Using Perl to send emails from remote "Mail-in-aBox" server - perl

Question

On DigitalOcean I've got a vps running MIAB ("Mail-in-aBox") at box.emailserver.com and a web app server on another vps at appserver.com.
I want to send emails from the web app using a Perl script.
I'm using the MIAB DNS server for both domain names. With the MIAB server I can send and receive email using my Mac Mini "Mail" app so that's working great.
I've edited a perl script I found on CPAN that attempts to authenticate a user and send a simple email from appserver.com but it is not passing the auth stage. I get this error:
Error sending email: failed AUTH: Command unknown: 'AUTH'
Anyone have any ideas on what I'm doing wrong?
Here's the script on the web app server, the mail.log from the MIAB, and what the script outputs when run:
#!/usr/bin/perl
use Email::Sender::Simple qw(sendmail);
use Email::Sender::Transport::SMTPS;
use Try::Tiny;
my $transport = Email::Sender::Transport::SMTPS->new(
host => 'box.emailserver.com',
ssl => 'starttls',
sasl_username => 'hostmaster#emailserver.com',
sasl_password => 'xxxx',
debug => 1, # or 1
);
use Email::Simple::Creator; # or other Email::
my $message = Email::Simple->create(
header => [
From => 'hostmaster#emailserver.com',
To => 'bill#my.com',
Subject => 'appserver.com perl test',
],
body => 'This is the test.',
);
try {
sendmail($message, { transport => $transport });
} catch {
die "Error sending email: $_";
};
MIAB mail.log:
Apr 16 13:17:10 box postfix/submission/smtpd[31729]: connect from appserver.com[45.55.229.99]
Apr 16 13:17:10 box postfix/submission/smtpd[31729]: lost connection after EHLO from appserver.com[45.55.229.99]
Apr 16 13:17:10 box postfix/submission/smtpd[31729]: disconnect from appserver.com[45.55.229.99]
appserver.com perl script output
root#appserver:/usr/lib/cgi-bin# perl test6.pl
Net::SMTPS>>> Net::SMTPS(0.06)
Net::SMTPS>>> IO::Socket::IP(0.37)
Net::SMTPS>>> IO::Socket(1.38)
Net::SMTPS>>> IO::Handle(1.35)
Net::SMTPS>>> Exporter(5.72)
Net::SMTPS>>> Net::SMTP(3.10)
Net::SMTPS>>> Net::Cmd(3.10)
Net::SMTPS=GLOB(0x33b7958)<<< 220 box.emailserver.com ESMTP Hi, I'm a Mail-in-a-Box (Ubuntu/Postfix; see https://mailinabox.email/)
Net::SMTPS=GLOB(0x33b7958)>>> EHLO localhost.localdomain
Net::SMTPS=GLOB(0x33b7958)<<< 250-box.emailserver.com
Net::SMTPS=GLOB(0x33b7958)<<< 250-PIPELINING
Net::SMTPS=GLOB(0x33b7958)<<< 250-SIZE 134217728
Net::SMTPS=GLOB(0x33b7958)<<< 250-VRFY
Net::SMTPS=GLOB(0x33b7958)<<< 250-ETRN
Net::SMTPS=GLOB(0x33b7958)<<< 250-STARTTLS
Net::SMTPS=GLOB(0x33b7958)<<< 250-ENHANCEDSTATUSCODES
Net::SMTPS=GLOB(0x33b7958)<<< 250-8BITMIME
Net::SMTPS=GLOB(0x33b7958)<<< 250 DSN
Error sending email: failed AUTH: Command unknown: 'AUTH'
Trace begun at /usr/local/share/perl/5.22.1/Email/Sender/Transport/SMTPS.pm line 98
Email::Sender::Transport::SMTPS::_throw('Email::Sender::Transport::SMTPS=HASH(0x24d8b80)', 'failed AUTH', 'Net::SMTPS=GLOB(0x33b7958)') called at /usr/local/share/perl/5.22.1/Email/Sender/Transport/SMTPS.pm line 71
Email::Sender::Transport::SMTPS::smtpclient('Email::Sender::Transport::SMTPS=HASH(0x24d8b80)') called at /usr/local/share/perl/5.22.1/Email/Sender/Transport/SMTPS.pm line 107
Email::Sender::Transport::SMTPS::send_email('Email::Sender::Transport::SMTPS=HASH(0x24d8b80)', 'Email::Abstract=ARRAY(0x3023ae0)', 'HASH(0x3023ca8)') called at /usr/local/share/perl/5.22.1/Email/Sender/Role/CommonSending.pm line 45
Email::Sender::Role::CommonSending::try {...} at /usr/share/perl5/Try/Tiny.pm line 92
eval {...} at /usr/share/perl5/Try/Tiny.pm line 83
Try::Tiny::try('CODE(0x307b370)', 'Try::Tiny::Catch=REF(0x3023d38)') called at /usr/local/share/perl/5.22.1/Email/Sender/Role/CommonSending.pm line 58
Email::Sender::Role::CommonSending::send('Email::Sender::Transport::SMTPS=HASH(0x24d8b80)', 'Email::Abstract=ARRAY(0x3023ae0)', 'HASH(0x3069a30)') called at /usr/local/share/perl/5.22.1/Email/Sender/Simple.pm line 119
Email::Sender::Simple::send_email('Email::Sender::Simple', 'Email::Abstract=ARRAY(0x3023ae0)', 'HASH(0x3023cf0)') called at /usr/local/share/perl/5.22.1/Email/Sender/Role/CommonSending.pm line 45
Email::Sender::Role::CommonSending::try {...} at /usr/share/perl5/Try/Tiny.pm line 92
eval {...} at /usr/share/perl5/Try/Tiny.pm line 83
Try::Tiny::try('CODE(0x3023b58)', 'Try::Tiny::Catch=REF(0x3005228)') called at /usr/local/share/perl/5.22.1/Email/Sender/Role/CommonSending.pm line 58
Email::Sender::Role::CommonSending::send('Email::Sender::Simple', 'Email::Simple=HASH(0x3004f88)', 'HASH(0x3004ee0)') called at /usr/share/perl5/Sub/Exporter/Util.pm line 18
Sub::Exporter::Util::ANON('Email::Simple=HASH(0x3004f88)', 'HASH(0x3004ee0)') called at test6.pl line 26
main::try {...} at /usr/share/perl5/Try/Tiny.pm line 92
eval {...} at /usr/share/perl5/Try/Tiny.pm line 83
Try::Tiny::try('CODE(0x2fd50b0)', 'Try::Tiny::Catch=REF(0x2f96d08)') called at test6.pl line 29

