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    HELP: cannot send email out after upgraded to 2.3.3

    Scheduled Pinned Locked Moved General pfSense Questions
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    • D
      dgcom
      last edited by

      How is it configured?
      Are you using well-known mail provider or your own?
      Are you using authentication?
      Using ports 25/587 with authentication need STARTTLS and 465 need SMTP over SSL/TLS.

      I suggest you also try packet capture and see if it even tries to connect.

      DG

      1 Reply Last reply Reply Quote 0
      • C
        caigeliu
        last edited by

        See attached picture. Besides options shown in the picture, I have also tried:
        untick "Disable SMTP notification"
        use 587, 25, 465 ports
        All input are correct, no typo.

        The email server I input is correct, I tested with "telnet email-server 587", etc.

        I don't know why the error msg is " Error: could not connect to the host … ??".  The same setting worked in the old version of pfsense 2.3.5.

        pfsense-email.PNG
        pfsense-email.PNG_thumb

        1 Reply Last reply Reply Quote 0
        • DerelictD
          Derelict LAYER 8 Netgate
          last edited by

          To repeat: Ports 25 and 587 generally need STARTTLS. SSL/TLS generally needs to be on port 465.

          The email server I input is correct, I tested with "telnet email-server 587", etc.

          The proper test for how you have that configured would be:

          openssl s_client -connect mail_server:587

          Which would almost certainly fail.

          Chattanooga, Tennessee, USA
          A comprehensive network diagram is worth 10,000 words and 15 conference calls.
          DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
          Do Not Chat For Help! NO_WAN_EGRESS(TM)

          1 Reply Last reply Reply Quote 0
          • C
            caigeliu
            last edited by

            You're right. port 25 no ssl/tls. port 465 for ssl, 587 for tls. I have tried many different combinations.

            I just tried your command from ssh console, testing is OK (see picture).

            The problem is why cannot connect the host from pfSense notification page? I can connect to the mail server host in ssh console.

            pfsense-email2.PNG
            pfsense-email2.PNG_thumb

            1 Reply Last reply Reply Quote 0
            • DerelictD
              Derelict LAYER 8 Netgate
              last edited by

              That is not a successful connection.

              To test a connection to that server using encryption on port 587 you would need:

              openssl s_client -connect mail.server:587 -starttls smtp

              IF YOU ARE CONNECTING ON PORT 25 or 587 AND WANT ENCRYPTION YOU NEED TO USE STARTTLS

              IF YOU WANT TO CONNECT USING SSL/TLS YOU NEED TO USE PORT 465

              Chattanooga, Tennessee, USA
              A comprehensive network diagram is worth 10,000 words and 15 conference calls.
              DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
              Do Not Chat For Help! NO_WAN_EGRESS(TM)

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

                The correct command for testing STARTTLS is:

                openssl s_client -starttls smtp -crlf -connect smtp.gmail.com:587

                (use either Ctrl+C or type QUIT+CrLf to end)
                Provide output (you can sanitize it a bit if it shows your cert info.

                To test different versions of SSL, try -ssl3, -tls1,  -tls1_1 and  -tls1_2

                Could be that your server is not supporting recent SSL versions which were disabled in pfSence…

                DG

                1 Reply Last reply Reply Quote 0
                • DerelictD
                  Derelict LAYER 8 Netgate
                  last edited by

                  He is connecting to port 587 using SSL/TLS. That will never work.

                  Chattanooga, Tennessee, USA
                  A comprehensive network diagram is worth 10,000 words and 15 conference calls.
                  DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
                  Do Not Chat For Help! NO_WAN_EGRESS(TM)

                  1 Reply Last reply Reply Quote 0
                  • C
                    caigeliu
                    last edited by

                    Thanks for all reply. If use 587:

                    pfsense-email3.PNG
                    pfsense-email3.PNG_thumb
                    pfsense-email5.PNG
                    pfsense-email5.PNG_thumb
                    pfsense-email6.PNG
                    pfsense-email6.PNG_thumb

                    1 Reply Last reply Reply Quote 0
                    • C
                      caigeliu
                      last edited by

                      If use 465,

                      pfsense-email7.PNG
                      pfsense-email7.PNG_thumb
                      pfsense-email8.PNG
                      pfsense-email8.PNG_thumb

                      1 Reply Last reply Reply Quote 0
                      • C
                        caigeliu
                        last edited by

                        All above errors are not caused by input parameters or our email server.

                        1 Reply Last reply Reply Quote 0
                        • P
                          phil.davis
                          last edited by

                          Note this bug https://redmine.pfsense.org/issues/7516 "Notify test buttons for smtp/growl should use new unsaved settings" and PR https://github.com/pfsense/pfsense/pull/3691 that fixes it.

                          In current releases (e.g. 2.3.3-p1) you have to save the settings first, then use the test buttons. It just tests the currently-saved settings, not the changes you may just have made in the form.

