I use this program to wrap putty, which doesn't support NTLM auth, setting the proxy type to telnet and create a SOCKS proxy to a remote SSH server.

hacked up ntlm proxy tunnel

package ntlmptunnel;

import java.io.IOException;
import java.io.InputStream;
import java.io.OutputStream;
import java.net.InetSocketAddress;
import java.net.ServerSocket;
import java.net.Socket;
import org.apache.commons.httpclient.HostConfiguration;
import org.apache.commons.httpclient.NTCredentials;
import org.apache.commons.httpclient.ProxyClient;
import org.apache.commons.httpclient.auth.AuthScope;

/*
 I use this program to wrap putty, which doesn't support NTLM auth, setting the proxy type to telnet and create a SOCKS proxy to a remote SSH server.
*/

public class Main 
{
 
    private static void pipe(final InputStream is, final OutputStream os)
    {
        Thread t = new Thread(new Runnable()
        {

            public void run()
            {
                try
                {
                    int read = -1;
                    byte[] bytes = new byte[8192];
                    while ((read = is.read(bytes)) != -1)
                        os.write(bytes, 0, read);
                }
                catch (IOException ex)
                {
                    ex.printStackTrace();
                }
            }
                
        });
        t.setDaemon(true);
        t.start();
    }
    
    public static void main(String[] args)
    {
        try
        {
            ServerSocket ss = new ServerSocket();
            ss.bind(new InetSocketAddress("localhost",localport));
            System.out.println("listening");
            Socket s = ss.accept();

            System.out.println("got connection");
            
            ProxyClient pc = new ProxyClient();
            HostConfiguration config = pc.getHostConfiguration();
            config.setHost("remote address", remote port);
            config.setProxy("proxy address", proxy port);
            
            pc.getState().setProxyCredentials(AuthScope.ANY, 
                                        new NTCredentials("username", "password", "", ""));
            
            ProxyClient.ConnectResponse r = pc.connect();
            
            System.out.println("connected to proxy...");
                
            OutputStream proxyOutput = r.getSocket().getOutputStream();
            InputStream proxyInput = r.getSocket().getInputStream();

            OutputStream outputToPutty  = s.getOutputStream();
            InputStream inputFromPutty = s.getInputStream();

            pipe(inputFromPutty,proxyOutput);
            pipe(proxyInput,outputToPutty);
            
            System.out.println("Running...");
            System.in.read();
            
        }
        catch(Exception e)
        {
            e.printStackTrace();
        }
    }

}