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  3. Outbound SMTP not working on my External Relay

Outbound SMTP not working on my External Relay

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  • S subtlecourage

    @girish Sent it your way!

    S Offline
    S Offline
    subtlecourage
    wrote on last edited by
    #10

    @subtlecourage Let me know what you think of those logs

    girishG 2 Replies Last reply
    0
    • S subtlecourage

      @subtlecourage Let me know what you think of those logs

      girishG Offline
      girishG Offline
      girish
      Staff
      wrote on last edited by
      #11

      @subtlecourage I didn't find the time today, but will take a look tomorrow.

      1 Reply Last reply
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      • S subtlecourage

        @subtlecourage Let me know what you think of those logs

        girishG Offline
        girishG Offline
        girish
        Staff
        wrote on last edited by
        #12

        @subtlecourage So, the connections are failing with "socket timeout waiting on connect" . Can you SSH into your server and check if "telnet smtp.xxx.com 465" works? If it doesn't , then it could either be the VPS provider is blocking it OR that the smtp provider is blocking it. I tried to connect from my server(s) and it connects fine. So, it's probably a VPS thing. Are you on linode by any chance? I recently learnt they block outbound port 465 and 587 by default on new accounts.

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        • S Offline
          S Offline
          subtlecourage
          wrote on last edited by
          #13

          @girish No, I am using hetzner

          I am getting a -bash: telnet: command not found

          Ok, just kidding.

          I installed it.

          I got this

          :~$ telnet smtp.fastmail.com 465
          Trying 66.111.4.140...
          Connected to smtp.fastmail.com.
          Escape character is '^]'.
          Connection closed by foreign host.

          girishG 1 Reply Last reply
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          • S subtlecourage

            @girish No, I am using hetzner

            I am getting a -bash: telnet: command not found

            Ok, just kidding.

            I installed it.

            I got this

            :~$ telnet smtp.fastmail.com 465
            Trying 66.111.4.140...
            Connected to smtp.fastmail.com.
            Escape character is '^]'.
            Connection closed by foreign host.

            girishG Offline
            girishG Offline
            girish
            Staff
            wrote on last edited by
            #14

            @subtlecourage Ah ok, so the smtp connection works well enough. Strange then, did you figure this one out already?

            S 1 Reply Last reply
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            • girishG girish

              @subtlecourage Ah ok, so the smtp connection works well enough. Strange then, did you figure this one out already?

              S Offline
              S Offline
              subtlecourage
              wrote on last edited by
              #15

              @girish said in Outbound SMTP not working on my External Relay:

              @subtlecourage Ah ok, so the smtp connection works well enough. Strange then, did you figure this one out already?

              Sadly, no.
              I keep getting these messages
              [outbound] Ongoing connection failed to 66.111.4.140:465 : socket timeout waiting on connect

              That is to fastmails servers

              Is there any DNS setting that could cause that?

              S 1 Reply Last reply
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              • S subtlecourage

                @girish said in Outbound SMTP not working on my External Relay:

                @subtlecourage Ah ok, so the smtp connection works well enough. Strange then, did you figure this one out already?

                Sadly, no.
                I keep getting these messages
                [outbound] Ongoing connection failed to 66.111.4.140:465 : socket timeout waiting on connect

                That is to fastmails servers

                Is there any DNS setting that could cause that?

                S Offline
                S Offline
                subtlecourage
                wrote on last edited by
                #16

                @subtlecourage

                I cant get any welcome emails to send, nor password reset emails. This is neutering my install.

                girishG 2 Replies Last reply
                0
                • S subtlecourage

                  @subtlecourage

                  I cant get any welcome emails to send, nor password reset emails. This is neutering my install.

                  girishG Offline
                  girishG Offline
                  girish
                  Staff
                  wrote on last edited by
                  #17

                  @subtlecourage Not sure what is going on here. Are you able to contact us on support@cloudron.io, so we can debug on the server?

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                  • S subtlecourage

                    @subtlecourage

                    I cant get any welcome emails to send, nor password reset emails. This is neutering my install.

                    girishG Offline
                    girishG Offline
                    girish
                    Staff
                    wrote on last edited by
                    #18

                    @subtlecourage my bad, I should have noticed. The issue here is that Cloudron's relay system only supports STARTTLS. This means that you have to use port 587 in your relay. Port 465 is pure "TLS" (as opposed to port 587 which is opportunistic TLS). Can you try with port 587? If that doesn't work, let me debug further.

                    S 1 Reply Last reply
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                    • girishG girish

                      @subtlecourage my bad, I should have noticed. The issue here is that Cloudron's relay system only supports STARTTLS. This means that you have to use port 587 in your relay. Port 465 is pure "TLS" (as opposed to port 587 which is opportunistic TLS). Can you try with port 587? If that doesn't work, let me debug further.

                      S Offline
                      S Offline
                      subtlecourage
                      wrote on last edited by
                      #19

                      @girish said in Outbound SMTP not working on my External Relay:

                      @subtlecourage my bad, I should have noticed. The issue here is that Cloudron's relay system only supports STARTTLS. This means that you have to use port 587 in your relay. Port 465 is pure "TLS" (as opposed to port 587 which is opportunistic TLS). Can you try with port 587? If that doesn't work, let me debug further.

                      Hah, that solved it.

                      Thank you.

                      S 1 Reply Last reply
                      1
                      • S subtlecourage

                        @girish said in Outbound SMTP not working on my External Relay:

                        @subtlecourage my bad, I should have noticed. The issue here is that Cloudron's relay system only supports STARTTLS. This means that you have to use port 587 in your relay. Port 465 is pure "TLS" (as opposed to port 587 which is opportunistic TLS). Can you try with port 587? If that doesn't work, let me debug further.

                        Hah, that solved it.

                        Thank you.

                        S Offline
                        S Offline
                        subtlecourage
                        wrote on last edited by subtlecourage
                        #20

                        @girish

                        It is doing something weird though.

                        It says it should be coming from noreplay@domain.com, but instead it is coming from imanalias@domain.com

                        Any ideas?

                        girishG 1 Reply Last reply
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                        • S subtlecourage

                          @girish

                          It is doing something weird though.

                          It says it should be coming from noreplay@domain.com, but instead it is coming from imanalias@domain.com

                          Any ideas?

                          girishG Offline
                          girishG Offline
                          girish
                          Staff
                          wrote on last edited by
                          #21

                          @subtlecourage said in Outbound SMTP not working on my External Relay:

                          It says it should be coming from noreplay@domain.com, but instead it is coming from imanalias@domain.com

                          Can you clarify what you mean by "it says"? Is there some error/warning somewhere? Also, I assume that you have put a custom domain in fastmail and also fastmail is able to relay mail as any email address i.e <anything>@domain.com ?

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