                          The fix is in 2.3.4 which is coming.

                          So maybe when you are trying lots of combinations and pressing "test", you are not actually getting an effective test.

                          As the Greek philosopher Isosceles used to say, "There are 3 sides to every triangle."
                          If I helped you, then help someone else - buy someone a gift from the INF catalog http://secure.inf.org/gifts/usd/

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

                            Looking at your screenshots, I believe that something else is corrupted, possibly in the config - look at pfsense-email6.PNG - it says that it could not start TLS.
                            I would suggest you take packet capture with this setting and look at it in Wireshark - make sure it goes to the right destination, connects and tries to negotiate SSL session.

                            DG

                            1 Reply Last reply Reply Quote 0
                            • C
                              caigeliu
                              last edited by

                              @phil.davis:

                              In current releases (e.g. 2.3.3-p1) you have to save the settings first, then use the test buttons.

                              I first click "save", then click test in above screenshots.

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

                                Please, review this forum thread - it may have an answer for you.
                                I did not read it in full, but it seems that there is an issue with certs used for SMTP, issued by private CA - pfSence has to trust them and some public CA certs might be missing in newer builds…

                                DG

                                1 Reply Last reply Reply Quote 0
                                • N
                                  NOYB
                                  last edited by

                                  Maybe it's time to simplify and apply isolation troubleshooting techniques.

                                  Remove encryption from the equation.  To protect authentication credentials, change the password or create a throwaway account for testing.

                                  From time to time some CA's are eliminated from the store.  Don't recall the error message that occurs when that happens so don't know if your error messages are due to that or not.

                                  1 Reply Last reply Reply Quote 0
                                  • C
                                    caigeliu
                                    last edited by

                                    Here  are complete packages for one testing of 465:

