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    cannot send email from Postfix to gmail

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    • IT-ADMINI
      IT-ADMIN
      last edited by

      hello everybody

      i have freePBX installed and i want it to send me notification (voicemails), after some researches i learned that i have to change this file in CentOS : /etc/postfix/main.cf, and because i don't have a SMTP server locally i decided to use gmail SMTP server like this howto : https://charlesauer.net/tutorials/centos/postfix-as-gmail-relay-centos.php
      but when i try to send an email for testing by using this command : mail [email protected], after i check my mailBox i receive an email telling that : Sign-in attempt prevented, and it is a one time email, i meant i receive it only one time no matter how much try i did.

      the log show :

      Aug 20 15:59:19 localhost postfix/pickup[12173]: 46732812CC: uid=0 from=<root>
      Aug 20 15:59:19 localhost postfix/cleanup[13616]: 46732812CC: message-id=[email protected]
      Aug 20 15:59:19 localhost postfix/qmgr[1537]: 46732812CC: from=[email protected], size=424, nrcpt=1 (queue active)
      Aug 20 15:59:20 localhost postfix/smtp[13618]: connect to smtp.gmail.com[2a00:1450:400c:c07::6c]:587: Network is unreachable
      Aug 20 15:59:21 localhost postfix/smtp[13618]: 46732812CC: SASL authentication failed; server smtp.gmail.com[64.233.166.109] said: 534-5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbvWI?534-5.7.14 zj2YGfQmgucVnJ9HrAFC6WCVSVHuyHESaYNUzIvrIqjfpm6SIzzvi4DLXnnxRd6KBOTIJj?534-5.7.14 kVTPzfD4joq3D9Q2v9KMxWGG4My_L8IVth64qZ-efP_oYhiX5wHubqUGfW0Od?534-5.7.14 1kRNMOkJvETTEHiGp8VBBhsxdhK_KIJL4slkDbDW3GQnIzn5TbZiqwEAiqQM71ZIK5WFJ2?534-5.7.14 Q2qVlbe07cy23exyVrRGy7IPWc68> Please log in via your web browser and?534-5.7.14 then try again.?534-5.7.14 Learn more at?534 5.7.14 https://support.google.com/mail/answer/78754 pg5sm5483950wjb.21 - gsmtp
      Aug 20 15:59:22 localhost postfix/smtp[13618]: 46732812CC: to=[email protected], relay=smtp.gmail.com[64.233.166.108]:587, delay=3.7, delays=0.07/0.11/3.5/0, dsn=4.7.14, status=deferred (SASL authentication failed; server smtp.gmail.com[64.233.166.108] said: 534-5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbsdq?534-5.7.14 TDH6yoR9TG_mfOM1lKfZ2GjiTY-zT9bJNPIl_w17A1MikQyOHl3VtUQQYJeXdnZ?534-5.7.14 xEy0na_j8xpck2pWl1Fg0vvsxzFhD8EKjzrhthen9owvZkBvmjOq1S2A_7z8a5uZXI7OHK?534-5.7.14 0BY662sxzm65-9UDBTIcg4jlZFvKYpxkadVDFFzTsqqAP_G_mQyHWVBM6HIMVqu0lUQDG4?534-5.7.14 kMCuF6Bu6LhODY28beu--zXhFNo0> Please log in via your web browser and?534-5.7.14 then try again.?534-5.7.14 Learn more at?534 5.7.14 https://support.google.com/mail/answer/78754 ho10sm5457453wjb.39 - gsmtp)

      1 Reply Last reply Reply Quote 1
      • IT-ADMINI
        IT-ADMIN
        last edited by

        the one time message i get in my inbox is :

        Untitled.png

        1 Reply Last reply Reply Quote 0
        • IT-ADMINI
          IT-ADMIN
          last edited by

          i want to highlight one important thing is the warning message i get is in my gmail account that exist in /etc/postfix/sasl_passwd not the recipient email """mail [email protected]"""

          1 Reply Last reply Reply Quote 0
          • scottalanmillerS
            scottalanmiller
            last edited by

            I believe that there is a setting that you have to change in Gmail to lower the security settings.

            1 Reply Last reply Reply Quote 0
            • IT-ADMINI
              IT-ADMIN
              last edited by

              do you know where is that setting in my gmail account??

              1 Reply Last reply Reply Quote 0
              • DashrenderD
                Dashrender
                last edited by

                Other than preventing SPAM, I've never understood why devices like this don't have their own SMTP mail server (actually I think they do, but don't seem to work as one might expect).

                For example - why can't my Copy machine just send an email to any email server on the planet? Why does it need to forward the email to my email server, then my server forwards to whomever?

