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    Email Send Error Research

    Water Closet
    smtp email imap
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    • W
      WrCombs @scottalanmiller
      last edited by

      @scottalanmiller said in Email Send Error Research:

      @wrcombs said in Email Send Error Research:

      SO they're running Postfix as a mail server?

      Yes, which most people do. Postfix powers the vast majority of non-Exchange email. It's the big leader.

      Okay great ..

      @JaredBusch They're running Postfix mail Server on outlook.

      J S 2 Replies Last reply Reply Quote 0
      • J
        JaredBusch @scottalanmiller
        last edited by

        @scottalanmiller said in Email Send Error Research:

        @wrcombs said in Email Send Error Research:

        SO they're running Postfix as a mail server?

        Yes, which most people do. Postfix powers the vast majority of non-Exchange email. It's the big leader.

        No, they are not. Their mail provider is running Postfix.

        Their provider is their ISP.

        1 Reply Last reply Reply Quote 0
        • J
          JaredBusch @WrCombs
          last edited by JaredBusch

          @wrcombs said in Email Send Error Research:

          @scottalanmiller said in Email Send Error Research:

          @wrcombs said in Email Send Error Research:

          SO they're running Postfix as a mail server?

          Yes, which most people do. Postfix powers the vast majority of non-Exchange email. It's the big leader.

          Okay great ..

          @JaredBusch They're running Postfix mail Server on outlook.

          No. They user is running outlook.

          They are connecting to their ISP’s domain email server, likely "free email" with domain purchase bullshit, which is running postfix

          Outlook connects to this type of server with SMTP

          1 Reply Last reply Reply Quote 2
          • J
            JaredBusch @WrCombs
            last edited by

            @wrcombs said in Email Send Error Research:

            Received: from localhost XXX-XX-XXX-XXXX.mobile.uscc.net [XXX.XXX.XXX.XXX]) (using TLSv1.3 with cipher TLS_AES_128_GCM_SHA256 (128/128 bits)) (No client certificate requested) by XXXX.XXXXXX.com (Postfix) with ESMTPSA id 80B013EC2E; Wed, 9 Jun 2021 22:47:05 +0000 (UTC)
            

            Let's break this down. This is the one that concerns you.

            The mail hit the email system from this IP address
            Received: from localhost XXX-XX-XXX-XXXX.mobile.uscc.net [XXX.XXX.XXX.XXX])

            The email was TLS encrypted
            (using TLSv1.3 with cipher TLS_AES_128_GCM_SHA256 (128/128 bits))

            The mail was recevied by this server running postfix.
            by XXXX.XXXXXX.com (Postfix)

            We can assume that this is showing his domain since you redacted it.

            Because it is his domain, this is likely shit "free email" from a cpanel webhost.

            Finally, this tell us that he authenticates to send SMTP to his host.
            with ESMTPSA

            W 1 Reply Last reply Reply Quote 1
            • W
              WrCombs @JaredBusch
              last edited by

              @jaredbusch Good information to know.. Thank you.

              1 Reply Last reply Reply Quote 0
              • S
                scottalanmiller @WrCombs
                last edited by

                @wrcombs said in Email Send Error Research:

                @scottalanmiller said in Email Send Error Research:

                @wrcombs said in Email Send Error Research:

                SO they're running Postfix as a mail server?

                Yes, which most people do. Postfix powers the vast majority of non-Exchange email. It's the big leader.

                Okay great ..

                @JaredBusch They're running Postfix mail Server on outlook.

                Outlook is an email client. It runs on your desktop. It's not a server or anything like that. Nothing runs "on it."

                J 1 Reply Last reply Reply Quote 0
                • J
                  JaredBusch
                  last edited by JaredBusch

                  Now that we know all of that, you can make some assumptions about the connection in Outlook.

                  SMTP can use any port.
                  Port 25 is the original, standard, unauthenticated port. But also blocked on most end user connections.

                  Typcially CPanel hosts use the standardized port 587 for inbound TLS connections.

                  So his Outlook is most likely configured to point to mail.domain.com:587 or simply domain.com:587 to send SMTP.

                  Adding in authentication means it is sent with a username and password. Username is typically the full email address.

                  W 1 Reply Last reply Reply Quote 0
                  • J
                    JaredBusch @scottalanmiller
                    last edited by

                    @scottalanmiller said in Email Send Error Research:

                    @wrcombs said in Email Send Error Research:

                    @scottalanmiller said in Email Send Error Research:

                    @wrcombs said in Email Send Error Research:

                    SO they're running Postfix as a mail server?

                    Yes, which most people do. Postfix powers the vast majority of non-Exchange email. It's the big leader.

                    Okay great ..

                    @JaredBusch They're running Postfix mail Server on outlook.

                    Outlook is an email client. It runs on your desktop. It's not a server or anything like that. Nothing runs "on it."

                    This entire discussion is about Outlook.

                    S 1 Reply Last reply Reply Quote 0
                    • W
                      WrCombs @JaredBusch
                      last edited by

                      @jaredbusch said in Email Send Error Research:

                      Now that we know all of that, you can make some assumptions about the connection in Outlook.

