HTTPS Proxy and LWP::UserAgent

I have read a number of threads on a number of sites and am still unable to make this work. I have a client machine (OSX) with OpenSSL 0.9.8r running perl 5.12.4, with LWP 6.0.4, updated Crypt::SSLeay, Net::SSL etc. I am trying to connect to an HTTPS site (https://github.com in the example) via a WinGate proxy that I have running on a Windows VM. Note that my actual application is attaching to an SSL webservice that I have no control over. From Firefox, pointed to the proxy everything is copacetic. The page loads successfully and I see the connections in the Proxy software Activity monitor. I'll be darned if I can make it work in Perl though. I've started with the code from this Stack Overflow Question : How do I force LWP to use Crypt::SSLeay for HTTPS requests? And added some debugging and additional output. Here's were I stand now: ``` #!/usr/bin/perl use strict; use warnings; use Net::SSL (); # From Crypt-SSLeay BEGIN { $Net::HTTPS::HTTPS_SSL_SOCKET_CLASS = "Net::SSL"; # Force use of Net::SSL $ENV{HTTPS_PROXY} = 'https://192.168.1.11:80'; # $ENV{PERL_LWP_SSL_VERIFY_HOSTNAME} = 0; $ENV{HTTPS_DEBUG} = 1; #Add debug output } use LWP::UserAgent; my $ua = LWP::UserAgent->new(); my $req = HTTP::Request->new('GET','https://github.com/'); my $response = $ua->request($req); print "--\n"; print "$_\n" for grep { $_ =~ /SSL/ } keys %INC; print "--\n"; if ($response->is_success) { print $response->decoded_content; # or whatever exit(0); } else { print "\nFail:\n"; print $response->status_line ."\n"; exit(1); } ``` Here's the output from this code: ``` -- Crypt/SSLeay.pm Crypt/SSLeay/X509.pm Net/SSL.pm -- Fail: 500 Can't connect to github.com:443 (Crypt-SSLeay can't verify hostnames) ``` If I then uncomment `$ENV{PERL_LWP_SSL_VERIFY_HOSTNAME} = 0;`, I do see a single connect to github.com:443 on the proxy and then nothing. (Note it works great from a web browser through the proxy). After much hanging I get the following output from the script: ``` SSL_connect:before/connect initialization SSL_connect:SSLv2/v3 write client hello A SSL_connect:before/connect initialization SSL_connect:SSLv3 write client hello A SSL_connect:failed in SSLv3 read server hello A SSL_connect:before/connect initialization SSL_connect:SSLv2 write client hello A SSL_connect:failed in SSLv2 read server hello A -- Crypt/SSLeay.pm Crypt/SSLeay/X509.pm Net/SSL.pm Crypt/SSLeay/CTX.pm Crypt/SSLeay/MainContext.pm -- Fail: 500 SSL negotiation failed: ``` If anyone can provide some direction here I would greatly appreciate it!