diff --git a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpClient.java b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpClient.java
index 224c16d464c..d4fc27fb973 100644
--- a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpClient.java
+++ b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpClient.java
@@ -46,6 +46,7 @@ import org.eclipse.jetty.client.api.Destination;
 import org.eclipse.jetty.client.api.Request;
 import org.eclipse.jetty.client.api.Response;
 import org.eclipse.jetty.http.HttpFields;
+import org.eclipse.jetty.http.HttpHeader;
 import org.eclipse.jetty.http.HttpMethod;
 import org.eclipse.jetty.io.ByteBufferPool;
 import org.eclipse.jetty.io.EndPoint;
@@ -273,7 +274,13 @@ public class HttpClient extends ContainerLifeCycle
                 .version(oldRequest.getVersion())
                 .content(oldRequest.getContent());
         for (HttpFields.Field header : oldRequest.getHeaders())
+        {
+            // We have a new URI, so skip the host header if present
+            if (HttpHeader.HOST == header.getHeader())
+                continue;
+
             newRequest.header(header.getName(), header.getValue());
+        }
         return newRequest;
     }
 
diff --git a/jetty-client/src/test/java/org/eclipse/jetty/client/ExternalSiteTest.java b/jetty-client/src/test/java/org/eclipse/jetty/client/ExternalSiteTest.java
new file mode 100644
index 00000000000..e21b73f5f13
--- /dev/null
+++ b/jetty-client/src/test/java/org/eclipse/jetty/client/ExternalSiteTest.java
@@ -0,0 +1,85 @@
+//
+//  ========================================================================
+//  Copyright (c) 1995-2012 Mort Bay Consulting Pty. Ltd.
+//  ------------------------------------------------------------------------
+//  All rights reserved. This program and the accompanying materials
+//  are made available under the terms of the Eclipse Public License v1.0
+//  and Apache License v2.0 which accompanies this distribution.
+//
+//      The Eclipse Public License is available at
+//      http://www.eclipse.org/legal/epl-v10.html
+//
+//      The Apache License v2.0 is available at
+//      http://www.opensource.org/licenses/apache2.0.php
+//
+//  You may elect to redistribute this code under either of these licenses.
+//  ========================================================================
+//
+
+package org.eclipse.jetty.client;
+
+import java.io.IOException;
+import java.net.Socket;
+import java.util.concurrent.CountDownLatch;
+import java.util.concurrent.TimeUnit;
+
+import org.eclipse.jetty.client.api.Response;
+import org.eclipse.jetty.client.api.Result;
+import org.eclipse.jetty.toolchain.test.TestTracker;
+import org.junit.After;
+import org.junit.Assert;
+import org.junit.Assume;
+import org.junit.Before;
+import org.junit.Rule;
+import org.junit.Test;
+
+public class ExternalSiteTest
+{
+    @Rule
+    public final TestTracker tracker = new TestTracker();
+
+    private HttpClient client;
+
+    @Before
+    public void prepare() throws Exception
+    {
+        client = new HttpClient();
+        client.start();
+    }
+
+    @After
+    public void dispose() throws Exception
+    {
+        client.stop();
+    }
+
+    @Test
+    public void testExternalSite() throws Exception
+    {
+        String host = "wikipedia.org";
+        int port = 80;
+
+        // Verify that we have connectivity
+        try
+        {
+            new Socket(host, port);
+        }
+        catch (IOException x)
+        {
+            Assume.assumeNoException(x);
+        }
+
+        final CountDownLatch latch = new CountDownLatch(1);
+        client.newRequest(host, port).send(new Response.CompleteListener()
+        {
+            @Override
+            public void onComplete(Result result)
+            {
+                if (!result.isFailed() && result.getResponse().getStatus() == 200)
+                    latch.countDown();
+            }
+        });
+
+        Assert.assertTrue(latch.await(10, TimeUnit.SECONDS));
+    }
+}