                      SMTP can use any port.
                      Port 25 is the original, standard, unauthenticated port. But also blocked on most end user connections.

                      Typcially CPanel hosts use the standardized port 587 for inbound TLS connections.

                      So his Outlook is most likely configured to point to mail.domain.com:587 or simply domain.com:587 to send SMTP.

                      Adding in authentication means it is sent with a username and password. Username is typically the full email address.

                      So would it likely to assume that Username and password are incorrect ?

                      not going to pretend here, I'm very much lost and confused.

                      J 1 Reply Last reply Reply Quote 0
                      • S
                        scottalanmiller @JaredBusch
                        last edited by

                        @jaredbusch said in Email Send Error Research:

                        @scottalanmiller said in Email Send Error Research:

                        @wrcombs said in Email Send Error Research:

                        @scottalanmiller said in Email Send Error Research:

                        @wrcombs said in Email Send Error Research:

                        SO they're running Postfix as a mail server?

                        Yes, which most people do. Postfix powers the vast majority of non-Exchange email. It's the big leader.

                        Okay great ..

                        @JaredBusch They're running Postfix mail Server on outlook.

                        Outlook is an email client. It runs on your desktop. It's not a server or anything like that. Nothing runs "on it."

                        This entire discussion is about Outlook.

                        I know, about what Outlook is talking to. Postfix (nor any other email server) does not run on Outlook.

                        1 Reply Last reply Reply Quote 1
                        • S
                          scottalanmiller @WrCombs
                          last edited by

                          @wrcombs said in Email Send Error Research:

                          We have a customer who is using a host firewall

                          FYI, it is an assumption that every computer has a host firewall. While some crazy people turn it off, it's not a special case.

                          By default, host firewalls (and regular firewalls) don't block outbound traffic.

                          W 1 Reply Last reply Reply Quote 0
                          • W
                            WrCombs @scottalanmiller
                            last edited by

                            @scottalanmiller said in Email Send Error Research:

                            @wrcombs said in Email Send Error Research:

                            We have a customer who is using a host firewall

                            FYI, it is an assumption that every computer has a host firewall. While some crazy people turn it off, it's not a special case.

                            By default, host firewalls (and regular firewalls) don't block outbound traffic.

                            what I mean by "hosted firewall" is we have our vendor's security team manage the firewall on the network. . .
                            meaning that we do not have access to it other than to the physical box it's self.

                            S 1 Reply Last reply Reply Quote 0
                            • S
                              scottalanmiller @WrCombs
                              last edited by

                              @wrcombs said in Email Send Error Research:

                              I've never touched email outside of being a user.

                              That's all that is likely going on here, user side settings are probably wrong. We don't have enough details to know for sure, but most likely that is all that this is. This isn't an email admin or admin thing at all, we suspect, just an MS Office configuration.

                              You should play with some email systems as an end user to see how they interact. Using Thunderbird and Outlook will give you a lot of exposure. Connect them to a couple different systems like O365 and Gmail and a more basic service to see what end users experience and how all of the configuration is for the end user.

                              Would also be recommended to run your own email server. That'll teach you a lot really quickly.

                              1 Reply Last reply Reply Quote 2
                              • J
                                JaredBusch @WrCombs
                                last edited by

                                @wrcombs said in Email Send Error Research:

                                So would it likely to assume that Username and password are incorrect ?

                                If the computer receives email, then the username and password were likely correct. Outlook's account setup wizard will only ask for the information one time by default.

                                If this system has never been able to send email, what is likely incorrect is the email server configuration details.

                                If it once sent email, then mostlikely Outlook had a connection problem once and popped up the credentials box, then the user put in the wrong info.

                                W DashrenderD 2 Replies Last reply Reply Quote 3
                                • S
                                  scottalanmiller @WrCombs
                                  last edited by

                                  @wrcombs said in Email Send Error Research:

                                  @scottalanmiller said in Email Send Error Research:

                                  @wrcombs said in Email Send Error Research:

                                  We have a customer who is using a host firewall

                                  FYI, it is an assumption that every computer has a host firewall. While some crazy people turn it off, it's not a special case.

                                  By default, host firewalls (and regular firewalls) don't block outbound traffic.

                                  what I mean by "hosted firewall" is we have our vendor's security team manage the firewall on the network. . .
                                  meaning that we do not have access to it other than to the physical box it's self.

                                  Oh, a "host firewall" and a "hosted firewall" are totally different things. However you don't have either in this case, you have a "managed firewall."

                                  A hosted firewall lives elsewhere, at someone else's datacenter. Because that's the "hosted" part of it. Hosted firewalls are pretty useless in general, you have to VPN to them from behind your own firewall and it's just a lot of latency.

                                  Managed firewalls are standard, we manage firewalls for every customer. You can test email like any other connection to see that the firewall is or isn't a problem. Just use your telnet as it is a TCP connection and that will tell you what is going on.

