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Network environment: Https Client<=============>Proxy Server<==============>Https Server 192.168.17.11<-----extranet------>192.168.17.22 10.100.21.10<----intranet----->10.100.21.11 ps: Http Client without default gateway, but it can ping to 10.100.21.11 Description: OS: Ubuntu 12.04 on 3 hosts Https Client: Implement with java(openjdk-6).Have one network-interface. Proxy Server: Apache2.2.Have two network-interfaces. Https Server: Tomcat6.Have one network-interface. I use two method to implement httpsurlconnection through proxy: (For facilitate I do not write down about ssl handle function for checking serverTrusted and hostnameVerifier issue.If need I will update.) 1.Proxy class InetSocketAddress proxyInet = new InetSocketAddress("10.100.21.11",80); Proxy proxy = new Proxy(Proxy.Type.HTTP, proxyInet); URL httpsUrl = new URL("https://192.168.17.22:8443/test"); HttpsURLConnection httpsCon = (HttpsURLConnection) httpsUrl.openConnection(proxy); httpsCon.setDoOutput(true); httpsCon.setDoInput(true); httpsCon.setRequestMethod("POST"); OutputStream out = httpsCon.getOutputStream(); OutputStreamWriter owriter = new OutputStreamWriter(out); owriter.write("<request>test</request>"); owriter.flush(); owriter.close(); ... This method workable and I observed packets flow also met my expectation. HttpClient ---> ProxyServer ---> HttpServer But when I use set Pro

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