1

I recently did a task for my development team's website (ironfi.st), in which I set us up an SMTP mail server on an apache2 web server. I used sendmail to complete the task along with a WordPress SMTP plugin called WP-MAIL-SMTP to allow for functionality of a contact page on our website. However, the current issue I am facing is that no mail will send out from the server.

One of the reasons I chose sendmail is due to it's simple setup steps. So I'm having trouble pinpointing what I might have done incorrectly. I connected to the server via Ubuntu and installed sendmail onto it. After which I ran the configuration setup and then went to edit the hosts file in /etc/hosts.

Below is a copy of what I put into the hosts file: 127.0.1.1 ironfi.st ironfi.st 127.0.0.1 localhost localhost.localdomain ironfi.st

Upon doing this I went and tested the SMTP server using the "send test email" feature that comes with the WP plugin I'm using. As stated previously, the email did not send. I began reading through the logs that the plugin spat out. However, this area is not necessarily my skilled area, so I may have missed something in the logs, which is why I'm attaching both the logs I took directly from the latest SMTP server log file mail.log from /var/log and the log files from the plugin below:

Logs from the plugin:

Test Message Sent

The result was:

bool(false)

The full debugging output is shown below:

object(PHPMailer)#445 (75) {
  ["Version"]=>
  string(6) "5.2.14"
  ["Priority"]=>
  NULL
  ["CharSet"]=>
  string(10) "iso-8859-1"
  ["ContentType"]=>
  string(10) "text/plain"
  ["Encoding"]=>
  string(4) "8bit"
  ["ErrorInfo"]=>
  string(0) ""
  ["From"]=>
  string(14) "root@localhost"
  ["FromName"]=>
  string(9) "Root User"
  ["Sender"]=>
  string(0) ""
  ["ReturnPath"]=>
  string(0) ""
  ["Subject"]=>
  string(0) ""
  ["Body"]=>
  string(0) ""
  ["AltBody"]=>
  string(0) ""
  ["Ical"]=>
  string(0) ""
  ["MIMEBody":protected]=>
  string(0) ""
  ["MIMEHeader":protected]=>
  string(0) ""
  ["mailHeader":protected]=>
  string(0) ""
  ["WordWrap"]=>
  int(0)
  ["Mailer"]=>
  string(4) "mail"
  ["Sendmail"]=>
  string(18) "/usr/sbin/sendmail"
  ["UseSendmailOptions"]=>
  bool(true)
  ["PluginDir"]=>
  string(0) ""
  ["ConfirmReadingTo"]=>
  string(0) ""
  ["Hostname"]=>
  string(0) ""
  ["MessageID"]=>
  string(0) ""
  ["MessageDate"]=>
  string(0) ""
  ["Host"]=>
  string(9) "localhost"
  ["Port"]=>
  int(25)
  ["Helo"]=>
  string(0) ""
  ["SMTPSecure"]=>
  string(0) ""
  ["SMTPAutoTLS"]=>
  bool(true)
  ["SMTPAuth"]=>
  bool(false)
  ["SMTPOptions"]=>
  array(0) {
  }
  ["Username"]=>
  string(0) ""
  ["Password"]=>
  string(0) ""
  ["AuthType"]=>
  string(0) ""
  ["Realm"]=>
  string(0) ""
  ["Workstation"]=>
  string(0) ""
  ["Timeout"]=>
  int(300)
  ["SMTPDebug"]=>
  bool(true)
  ["Debugoutput"]=>
  string(4) "echo"
  ["SMTPKeepAlive"]=>
  bool(false)
  ["SingleTo"]=>
  bool(false)
  ["SingleToArray"]=>
  array(0) {
  }
  ["do_verp"]=>
  bool(false)
  ["AllowEmpty"]=>
  bool(false)
  ["LE"]=>
  string(1) "
"
  ["DKIM_selector"]=>
  string(0) ""
  ["DKIM_identity"]=>
  string(0) ""
  ["DKIM_passphrase"]=>
  string(0) ""
  ["DKIM_domain"]=>
  string(0) ""
  ["DKIM_private"]=>
  string(0) ""
  ["action_function"]=>
  string(0) ""
  ["XMailer"]=>
  string(0) ""
  ["smtp":protected]=>
  NULL
  ["to":protected]=>
  array(0) {
  }
  ["cc":protected]=>
  array(0) {
  }
  ["bcc":protected]=>
  array(0) {
  }
  ["ReplyTo":protected]=>
  array(0) {
  }
  ["all_recipients":protected]=>
  array(0) {
  }
  ["RecipientsQueue":protected]=>
  array(0) {
  }
  ["ReplyToQueue":protected]=>
  array(0) {
  }
  ["attachment":protected]=>
  array(0) {
  }
  ["CustomHeader":protected]=>
  array(0) {
  }
  ["lastMessageID":protected]=>
  string(0) ""
  ["message_type":protected]=>
  string(0) ""
  ["boundary":protected]=>
  array(0) {
  }
  ["language":protected]=>
  array(0) {
  }
  ["error_count":protected]=>
  int(0)
  ["sign_cert_file":protected]=>
  string(0) ""
  ["sign_key_file":protected]=>
  string(0) ""
  ["sign_extracerts_file":protected]=>
  string(0) ""
  ["sign_key_pass":protected]=>
  string(0) ""
  ["exceptions":protected]=>
  bool(true)
  ["uniqueid":protected]=>
  string(0) ""
}

