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    Tailscale with pfsense exit node, no DNS

    Scheduled Pinned Locked Moved Tailscale
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    • SoloamS
      Soloam @michmoor
      last edited by

      @michmoor not using headscale, the main reason for me to upgrade the tailscale client was to be able to connect to headscale!

      1 Reply Last reply Reply Quote 1
      • D
        Defiling2063
        last edited by

        I experienced the same problem (couldn't resolve names) using pfsense as exit node after I upgraded tailscale client on pfsense connecting to headscale. To troubleshoot:

        • I turned off and on advertise-exit-node on pfsense.
        • on headscale, I disable / enable the route

        It worked for a few hours and then stopped working.

        I also experienced routing problem from hosts behind pfsense to other hosts meshed through tailscale. I downgraded headscale and tailscale client on pfsense. It has been working fine since this morning.

        SoloamS 1 Reply Last reply Reply Quote 0
        • SoloamS
          Soloam @Defiling2063
          last edited by

          @Defiling2063 What version did you downgraded headscale to make it work with default tailscale client?

          1 Reply Last reply Reply Quote 0
          • D
            Defiling2063
            last edited by Defiling2063

            0.23.0.

            I may be able to run an later version but that was the version I upgraded from before thing went south. I reverted the upgrade.

            p/s wish I saw this thread before I upgraded headscale and tailscale client on pfsense. That would have saved me a week of pulling hair. Cheers.

            1 Reply Last reply Reply Quote 0
            • J
              jacobhall
              last edited by

              I believe I am experiencing the same issue. I recently set up a fresh tailnet and added pfsense as an exit node. The exit node works except when Tailscale DNS is enabled on the client, in which case DNS breaks. This problem doesn't occur when other exit nodes are used.

              Package Versions:
              headscale 0.25.1
              pfSense-pkg-Tailscale 0.1.4
              tailscale (freebsd pkg on pfsense) 1.80.3

              J 1 Reply Last reply Reply Quote 0
              • J
                jacobhall @jacobhall
                last edited by

                Linking relevant threads on the Tailscale GitHub and Lawrence Systems forum which describe related issues (it looks like @Soloam has participated in all of these).

                If anyone having a similar problem bumps into this, please take a minute to document your experience so that we can collect more information and try to solve this. Thanks

                SoloamS D 2 Replies Last reply Reply Quote 0
                • SoloamS
                  Soloam @jacobhall
                  last edited by

                  @jacobhall said in Tailscale with pfsense exit node, no DNS:

                  Linking relevant threads on the Tailscale GitHub and Lawrence Systems forum which describe related issues (it looks like @Soloam has participated in all of these).

                  If anyone having a similar problem bumps into this, please take a minute to document your experience so that we can collect more information and try to solve this. Thanks

                  This problem, from what I can tell, only happens on people using headscale, because we have to change the tailscale client version on pfsense...With Tailscale services the tailscale client on the pfsense package works and it seams to be imune to this problem

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                  • E
                    elvisimprsntr
                    last edited by elvisimprsntr

                    Not sure if related, but there are some TestFlight builds which include DNS fixes.

                    Screenshot 2025-03-25 at 12.42.22 PM.png Screenshot 2025-03-25 at 12.42.32 PM.png

                    J 1 Reply Last reply Reply Quote 0
                    • J
                      jacobhall @elvisimprsntr
                      last edited by

                      @elvisimprsntr I'd be willing to try it out. When my client uses pfSense as an exit node, it can ping 100.100.100.100, but DNS queries to the same IP address time out. This makes me think there is an issue with the pfSense/FreeBSD implementation specifically.

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                      • E
                        elvisimprsntr
                        last edited by elvisimprsntr

                        I don't seem to have a problem with DNS when using pfSense or NAS docker container as an exit node, but I am not using headscale.

                        PFSENSE

                        • 2.7.2 CE
                        • Tailscale package 1.4.0
                        • Tailscale 1.80.3_1
                        • Advertise sub-net routes and exit node enabled
                        • Accept DNS from control server enabled

                        NAS

                        • TrueNAS SCALE 24.10.2
                        • Tailscale docker app 1.2.14
                        • Tailscale 1.80.3
                        • Advertise sub-net routes and exit node enabled
                        • Accept DNS from control server enabled

                        ADMIN CONSOLE

                        • Nameservers: Magic DNS
                        • Global nameservers, Local DNS settings: pfSense LAN IP
                        • Search domains: tailnet, pfSense domain
                        • Advertise sub-net routes and exit node enabled for both pfSense and NAS

                        CLIENT

                        • iOS 18.4 RC
                        • Tailscale 1.81.193 via TestFlight

                        IMG_3055.png

                        IMG_3057.jpeg

                        1 Reply Last reply Reply Quote 1
                        • E
                          elvisimprsntr
                          last edited by elvisimprsntr

                          1.82.0 is released with some MagicDNS fixes.

                          Changelog

                          Screenshot 2025-03-28 at 3.25.00 AM.png

                          I manually updated my NAS docker container.

                          tailscale update
                          reboot
                          

                          Give it a few days for a FreeBSD package to be available.

                          Freshports

                          J E 2 Replies Last reply Reply Quote 0
                          • J
                            jacobhall @elvisimprsntr
                            last edited by

                            @elvisimprsntr I'll give it another try once that version makes it to Google Play, but at first glance this appears to be an unrelated bugfix. I have been experiencing this issue using a v1.82.0 client on Linux, which should include the patch you mention. My pfSense box is currently running 1.80.3, so maybe it's worth testing 1.80.3_1 in case that makes a difference.

                            I agree with @Soloam above that this is likely an issue only experienced by headscale users. Regardless, I think it's the pfSense package that requires fixing as my other exit nodes running Linux have not had any issues. I don't have the time right now to delve into the Tailscale, FreeBSD, and pfSense codebases at the moment, but I hope to support this bugfix however I can.

                            I am hopeful someone on this forum can help contextualize this issue in terms of pfSense's DNS system and point us (me) in the right direction for contributing a fix.

                            1 Reply Last reply Reply Quote 0
                            • E
                              elvisimprsntr @elvisimprsntr
                              last edited by elvisimprsntr

                              I upgraded 2.7.2 CE to TS 1.82.0

                              No issues so far.

                              1 Reply Last reply Reply Quote 0
                              • D
                                Defiling2063 @jacobhall
                                last edited by

                                @jacobhall

                                I was on the stock version (pfsense community 2.7.2) of tailslcale connecting to headscale.

                                I upgraded tailscale client on pfsense to 1.82.5 while leaving headscale unchanged. I was able to reproduce the problem -- my android tailscale client cannot resolve dns when using the tailscale client on pfsense as an exit node. If I disable "Use tailscale DNS" on my android client, internet connectivity works.

                                I am going to leave it broken for now, if anyone wants me to try different things. Thanks.

                                1 Reply Last reply Reply Quote 0
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