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";
[download]

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.