mail.log:

Feb  5 10:56:28 ironfist-droplet sendmail[27655]: v15FuS0k027655: from=root, size=196, class=0, nrcpts=1, msgid=<201702051556.v15FuS0k027655@ironfist-droplet>, relay=root@localhost
Feb  5 10:56:28 ironfist-droplet sm-mta[27657]: v15FuSaG027657: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 10:56:28 ironfist-droplet sendmail[27655]: v15FuS0k027655: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 10:56:28 ironfist-droplet sm-mta[27657]: v15FuSaG027657: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 10:56:28 ironfist-droplet sendmail[27655]: v15FuS0k027655: v15FuS0l027655: DSN: User unknown
Feb  5 10:56:28 ironfist-droplet sm-mta[27657]: v15FuSaI027657: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051556.v15FuS0l027655@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 10:56:28 ironfist-droplet sendmail[27655]: v15FuS0l027655: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15FuSaI027657 Message accepted for delivery)
Feb  5 10:56:28 ironfist-droplet sm-mta[27658]: v15FuSaI027657: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:03:40 ironfist-droplet sendmail[27694]: v15G3ehZ027694: from=root, size=196, class=0, nrcpts=1, msgid=<201702051603.v15G3ehZ027694@ironfist-droplet>, relay=root@localhost
Feb  5 11:03:40 ironfist-droplet sm-mta[27696]: v15G3e0P027696: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:03:40 ironfist-droplet sendmail[27694]: v15G3ehZ027694: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:03:40 ironfist-droplet sm-mta[27696]: v15G3e0P027696: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:03:40 ironfist-droplet sendmail[27694]: v15G3ehZ027694: v15G3eha027694: DSN: User unknown
Feb  5 11:03:40 ironfist-droplet sm-mta[27696]: v15G3e0R027696: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051603.v15G3eha027694@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:03:40 ironfist-droplet sendmail[27694]: v15G3eha027694: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G3e0R027696 Message accepted for delivery)
Feb  5 11:03:40 ironfist-droplet sm-mta[27697]: v15G3e0R027696: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:04:30 ironfist-droplet sendmail[27702]: v15G4Uxv027702: from=root, size=196, class=0, nrcpts=1, msgid=<201702051604.v15G4Uxv027702@ironfist-droplet>, relay=root@localhost
Feb  5 11:04:30 ironfist-droplet sm-mta[27704]: v15G4UL7027704: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:04:30 ironfist-droplet sendmail[27702]: v15G4Uxv027702: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:04:30 ironfist-droplet sm-mta[27704]: v15G4UL7027704: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:04:30 ironfist-droplet sendmail[27702]: v15G4Uxv027702: v15G4Uxw027702: DSN: User unknown
Feb  5 11:04:30 ironfist-droplet sm-mta[27704]: v15G4UL9027704: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051604.v15G4Uxw027702@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:04:30 ironfist-droplet sendmail[27702]: v15G4Uxw027702: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G4UL9027704 Message accepted for delivery)
Feb  5 11:04:30 ironfist-droplet sm-mta[27705]: v15G4UL9027704: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:04:43 ironfist-droplet sendmail[27710]: v15G4hPh027710: from=root, size=196, class=0, nrcpts=1, msgid=<201702051604.v15G4hPh027710@ironfist-droplet>, relay=root@localhost
Feb  5 11:04:43 ironfist-droplet sm-mta[27712]: v15G4hZC027712: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:04:43 ironfist-droplet sendmail[27710]: v15G4hPh027710: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:04:43 ironfist-droplet sm-mta[27712]: v15G4hZC027712: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:04:43 ironfist-droplet sendmail[27710]: v15G4hPh027710: v15G4hPi027710: DSN: User unknown
Feb  5 11:04:43 ironfist-droplet sm-mta[27712]: v15G4hZE027712: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051604.v15G4hPi027710@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:04:43 ironfist-droplet sendmail[27710]: v15G4hPi027710: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G4hZE027712 Message accepted for delivery)
Feb  5 11:04:43 ironfist-droplet sm-mta[27713]: v15G4hZE027712: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:06:52 ironfist-droplet sendmail[27722]: v15G6qmc027722: from=root, size=196, class=0, nrcpts=1, msgid=<201702051606.v15G6qmc027722@ironfist-droplet>, relay=root@localhost
