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    Mail servers imap behind pfsense not reachable

    Scheduled Pinned Locked Moved Firewalling
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    • D
      daan
      last edited by

      The mail server is on my current IP, but with my previous router it worked fine (Non pfsense).
      And yes I am 1000% sure my pfsense WAN IP is my public IP, because all of my websites running from this network are up and reachable.

      V 1 Reply Last reply Reply Quote 0
      • johnpozJ
        johnpoz LAYER 8 Global Moderator
        last edited by johnpoz

        Well something is answering on his IP he is connecting to the forum with, which I would assume his IP... But from his packet capture - nothing is getting to pfsense..

        Pfsense can not forward what it does not see.. This is basic 101 stuff here..

        edit: I do not know what to tell you.. This is basic 101 stuff here, if you can not show us pfsense seeing the traffic on its wan... How could it ever do anything with it.. All I can tell you is something answers on 143 when I hit the IP you connected to the forum from..

        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 @daan
          last edited by

          @daan said in Mail servers imap behind pfsense not reachable:

          When I do not specify a port I see loads of traffic, HTTPS traffic

          You can also limit the capture to multiple port by entering "143|587|993" for instance to take all IMAP ports.

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          • V
            viragomann @daan
            last edited by

            @daan
            You can check your real public IP on web services like https://whatismyipaddress.com

            The IP you get displayed there must match your pfSense WAN IP, otherwise there is a router in front of pfSense.

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            • D
              daan
              last edited by

              @viragomann I know my it is the same IP as the pfsense WAN interface IP

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              • D
                daan
                last edited by

                @johnpoz this is my capture with 143|465|587|993 as ports
                Screenshot 2020-09-25 1449523.png

                V P 2 Replies Last reply Reply Quote 0
                • johnpozJ
                  johnpoz LAYER 8 Global Moderator
                  last edited by johnpoz

                  Do a simple sniff on 143 then..

                  Then go to can you see me . org and put in 143..

                  You should see this traffic. Clearly sniffing is working.. But I don't see any traffic for 143.

                  To be honest, sure looks to be working to me.. Whatever issues you might be having with imap has nothing to do with pfsense. I get a connection to 143, and sure seems to be whatever server your running behind pfsense.. reports Dovecot (Debian), which is what your Poste.io server uses for imap..

                  btw I see 993 there in your sniff which would be imap over tls. Maybe your client is just not using 143 when you tested which is why you didn't see on sniff.. Do can you see me . org so you know exactly what port is being sent.

                  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

                  D 1 Reply Last reply Reply Quote 0
                  • V
                    viragomann @daan
                    last edited by viragomann

                    @daan said in Mail servers imap behind pfsense not reachable:

                    this is my capture with 143|465|587|993 as ports

                    Ther is obviously a communiction on 993. Possibly your client switches automatically to 993 (SSL)?

                    However, the traffic may be outbound as well. You're the only one who knows the destination IP, we cannot see it.

                    GertjanG D 2 Replies Last reply Reply Quote 0
                    • GertjanG
                      Gertjan @viragomann
                      last edited by

                      @viragomann said in Mail servers imap behind pfsense not reachable:

                      Ther is obviously a communiction on 993. Possibly your client switches automatically to 993 (SSL)?

                      Hummm : 993 was already mentioned above.
                      Check if the mail server "IMAPS" is listening on port 993 on the IMAP server before you NAT that port (TCP).

                      No "help me" PM's please. Use the forum, the community will thank you.
                      Edit : and where are the logs ??

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                      • D
                        daan @johnpoz
                        last edited by daan

                        @johnpoz These are my client settings, the settings worked fine with my previous router.
                        Screenshot 2020-09-25 151153.png

                        And yes I am using poste.io

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                        • D
                          daan @viragomann
                          last edited by

                          @viragomann My public IP reports in inbound as well as outbound traffic on port 993

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                          • johnpozJ
                            johnpoz LAYER 8 Global Moderator
                            last edited by

                            Well your client not set to use 143 in that setup. So why would you think you would see traffic on 143?

                            Not sure what to tell you... Pfsense only job in this is sending the traffic on to where you tell it to send it. Clearly from your sniff that is happening on 993.. So whatever issues you have with imap has nothing to do with pfsense.. Its a dumb doorman in the big picture.. It sees traffic on port X, and sends it on to where you told it to send it.. And then sends the answer back - it has nothing to do with the workings of the conversation.. Nor does it care..

                            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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                            • D
                              daan @Gertjan
                              last edited by

                              @Gertjan Yes I did I uploaded a screenshot of it
                              alt text

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                              • GertjanG
                                Gertjan
                                last edited by

                                1e7b2090-74e1-4446-8e3b-ca3df2f86c2b-image.png

                                STARTTLS seems strange when using 993 as there can't be a TLS negotiation - it will be a direct SSL/TLS connection, like your 465 = SMTPS outgoing mail connection.

                                No "help me" PM's please. Use the forum, the community will thank you.
                                Edit : and where are the logs ??

                                D 1 Reply Last reply Reply Quote 0
                                • D
                                  daan @johnpoz
                                  last edited by

                                  @johnpoz Same story when I use port 143, it does not connect.
                                  Yes I know what pfsense does, but why did it work fine on my previous router and not on my pfsense router?

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                                  • D
                                    daan @Gertjan
                                    last edited by

                                    @Gertjan My mail server does TLS over port 993
                                    df9c81dd-cd73-48c9-928b-5ae0cd9c6053-image.png
                                    (POP, HTTP and HTTPS are not forwarded)

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                                    • johnpozJ
                                      johnpoz LAYER 8 Global Moderator
                                      last edited by

                                      @daan said in Mail servers imap behind pfsense not reachable:

                                      Same story when I use port 143, it does not connect.

                                      It does connect.. I have connected via 143..

                                      connect.png

                                      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

                                      D 1 Reply Last reply Reply Quote 0
                                      • V
                                        viragomann
                                        last edited by

                                        Since we cannot see any unencryted connection attempts, I think it's a legitimate question, if there is a valid SSL certificate installed on the IMAP server.

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                                        • D
                                          daan @johnpoz
                                          last edited by

                                          @johnpoz Wattt the hell, when I do the same it returns
                                          29d7ebdc-0255-441d-a993-44ac60e67925-image.png

                                          bmeeksB 1 Reply Last reply Reply Quote 0
                                          • D
                                            daan @viragomann
                                            last edited by

                                            @viragomann Yes there is, I am using Let's encrypt mail certificates.

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