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I am trying to send automated emails from my server to my gmail account, so that I can get important notices like when my webserver is not responding, or just some daily statistics.

As email sending program I am using exim4 on my debian6 server. Whenever an email is beeing sent I get the following error log in /var/log/exim4/mainlog:

    2016-04-24 12:48:34 1auHac-0000Mr-G3 ** [email protected] R=dnslookup T=remote_smtp X=TLS1.2:ECDHE_RSA_AES_128_GCM_SHA256:128 DN="C=US,ST=California,L=Mountain View,O=Google Inc,CN=mx.google.com": SMTP error from remote mail server after end of data: host gmail-smtp-in.l.google.com [2a00:1450:400c:c09::1b]: 550-5.7.1 [2a02:c200:1:10:2:6:6291:1] Our system has detected that this message\n550-5.7.1 does not meet IPv6 sending guidelines regarding PTR records and\n550-5.7.1 authentication. Please review\n550-5.7.1  https://support.google.com/mail/?p=ipv6_authentication_error for more\n550 5.7.1 information. sw5si18679304wjc.113 - gsmtp

With the important part beeing

 Our system has detected that this message\n550-5.7.1 does not meet IPv6 sending guidelines regarding PTR records and\n550-5.7.1 authentication.

I reviewed this guidelines and tried to set everything up as required, but something seems to be sill not correct.

What I tried:

First I set up a PTR entry for the IPv6 address on the control panel of my hosting provider:

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Since this didn't change anything I tried to force exim to use Ipv4 instead hoping to solve the issue.

In my update-exim4.conf.conf I added my Ip4 address to the dc_smarthost entry and set dc_local_interfaces to dc_local_interfaces='127.0.0.1'

This configuration change didn't help either, and since I don't really know what I am doing I decided to ask this question for further help.

1 Answer 1

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As you are trying to send the messages to yourself, configure Exim to authenticate with your gmail credentials when sending the messages. This should work for low volumes that are not being forwarded.

Add your credentials to /etc/exim/passwd.client. You should secure this file so that Exim can read it but not general users. I would not recommend this for high volumes of email or for email forwarding to other users.

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