Well, in my case there is a problem! I am using LWP:UserAgent module with perl 5.8.8 on a FreeBSD 6.1 system. And have configured Apache web server as the proxy. I have set the following environment variable to use SSLeay proxy capabilities: https_proxy=http://<Proxy server IP>:80 When I conenct to a HTTPS server over the proxy, I see from the Wireshark trace the following request sent from my machine to the proxy. CONNECT <remote HTTPS server IP>:443 HTTP/1.0 It starts to do the SSL negotiation, but in the middle of it, I see the following unexpected request from my machine to the proxy: CONNECT <Proxy server IP>:80 HTTP/1.0 My machine to trying to connect to the proxy server itself! This is somehow messing up with the previous connection to the remote HTTPS server and the SSL negotiation fails. Once in a while after many failed attempts, SSL negotiation succeeds. From the trace I see that it is successful ONLY when the second CONNECT to the proxy is not done. There is only a single CONNECT to the remote server. So this leads me to believe that the unexpected CONNECT to the proxy is an issue. The original thread mentioned that it could be a bug in LWP:UserAgent. So was wondering if it indeed is and if so, what is the solution? Thanks