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    Emails being blocked sending out

    Scheduled Pinned Locked Moved Firewalling
    14 Posts 5 Posters 2.0k Views
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    • S
      sdp0024
      last edited by

      Scotts-MacBook-Pro:~ ScottParks$ telnet smtp.gmail.com 465
      Trying 74.125.20.108…
      Connected to gmail-smtp-msa.l.google.com.
      Escape character is '^]'.

      Scotts-MacBook-Pro:~ ScottParks$ telnet smtp.gmail.com 587
      Trying 74.125.20.109...
      Connected to gmail-smtp-msa.l.google.com.
      Escape character is '^]'.
      220 smtp.gmail.com ESMTP hh3sm8662756pbc.8 - gsmtp

      Scotts-MacBook-Pro:~ ScottParks$ telnet smtp.gmail.com 25
      Trying 74.125.20.108...
      telnet: connect to address 74.125.20.108: Operation timed out
      Trying 74.125.20.109...
      telnet: connect to address 74.125.20.109: Operation timed out
      Trying 2607:f8b0:400e:c01::6c...
      telnet: connect to address 2607:f8b0:400e:c01::6c: No route to host
      telnet: Unable to connect to remote host

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

        ISP's blocking it most likely.  Interesting they pass 465.

        Your best bet is probably tcp/587 + STARTTLS + authentication.

        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
        • S
          sdp0024
          last edited by

          I've tried both 465 and 587 and use IP auth with google apps.

          Google is saying they never get the request from our public IP.

          Is there any proof I can provide to AT&T that they aren't allowing my traffic to pass? Otherwise they are just going to play dumb.

          ![Screen Shot 2015-08-21 at 12.33.27 PM.png](/public/imported_attachments/1/Screen Shot 2015-08-21 at 12.33.27 PM.png)
          ![Screen Shot 2015-08-21 at 12.33.27 PM.png_thumb](/public/imported_attachments/1/Screen Shot 2015-08-21 at 12.33.27 PM.png_thumb)

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

            You have proof?  It's not going to be a secret to them that they block outbound tcp/25.  You might just have to ask for it to be opened.

            This is not a pfSense problem.

            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
              cyberbot
              last edited by

              Had a similar issue before
              My ISP appear to block port 25
              I've used port 587 and it works
              Make sure to nat the port to the app server

              1 Reply Last reply Reply Quote 0
              • S
                sdp0024
                last edited by

                Here's an update. I was able to configure MacBook Outlook to connect to google apps with 465 and was able to send test mail out.

                So theoretically it should be the same and not a pfsense or ISP problem, right???

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

                  Dude -

                  How do the devices you're trying to send mail with send mail?

                  25 Starts Clear - STARTTLS sometimes supported - authentication might be required
                  465 Starts with SSL - authentication might be required
                  587 Starts Clear - STARTTLS sometimes supported - authentication required before email submission

                  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
                  • S
                    sdp0024
                    last edited by

                    SuiteCRM and OwnCloud both worked with current settings using port 465 and google apps IP auth when it was being hosted on EC2 but since we moved it back locally it doesn't work. All settings are the same. Only thing I had to change was of course the auth IP that google apps had to allow from EC2 IP to my WAN IP.

                    1 Reply Last reply Reply Quote 0
                    • D
                      doktornotor Banned
                      last edited by

                      Dude. I already gave you a link to provide some useful testing and debugging info on the other thread. Why don't you just do it?

                      1 Reply Last reply Reply Quote 0
                      • chpalmerC
                        chpalmer
                        last edited by

                        Start here-

                        https://forum.pfsense.org/index.php?topic=70.0

                        Triggering snowflakes one by one..
                        Intel(R) Core(TM) i5-4590T CPU @ 2.00GHz on an M400 WG box.

                        1 Reply Last reply Reply Quote 0
                        • S
                          sdp0024
                          last edited by

                          Scotts-MacBook-Pro:~ ScottParks$ openssl s_client -connect smtp-relay.gmail.com:587 -starttls smtp
                          CONNECTED(00000003)
                          depth=2 /C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
                          verify error:num=20:unable to get local issuer certificate
                          verify return:0
                          –-
                          Certificate chain
                          0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp-relay.gmail.com
                            i:/C=US/O=Google Inc/CN=Google Internet Authority G2
                          1 s:/C=US/O=Google Inc/CN=Google Internet Authority G2
                            i:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
                          2 s:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
                            i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority

                          Server certificate
                          -----BEGIN CERTIFICATE-----
                          MIIEgjCCA2qgAwIBAgIIODBLubr9A2MwDQYJKoZIhvcNAQEFBQAwSTELMAkGA1UE
                          BhMCVVMxEzARBgNVBAoTCkdvb2dsZSBJbmMxJTAjBgNVBAMTHEdvb2dsZSBJbnRl
                          cm5ldCBBdXRob3JpdHkgRzIwHhcNMTUwMjE4MTAyMDU3WhcNMTUxMjMxMDAwMDAw
                          WjBuMQswCQYDVQQGEwJVUzETMBEGA1UECAwKQ2FsaWZvcm5pYTEWMBQGA1UEBwwN
                          TW91bnRhaW4gVmlldzETMBEGA1UECgwKR29vZ2xlIEluYzEdMBsGA1UEAwwUc210
                          cC1yZWxheS5nbWFpbC5jb20wggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIB
                          AQDE+bjFuGH62y341P0icz1L2SKpRS0pt1PvVGtru1g3t35IDUarI36+/duBX6W5
                          CtJmkPOiHfH/mbT/EN/+zI1RD8hzR4sH6wDcLSp42DvodWRfpz9P/1HShpOO84BZ
                          IJBj+um6+lnBq4Rb/JukDE7mGc9T/UeagR+o9b64HqaOHkzO+CWcLnAlqyu6UXq9
                          5clpkd+7uyKkl+wifGzbQI6Hnt+Ssb2DhjTSDHH0f9Ae7RJKWKnQlizsrKI52WSj
                          bfLlvRxf7Zz8aKhX1wQ17ICkJa/aHTswWH4M7uliJhRi5UhNi4CYFh8pfkgp6bAV
                          usH4lHAj/Lpq0mQ6EnNbsoVzAgMBAAGjggFHMIIBQzAdBgNVHSUEFjAUBggrBgEF
                          BQcDAQYIKwYBBQUHAwIwHwYDVR0RBBgwFoIUc210cC1yZWxheS5nbWFpbC5jb20w
                          aAYIKwYBBQUHAQEEXDBaMCsGCCsGAQUFBzAChh9odHRwOi8vcGtpLmdvb2dsZS5j
                          b20vR0lBRzIuY3J0MCsGCCsGAQUFBzABhh9odHRwOi8vY2xpZW50czEuZ29vZ2xl
                          LmNvbS9vY3NwMB0GA1UdDgQWBBRq4wUieE4jUdsQGeM8atDb98lSPDAMBgNVHRMB
                          Af8EAjAAMB8GA1UdIwQYMBaAFErdBhYbvPZotXb1gba7Yhq6WoEvMBcGA1UdIAQQ
                          MA4wDAYKKwYBBAHWeQIFATAwBgNVHR8EKTAnMCWgI6Ahhh9odHRwOi8vcGtpLmdv
                          b2dsZS5jb20vR0lBRzIuY3JsMA0GCSqGSIb3DQEBBQUAA4IBAQATjUExdKa1G4p4
                          MwOnPORkMZTj0N6tU6diUzKeAtHE8K51q5HCmz9d6JIIt2UoJ0E2KXReBX4sKmQQ
                          7R1RhcUhy6Bie25QvDAniWQhTbI7AbTCvqDl0I242wYQ5aIOTeWYcR6RvOsZigLo
                          qHHoTROhumKcMST8+zHNmI4IZbry7Oq4hlqNb6UYPAd32jV59lJPU0xvW/Vlzj9K
                          ttOFYq6jw1DUImeJp7Zfh2s7yMVSSe8XwDcEfbJZA9U10/8S2B8YYwB0cVetjo/Q
                          b6koiKE5gbfE58TLMKKW/YOJ/xqZiu1LMQV67RpI9VzF6UP/dVlEUh+Jw2N/p0nM
                          MvOK1pqd
                          -----END CERTIFICATE-----
                          subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp-relay.gmail.com
                          issuer=/C=US/O=Google Inc/CN=Google Internet Authority G2

                          No client certificate CA names sent

                          SSL handshake has read 3492 bytes and written 479 bytes

                          New, TLSv1/SSLv3, Cipher is RC4-SHA
                          Server public key is 2048 bit
                          Secure Renegotiation IS supported
                          Compression: NONE
                          Expansion: NONE
                          SSL-Session:
                              Protocol  : TLSv1
                              Cipher    : RC4-SHA
                              Session-ID: 21900F806CB079425019879EF325A4CF74D08715C6298AF1EFAD447E5980F4AA
                              Session-ID-ctx:
                              Master-Key: 8AD0BBF7C086A831DB2D4FD80293AC72AAC90A855834C129C51046BF7DDAD9522B6BE2B9CB9C7804A826A0EFBFE84BAA
                              Key-Arg  : None
                              Start Time: 1440296241
                              Timeout  : 300 (sec)
                              Verify return code: 0 (ok)

                          250 SMTPUTF8

                          1 Reply Last reply Reply Quote 0
                          • D
                            doktornotor Banned
                            last edited by

                            Awesome. So, pfSense is completely out of business as far as this goes. It blocks nothing. Please, focus your debugging elsewhere and follow up in the proper forum. (That is, the one for software you are having trouble with. It's not pfSense.)

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