Feb  5 11:06:52 ironfist-droplet sm-mta[27724]: v15G6qtl027724: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:06:52 ironfist-droplet sendmail[27722]: v15G6qmc027722: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:06:52 ironfist-droplet sm-mta[27724]: v15G6qtl027724: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:06:52 ironfist-droplet sendmail[27722]: v15G6qmc027722: v15G6qmd027722: DSN: User unknown
Feb  5 11:06:52 ironfist-droplet sm-mta[27724]: v15G6qtn027724: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051606.v15G6qmd027722@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:06:52 ironfist-droplet sendmail[27722]: v15G6qmd027722: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G6qtn027724 Message accepted for delivery)
Feb  5 11:06:52 ironfist-droplet sm-mta[27725]: v15G6qtn027724: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:06:57 ironfist-droplet sendmail[27730]: v15G6vDO027730: from=root, size=196, class=0, nrcpts=1, msgid=<201702051606.v15G6vDO027730@ironfist-droplet>, relay=root@localhost
Feb  5 11:06:57 ironfist-droplet sm-mta[27732]: v15G6vBt027732: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:06:57 ironfist-droplet sendmail[27730]: v15G6vDO027730: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:06:57 ironfist-droplet sm-mta[27732]: v15G6vBt027732: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:06:57 ironfist-droplet sendmail[27730]: v15G6vDO027730: v15G6vDP027730: DSN: User unknown
Feb  5 11:06:57 ironfist-droplet sm-mta[27732]: v15G6vBv027732: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051606.v15G6vDP027730@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:06:57 ironfist-droplet sendmail[27730]: v15G6vDP027730: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G6vBv027732 Message accepted for delivery)
Feb  5 11:06:57 ironfist-droplet sm-mta[27733]: v15G6vBv027732: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:08:43 ironfist-droplet sendmail[27745]: v15G8hA4027745: from=root, size=196, class=0, nrcpts=1, msgid=<201702051608.v15G8hA4027745@ironfist-droplet>, relay=root@localhost
Feb  5 11:08:43 ironfist-droplet sm-mta[27747]: v15G8hUp027747: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:08:43 ironfist-droplet sendmail[27745]: v15G8hA4027745: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:08:43 ironfist-droplet sm-mta[27747]: v15G8hUp027747: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:08:43 ironfist-droplet sendmail[27745]: v15G8hA4027745: v15G8hA5027745: DSN: User unknown
Feb  5 11:08:43 ironfist-droplet sm-mta[27747]: v15G8hUr027747: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051608.v15G8hA5027745@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:08:43 ironfist-droplet sendmail[27745]: v15G8hA5027745: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G8hUr027747 Message accepted for delivery)
Feb  5 11:08:43 ironfist-droplet sm-mta[27748]: v15G8hUr027747: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 11:09:30 ironfist-droplet sendmail[27772]: v15G9U0s027772: from=root, size=196, class=0, nrcpts=1, msgid=<201702051609.v15G9U0s027772@ironfist-droplet>, relay=root@localhost
Feb  5 11:09:30 ironfist-droplet sm-mta[27774]: v15G9UTw027774: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 11:09:30 ironfist-droplet sendmail[27772]: v15G9U0s027772: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 11:09:30 ironfist-droplet sm-mta[27774]: v15G9UTw027774: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:09:30 ironfist-droplet sendmail[27772]: v15G9U0s027772: v15G9U0t027772: DSN: User unknown
Feb  5 11:09:30 ironfist-droplet sm-mta[27774]: v15G9UU0027774: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702051609.v15G9U0t027772@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 11:09:30 ironfist-droplet sendmail[27772]: v15G9U0t027772: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15G9UU0027774 Message accepted for delivery)
Feb  5 11:09:30 ironfist-droplet sm-mta[27775]: v15G9UU0027774: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 15:34:09 ironfist-droplet sendmail[29166]: v15KY9ME029166: from=root, size=196, class=0, nrcpts=1, msgid=<201702052034.v15KY9ME029166@ironfist-droplet>, relay=root@localhost
