sendmail from a jail - intermittent problems

Tue May 31 01:41:47 UTC 2016

On Mon, May 30, 2016 at 6:32 PM, Kelly Martin <kellymartin at gmail.com> wrote:
>
> I have a web server running in a jail that needs to send mail. The web
> server script is configured properly and I get mail from it
> intermittently... meaning, every once and a while but not reliably at all.
> Here's the kicker: all the sendmail requests show up properly in
> /var/log/maillog but most are just never received. They seem to vanish. I'm
> confused how this could happen. I can reliably send mail from the command
> line inside the jail.
>
> Here is a recent snipped from the log entries trying to send mail from the
> script. I've anonymized the email and domains to protect the innocent:
>
> May 30 16:15:03 webjail sendmail[54383]: u4UMF24X054383: from=www,
> size=1911, class=0, nrcpts=1, msgid=<
> 54bd126df09223d3801a199e5d72f22a at my.securesite.com>, relay=www at localhost
> May 30 16:15:03 webjail sm-mta[54384]: STARTTLS=server, relay=[10.0.0.1],
> version=TLSv1.2, verify=NO, cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 16:15:03 webjail sendmail[54383]: STARTTLS=client,
> relay=[127.0.0.1], version=TLSv1.2, verify=FAIL,
> cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 16:15:03 webjail sm-mta[54384]: u4UMF38c054384: from=<www at webjail>,
> size=2021, class=0, nrcpts=1, msgid=<
> 54bd126df09223d3801a199e5d72f22a at my.securesite.com>, proto=ESMTPS,
> daemon=Daemon0, relay=[10.0.0.1]
> May 30 16:15:03 webjail sendmail[54383]: u4UMF24X054383: to=Noreen Somebody
> <noreensomebody at gmail.com>, ctladdr=www (80/80), delay=00:00:00,
> xdelay=00:00:00, mailer=relay, pri=31911, relay=[127.0.0.1] [127.0.0.1],
> dsn=2.0.0, stat=Sent (u4UMF38c054384 Message accepted for delivery)
> May 30 16:15:03 webjail sendmail[54387]: u4UMF31m054387: from=www,
> size=1128, class=0, nrcpts=1, msgid=<
> 7ecf1131971053c7881ba0295d547c7e at my.securesite.com>, relay=www at localhost
> May 30 16:15:03 webjail sm-mta[54388]: STARTTLS=server, relay=[10.0.0.1],
> version=TLSv1.2, verify=NO, cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 16:15:03 webjail sendmail[54387]: STARTTLS=client,
> relay=[127.0.0.1], version=TLSv1.2, verify=FAIL,
> cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 16:15:03 webjail sm-mta[54386]: STARTTLS=client, relay=
> gmail-smtp-in.l.google.com., version=TLSv1.2, verify=FAIL,
> cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
> May 30 16:15:03 webjail sm-mta[54388]: u4UMF3lu054388: from=<www at webjail>,
> size=1238, class=0, nrcpts=1, msgid=<
> 7ecf1131971053c7881ba0295d547c7e at my.securesite.com>, proto=ESMTPS,
> daemon=Daemon0, relay=[10.0.0.1]
> May 30 16:15:03 webjail sendmail[54387]: u4UMF31m054387: to=Noreen Somebody
> <noreensomebody at gmail.com>, ctladdr=www (80/80), delay=00:00:00,
> xdelay=00:00:00, mailer=relay, pri=31128, relay=[127.0.0.1] [127.0.0.1],
> dsn=2.0.0, stat=Sent (u4UMF3lu054388 Message accepted for delivery)
> May 30 16:15:04 webjail sendmail[54391]: u4UMF3W9054391: from=www,
> size=987, class=0, nrcpts=2, msgid=<
> 9b64a1b5489988ac34a99a92bb95d501 at my.securesite.com>, relay=www at localhost
> May 30 16:15:04 webjail sendmail[54391]: STARTTLS=client,
> relay=[127.0.0.1], version=TLSv1.2, verify=FAIL,
> cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 16:15:04 webjail sm-mta[54392]: STARTTLS=server, relay=[10.0.0.1],
> version=TLSv1.2, verify=NO, cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 16:15:04 webjail sm-mta[54390]: STARTTLS=client, relay=
> gmail-smtp-in.l.google.com., version=TLSv1.2, verify=FAIL,
> cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
> May 30 16:15:04 webjail sm-mta[54386]: u4UMF38c054384: to=<
> noreensomebody at gmail.com>, ctladdr=<www at webjail> (80/80), delay=00:00:01,
> xdelay=00:00:01, mailer=esmtp, pri=32021, relay=gmail-smtp-in.l.google.com.
> [74.125.126.26], dsn=2.0.0, stat=Sent (OK 1464646504 127si27813404itv.11 -
> gsmtp)
> May 30 16:15:04 webjail sm-mta[54392]: u4UMF4Dq054392: from=<www at webjail>,
> size=1070, class=0, nrcpts=2, msgid=<
