How to enable SSL support in sockets connected with a sock5 server?

[dxxd116]

Hello, Guys: Does anyone have experience in this situation? First, I established a socket connection to a socks5 proxy Server through the use of Net::SOCKS module. Then I realized that I try to enable SSL in order to communicate with the gmail smtp server through the "STARTTLS" command. Then I am lost, what should be done next in order to send an email through the socket? Codes are as below:

use Net::SOCKS;
use Net::SSLeay;
use IO::Socket::INET;
use IO::Socket::SSL;
use MIME::Base64 qw[encode_base64 decode_base64];
use Digest::HMAC_MD5 qw[hmac_md5_hex];


my $sock = new Net::SOCKS(socks_addr => '211.239.124.76',
                socks_port =>9188,
                #user_id => 'the_user',
                #user_password => 'the_password',
                #force_nonanonymous => 0,
                protocol_version => 5);
print "Cannot establish connection using socks!\n" if !$sock;
print "Connecting to google gmail now!\n";
my $f= $sock->connect(peer_addr => 'smtp.gmail.com',
 peer_port => 587);

 open FH, ">:utf8","socks.txt";
 
     my $line=<$f>;
     print $line ;
     print FH $line;

     print $f "EHLO localhost\n";
     $line=<$f>;
     print $line;
     print FH $line;

     print $f "StartTLS\n";
     $line=<$f>;
     print $line;
     print FH $line;
#What is next?...

Thanks.

[Corion]

IO::Socket::SSL has a ->start_SSL method, which will upgrade your "plain" socket to a SSL-encrypted connection. I think this is what all the other things that use StartTLS use (Google Code Search), but if not, maybe you find the appropriate things there. Also, have you looked at what CPAN has to offer for ESMTP, which seems what you're implementing?

[dxxd116]

Connecting to google gmail now!
220 mx.google.com ESMTP q18sm34685365pog.9
250-mx.google.com at your service, [121.15.233.169]
250-SIZE 35651584
Usage: IO::Handle::error(handle) at C:/Perl/site/lib/IO/Socket/SSL.pm 
+line 611, <GEN0> line 3.

Above is the reponse I got after I use IO::Socket::SSL::start_SSL method on the socket connected through a socks5 server. Code added are as below

if(not IO::Socket::SSL::start_SSL($f,
        SSL_version    =>    "SSLv3 TLSv1")){
        die "Couldn't start TLS: \n" . IO::Socket::SSL::errstr ."\n";
    }
    print $f "EHLO localhost\n";
    $line=<$f>;
     print $line;
     print FH $line;
     
     print $f "AUTH LOGIN\n";
    $line=<$f>;
     print $line;
     print FH $line;

Any ideas? Thank you very much!

[kennethk]

Specifically in connection to the gmail servers, I had significantly more luck a few months back when I wrote an automailer using Net::SMTP::TLS - the final code is published here.