                                  1 Reply Last reply Reply Quote 0
                                  • W
                                    WrCombs @JaredBusch
                                    last edited by

                                    @jaredbusch said in Email Send Error Research:

                                    @wrcombs said in Email Send Error Research:

                                    So would it likely to assume that Username and password are incorrect ?

                                    If the computer receives email, then the username and password were likely correct. Outlook's account setup wizard will only ask for the information one time by default.

                                    Customer claims everything worked up unitl Feb. 18th (just heard this today..) then it stopped working

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

                                      @wrcombs said in Email Send Error Research:

                                      @jaredbusch said in Email Send Error Research:

                                      @wrcombs said in Email Send Error Research:

                                      So would it likely to assume that Username and password are incorrect ?

                                      If the computer receives email, then the username and password were likely correct. Outlook's account setup wizard will only ask for the information one time by default.

                                      Customer claims everything worked up unitl Feb. 18th (just heard this today..) then it stopped working

                                      you mentioned three locations before - is this person using a laptop and traveling between these locations?
                                      You also mentioned that it worked at the other locations just not at this one location - is that still accurate?

                                      W 1 Reply Last reply Reply Quote 1
                                      • W
                                        WrCombs @Dashrender
                                        last edited by

                                        @dashrender said in Email Send Error Research:

                                        @wrcombs said in Email Send Error Research:

                                        @jaredbusch said in Email Send Error Research:

                                        @wrcombs said in Email Send Error Research:

                                        So would it likely to assume that Username and password are incorrect ?

                                        If the computer receives email, then the username and password were likely correct. Outlook's account setup wizard will only ask for the information one time by default.

                                        Customer claims everything worked up unitl Feb. 18th (just heard this today..) then it stopped working

                                        you mentioned three locations before - is this person using a laptop and traveling between these locations?
                                        You also mentioned that it worked at the other locations just not at this one location - is that still accurate?

                                        This is still accurate - yes.
                                        3 locations - all similar hardware setup -
                                        Back office Manager PC, Server, Rack and hosted firewall.

                                        He has 3 different email accounts setup - 1 for each restaurant location .

                                        he travels with a laptop and can't send emails from this 1 location neither on his laptop over Wifi , nor on the Manager PC.

                                        S DashrenderD 2 Replies Last reply Reply Quote 0
                                        • S
                                          scottalanmiller @WrCombs
                                          last edited by

                                          @wrcombs said in Email Send Error Research:

                                          @dashrender said in Email Send Error Research:

                                          @wrcombs said in Email Send Error Research:

                                          @jaredbusch said in Email Send Error Research:

                                          @wrcombs said in Email Send Error Research:

                                          So would it likely to assume that Username and password are incorrect ?

                                          If the computer receives email, then the username and password were likely correct. Outlook's account setup wizard will only ask for the information one time by default.

                                          Customer claims everything worked up unitl Feb. 18th (just heard this today..) then it stopped working

                                          you mentioned three locations before - is this person using a laptop and traveling between these locations?
                                          You also mentioned that it worked at the other locations just not at this one location - is that still accurate?

                                          This is still accurate - yes.
                                          3 locations - all similar hardware setup -
                                          Back office Manager PC, Server, Rack and hosted firewall.

                                          He has 3 different email accounts setup - 1 for each restaurant location .

                                          he travels with a laptop and can't send emails from this 1 location neither on his laptop over Wifi , nor on the Manager PC.

                                          Ah, if it is location based, that certainly sounds like the firewall managers have gotten heavy handed and decided that email apps like Outlook are going to be blocked at a network level.

                                          W 1 Reply Last reply Reply Quote 0
                                          • W
                                            WrCombs @scottalanmiller
                                            last edited by

                                            @scottalanmiller said in Email Send Error Research:

                                            @wrcombs said in Email Send Error Research:

                                            @dashrender said in Email Send Error Research:

                                            @wrcombs said in Email Send Error Research:

                                            @jaredbusch said in Email Send Error Research:

                                            @wrcombs said in Email Send Error Research:

                                            So would it likely to assume that Username and password are incorrect ?

                                            If the computer receives email, then the username and password were likely correct. Outlook's account setup wizard will only ask for the information one time by default.

                                            Customer claims everything worked up unitl Feb. 18th (just heard this today..) then it stopped working

                                            you mentioned three locations before - is this person using a laptop and traveling between these locations?
                                            You also mentioned that it worked at the other locations just not at this one location - is that still accurate?

                                            This is still accurate - yes.
                                            3 locations - all similar hardware setup -
                                            Back office Manager PC, Server, Rack and hosted firewall.

                                            He has 3 different email accounts setup - 1 for each restaurant location .

                                            he travels with a laptop and can't send emails from this 1 location neither on his laptop over Wifi , nor on the Manager PC.

                                            Ah, if it is location based, that certainly sounds like the firewall managers have gotten heavy handed and decided that email apps like Outlook are going to be blocked at a network level.

                                            Was on the phone with the firewall admin team yesterday, and they showed that emails were leaving the site through the firewall ....

                                            S 1 Reply Last reply Reply Quote 0
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