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Trying to send an email from Perl. Both programs I've tried to use end up with the same error message: ".../IO/Socket/SSL.pm:1177: global error: Undefined SSL object". If I understand the messages correctly it appears that in both cases Net::SMTPS sends information to IO::Socket::SSL which clearly SSL.pm doesn't like. Since I'm at the limit of what I know, I thought I would ask for any information I could get.

Program 1

use Email::Sender::Simple qw(sendmail);
use Email::Sender::Transport::SMTPS;
use Email::Simple ();
use Email::Simple::Creator ();

my $smtpserver = 'ddd.com';
my $smtpport = 587;
my $smtpuser   = 'xxx@ddd.com';
my $smtppassword = 'yyyyyy';

my $transport = Email::Sender::Transport::SMTPS->new({
    host => $smtpserver,
    ssl  => 'starttls',
    port => $smtpport,
    sasl_username => $smtpuser,
    sasl_password => $smtppassword,
    debug => 1,
});


my $email = Email::Simple->create(
    header => [
    To      => 'xxx@ddd.com',
    From    => 'xxx@ddd.com',
    Subject => 'Hi!',
  ],
    body => "This is my message\n",
);

sendmail($email, { transport => $transport });

[download]

The debug flag returns the following information:

Net::SMTPS>>> Net::SMTPS(0.10)
Net::SMTPS>>>   IO::Socket::IP(0.39)
Net::SMTPS>>>     IO::Socket(1.40)
Net::SMTPS>>>       IO::Handle(1.40)
Net::SMTPS>>>         Exporter(5.74)
Net::SMTPS>>>   Net::SMTP(3.11)
Net::SMTPS>>>     Net::Cmd(3.11)
Net::SMTPS=GLOB(0x556317f13e28)<<< 220-ddd.com ESMTP Exim 4.92 #2 Mon,
+ 01 Jun 2020 07:42:59 -0600 
Net::SMTPS=GLOB(0x556317f13e28)<<< 220-We do not authorize the use of 
+this system to transport unsolicited, 
Net::SMTPS=GLOB(0x556317f13e28)<<< 220 and/or bulk e-mail.
Net::SMTPS=GLOB(0x556317f13e28)>>> EHLO localhost.localdomain
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-ddd.com Hello dsl-ip.fuse.net [
+ipaddr]
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-SIZE 52428800
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-8BITMIME
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-PIPELINING
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-AUTH PLAIN LOGIN
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-STARTTLS
Net::SMTPS=GLOB(0x556317f13e28)<<< 250 HELP
Net::SMTPS=GLOB(0x556317f13e28)>>> STARTTLS
Net::SMTPS=GLOB(0x556317f13e28)<<< 220 TLS go ahead
DEBUG: .../IO/Socket/SSL.pm:1177: global error: Undefined SSL object
Net::SMTPS=GLOB(0x556317f13e28)>>> EHLO localhost.localdomain
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-ddd.com Hello dsl-ip.fuse.net [
+ipaddr]
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-SIZE 52428800
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-8BITMIME
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-PIPELINING
Net::SMTPS=GLOB(0x556317f13e28)<<< 250-AUTH PLAIN LOGIN
Net::SMTPS=GLOB(0x556317f13e28)<<< 250 HELP
Net::SMTPS=GLOB(0x556317f13e28)>>> AUTH PLAIN -stuff here-
Net::SMTPS=GLOB(0x556317f13e28)<<< 535 Incorrect authentication data
failed AUTH: Incorrect authentication data

[download]

Program 2 is:

use Net::SMTPS ;
use MIME::Lite ;

my $msg = MIME::Lite ->new (  
From => 'xxx@ddd.com',
To => 'xxx@ddd.com',
Subject => 'Test Message',
Data => 'This is a test',
Type => 'text/html'
);

my $USERNAME = 'xxx@ddd.com';
my $PASSWORD = 'yyyyyyyy'; 

my $smtps = Net::SMTPS->new("ddd.com", Port => 587,  doSSL => 'starttl
+s', Debug => 1, Debug_SSL => 3);


$smtps->auth ( $USERNAME, $PASSWORD ) or die("Could not authenticate\n
+");

$smtps->mail('xxx@ddd.com');
$smtps->to('xxx@ddd.com');
$smtps->data();
$smtps->datasend( $msg->as_string() );  
$smtps->dataend();  
$smtps->quit;

[download]

The debug flags return the following information:

