How do a send an HTTPS request through a proxy in Java?

HTTPS proxy doesn’t make sense because you can’t terminate your HTTP connection at the proxy for security reasons. With your trust policy, it might work if the proxy server has a HTTPS port. Your error is caused by connecting to HTTP proxy port with HTTPS.

You can connect through a proxy using SSL tunneling (many people call that proxy) using proxy CONNECT command. However, Java doesn’t support newer version of proxy tunneling. In that case, you need to handle the tunneling yourself. You can find sample code here,

http://www.javaworld.com/javaworld/javatips/jw-javatip111.html

EDIT: If you want defeat all the security measures in JSSE, you still need your own TrustManager. Something like this,

 public SSLTunnelSocketFactory(String proxyhost, String proxyport){
      tunnelHost = proxyhost;
      tunnelPort = Integer.parseInt(proxyport);
      dfactory = (SSLSocketFactory)sslContext.getSocketFactory();
 }

 ...

 connection.setSSLSocketFactory( new SSLTunnelSocketFactory( proxyHost, proxyPort ) );
 connection.setDefaultHostnameVerifier( new HostnameVerifier()
 {
    public boolean verify( String arg0, SSLSession arg1 )
    {
        return true;
    }
 }  );

EDIT 2: I just tried my program I wrote a few years ago using SSLTunnelSocketFactory and it doesn’t work either. Apparently, Sun introduced a new bug sometime in Java 5. See this bug report,

http://bugs.sun.com/view_bug.do?bug_id=6614957

The good news is that the SSL tunneling bug is fixed so you can just use the default factory. I just tried with a proxy and everything works as expected. See my code,

public class SSLContextTest {

    public static void main(String[] args) {

        System.setProperty("https.proxyHost", "proxy.xxx.com");
        System.setProperty("https.proxyPort", "8888");

        try {

            SSLContext sslContext = SSLContext.getInstance("SSL");

            // set up a TrustManager that trusts everything
            sslContext.init(null, new TrustManager[] { new X509TrustManager() {
                public X509Certificate[] getAcceptedIssuers() {
                    System.out.println("getAcceptedIssuers =============");
                    return null;
                }

                public void checkClientTrusted(X509Certificate[] certs,
                        String authType) {
                    System.out.println("checkClientTrusted =============");
                }

                public void checkServerTrusted(X509Certificate[] certs,
                        String authType) {
                    System.out.println("checkServerTrusted =============");
                }
            } }, new SecureRandom());

            HttpsURLConnection.setDefaultSSLSocketFactory(
                    sslContext.getSocketFactory());

            HttpsURLConnection
                    .setDefaultHostnameVerifier(new HostnameVerifier() {
                        public boolean verify(String arg0, SSLSession arg1) {
                            System.out.println("hostnameVerifier =============");
                            return true;
                        }
                    });

            URL url = new URL("https://www.verisign.net");
            URLConnection conn = url.openConnection();
            BufferedReader reader = 
                new BufferedReader(new InputStreamReader(conn.getInputStream()));
            String line;
            while ((line = reader.readLine()) != null) {
                System.out.println(line);
            }
        } catch (Exception e) {
            e.printStackTrace();
        } 
    }
}

This is what I get when I run the program,

checkServerTrusted =============
hostnameVerifier =============
<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.1//EN" "http://www.w3.org/TR/xhtml11/DTD/xhtml11.dtd">
......

As you can see, both SSLContext and hostnameVerifier are getting called. HostnameVerifier is only involved when the hostname doesn’t match the cert. I used “www.verisign.net” to trigger this.

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