sendmail from a jail - intermittent problems

Tue May 31 01:32:23 UTC 2016

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