I am attempting to debug the problem I am hitting. Looking at this, I am not sure if squid or target server doesn't like client's ssl handshaking request. Also, I am not sure how to interpret local or remote addresses as what says remote is the client machine that is trying to acces the target site which is identified as local. Also, if you could shed some light as to what these messages are all about, I would greatly appreciate it. 2013/01/31 12:11:38.007 kid1| TcpAcceptor.cc(197) doAccept: New connection on FD 29 2013/01/31 12:11:38.009 kid1| TcpAcceptor.cc(272) acceptNext: connection on local=0.0.0.0:3229 remote=[::] FD 29 flags=41 2013/01/31 12:11:38.014 kid1| client_side.cc(2582) clientProcessRequest: clientProcessRequest: Invalid Request 2013/01/31 12:11:38.017 kid1| errorpage.cc(1282) BuildContent: No existing error page language negotiated for ERR_INVALID_REQ. Using default error file. 2013/01/31 12:11:38.019 kid1| store.cc(994) checkCachable: StoreEntry::checkCachable: NO: not cachable 2013/01/31 12:11:38.022 kid1| client_side_reply.cc(1966) processReplyAccessResult: The reply for NONE error:invalid-request is ALLOWED, because it matched 'NO ACL's' 2013/01/31 12:11:38.024 kid1| client_side.cc(1386) sendStartOfMessage: HTTP Client local=173.194.75.106:443 remote=192.168.5.35:38723 FD 11 flags=33 2013/01/31 12:11:38.026 kid1| client_side.cc(1387) sendStartOfMessage: HTTP Client REPLY: --------- HTTP/1.1 400 Bad Request Server: squid Mime-Version: 1.0 Date: Thu, 31 Jan 2013 17:11:38 GMT Content-Type: text/html Content-Length: 3662 X-Squid-Error: ERR_INVALID_REQ 0 Vary: Accept-Language Content-Language: en X-Cache: MISS from server X-Cache-Lookup: NONE from server:80 Via: 1.1 server (squid) Connection: close Thanks in advance