Feb  5 15:34:09 ironfist-droplet sm-mta[29168]: v15KY9Bg029168: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 15:34:09 ironfist-droplet sendmail[29166]: v15KY9ME029166: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 15:34:09 ironfist-droplet sm-mta[29168]: v15KY9Bg029168: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:34:09 ironfist-droplet sendmail[29166]: v15KY9ME029166: v15KY9MF029166: DSN: User unknown
Feb  5 15:34:09 ironfist-droplet sm-mta[29168]: v15KY9Bi029168: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702052034.v15KY9MF029166@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:34:09 ironfist-droplet sendmail[29166]: v15KY9MF029166: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15KY9Bi029168 Message accepted for delivery)
Feb  5 15:34:09 ironfist-droplet sm-mta[29169]: v15KY9Bi029168: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 15:34:59 ironfist-droplet sendmail[29179]: v15KYxAq029179: from=root, size=196, class=0, nrcpts=1, msgid=<201702052034.v15KYxAq029179@ironfist-droplet>, relay=root@localhost
Feb  5 15:34:59 ironfist-droplet sm-mta[29181]: v15KYx21029181: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 15:34:59 ironfist-droplet sendmail[29179]: v15KYxAq029179: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 15:34:59 ironfist-droplet sm-mta[29181]: v15KYx21029181: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:34:59 ironfist-droplet sendmail[29179]: v15KYxAq029179: v15KYxAr029179: DSN: User unknown
Feb  5 15:34:59 ironfist-droplet sm-mta[29181]: v15KYx23029181: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702052034.v15KYxAr029179@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:34:59 ironfist-droplet sendmail[29179]: v15KYxAr029179: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15KYx23029181 Message accepted for delivery)
Feb  5 15:34:59 ironfist-droplet sm-mta[29182]: v15KYx23029181: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 15:35:24 ironfist-droplet sendmail[29189]: v15KZNKB029189: from=root, size=196, class=0, nrcpts=1, msgid=<201702052035.v15KZNKB029189@ironfist-droplet>, relay=root@localhost
Feb  5 15:35:24 ironfist-droplet sm-mta[29191]: v15KZOSx029191: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 15:35:24 ironfist-droplet sendmail[29189]: v15KZNKB029189: to=root, ctladdr=root (0/0), delay=00:00:01, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 15:35:24 ironfist-droplet sm-mta[29191]: v15KZOSx029191: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:35:24 ironfist-droplet sendmail[29189]: v15KZNKB029189: v15KZNKC029189: DSN: User unknown
Feb  5 15:35:24 ironfist-droplet sm-mta[29191]: v15KZOT1029191: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702052035.v15KZNKC029189@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:35:24 ironfist-droplet sendmail[29189]: v15KZNKC029189: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15KZOT1029191 Message accepted for delivery)
Feb  5 15:35:24 ironfist-droplet sm-mta[29192]: v15KZOT1029191: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent
Feb  5 15:35:34 ironfist-droplet sendmail[29199]: v15KZYoU029199: from=root, size=196, class=0, nrcpts=1, msgid=<201702052035.v15KZYoU029199@ironfist-droplet>, relay=root@localhost
Feb  5 15:35:34 ironfist-droplet sm-mta[29201]: v15KZYQ4029201: ruleset=check_rcpt, arg1=<root@ironfist-droplet>, relay=localhost [127.0.0.1], reject=553 5.1.8 <root@ironfist-droplet>... Domain of sender address root@ironfist-droplet does not exist
Feb  5 15:35:34 ironfist-droplet sendmail[29199]: v15KZYoU029199: to=root, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30196, relay=[127.0.0.1] [127.0.0.1], dsn=5.1.8, stat=User unknown
Feb  5 15:35:34 ironfist-droplet sm-mta[29201]: v15KZYQ4029201: from=<root@ironfist-droplet>, size=196, class=0, nrcpts=0, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:35:34 ironfist-droplet sendmail[29199]: v15KZYoU029199: v15KZYoV029199: DSN: User unknown
Feb  5 15:35:34 ironfist-droplet sm-mta[29201]: v15KZYQ6029201: from=<>, size=2194, class=0, nrcpts=1, msgid=<201702052035.v15KZYoV029199@ironfist-droplet>, proto=ESMTP, daemon=MTA-v4, relay=localhost [127.0.0.1]
Feb  5 15:35:34 ironfist-droplet sendmail[29199]: v15KZYoV029199: to=root, delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=31220, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v15KZYQ6029201 Message accepted for delivery)
Feb  5 15:35:34 ironfist-droplet sm-mta[29202]: v15KZYQ6029201: to=<root@ironfist-droplet>, delay=00:00:00, xdelay=00:00:00, mailer=local, pri=32407, dsn=2.0.0, stat=Sent

