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I have a form on a webpage that sends an email using sendmail on the same server. The recipient is a client that uses Google Apps for their email. In the form, I enter my email address. If I enter *@aol.com or *@yahoo.com (where "*" is anything, not a literal asterisk, of course), the email fails to send with the following dump in /var/log/mail.log:

Sep 22 14:01:12 localhost sendmail[16522]: t8ME1CSU016522: Authentication-Warning: localhost.local: www-data set sender to [email protected] using -f
Sep 22 14:01:12 localhost sendmail[16522]: t8ME1CSU016522: [email protected], size=1099, class=0, nrcpts=1, msgid=<[email protected]>, relay=www-data@localhost
Sep 22 14:01:12 localhost sm-mta[16523]: t8ME1CIi016523: from=<[email protected]>, size=1418, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA-v4, relay=localhost.local [127.0.0.1]
Sep 22 14:01:12 localhost sendmail[16522]: t8ME1CSU016522: [email protected], [email protected] (33/33), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31099, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (t8ME1CIi016523 Message accepted for delivery)
Sep 22 14:01:12 localhost sendmail[16527]: t8ME1CjK016527: Authentication-Warning: localhost.local: www-data set sender to [email protected] using -f
Sep 22 14:01:12 localhost sendmail[16527]: t8ME1CjK016527: [email protected], size=1224, class=0, nrcpts=1, msgid=<[email protected]>, relay=www-data@localhost
Sep 22 14:01:12 localhost sm-mta[16528]: t8ME1CK4016528: from=<[email protected]>, size=1543, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA-v4, relay=localhost.local [127.0.0.1]
Sep 22 14:01:12 localhost sendmail[16527]: t8ME1CjK016527: [email protected], [email protected] (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 (t8ME1CK4016528 Message accepted for delivery)
Sep 22 14:01:13 localhost sm-mta[16530]: STARTTLS=client, relay=aspmx.l.google.com., version=TLSv1/SSLv3, verify=FAIL, cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
Sep 22 14:01:13 localhost sm-mta[16525]: STARTTLS=client, relay=aspmx.l.google.com., version=TLSv1/SSLv3, verify=FAIL, cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
Sep 22 14:01:13 localhost sm-mta[16530]: t8ME1CK4016528: to=<[email protected]>, delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=121543, relay=aspmx.l.google.com. [173.194.205.27], dsn=5.0.0, stat=Service unavailable
Sep 22 14:01:13 localhost sm-mta[16530]: t8ME1CK4016528: t8ME1DK4016530: DSN: Service unavailable
Sep 22 14:01:13 localhost sm-mta[16530]: t8ME1DK4016530: to=<[email protected]>, delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=30000, relay=aspmx.l.google.com. [173.194.205.27], dsn=5.1.1, stat=User unknown
Sep 22 14:01:13 localhost sm-mta[16530]: t8ME1DK4016530: t8ME1DK5016530: return to sender: User unknown
Sep 22 14:01:13 localhost sm-mta[16530]: t8ME1DK5016530: to=root, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=30000, dsn=2.0.0, stat=Sent
Sep 22 14:01:13 localhost sm-mta[16525]: t8ME1CIi016523: to=<[email protected]>, delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=121418, relay=aspmx.l.google.com. [173.194.205.27], dsn=5.0.0, stat=Service unavailable
Sep 22 14:01:13 localhost sm-mta[16525]: t8ME1CIi016523: t8ME1DIi016525: DSN: Service unavailable
Sep 22 14:01:13 localhost sm-mta[16525]: t8ME1DIi016525: to=<[email protected]>, delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=30000, relay=aspmx.l.google.com. [173.194.205.27], dsn=5.1.1, stat=User unknown
Sep 22 14:01:13 localhost sm-mta[16525]: t8ME1DIi016525: t8ME1DIj016525: return to sender: User unknown
Sep 22 14:01:13 localhost sm-mta[16525]: t8ME1DIj016525: to=root, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=30000, dsn=2.0.0, stat=Sent

Every other email address that I've tried seems to work fine and the logs indicate success. Both seem to connect to the relay, but the failures fall apart right after that.

I can see that a service is unavailable, but I'm not entirely sure which one nor am I sure why it's only unavailable when I enter those addresses - especially when the sender is being forced to a no_reply email address. Why would the value I enter on the form matter at all? I'm clearly missing something.

I'm not a sysadmin and I'm certainly not well-versed in email troubleshooting so I'm hoping someone can give me a hand understanding what I'm looking at here. What could be causing these failures?

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  • What makes you think the destination address(es) exist? [email protected] also gives me a bounce, from google, as does [email protected].
    – MadHatter
    Sep 22, 2015 at 17:15
  • Sorry, myclient.com is a placeholder. I didn't want to publish the actual client address. I know it works because email arrives when sent in non-yahoo, non-aol cases. Sep 22, 2015 at 17:45
  • I very strongly advise you to read the meta post on whether and how to obfuscate information - and tell us everything about the problem, not just what you think we should need.
    – MadHatter
    Sep 22, 2015 at 17:48
  • Fair enough and point taken. In this case, I'm just looking for help understanding what these logs are telling me. I know the end result: the email send recorded here fails. I don't know how to read these logs well enough to understand why or where to look next. Sep 22, 2015 at 17:54
  • I also know that the same email does send if I enter non-aol, non-yahoo info on the form. Sep 22, 2015 at 17:55

2 Answers 2

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Sendmail: send a test message with full SMTP transcript

You can make sendmail send a test message with full transcript of the SMTP session.
Usually it provides more clues why delivery fails.

Execute the following script as root after changing SENDER and RECIPIENT.

#!/bin/sh
[email protected]
ENVELOPE_SENDER=$SENDER
[email protected]

/usr/sbin/sendmail -i -v -f$ENVELOPE_SENDER -- $RECIPIENT <<END
from: $SENDER
to: $RECIPIENT
subject: delivery test

Delivery test -- ignore it.
END
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Signup for feedback loops and find out from aol and yahoo, also make sure you are complaint.

make sure you respect NDR's (which I see a few), you might also want to use a smarthost like sendgrid to help you out.

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  • I'm waiting on confirmation, but I was told that the app in question did send the email with a from address entered on the form. That would lead me to believe that DMARC is the problem. The messages weren't originating from the yahoo/aol servers. Sep 22, 2015 at 21:32
  • Send an email to your gmail account and post the headers from 'view original' that may help too Sep 22, 2015 at 23:18

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