                                    13:07:21.615841 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32106, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x97b0 (correct), seq 2191407335:2191408795, ack 2273860481, win 16309, length 1460
                                    13:07:21.643670 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 60: (tos 0x0, ttl 59, id 43376, offset 0, flags [DF], proto TCP (6), length 40)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0xd3da (correct), seq 1, ack 11680, win 1748, length 0
                                    13:07:21.643920 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 526: (tos 0x0, ttl 63, id 32107, offset 0, flags [DF], proto TCP (6), length 512)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [P.], cksum 0xe604 (correct), seq 11680:12152, ack 1, win 16309, length 472
                                    13:07:21.650116 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 60: (tos 0x0, ttl 59, id 43377, offset 0, flags [DF], proto TCP (6), length 40)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0xd1c5 (correct), seq 1, ack 12152, win 1809, length 0
                                    13:07:21.650363 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32113, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x6236 (correct), seq 17992:19452, ack 1, win 16309, length 1460
                                    13:07:21.657134 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43378, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x925e (correct), seq 1, ack 12152, win 1809, options [nop,nop,sack 1 {17992:19452}], length 0
                                    13:07:21.958969 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32114, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0xd8ef (correct), seq 12152:13612, ack 1, win 16309, length 1460
                                    13:07:21.965808 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43379, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x8caa (correct), seq 1, ack 13612, win 1809, options [nop,nop,sack 1 {17992:19452}], length 0
                                    13:07:21.966116 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32115, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [P.], cksum 0x09f4 (correct), seq 19452:20912, ack 1, win 16309, length 1460
                                    13:07:21.966144 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32116, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x4330 (correct), seq 20912:22372, ack 1, win 16309, length 1460
                                    13:07:21.972885 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43380, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x86f6 (correct), seq 1, ack 13612, win 1809, options [nop,nop,sack 1 {17992:20912}], length 0
                                    13:07:21.974129 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43381, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x8142 (correct), seq 1, ack 13612, win 1809, options [nop,nop,sack 1 {17992:22372}], length 0
                                    13:07:22.308207 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 74: (tos 0x0, ttl 64, id 1868, offset 0, flags [DF], proto TCP (6), length 60)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags , cksum 0x4e45 (incorrect -> 0xc40a), seq 2198535874, win 65228, options [mss 1460,nop,wscale 7,sackOK,TS val 3724690981 ecr 0], length 0
                                    13:07:22.330747 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 74: (tos 0x0, ttl 59, id 0, offset 0, flags [DF], proto TCP (6), length 60)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [S.], cksum 0x6922 (correct), seq 2017900417, ack 2198535875, win 14480, options [mss 1460,sackOK,TS val 1841922946 ecr 3724690981,nop,wscale 7], length 0
                                    13:07:22.330792 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 64, id 4415, offset 0, flags [DF], proto TCP (6), length 52)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [.], cksum 0x4e3d (incorrect -> 0xce60), seq 1, ack 1, win 520, options [nop,nop,TS val 3724691003 ecr 1841922946], length 0
                                    13:07:22.359282 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 583: (tos 0x0, ttl 64, id 25093, offset 0, flags [DF], proto TCP (6), length 569)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [P.], cksum 0x5042 (incorrect -> 0x1caf), seq 1:518, ack 1, win 520, options [nop,nop,TS val 3724691032 ecr 1841922946], length 517
                                    13:07:22.365140 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 13339, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [.], cksum 0xcd98 (correct), seq 1, ack 518, win 122, options [nop,nop,TS val 1841922998 ecr 3724691032], length 0
                                    13:07:22.369283 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 59, id 13340, offset 0, flags [DF], proto TCP (6), length 1500)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [.], cksum 0x40c3 (correct), seq 1:1449, ack 518, win 122, options [nop,nop,TS val 1841923000 ecr 3724691032], length 1448
                                    13:07:22.369318 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 64, id 44488, offset 0, flags [DF], proto TCP (6), length 52)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [.], cksum 0x4e3d (incorrect -> 0xc661), seq 518, ack 1449, win 509, options [nop,nop,TS val 3724691042 ecr 1841923000], length 0
                                    13:07:22.370515 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 59, id 13341, offset 0, flags [DF], proto TCP (6), length 1500)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [.], cksum 0xba14 (correct), seq 1449:2897, ack 518, win 122, options [nop,nop,TS val 1841923000 ecr 3724691032], length 1448
                                    13:07:22.370549 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 64, id 11179, offset 0, flags [DF], proto TCP (6), length 52)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [.], cksum 0x4e3d (incorrect -> 0xc0b8), seq 518, ack 2897, win 509, options [nop,nop,TS val 3724691043 ecr 1841923000], length 0
                                    13:07:22.371468 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 1259: (tos 0x0, ttl 59, id 13342, offset 0, flags [DF], proto TCP (6), length 1245)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [P.], cksum 0xf721 (correct), seq 2897:4090, ack 518, win 122, options [nop,nop,TS val 1841923000 ecr 3724691032], length 1193
                                    13:07:22.371500 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 64, id 51963, offset 0, flags [DF], proto TCP (6), length 52)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [.], cksum 0x4e3d (incorrect -> 0xbc0c), seq 518, ack 4090, win 511, options [nop,nop,TS val 3724691044 ecr 1841923000], length 0
                                    13:07:22.378422 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 268: (tos 0x0, ttl 64, id 26698, offset 0, flags [DF], proto TCP (6), length 254)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [P.], cksum 0x4f07 (incorrect -> 0xe7bc), seq 518:720, ack 4090, win 520, options [nop,nop,TS val 3724691051 ecr 1841923000], length 202
                                    13:07:22.384517 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 324: (tos 0x0, ttl 59, id 13343, offset 0, flags [DF], proto TCP (6), length 310)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [P.], cksum 0x1909 (correct), seq 4090:4348, ack 720, win 130, options [nop,nop,TS val 1841923017 ecr 3724691051], length 258
                                    13:07:22.384548 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 64, id 11560, offset 0, flags [DF], proto TCP (6), length 52)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [.], cksum 0x4e3d (incorrect -> 0xba1b), seq 720, ack 4348, win 518, options [nop,nop,TS val 3724691057 ecr 1841923017], length 0
                                    13:07:22.384753 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 97: (tos 0x0, ttl 64, id 43524, offset 0, flags [DF], proto TCP (6), length 83)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [P.], cksum 0x4e5c (incorrect -> 0x64db), seq 720:751, ack 4348, win 520, options [nop,nop,TS val 3724691057 ecr 1841923017], length 31