If anyone finds anything that could be of help in the logs, please don't hesitate to let me know. I'm still doing research and trying to find what might be wrong and going through the logs, however, since I'm not as skilled in this area, all help in any form is appreciated.

Mail.err.1 log:

Jan 24 23:21:47 ironfist-droplet sendmail[2417]: My unqualified host name (ironfist-droplet) unknown; sleeping for retry
Jan 24 23:22:47 ironfist-droplet sendmail[2417]: unable to qualify my own domain name (ironfist-droplet) -- using short name
Jan 24 23:22:47 ironfist-droplet sm-mta[2486]: My unqualified host name (ironfist-droplet) unknown; sleeping for retry
Jan 24 23:22:50 ironfist-droplet sm-msp-queue[2491]: My unqualified host name (ironfist-droplet) unknown; sleeping for retry
Jan 24 23:23:47 ironfist-droplet sm-mta[2486]: unable to qualify my own domain name (ironfist-droplet) -- using short name
Jan 24 23:23:50 ironfist-droplet sm-msp-queue[2491]: unable to qualify my own domain name (ironfist-droplet) -- using short name

Thank you.

  • Do you have a chance not to cut the logfile entries at the end of the line? Don't use nano, just cat mail.log.2 or similar. There is a problem with the hostname and the reverse name resolution, but we need the complete lines. – ridgy Feb 5 '17 at 18:30
  • Hey, thanks for letting me know that. I copied the logs using cat now instead of nano. It should be corrected now! – Matt Jones Feb 5 '17 at 20:37
  • The most important messages seem to be unable to qualify my own domain name (ironfist-droplet) and gethostbyaddr(104.236.90.239) failed. Why does sendmail mean your hostname is ironfist-droplet, and where does IP 104.236.90.239come from? Please check your sendmail configuration! – ridgy Feb 5 '17 at 21:52
  • I'm not quite sure! For awhile I had ironfist-droplet (the server name) in as the hosts name, however I realized this was an error and removed ironfist-droplet from the hosts list and put the site ironfi.st in it's place (which I believe is correct, again this area is not my forte). So I'm not sure why it's saying that? Perhaps I copied the wrong mail log? I had mail.log, mail.log.1, mail.log.2 and mail.log.2 was the latest copy of the logs so I figured that would be the most up to date! – Matt Jones Feb 6 '17 at 0:13
  • Usually with logrotation the file without digit is the actual one, log.1 the next older, etc. So mail.log should be the actual one (ls -ltr /var/log/mail* should show) – ridgy Feb 6 '17 at 12:46
1

It's been a very long time since I was working with sendmailand postfix, so I am not able to give you qualified advice in the configuration of your MTA.

As far as I can see your internet domain name is ironfi.st (see which ironfi.st), which is as well the name of your HTTP server when accessed from the internet (host ironfi.st), with (at minimum) an additional name/alias as www.ironfi.st.

There is also an MX record for ironfi.st, pointing to mx-caprica.easydns.com, so mails could be delivered to the address someone@ironfi.st. These informations are all publicly available by querying the DNS.

