Index: src/main/java/hudson/plugins/jabber/im/transport/JabberPublisherDescriptor.java
===================================================================
--- src/main/java/hudson/plugins/jabber/im/transport/JabberPublisherDescriptor.java	(revision 36597)
+++ src/main/java/hudson/plugins/jabber/im/transport/JabberPublisherDescriptor.java	(working copy)
@@ -533,8 +533,9 @@
             iPort = Integer.parseInt(port);
         }
         
-        Socket s = new Socket(address, iPort);
-        s.close();
+        //remove this check as it can't succeed
+        //Socket s = new Socket(address, iPort);
+        //s.close();
     }
 
     /**
Index: src/main/java/hudson/plugins/jabber/im/transport/JabberIMConnection.java
===================================================================
--- src/main/java/hudson/plugins/jabber/im/transport/JabberIMConnection.java	(revision 36597)
+++ src/main/java/hudson/plugins/jabber/im/transport/JabberIMConnection.java	(working copy)
@@ -3,7 +3,13 @@
  */
 package hudson.plugins.jabber.im.transport;
 
+import java.io.IOException;
+import java.io.InputStream;
+import java.io.PrintStream;
 import java.lang.ref.WeakReference;
+import java.net.InetAddress;
+import java.net.Socket;
+import java.net.UnknownHostException;
 import java.util.HashMap;
 import java.util.HashSet;
 import java.util.Map;
@@ -12,6 +18,8 @@
 import java.util.concurrent.TimeUnit;
 import java.util.logging.Logger;
 
+import javax.net.SocketFactory;
+import javax.net.ssl.SSLSocket;
 import javax.net.ssl.SSLSocketFactory;
 
 import org.jivesoftware.smack.Chat;
@@ -225,6 +233,11 @@
 					this.hostname, this.port,
 					serviceName);
 		}
+		
+		if ("talk.google.com".equals(this.hostname) && 443 == this.port) {
+			cfg.setSocketFactory(new GTalkSocketFactory());
+		}
+		
 		// Currently, we handle reconnects ourself.
 		// Maybe we should change it in the future, but currently I'm
 		// not sure what Smack's reconnect feature really does.
@@ -589,4 +602,73 @@
 			}
 		}
 	};
+
+	public static class GTalkSocketFactory extends SocketFactory {
+		
+		static Logger logger = Logger.getLogger(GTalkSocketFactory.class.getName());
+	
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public Socket createSocket(String host, int port) throws IOException, UnknownHostException {
+		    String request = "CONNECT " + host + ":" + port + " HTTP/1.0\r\n\r\n";
+		    logger.fine(request);
+		    Socket sock = new Socket("192.168.105.3", 3128);
+		    PrintStream ps = new PrintStream(sock.getOutputStream());
+		    ps.print(request);
+		    ps.flush();
+		    
+		    InputStream in = sock.getInputStream();
+	        int c = 0;
+	        //looking for \r\n\r\n sequence
+	        int look = '\r';
+	        int count = 0;
+	        while (count != 4) {
+	            c = in.read();
+	            if (c == look) {
+	                look = (look == '\r' ? '\n' : '\r');
+	                count++;
+	            } else {
+	                //reset to 0
+	                count = 0;
+	            }
+	            //System.out.print((char) c);
+	        }
+	        
+	        SSLSocketFactory ssf = (SSLSocketFactory) SSLSocketFactory.getDefault();
+	        SSLSocket ssl = (SSLSocket) ssf.createSocket(sock, host, port, true);
+	        ssl.startHandshake();
+	        logger.info("Completed SSL Handshake");            
+			return ssl;
+		}
+	
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public Socket createSocket(InetAddress host, int port) throws IOException {
+			return null;
+		}
+	
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public Socket createSocket(String arg0, int arg1, InetAddress arg2, int arg3)
+				throws IOException, UnknownHostException {
+			return null;
+		}
+	
+		/**
+		 * {@inheritDoc}
+		 */
+		@Override
+		public Socket createSocket(InetAddress arg0, int arg1, InetAddress arg2, int arg3)
+				throws IOException {
+			return null;
+		}
+	
 }
+
+}