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

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?

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Re^2: How to enable SSL support in sockets connected with a sock5 server?
by dxxd116 (Beadle) on Jan 12, 2009 at 12:34 UTC
    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!
      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.