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  3. Gmail has detected that this message does not meet IPv6 sending guidelines regarding PTR records and authentication

Gmail has detected that this message does not meet IPv6 sending guidelines regarding PTR records and authentication

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  • andreasduerenA Offline
    andreasduerenA Offline
    andreasdueren
    wrote on last edited by joseph
    #1

    I got a problem sending emails to gmail. Apparently Cloudron tries to send them via IPv6, even though I have disabled it in the network settings. But even then, I manually set it up but it still doesn't work. Does anyone else have a similar problem?

    Failure Reason: Error: 550 5.7.1 [my IPv6] Gmail has detected that this message does not meet IPv6 sending guidelines regarding PTR records and authentication . For more information, go to  https://support.google.com/mail/?p=IPv6AuthError 2adb3069b0e04-5422382618esi2729121e87.370 - gsmtp
    

    The cloudron checks in the E-Mail section are not throwing any errors and neither are external tools. I am not able to recreate this issue on a secondary cloudron instance.

    1 Reply Last reply
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    • andreasduerenA Offline
      andreasduerenA Offline
      andreasdueren
      wrote on last edited by
      #2

      @nebulon unfortunately this came up again. IPv6 is disabled in the GUI and I had run sysctl -w net.ipv6.conf.all.disable_ipv6=1 but now the server is sending mail via my IPv6 address again, resulting in declines. Google tells me in the error that the PTR record isn't set

      "message": "Upstream error: 421 4.7.23 [my IPv6] The IP address sending this message does not 4.7.23 have a PTR record, or the corresponding forward DNS entry does not 4.7.23 match the sending IP. To protect our users from spam, mail has been 4.7.23 temporarily rate limited. To learn more about IP address requirement 4.7.23 s for sending to Gmail, visit  4.7.23  https://support.google.com/a?p=sender-guidelines-ip  4.7.23 To learn more about Gmail requirements for bulk senders, visit 4.7.23  https://support.google.com/a?p=sender-guidelines. 4fb4d7f45d1cf-5dc723cedd9si4923716a12.77 - gsmtp",
      

      But that doesn't seem to be the issue. Unspam tells me that the email is not signed with a valid DKIM signature, which probably makes more sense.

      andreasduerenA 1 Reply Last reply
      0
      • andreasduerenA andreasdueren

        @nebulon unfortunately this came up again. IPv6 is disabled in the GUI and I had run sysctl -w net.ipv6.conf.all.disable_ipv6=1 but now the server is sending mail via my IPv6 address again, resulting in declines. Google tells me in the error that the PTR record isn't set

        "message": "Upstream error: 421 4.7.23 [my IPv6] The IP address sending this message does not 4.7.23 have a PTR record, or the corresponding forward DNS entry does not 4.7.23 match the sending IP. To protect our users from spam, mail has been 4.7.23 temporarily rate limited. To learn more about IP address requirement 4.7.23 s for sending to Gmail, visit  4.7.23  https://support.google.com/a?p=sender-guidelines-ip  4.7.23 To learn more about Gmail requirements for bulk senders, visit 4.7.23  https://support.google.com/a?p=sender-guidelines. 4fb4d7f45d1cf-5dc723cedd9si4923716a12.77 - gsmtp",
        

        But that doesn't seem to be the issue. Unspam tells me that the email is not signed with a valid DKIM signature, which probably makes more sense.

        andreasduerenA Offline
        andreasduerenA Offline
        andreasdueren
        wrote on last edited by
        #3

        @andreasdueren Seems to work again now. I had to enable IPv6 (I think rebooting enables this anyways?) reboot the server, redo DNS and mail server location.

        jdaviescoatesJ 1 Reply Last reply
        1
        • andreasduerenA andreasdueren

          @andreasdueren Seems to work again now. I had to enable IPv6 (I think rebooting enables this anyways?) reboot the server, redo DNS and mail server location.

          jdaviescoatesJ Online
          jdaviescoatesJ Online
          jdaviescoates
          wrote on last edited by
          #4

          @andreasdueren be sure to set your IPv6 PTR too if you've not already done so

          I use Cloudron with Gandi & Hetzner

          andreasduerenA 1 Reply Last reply
          1
          • J joseph has marked this topic as solved on
          • jdaviescoatesJ jdaviescoates

            @andreasdueren be sure to set your IPv6 PTR too if you've not already done so

            andreasduerenA Offline
            andreasduerenA Offline
            andreasdueren
            wrote on last edited by
            #5

            @jdaviescoates Yes I had done that a while ago

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