What I am not really sure is the organisation of your local network/server, as I assume your server lives behind a router using NAS with some ports passed to your server (anything else would be heavily insecure). So, your host should have the loopback network (127.0.0.x) and at least one other private network to connect to the router. Here and in the following I assume your apache server is based on Linux OS, and I only refer to configuring IPV4.

What at a first glance looks odd is your /etc/hosts. It usually defaults to something like

127.0.0.1   localhost
<privateIP> <hostname> <hostname.domainname>

As from your mail.logI suppose your hostname is ironfist-droplet; I don't know if your DNS-domainname is set. You may check this with hostname -fand dnsdomainname. Assuming your private IP is 192.168.1.10(just an assumption!) and hostname -freturns ironfist-droplet.ironfi.st, the second line should read

192.168.1.10 ironfist-droplet ironfist-droplet.ironfi.st

and for completeness you might have

192.168.1.10 ironfist-droplet ironfist-droplet.ironfi.st ironfi.st

Now you can test with

ping localhost
ping ironfist-droplet
ping ironfist-droplet.ironfi.st
ping ironfi.st

which should return the correct IP and have no packet loss.

Now to the entries in your mail.log:

You are sending mails from rootto root (don't know why) via relay root@localhost. The sender then is coded as root@ironfist-droplet, which is rejected as the domain of the sender address does not exist. There is a mail returned from <> to root@ironfist-droplet via relay localhost, what is the delivered; I think this is the message of the MTA to the sender that the mail could not be sent. Look into the local mailbox of root using mailxor s-nail or some other program like that.

You should thoroughly reflect the configuration of your WP-MAIL-SMTP plugin (who shall be the sender, who shall be the recipient) and your sendmail (what domain is it responsible for, which senders are allowed to send mails, where to relay mails to). As I said, I am not able to advice here. If e.g. you want the mails sent to someone@ironfi.st you should configure it that way with a valid sender; just from rootto rootis not a good idea.

And look in /var/log/mail.err if it exists, maybe there are some more hints. It usually only contains error messages, whereas mail.logcontains success messages as well.

  • Thank you for the comprehensive reply! I shall try all these things and respond with an update of progress! Thank you so much! – Matt Jones Feb 17 '17 at 16:08
  • hotsname -f returns ironfist-droplet but not ironfist-droplet.ironfi.st should my hosts file look like this then: 192.168.1.10 ironfist-droplet ironfist-droplet.ironfi.st – Matt Jones Feb 18 '17 at 14:47
  • I've updated my post with the info from mail.err.1 (as mail.err was empty) – Matt Jones Feb 18 '17 at 17:03

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