                                    13:07:22.387929 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 64, id 24108, offset 0, flags [DF], proto TCP (6), length 52)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [F.], cksum 0x4e3d (incorrect -> 0xb9f6), seq 751, ack 4348, win 520, options [nop,nop,TS val 3724691060 ecr 1841923017], length 0
                                    13:07:22.389948 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 174: (tos 0x0, ttl 59, id 13344, offset 0, flags [DF], proto TCP (6), length 160)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [P.], cksum 0x5a0d (correct), seq 4348:4456, ack 720, win 130, options [nop,nop,TS val 1841923022 ecr 3724691057], length 108
                                    13:07:22.389982 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 54: (tos 0x0, ttl 64, id 2526, offset 0, flags [DF], proto TCP (6), length 40)
                                        pfsense-ip.36683 > mail-sever-ip.465: Flags [R], cksum 0x4e31 (incorrect -> 0x4c10), seq 2198536594, win 0, length 0
                                    13:07:22.390025 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 13345, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [F.], cksum 0xbb0d (correct), seq 4456, ack 751, win 130, options [nop,nop,TS val 1841923023 ecr 3724691057], length 0
                                    13:07:22.393318 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 13346, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [.], cksum 0xbb06 (correct), seq 4457, ack 752, win 130, options [nop,nop,TS val 1841923026 ecr 3724691060], length 0
                                    13:07:22.879497 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32127, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0xda47 (correct), seq 13612:15072, ack 1, win 16309, length 1460
                                    13:07:22.947930 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 174: (tos 0x0, ttl 59, id 13347, offset 0, flags [DF], proto TCP (6), length 160)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [P.], cksum 0x5835 (correct), seq 4348:4456, ack 752, win 130, options [nop,nop,TS val 1841923459 ecr 3724691060], length 108
                                    13:07:22.948379 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43382, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x7b99 (correct), seq 1, ack 15072, win 1798, options [nop,nop,sack 1 {17992:22372}], length 0
                                    13:07:22.948869 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32128, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0xe265 (correct), seq 22372:23832, ack 1, win 16309, length 1460
                                    13:07:22.948886 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32129, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x1c25 (correct), seq 23832:25292, ack 1, win 16309, length 1460
                                    13:07:22.955779 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43383, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x75e5 (correct), seq 1, ack 15072, win 1798, options [nop,nop,sack 1 {17992:23832}], length 0
                                    13:07:22.956866 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43384, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x7031 (correct), seq 1, ack 15072, win 1798, options [nop,nop,sack 1 {17992:25292}], length 0
                                    13:07:23.874785 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 174: (tos 0x0, ttl 59, id 13348, offset 0, flags [DF], proto TCP (6), length 160)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [P.], cksum 0x54cb (correct), seq 4348:4456, ack 752, win 130, options [nop,nop,TS val 1841924333 ecr 3724691060], length 108
                                    13:07:25.504447 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 174: (tos 0x0, ttl 59, id 13349, offset 0, flags [DF], proto TCP (6), length 160)
                                        mail-sever-ip.465 > pfsense-ip.36683: Flags [P.], cksum 0x4df7 (correct), seq 4348:4456, ack 752, win 130, options [nop,nop,TS val 1841926081 ecr 3724691060], length 108
                                    13:07:25.968249 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32150, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x8d20 (correct), seq 15072:16532, ack 1, win 16309, length 1460
                                    13:07:26.311212 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43385, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x6a88 (correct), seq 1, ack 16532, win 1787, options [nop,nop,sack 1 {17992:25292}], length 0
                                    13:07:26.311668 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32151, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x4617 (correct), seq 25292:26752, ack 1, win 16309, length 1460
                                    13:07:26.311692 00:08:a2:09:4b:7f > 00:31:46:3d:ab:84, ethertype IPv4 (0x0800), length 1514: (tos 0x0, ttl 63, id 32152, offset 0, flags [DF], proto TCP (6), length 1500)
                                        pfsense-ip.47374 > mail-sever-ip.465: Flags [.], cksum 0x5bf6 (correct), seq 26752:28212, ack 1, win 16309, length 1460
                                    13:07:26.442459 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43386, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x64d4 (correct), seq 1, ack 16532, win 1787, options [nop,nop,sack 1 {17992:26752}], length 0
                                    13:07:26.442489 00:31:46:3d:ab:84 > 00:08:a2:09:4b:7f, ethertype IPv4 (0x0800), length 66: (tos 0x0, ttl 59, id 43387, offset 0, flags [DF], proto TCP (6), length 52)
                                        mail-sever-ip.465 > pfsense-ip.47374: Flags [.], cksum 0x5f20 (correct), seq 1, ack 16532, win 1787, options [nop,nop,sack 1 {17992:28212}], length 0

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                                    • D
                                      dgcom
                                      last edited by

                                      You should really do this with port 587, save pcap file and review it in Wireshark.
                                      But even with this capture - it looks like it connects, but can't authenticate or negotiate proper SSL channel.

                                      DG

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                                      • N
                                        NOYB
                                        last edited by

                                        @dgcom:

                                        You should really do this with port 587, save pcap file and review it in Wireshark.
                                        But even with this capture - it looks like it connects, but can't authenticate or negotiate proper SSL channel.

                                        pfSense likely missing the CA for the server cert.  As is pointed out in that thread you linked to a few posts ago.

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                                        • D
                                          dgcom
                                          last edited by

                                          @NOYB:

                                          pfSense likely missing the CA for the server cert.

                                          I agree. But that needs to be tested/verified :)

                                          DG

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                                          • N
                                            NOYB
                                            last edited by

                                            @dgcom:

                                            @NOYB:

                                            pfSense likely missing the CA for the server cert.

                                            I agree. But that needs to be tested/verified :)

                                            Which is not that difficult to do and the start tls error message being thrown is exactly what happens when the CA is missing.

                                            Error: could not start TLS connection encryption protocol

                                            Going on a week and 2 forum pages for this without looking at the certs is nonsense.

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