.  See my example where I have a johnpoz cert as the user cert.

                    samecert.png
                    samecert.png_thumb

                    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 2.7.2, 24.11

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