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    Emails being blocked sending out

    Firewalling
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    • S
      sdp0024 last edited by

      We have App server trying to connect to google apps SMTP relay but they aren't getting to them and our server admin looked and believes it's the FW not allowing to pass through. Logs show permission error on either suitecrm or owncloud which are the two applications needing to send out emails.

      We have two interfaces (WAN, LAN) and I've attached screenshot of both rules

      Any ideas or help would be greatly appreciated.

      FYI, it all worked when we had hosted on AWS EC2 and just moved to local hosting.
      ![Screen Shot 2015-08-21 at 11.45.26 AM.png](/public/imported_attachments/1/Screen Shot 2015-08-21 at 11.45.26 AM.png)
      ![Screen Shot 2015-08-21 at 11.45.26 AM.png_thumb](/public/imported_attachments/1/Screen Shot 2015-08-21 at 11.45.26 AM.png_thumb)
      ![Screen Shot 2015-08-21 at 11.45.36 AM.png](/public/imported_attachments/1/Screen Shot 2015-08-21 at 11.45.36 AM.png)
      ![Screen Shot 2015-08-21 at 11.45.36 AM.png_thumb](/public/imported_attachments/1/Screen Shot 2015-08-21 at 11.45.36 AM.png_thumb)

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      • Derelict
        Derelict LAYER 8 Netgate last edited by

        outbound connections are governed by rules on LAN, not WAN.  That rule passes everything and so it's not the problem.

        My first guess is your ISP is blocking outbound tcp/25 connections.

        from a host on LAN:

        telnet smtp.gmail.com 25

        what happens?

        telnet smtp.gmail.com 587

        what happens?

        Chattanooga, Tennessee, USA
        The pfSense Book is free of charge!
        DO NOT set a source 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

          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
          • Derelict
            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
            The pfSense Book is free of charge!
            DO NOT set a source 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)

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              • Derelict
                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
                The pfSense Book is free of charge!
                DO NOT set a source 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
                    • Derelict
                      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
                      The pfSense Book is free of charge!
                      DO NOT set a source 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.

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                        • 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
                          • chpalmer
                            chpalmer last edited by

                            Start here-

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

                            Triggering snowflakes one by one..

                            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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