Net::SMTPS>>> Net::SMTPS(0.10)
Net::SMTPS>>>   IO::Socket::IP(0.39)
Net::SMTPS>>>     IO::Socket(1.40)
Net::SMTPS>>>       IO::Handle(1.40)
Net::SMTPS>>>         Exporter(5.74)
Net::SMTPS>>>   Net::SMTP(3.11)
Net::SMTPS>>>     Net::Cmd(3.11)
Net::SMTPS=GLOB(0x5609e794aac0)<<< 220-ddd.com ESMTP Exim 4.92 #2 Mon,
+ 01 Jun 2020 08:30:01 -0600 
Net::SMTPS=GLOB(0x5609e794aac0)<<< 220-We do not authorize the use of 
+this system to transport unsolicited, 
Net::SMTPS=GLOB(0x5609e794aac0)<<< 220 and/or bulk e-mail.
Net::SMTPS=GLOB(0x5609e794aac0)>>> EHLO localhost.localdomain
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-ddd.com Hello dsl-ip.fuse.net [
+ipaddr]
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-SIZE 52428800
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-8BITMIME
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-PIPELINING
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-AUTH PLAIN LOGIN
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-STARTTLS
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250 HELP
Net::SMTPS=GLOB(0x5609e794aac0)>>> STARTTLS
Net::SMTPS=GLOB(0x5609e794aac0)<<< 220 TLS go ahead
DEBUG: .../IO/Socket/SSL.pm:3010: new ctx 94600543851488
DEBUG: .../IO/Socket/SSL.pm:1620: start handshake
DEBUG: .../IO/Socket/SSL.pm:1177: global error: Undefined SSL object
DEBUG: .../IO/Socket/SSL.pm:787: ssl handshake not started
DEBUG: .../IO/Socket/SSL.pm:832: not using SNI because hostname is unk
+nown
DEBUG: .../IO/Socket/SSL.pm:864: request OCSP stapling
DEBUG: .../IO/Socket/SSL.pm:880: set socket to non-blocking to enforce
+ timeout=120
DEBUG: .../IO/Socket/SSL.pm:894: call Net::SSLeay::connect
DEBUG: .../IO/Socket/SSL.pm:897: done Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:907: ssl handshake in progress
DEBUG: .../IO/Socket/SSL.pm:917: waiting for fd to become ready: SSL w
+ants a read first
DEBUG: .../IO/Socket/SSL.pm:937: socket ready, retrying connect
DEBUG: .../IO/Socket/SSL.pm:894: call Net::SSLeay::connect
DEBUG: .../IO/Socket/SSL.pm:897: done Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:907: ssl handshake in progress
DEBUG: .../IO/Socket/SSL.pm:917: waiting for fd to become ready: SSL w
+ants a read first
DEBUG: .../IO/Socket/SSL.pm:937: socket ready, retrying connect
DEBUG: .../IO/Socket/SSL.pm:894: call Net::SSLeay::connect
DEBUG: .../IO/Socket/SSL.pm:897: done Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:907: ssl handshake in progress
DEBUG: .../IO/Socket/SSL.pm:917: waiting for fd to become ready: SSL w
+ants a read first
DEBUG: .../IO/Socket/SSL.pm:937: socket ready, retrying connect
DEBUG: .../IO/Socket/SSL.pm:894: call Net::SSLeay::connect
DEBUG: .../IO/Socket/SSL.pm:897: done Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:907: ssl handshake in progress
DEBUG: .../IO/Socket/SSL.pm:917: waiting for fd to become ready: SSL w
+ants a read first
DEBUG: .../IO/Socket/SSL.pm:937: socket ready, retrying connect
DEBUG: .../IO/Socket/SSL.pm:894: call Net::SSLeay::connect
DEBUG: .../IO/Socket/SSL.pm:2864: ok=1 [2] /C=GB/ST=Greater Manchester
+/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Certification Authority/
+C=GB/ST=Greater Manchester/L=Salford/O=COMODO CA Limited/CN=COMODO RS
+A Certification Authority
DEBUG: .../IO/Socket/SSL.pm:2864: ok=1 [1] /C=GB/ST=Greater Manchester
+/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Certification Authority/
+C=US/ST=TX/L=Houston/O=cPanel, Inc./CN=cPanel, Inc. Certification Aut
+hority
DEBUG: .../IO/Socket/SSL.pm:2864: ok=1 [0] /C=US/ST=TX/L=Houston/O=cPa
+nel, Inc./CN=cPanel, Inc. Certification Authority/CN=box826.bluehost.
+com
DEBUG: .../IO/Socket/SSL.pm:2911: did not get stapled OCSP response
DEBUG: .../IO/Socket/SSL.pm:897: done Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:907: ssl handshake in progress
DEBUG: .../IO/Socket/SSL.pm:917: waiting for fd to become ready: SSL w
+ants a read first
DEBUG: .../IO/Socket/SSL.pm:937: socket ready, retrying connect
DEBUG: .../IO/Socket/SSL.pm:894: call Net::SSLeay::connect
DEBUG: .../IO/Socket/SSL.pm:897: done Net::SSLeay::connect -> 1
DEBUG: .../IO/Socket/SSL.pm:952: ssl handshake done
Net::SMTPS=GLOB(0x5609e794aac0)>>> EHLO localhost.localdomain
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-ddd.com Hello dsl-ip.fuse.net [
+ipaddr]
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-SIZE 52428800
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-8BITMIME
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-PIPELINING
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250-AUTH PLAIN LOGIN
Net::SMTPS=GLOB(0x5609e794aac0)<<< 250 HELP
Net::SMTPS=GLOB(0x5609e794aac0)>>> AUTH PLAIN -stuff here
Net::SMTPS=GLOB(0x5609e794aac0)<<< 535 Incorrect authentication data
Could not authenticate

[download]

It has been a long time since I did any programming and I am not sure how to proceed to fix this. Any thoughts welcome and Thanks

In reply to sending email with starttls not working by jfwell

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