I know there are a some threads about sending an email on Windows but those are focused for people that use ActivePerl, but in my case I build Perl from the source.

You should study those threads, they apply to you as well, perl is perl

Well, I did study them, I did try their solutions and one of those I mentioned above with out success. Since networking is not my specialty and the only thing I need is just to send a email with or without attachments, so I was just looking for help on what I may be doing wrong or what am I missing with my configuration from someone who has experience in this field.

You don't tell us how the different approaches from different nodes here fail for you. You don't show code we can try ourselves. It will help us help you better if you provide us an easy way to replicate your problem.

See the following nodes, all of which have code or alternative approaches:

• gmail -- sending out html messages
• MIME::Lite error => SMTP auth() command not supported on smtp.gmail.com
• Bad file descriptor with mail to Gmail using MIME::Lite.
• Sending Mail trough Perl using ActivePerl on windows (but that one might be a bit out of date)

Thanks and yes would like to try your solution.

I had to do the login in this manual way because I had problems with the authentication (the method provided by the SMTP object simply did not work: I did some research and turned out that others are having similar problems on Win32). My original code has hard coded server and user names. Now I've tried to comprise things in one sub called 'sendmail'. I've tested this sub to the extent of sending one e-mail and it worked. The parameters to the sub should be obvious (set 'debug' to '0' if everything works fine, set it to '1' and you will get a verbose debug info with the commands the SMTP object sends to the server and the responses - in my case this proved to be very helpful):

use Net::SMTP;
use MIME::Base64;

# usage: sendmail(mailserver,username,password,from,to,subject,content
+,debug);
sub sendmail
{

my ($mail_server,$username,$password,$from,$to,$subject,$content,$debu
+g)=@_;

$smtp = Net::SMTP->new(
    $mail_server,
    Timeout => 30,
    Debug   => $debug,
    );

$smtp->datasend("AUTH LOGIN\n");
$smtp->response();
$smtp->datasend(encode_base64($username));
$smtp->response();
$smtp->datasend(encode_base64($password));
$smtp->response();
$smtp->mail($from);
$smtp->to($to);
$smtp->data();
$smtp->datasend("To: $to\n");
$smtp->datasend("From: $from\n");
$smtp->datasend("Content-Type: text/html\n");
$smtp->datasend("Subject: $subject");
$smtp->datasend("\n");
$smtp->datasend($content);
$smtp->datasend("\n");
$smtp->dataend();
$smtp->quit;

}
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