> 9b64a1b5489988ac34a99a92bb95d501 at my.securesite.com>, proto=ESMTPS,
> daemon=Daemon0, relay=[10.0.0.1]
> May 30 16:15:04 webjail sendmail[54391]: u4UMF3W9054391: to=
> info at securesite.com,"SecureSite Admin" <admin at securesite.com>, ctladdr=www
> (80/80), delay=00:00:01, xdelay=00:00:00, mailer=relay, pri=60987,
> relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (u4UMF4Dq054392 Message
> accepted for delivery)
> May 30 16:15:04 webjail sm-mta[54390]: u4UMF3lu054388: to=<
> noreensomebody at gmail.com>, ctladdr=<www at webjail> (80/80), delay=00:00:01,
> xdelay=00:00:01, mailer=esmtp, pri=31238, relay=gmail-smtp-in.l.google.com.
> [173.194.198.26], dsn=2.0.0, stat=Sent (OK 1464646505 69si3936877ioe.191 -
> gsmtp)
> May 30 16:15:04 webjail sm-mta[54394]: STARTTLS=client, relay=
> aspmx.l.google.com., version=TLSv1.2, verify=FAIL,
> cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
> May 30 16:15:04 webjail sm-mta[54394]: u4UMF4Dq054392: to=<
> admin at securesite.com>,<info at securesite.com>, ctladdr=<www at webjail> (80/80),
> delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=61070, relay=
> aspmx.l.google.com. [74.125.70.27], dsn=2.0.0, stat=Sent (OK 1464646505
> f3si40822457ioa.19 - gsmtp)
>
> From what I can see the mail is going out fine but I never receive it. In
> this case it's To: noreensomebody at gmail.com, who is a customer, and BCC: or
> CC: admin at securesite.com which is my email.
>
> Some details:
> - FreeBSD 10.x with latest patches
> - jail only runs Apache/PHP, sendmail, cron and syslog
> - jail bound to lo1 as 10.0.0.1, no external interfaces
> - Internal Sendmail running as a daemon
> - no sendmail entry in the jail's /etc/rc.conf or /etc/rc.local
> - mail is not being blocked by the firewall on the host
> - host is running on DigitalOcean's public cloud. I don't know if they do
> any outbound mail filtering to hosted customer services (doubtful)
>
> Any thoughts on how to better diagnose this issue? Should I try to use an
> external SMTP server? Ultimately I need to get the built-in Sendmail
> working reliably however.
>
> If I send mail to one of my own email addresses from the command line, I do
> get the email. Here's what that log looks like. Maybe I'm missing something
> obvious in the previous log.
>
> [CODE]May 30 18:12:33 webjail sendmail[54911]: u4V0CWsL054911: from=root,
> size=95, class=0, nrcpts=1, msgid=<201605310012.u4V0CWsL054911 at webjail>,
> relay=root at localhost
> May 30 18:12:33 webjail sendmail[54911]: STARTTLS=client,
> relay=[127.0.0.1], version=TLSv1.2, verify=FAIL,
> cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 18:12:33 webjail sm-mta[54912]: STARTTLS=server, relay=[10.0.0.1],
> version=TLSv1.2, verify=NO, cipher=DHE-RSA-AES256-GCM-SHA384, bits=256/256
> May 30 18:12:33 webjail sm-mta[54912]: u4V0CXLL054912: from=<root at webjail>,
> size=395, class=0, nrcpts=1, msgid=<201605310012.u4V0CWsL054911 at webjail>,
> proto=ESMTPS, daemon=Daemon0, relay=[10.0.0.1]
> May 30 18:12:33 webjail sendmail[54911]: u4V0CWsL054911: to=
> me at mytestsite.com, ctladdr=root (0/0), delay=00:00:01, xdelay=00:00:00,
> mailer=relay, pri=30095, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0,
> stat=Sent (u4V0CXLL054912 Message accepted for delivery)
> May 30 18:12:33 webjail sm-mta[54914]: STARTTLS=client, relay=
> aspmx.l.google.com., version=TLSv1.2, verify=FAIL,
> cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
> May 30 18:12:34 webjail sm-mta[54914]: u4V0CXLL054912: to=<me at mytestsite.com>,
> ctladdr=<root at webjail> (0/0), delay=00:00:01, xdelay=00:00:01,
> mailer=esmtp, pri=30395, relay=aspmx.l.google.com. [74.125.193.26],
> dsn=2.0.0, stat=Sent (OK 1464653554 i78si28053286ita.45 - gsmtp)
>
> Thanks,
> Kelly
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Could be SPF or spam filtering type of issue? Take a look at the
headers on the mail you do receive.  Did you try using telnet /
openssl s_client to send email from the jail?

An SMTP service might be a good idea, there are many which offer
free/gratis accounts for low/small volumes.

-- 
Waitman Gobble
Los Altos California USA
510-830-7975