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    OpenVPN bad encapsulated packet length question

    Scheduled Pinned Locked Moved General pfSense Questions
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    • A Offline
      amrogers3 @netblues
      last edited by amrogers3

      @netblues

      UDP using port 443 ok?
      Had no idea there was ai driven spam now. Thought that was one weird post.

      Going to change it here to UDP over 443 and download a new client Viscosity bundle. Glad I posted about the TCP error. I learned a bit.
      Screenshot 2025-08-03 at 7.19.42 PM.png

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      • N Offline
        netblues @amrogers3
        last edited by

        @amrogers3
        Well, you can do that, technically all ports are the same , however quic will be using udp on 443.
        And if it is a firewall that you need to bypass, udp won't cut it either.
        Most todays firewals can do dpi and will detect openvpn on any port.

        Unless you have other reasons, consider using the default 1194 port, or maybe 1193 or 1195, just to avoid random scans.
        Obscurity is not security, and sometimes creates more issues than it solves, e.g. in a penetration test audit.

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        • stephenw10S Online
          stephenw10 Netgate Administrator
          last edited by

          It should work using TCP on port 443. It's relatively common to use that combination to avoid restrictive networks.

          But I too would advice starting out at something close to the default values setup by the wizard and make sure it works as expected there first.

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          • A Offline
            amrogers3 @netblues
            last edited by amrogers3

            @netblues
            Thank you, I was using 443 because I sometimes log into my VPN through different networks and never know how restrictive firewalls will be and if they lockdown anything other than 80/443.

            I wasn't trying to do security through obscurity, it was what port would be the most unrestricted. I figured 443 is pretty universal and would be allowed everywhere. My other option I was thinking about was 80. I was unaware of the speed degradation issues with TCP but it makes sense because all of the handshakes and overhead with TCP. Also, if DPI is utilized I guess it really doesn't matter what port I use, they can block openvpn if they see it, although it seems openvpn over encrypted connection be be harder to inspect??? maybe it would be the handshake that alerts?

            Have you had any issues using 1194 through various networks?

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            • N Offline
              netblues @amrogers3
              last edited by

              @amrogers3 Depends on the network and the admin
              Fortigate firewalls detect openvpn and block it by default for one.

              Blocking outbound ports is found in medium to high security since it requires much more administrative effort.
              And then, usually such shops opt for a proxy approach which gives much better control anyway.

              You can always run two instances on the same box, one on 1194 udp and another on 443 tcp
              And see how it goes.

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              • A Offline
                amrogers3 @netblues
                last edited by

                @netblues said in OpenVPN bad encapsulated packet length question:

                You can always run two instances on the same box, one on 1194 udp and another on 443 tcp
                And see how it goes.

                That is a good idea. I will give that a try. Forum won't let me thumbs up your post so I will give you a thumbs up here.
                Appreciate all the help!
                👍

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                • stephenw10S Online
                  stephenw10 Netgate Administrator
                  last edited by

                  You can even get extra sneaky: https://docs.netgate.com/pfsense/en/latest/vpn/openvpn/port-share.html

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                  • A Offline
                    amrogers3 @stephenw10
                    last edited by

                    @stephenw10

                    That is interesting. So if I am not running a web server, I can just redirect to a IP to an internal IP that doesn't exist?

                    I have a 192.168.1.x network but not 192.168.2.x.

                    port-share 192.168.2.111 443;
                    
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                    • stephenw10S Online
                      stephenw10 Netgate Administrator
                      last edited by

                      Yup you could though I'm not sure what advantage that might give.

                      But I certainly wouldn't try that until you have a basic UDP server setup and working as expected. Any custom server config is likely to make diagnosing issue more difficult. Start simple, add fun stuff later! 😉

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                      • A Offline
                        amrogers3 @stephenw10
                        last edited by amrogers3

                        @stephenw10

                        I think I may be dealing with the issue @netblues mentioned that on one particular network, it is blocking VPN.

                        I am not sure what that would look like in the logs but I can create a new post on the topic if that would be more appropriate. What would a Firewall block on VPN look like in the logs? Would it hang the connection? Would it look like this?
                        It can find the VPN server but cannot connect.

                        ffc5835c-5231-4770-bd2a-3435c8b50f21-image.png

                        It then hangs on attempting to establish a TCP connection.

                        My VPN is functional over other networks, this is the only network that is giving me issues.

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                        • stephenw10S Online
                          stephenw10 Netgate Administrator
                          last edited by

                          Yes you would likely just see no replies at all because the server never sees the incoming connection.

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                          • A Offline
                            amrogers3 @stephenw10
                            last edited by

                            @stephenw10

                            Ok, I will do some research on VPN port share tonight and do some testing.

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                            • stephenw10S Online
                              stephenw10 Netgate Administrator
                              last edited by

                              I would not expect that to help in this situation, just FYI.

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                              • A Offline
                                amrogers3
                                last edited by

                                Good to know. Is there a way around DPI?

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                                • stephenw10S Online
                                  stephenw10 Netgate Administrator
                                  last edited by

                                  It depends. Probably not if it's any good. Not easily at least.

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                                  • A Offline
                                    amrogers3
                                    last edited by amrogers3

                                    yep, looks like I am done. I checked 443 and 1194 from another network and both are connecting. The network I need openVPN to work appears to be blocking both ports. Port 443 wasn't working before so I gave 1194 a shot just to check if default was allowed, however, the firewall appears to also block 1194.
                                    Bummer 😢

                                    Screenshot 2025-08-06 at 12.18.16 PM.png

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                                    • stephenw10S Online
                                      stephenw10 Netgate Administrator
                                      last edited by

                                      You can try something like UDP port 53 or 123 which are commonly passed. But you would need to do some shuffling for that since pfSense is already listening on those ports for DNS and NTP. You could forward traffic incoming on those to port 1194 on localhost for example.

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                                      • stephenw10S Online
                                        stephenw10 Netgate Administrator
                                        last edited by

                                        Though 'no route to host' there could be a local networking issue rather than a firewall blocking anything.

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                                        • A Offline
                                          amrogers3 @stephenw10
                                          last edited by

                                          @stephenw10

                                          Thank you. I will do some research on this option

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