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 c9ce6f258ed1..e6e71096bd69 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
@@ -562,7 +562,13 @@ protected Origin createOrigin(String scheme, String host, int port, Object tag)
         return new Origin(scheme, host, port, tag);
     }
 
-    protected HttpDestination resolveDestination(Origin origin)
+    /**
+     * <p>Returns, creating it if absent, the destination with the given origin.</p>
+     *
+     * @param origin the origin that identifies the destination
+     * @return the destination for the given origin
+     */
+    public HttpDestination resolveDestination(Origin origin)
     {
         return destinations.computeIfAbsent(origin, o ->
         {
diff --git a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java
index 6930ca19b6b7..8ab4f21e1f79 100644
--- a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java
+++ b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java
@@ -120,7 +120,13 @@ protected void normalizeRequest(Request request)
         if (version.getVersion() <= 11)
         {
             if (!headers.containsKey(HttpHeader.HOST.asString()))
-                headers.put(getHttpDestination().getHostField());
+            {
+                URI uri = request.getURI();
+                if (uri != null)
+                    headers.put(HttpHeader.HOST, uri.getAuthority());
+                else
+                    headers.put(getHttpDestination().getHostField());
+            }
         }
 
         // Add content headers
diff --git a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpDestination.java b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpDestination.java
index fd8ae0bb52b5..c8866e6dc00e 100644
--- a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpDestination.java
+++ b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpDestination.java
@@ -253,15 +253,13 @@ public void failed(Throwable x)
         abort(x);
     }
 
+    public void send(Request request, