2

My debian server sends email to yahoo, hotmail but not to gmail !

tail /etc/log/mail.log

95.211.117.206], dsn=4.0.0, stat=Deferred: Connection timed out with 75gmail.com.
Nov 23 23:07:52 sitechat sendmail[1837]: tANM7qEk001837: from=www-data, size=1224, class=0, nrcpts=1, msgid=<201511232207.tANM7qEk001837@sitechat.com>, relay=www-data@localhost
Nov 23 23:07:52 sitechat sm-mta[1838]: tANM7q7O001838: from=<www-data@sitechat.com>, size=1476, class=0, nrcpts=1, msgid=<201511232207.tANM7qEk001837@sitechat.com>, proto=ESMTP, daemon=MTA-v4, relay=localhost.localdomain [127.0.0.1]
Nov 23 23:07:52 sitechat sendmail[1837]: tANM7qEk001837: to=hidden@gmail.com, ctladdr=www-data (33/33), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31224, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (tANM7q7O001838 Message accepted for delivery)
Nov 23 23:07:52 sitechat sm-mta[1840]: STARTTLS=client, relay=gmail-smtp-in.l.google.com., version=TLSv1/SSLv3, verify=FAIL, cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
Nov 23 23:07:52 sitechat sm-mta[1840]: tANM7q7O001838: to=<hidden@gmail.com>, ctladdr=<www-data@sitechat.com> (33/33), delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=121476, relay=gmail-smtp-in.l.google.com. [IPv6:2a00:1450:400c:c02::1b], dsn=5.0.0, stat=Service unavailable
Nov 23 23:07:52 sitechat sm-mta[1840]: tANM7q7O001838: tANM7q7O001840: DSN: Service unavailable
Nov 23 23:07:53 sitechat sm-mta[1840]: tANM7q7O001840: to=<www-data@sitechat.com>, delay=00:00:01, xdelay=00:00:01, mailer=local, pri=30000, dsn=2.0.0, stat=Sent

I configured the reverse, change the hostname, made tests with test-mail.com where I receive score 9/10 (a very high one)

What else should I do ?

  • Try pasting your logs again, with the correct (code) button this time. They are unreadable and unrepairable as is. – Michael Hampton Nov 23 '15 at 22:18
  • sorry: corrected – yarek Nov 23 '15 at 22:24
2

At first i thought the remote server was grey listing you (the time out could still be some form of grey listing or the server is just not reachable for you, who knows). But at closer look it appears your server is not able to reach the IPv4 address of the remote server, and then tries the IPv6 address instead:

95.211.117.206], dsn=4.0.0, stat=Deferred: Connection timed out with 75gmail.com.
Nov 23 23:07:52 sitechat sm-mta[1840]: tANM7q7O001838: to=<hidden@gmail.com>, ctladdr=<www-data@sitechat.com> (33/33), delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=121476, relay=gmail-smtp-in.l.google.com. [IPv6:2a00:1450:400c:c02::1b], dsn=5.0.0, stat=Service unavailable

I have noticed that gmail servers tend to refuse emails on their IPv6 addresses if you have not configured a correct reverse DNS for the IPv6 address. I also noticed that this check can be more picky (or maybe broken).

I would suggest to try and fix the rDNS of your IPv6 address and if that doesn't work or already is correct, try to configure your MTA to use gmail's Ipv4 addresses exclusively.

And perhaps this is not the problem and the remote server is just grey listing you on both IPv4 and IPv6 and if your MTA will retry long enough it will eventually succeed.

  • I solved the problem using postfix insread of sendmail and disabling ipv6 – yarek Nov 24 '15 at 13:33

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