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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 tks for the replay.

      I have it simple, no acl, and i'm using the tailscale dns (100.100.100.100), is there any config on the pfsense nat outbound that you added?

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

        I added a new vm only to act as exit node and it works... I have it all, access to my private network (actually is beeing provided by pfsese sharred routes, but I could add it to the other node also)... I have exit node capability (on the lxc) and inside the exit node I allso can access all my private network and dns!

        So I don't see this as a headscale problem! It could be bad configuration on pfsense.

        @michmoor do you use the native interface or did you assigned it to a pfsesne interface? Can you shere with me all the rules, nat and settings that you added to make this work? Also, do you use dns unbound?

        Thank you

        M 1 Reply Last reply Reply Quote 0
        • M
          michmoor LAYER 8 Rebel Alliance @Soloam
          last edited by michmoor

          @Soloam

          You do not assign a tailscale interface. For NAT, i do have an outbound NAT as so.
          That is the Tailscale IP i received when i added my pfsense as an exit node. Because you do not assign an IP, the Interface wont be listed in the outbound NAT rule for the NAT address but that's ok you just add the pfsense TS address.

          d1ca8092-98ce-429a-b04f-e96741acc20b-image.png

          3d96b285-7368-4cc3-9bec-84b758da4d37-image.png

          Firewall: NetGate,Palo Alto-VM,Juniper SRX
          Routing: Juniper, Arista, Cisco
          Switching: Juniper, Arista, Cisco
          Wireless: Unifi, Aruba IAP
          JNCIP,CCNP Enterprise

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

            @michmoor I tried to add it and same result, no dns when useing exit node! I can ping all ip's and I can acess all ip's by direct ip... but no dns resolved...

            Is that the only rule? you don't need to add rules to the intercace? And in outbound didn't you add rules with the tailscale IP to other interfaces?

            Are you using dns unbound?

            Thank you

            M 1 Reply Last reply Reply Quote 0
            • M
              michmoor LAYER 8 Rebel Alliance @Soloam
              last edited by michmoor

              @Soloam I dont need rules on the interface because traffic isn't directed to pfsense itself.
              I only needed an outbound NAT if i am trying to reach other devices in my tailnet coming from my LAN behind my firewall. Thats the reason for the Outbound NAT. I don't fully know your topology so that "may" be required or not in your case.

              When i select my pfsense as an exit node all that is happening is that DNS resolution gets done by the tailscale DNS server which in my case is 100.100.100.100. After that , traffic is simply forwarded to pfsense and out to the Internet. Traffic leaving your pfsense to the internet will be sourced as coming from the WAN address itself hence no reason for any additional NAT rules.

              Are you using split DNS? In other words, are you trying to access internal domains to your LAN? Or is internal and external domains not resolving? With internal domains, you would use tailscale split DNS feature and that should point to your pfsense if your pfsense is doing DNS for you internally.

              Lastly, is pfsense offering itself to be an exit node?

              1bba38ee-985e-4e07-96f5-d7ec8eb92308-image.png

              Firewall: NetGate,Palo Alto-VM,Juniper SRX
              Routing: Juniper, Arista, Cisco
              Switching: Juniper, Arista, Cisco
              Wireless: Unifi, Aruba IAP
              JNCIP,CCNP Enterprise

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

                @michmoor yes my pfsense is advertised as exit node and I use spli dns to my local network... Dns resolution does not work with public and private dns... One thing that I noticed with a tcpdump is that no request arrive to my pfsese 100.100.100.100 on port 53 when I'm on exit onde on another node!

                I found somthing interresting!

                On my vm taht i use as a exit node... when I turn on exit node on my phone, I see this connections appear on pfsense:

                d8217c03-e2a8-46cc-9c0d-42a7db9e3672-image.png

                When I do the same with pfsense I don't see any connection!

                M 1 Reply Last reply Reply Quote 0
                • M
                  michmoor LAYER 8 Rebel Alliance @Soloam
                  last edited by

                  @Soloam This is why i said earlier this seems more of a headscale than pfsense.
                  Trying to understand your pcap but who is 100.100.100.100? Is that your controller?
                  Just looking at the 2nd row in the states snippet, traffic from 192.168.2.159 gets SNAT to 100.64.0.1 which makes sense for traffic leaving your pfsense and towards your tailnet. The destination is 100.100.100.100:853 but SYN_SENT:CLOSED indicates that the client is not responding to those TCP SYN messages (3way handshake). Thats a question for you. Why isn't that IP responding if that is your DNS server? If your DNS server is your pfsense as you stated then why isn't it responding.
                  Something seems off but don't know where.

                  UDP on port 53 seems to work according to the states.

                  Forgetting headscale for a moment.
                  If your client is on your tailnet, it should send DNS to pfsense which is the tailnet DNS controller in your set up?

                  Firewall: NetGate,Palo Alto-VM,Juniper SRX
                  Routing: Juniper, Arista, Cisco
                  Switching: Juniper, Arista, Cisco
                  Wireless: Unifi, Aruba IAP
                  JNCIP,CCNP Enterprise

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

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

                    eems to work according to the sta

                    100.100.100.100 is the dns server used by tailscale, it's the dns responsible for all the responses inside a tailscale network...

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

                      I'm starting to belive that this might be related to the fact that I updated the tailscale client on pfsense! The package version is outdated and was not compatible with headscale that required a minimum version of 1.80.2, the one installed was 1.79. I'll wait for the package to be updated before investing more time into this!

                      Thank you for the help

                      M 1 Reply Last reply Reply Quote 0
                      • M
                        michmoor LAYER 8 Rebel Alliance @Soloam
                        last edited by

                        @Soloam can you downgrade the pfsense package? If so that would rule out some things

                        Firewall: NetGate,Palo Alto-VM,Juniper SRX
                        Routing: Juniper, Arista, Cisco
                        Switching: Juniper, Arista, Cisco
                        Wireless: Unifi, Aruba IAP
                        JNCIP,CCNP Enterprise

                        SoloamS 1 Reply Last reply Reply Quote 0
                        • 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

                                      1 Reply Last reply Reply Quote 0
                                      • 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.

                                          1 Reply Last reply Reply Quote 0
                                          • 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
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