Thanks for your reply. We have our app-server that uses Sun's HttpURLConnection to send an outbound request to an endpoint, via a Squid 2.7 proxy. Timeouts are all default. We see that the HTTP CONNECT is sent the first time (over http), and thereafter communication is encrypted. The endpoint gets the POST request (does NOT get the first CONNECT). Everything works fine when we send POST requests subsequently. However, between 2 successive POSTs, if we wait for 5 minutes, we see a new CONNECT sent from the client, but the endpoint gets this CONNECT (through SSL). As if Squid uses the existing server connection to relay the CONNECT. The architecture is somewhat like this: Client -> Squid -> Internet -> FW (Cisco) -> LB -> Apache (mod_proxy) -> endpoint (Tomcat) Thoughts? -- View this message in context: http://squid-web-proxy-cache.1019090.n4.nabble.com/Can-Squid-2-7-send-an-HTTP-Connect-to-the-server-tp4661032p4661042.html Sent from the Squid - Users mailing list archive at Nabble.com.