Answer 1

Net::SMTPS=GLOB(0x33b7958)<<< 220 box.emailserver.com ESMTP Hi, I'm a Mail-in-a-Box (Ubuntu/Postfix; see https://mailinabox.email/)
Net::SMTPS=GLOB(0x33b7958)>>> EHLO localhost.localdomain
Net::SMTPS=GLOB(0x33b7958)<<< 250-box.emailserver.com
Net::SMTPS=GLOB(0x33b7958)<<< 250-PIPELINING
Net::SMTPS=GLOB(0x33b7958)<<< 250-SIZE 134217728
Net::SMTPS=GLOB(0x33b7958)<<< 250-VRFY
Net::SMTPS=GLOB(0x33b7958)<<< 250-ETRN
Net::SMTPS=GLOB(0x33b7958)<<< 250-STARTTLS
Net::SMTPS=GLOB(0x33b7958)<<< 250-ENHANCEDSTATUSCODES
Net::SMTPS=GLOB(0x33b7958)<<< 250-8BITMIME
Net::SMTPS=GLOB(0x33b7958)<<< 250 DSN
Based on this output from the EHLO command the server does not support any kind of authentication. If it would there would be a line like 250-AUTH LOGIN PLAIN ..., i.e. a line which declares support for the AUTH command and shows which authentication methods are supported. But since there is no such line the server does not support authentication.
If you want to use authentication you need to fix this at the server setup. While I can find no information about it in the setup guid of MIAB it uses Postfix underneath which support authentication and there are various tutorials online which describe the process. But, any questions for this server setup are probably more on-topic at serverfault.com.

Answer 2

None of the instructions here or elsewhere worked for me, so I crafted my own solution using Net::SMTP. I have Mail-In-A-Box working successfully on Namecheap with full STARTTLS support using a Perl script. The e-mails pass Gmail's spam folder, passing all their authenticity tests. Once you have your mailinabox server fully configured, this script can be used to send e-mails via SMTP.
#!/usr/bin/perl
use warnings;
use strict;
use Net::SMTP;
use Authen::SASL;
my $host = 'box.yoursite.com'; #server1.yoursite.com if on namecheap
my $port = 587;
my $username = 'you#yoursite.com';
my $password = 'yourpassword';
my $sendto = 'your#friend.com';
my $smtp = Net::SMTP->new(
$host,
Port => $port,
SSL => 0, #No SSL on initial handshake.
Timeout => 10,
Debug => 1
);
#Postfix has no AUTH option until STARTTLS.
$smtp->starttls();
$smtp->auth($username, $password);
$smtp->mail($username);
if ($smtp->to($sendto)) {
$smtp->data();
$smtp->datasend("From: $username\n");
$smtp->datasend("To: $sendto\n");
$smtp->datasend("Subject: Test message\n");
$smtp->datasend("\n");
$smtp->datasend("The test works!\n");
$smtp->dataend();
} else {
print "Error: ", $smtp->message();
}
$smtp->quit;
A few notes:
The first EHLO handshake needs to be performed without SSL (SSL=>0), and once initiated, a STARTTLS connection can then be established. Hence, this initial EHLO handshake fails to return a 250-AUTH response from the mailinabox server, but upgrading the SMTP connection constructor to STARTTLS ($smtp->starttls()) succeeds in returning 250-AUTH PLAIN LOGIN, at which point, you can proceed to authenticate with the SMTP server in the normal way.
Make sure both the Net::SMTP and Authen::SASL cpan modules are both installed/upgraded.
I added the server IP address to mynetworks as described by Bill Stephenson, but did not find it to be necessary.