Further research: There's a utility called http-ping.exe that pings http for a response. This shows a timeout from location 2 to location 1 calling google.com through the proxy. Vice versa, no timeout. *From Location 1 --> 2* <http://squid-web-proxy-cache.1019090.n4.nabble.com/file/n4664343/loc1-2.png> *From Location 2 --> 1* <http://squid-web-proxy-cache.1019090.n4.nabble.com/file/n4664343/loc2-1.png> -- View this message in context: http://squid-web-proxy-cache.1019090.n4.nabble.com/Issue-with-Web-Traffic-through-IPSEC-Tunnel-to-a-Squid-Proxy-tp4664319p4664343.html Sent from the Squid - Users mailing list archive at Nabble.com.