I ended up spliting up the call string in order to intervene in the setup steps:

my  $objst = Email::Stuff
        ->to('tshinnic@io.com')
        ->from('tshinnic@gmail.com')
        ->subject('Test Subject')
        ->text_body('This is a test.');
# This forces Net::SMTP::SSL to be loaded
    $objst->using( 'SMTP', ssl => 1 );
# Which allows us to do this ...
    $IO::Socket::SSL::DEBUG = 1;
my  $rc = $objst->send('SMTP',
        ssl      => 1,
        Host     => 'smtp.gmail.com',
        PeerPort => 465,
        username => 'tshinnic',
        password => 'xxx',
        Debug    => 1,
    );
[download]

CA file certs/my-ca.pem not found, using CA path instead.
IO::Socket::INET configuration failederror:00000000:lib(0):func(0):rea
+son(0)
 at C:/Perl587/site/lib/Email/Send/SMTP.pm line 37
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After taking the same extraordinary measures, what error messages do you see?

Doesn't matter if it is on Win32 or *nix, I could not build Email::Stuff onWin32, so I tried it on one of my CentOS testing servers:

#!/usr/bin/perl
use warnings;
use strict;
use Email::Stuff;
my  $objst = Email::Stuff
        ->to('jophnday@wordsnimages.com')
        ->from('praecipuus@gmail.com')
        ->subject('Test Subject')
        ->text_body('This is a test.');
# This forces Net::SMTP::SSL to be loaded
    $objst->using( 'SMTP', ssl => 1 );
# Which allows us to do this ...
    $IO::Socket::SSL::DEBUG = 1;
my  $rc = $objst->send('SMTP',
        ssl      => 1,
        Host     => 'smtp.gmail.com',
        PeerPort => 465,
        username => 'praecipuus',
        password => 'xx***xx',
        Debug    => 1,
    );
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Result:

Name "IO::Socket::SSL::DEBUG" used only once: possible typo at emailst
+uff.pl line 13.
CA file certs/my-ca.pem not found, using CA path instead.
IO::Socket::INET configuration failederror:00000000:lib(0):func(0):rea
+son(0)
 at /usr/lib/perl5/site_perl/5.8.7/Email/Send/SMTP.pm line 37
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jdtoronto

Same here. Exact same error message. My research has led me nowhere to debug that.

That is exactly the same error message I get now. Off the top of my head, I have no idea what it means. Off to figure it out!

#!/usr/bin/perl
use warnings;
use strict;
use Net::SMTP::SSL;


  my $smtp = Net::SMTP::SSL->new(
    'smtp.gmail.com',
    Port => 465,
    Timeout => 30,
    Debug   => 1,
  );
  
print $@;
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Net::SMTP::SSL: Bad service ''
[download]

I don't have time to try more now, but this might give you some more thngs to follow up.

jdtoronto

First off, testing the socket connection to smtp.gmail.com:465 works great using IO::Socket::SSL:

use IO::Socket::SSL;

my $client = IO::Socket::SSL->new("smtp.gmail.com:465");

if ($client) {
  print $client "GET / HTTP/1.0\r\n\r\n";
  print <$client>;
  close $client;
} else {
  warn "I encountered a problem: ",
    IO::Socket::SSL::errstr();
}
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Result:

220 mx.gmail.com ESMTP c18sm62410hub

Then a really simple test with Net::SMTP::SSL yields a bad result:

use Net::SMTP::SSL;
use Data::Dumper;
my $smtps = Net::SMTP::SSL->new("smtp.gmail.com", Port => 465);
print Dumper($smtps);
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Result:

$VAR1 = undef;

What puzzles me is that these are very established modules. I'll report more here when I know more.

Indeed, Email::Stuff is just a usability wrapper (I wrote it that way intentionally).

Trouble with IO::Socket::(Anything) on Win32 would not surprise me at all, there's a few dragons there.

What Perl distribution are you using?

The first step might be to just write a simple test script that tries to connect via SSL, then immediately drops the connect once established, to GMail's server and see if that works.

That would isolate the problem to the connectivity layer. If you can get that working, then lets look at Email::Stuff and friends.

Until then though, I consider the entire Email:: family to be blameless here.

I am on Linux, Perl 5.8.8.

I must be missing something. I don't see how your suggestion differs from what I did at the outset. I have a simple test script that tries to connect via SSL. But I don't understand enough about the mechanism in the connectivity layer to troubleshoot what is happening in the interim between my script and their servers.

I tried to break it down by just using Email::Send::SMTP to send a message:

#!/usr/bin/perl
use warnings;
use strict;
use Email::Send;
my $mailer = Email::Send->new({mailer => 'SMTP'});
$mailer->mailer_args([Host => 'smtp.gmail.com:465',
                      ssl => 1,
                      username => 'mike@mikebaas.com',
                      password => 'xxx']);

my $message = "From: mike\@mikebaas.com
To: test\@mikebaas.com
Subject: testing

This is the test message body.";

my $result = $mailer->send($message);
print "$result\n";
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The value of $result is:

Couldn't connect to smtp.gmail.com:465

Not quite sure how to get more detail out of the module.