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  3. SMTP timeout after updating to 8.3.1

SMTP timeout after updating to 8.3.1

Scheduled Pinned Locked Moved Solved Support
emailsmtprelayipv6
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  • robiR Offline
    robiR Offline
    robi
    wrote on last edited by
    #4

    Check the other threads on the forum about ipv6 issues, it's best to disable it on the entire OS until a solution is found.

    Conscious tech

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    • J Offline
      J Offline
      joseph
      Staff
      wrote on last edited by
      #5

      @rupertsworld can you try curl -6 https://ipv6.api.cloudron.io/api/v1/helper/public_ip on the server ? Looks like that fails. Next step is to see if host ipv6.api.cloudron.io works or not.

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      • R Offline
        R Offline
        rupertsworld
        wrote on last edited by rupertsworld
        #6

        For the first command (curl):

        curl: (7) Failed to connect to ipv6.api.cloudron.io port 443 after 1055 ms: Couldn't connect to server

        For the second command (host):

        ipv6.api.cloudron.io has IPv6 address 2604:a880:800:10::b66:f001

        @joseph

        J 1 Reply Last reply
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        • R rupertsworld

          For the first command (curl):

          curl: (7) Failed to connect to ipv6.api.cloudron.io port 443 after 1055 ms: Couldn't connect to server

          For the second command (host):

          ipv6.api.cloudron.io has IPv6 address 2604:a880:800:10::b66:f001

          @joseph

          J Offline
          J Offline
          joseph
          Staff
          wrote on last edited by
          #7

          @rupertsworld so DNS resolution is working. You can try ping6 2604:a880:800:10::b66:f001 . It looks like there is some IPv6 networking issue in your server. Maybe you can disable IPv6 altogether and also in Cloudron Network -> IPv6 disable it (then Sync DNS as well to remove the AAAA DNS entries).

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          • R Offline
            R Offline
            rupertsworld
            wrote on last edited by
            #8

            I disabled IPv6 & synced everything, but still cannot connect to an SMTP server (having major problems sending people calendar invites at the moment)

            J 1 Reply Last reply
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            • R rupertsworld

              I disabled IPv6 & synced everything, but still cannot connect to an SMTP server (having major problems sending people calendar invites at the moment)

              J Offline
              J Offline
              joseph
              Staff
              wrote on last edited by
              #9

              @rupertsworld you have to disable IPv6 on the server (and not just in Cloudron UI). The Cloudron UI only does not set up AAAA records, does not remove IPv6 on the server as such .

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              • R Offline
                R Offline
                rupertsworld
                wrote on last edited by
                #10

                OK so I need to go through some steps to disable IPv6 on the command line of my Droplet.

                But I'm confused – I only enabled IPv6 in response to the first comment here, which I interpreted as suggesting I enable it. So, is IPv6 responsible for the SMTP server connection failures?

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                • R Offline
                  R Offline
                  rupertsworld
                  wrote on last edited by
                  #11

                  I've disabled IPv6 on the server and am still getting connection timeout issues for any SMTP server.

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                  • R Offline
                    R Offline
                    rupertsworld
                    wrote on last edited by
                    #12

                    I've now also tried with Mailgun following their setup instructions and get the same timeout error

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                    • R Offline
                      R Offline
                      rupertsworld
                      wrote on last edited by
                      #13

                      There are also some AAAA records I cannot delete

                      Screenshot 2025-04-01 at 10.40.01 AM.png

                      J 1 Reply Last reply
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                      • nebulonN Offline
                        nebulonN Offline
                        nebulon
                        Staff
                        wrote on last edited by
                        #14

                        The initial error was the outbound ipv6 connection which failed, so you have to disable ipv6 on the server itself. This has little to do with the AAAA record, as that would be for incomming connections!
                        You may have to contact your server provider on how to disable ipv6 (network wise) on the server. Just to get ipv6 issues out of the way first. Ipv4 is totally sufficient anyways for the moment, so best to get those potential issues out of the way.

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                        • R rupertsworld

                          There are also some AAAA records I cannot delete

                          Screenshot 2025-04-01 at 10.40.01 AM.png

                          J Offline
                          J Offline
                          joseph
                          Staff
                          wrote on last edited by
                          #15

                          @rupertsworld where is this screenshot from?

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                          • R Offline
                            R Offline
                            rupertsworld
                            wrote on last edited by
                            #16

                            Apologies for the lack of context – this is through the Digital Ocean app integration with Cloudron

                            J 1 Reply Last reply
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                            • R rupertsworld

                              Apologies for the lack of context – this is through the Digital Ocean app integration with Cloudron

                              J Offline
                              J Offline
                              joseph
                              Staff
                              wrote on last edited by
                              #17

                              @rupertsworld Interesting... Cloudron only has a marketplace image on Digital Ocean . AFAIK, we don't have any app integration . It could be that DO implemented some features on their side without our knowledge .

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                              • J Offline
                                J Offline
                                joseph
                                Staff
                                wrote on last edited by
                                #18

                                This is/was an issue with DO blocking outbound 587.

                                See also https://docs.digitalocean.com/support/why-is-smtp-blocked/ . Bit ironic they want to use all these sketchy SaaS email providers. They keep changing ownership to various marketing companies. I thought DO being an infra company will know better..

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                                • R Offline
                                  R Offline
                                  rupertsworld
                                  wrote on last edited by
                                  #19

                                  Yeah can confirm, and thanks for the help diagnosing. I wasn't given any advanced notice of the SMTP block, it was hidden in release notes somewhere. This is now unblocked.

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