                Did I answer my own question in the first sentence, because of SPAM?

                scottalanmillerS 2 Replies Last reply Reply Quote 0
                • scottalanmillerS
                  scottalanmiller @Dashrender
                  last edited by

                  @Dashrender said:

                  Did I answer my own question in the first sentence, because of SPAM?

                  Yup. All of those devices can send. Nearly nothing accepts it.

                  This goes back to our discussions about why trying to host your own email server is problematic. Didn't you state that you didn't have these problems?

                  DashrenderD 1 Reply Last reply Reply Quote 0
                  • scottalanmillerS
                    scottalanmiller
                    last edited by

                    I have devices like this send to us through whitelisting. If you don't whitelist it, any commercial SPAM filter will normally catch it.

                    DashrenderD 1 Reply Last reply Reply Quote 0
                    • DashrenderD
                      Dashrender @scottalanmiller
                      last edited by

                      @scottalanmiller said:

                      Didn't you state that you didn't have these problems?

                      I don't have these problems because I host my own email. Of course assuming I move to O365, then I will begin to have these problems.

                      scottalanmillerS 2 Replies Last reply Reply Quote 0
                      • scottalanmillerS
                        scottalanmiller @Dashrender
                        last edited by

                        @Dashrender said:

                        I don't have these problems because I host my own email. Of course assuming I move to O365, then I will begin to have these problems.

                        But you just said that you can't send out from these devices, which are each hosting your own email. You wanted to send to other people and couldn't, I thought.

                        1 Reply Last reply Reply Quote 0
                        • DashrenderD
                          Dashrender @scottalanmiller
                          last edited by

                          @scottalanmiller said:

                          I have devices like this send to us through whitelisting. If you don't whitelist it, any commercial SPAM filter will normally catch it.

                          I too whitelist my internal devices for receiving/forwarding SMTP mail from these types of devices.

                          1 Reply Last reply Reply Quote 0
                          • scottalanmillerS
                            scottalanmiller @Dashrender
                            last edited by

                            @Dashrender said:

                            For example - why can't my Copy machine just send an email to any email server on the planet?

                            This line. in one breath you are asking why you can't. In the next you are saying that you can.

                            1 Reply Last reply Reply Quote 0
                            • scottalanmillerS
                              scottalanmiller
                              last edited by

                              When I host my own Postfix servers I can put in a lot of effort and get them to sometimes get mail accepted if I give each their own IP address, but it is not super reliable. Or I can send through our existing email infrastructure. But running each as its own is very problematic for reliable third party delivery.

                              1 Reply Last reply Reply Quote 0
                              • scottalanmillerS
                                scottalanmiller @Dashrender
                                last edited by

                                @Dashrender said:

                                Of course assuming I move to O365, then I will begin to have these problems.

                                Why would you assume that?

                                DashrenderD 1 Reply Last reply Reply Quote 0
                                • IT-ADMINI
                                  IT-ADMIN
                                  last edited by

                                  anyone know how to solve this problem ??

                                  1 Reply Last reply Reply Quote 0
                                  • IT-ADMINI
                                    IT-ADMIN
                                    last edited by

                                    how can i inform my gmail account to allow postfix to use it as a relay ??

                                    1 Reply Last reply Reply Quote 0
                                    • scottalanmillerS
                                      scottalanmiller
                                      last edited by

                                      Does this line tell us anything...

                                      Aug 20 15:59:20 localhost postfix/smtp[13618]: connect to smtp.gmail.com[2a00:1450:400c:c07::6c]:587: Network is unreachable

                                      Maybe there is a network error here? Test that port with telnet.

                                      IT-ADMINI 1 Reply Last reply Reply Quote 0
                                      • DashrenderD
                                        Dashrender @scottalanmiller
                                        last edited by

                                        @scottalanmiller said:

                                        @Dashrender said:

                                        Of course assuming I move to O365, then I will begin to have these problems.

                                        Why would you assume that?

                                        Because of posts like this. Of course we could get lucky and things like this might be working better.

                                        scottalanmillerS 1 Reply Last reply Reply Quote 0
                                        • scottalanmillerS
                                          scottalanmiller @Dashrender
                                          last edited by

                                          @Dashrender said:

                                          Because of posts like this. Of course we could get lucky and things like this might be working better.

                                          But this is about GMail. Did someone talk about Office 365, which is unrelated to Gmail.

                                          DashrenderD 1 Reply Last reply Reply Quote 0
                                          • IT-ADMINI
                                            IT-ADMIN @scottalanmiller
                                            last edited by

                                            @scottalanmiller said:

                                            Does this line tell us anything...

                                            Aug 20 15:59:20 localhost postfix/smtp[13618]: connect to smtp.gmail.com[2a00:1450:400c:c07::6c]:587: Network is unreachable

                                            Maybe there is a network error here? Test that port with telnet.

                                            can you explain what do you mean please

                                            scottalanmillerS 1 Reply Last reply Reply Quote 0
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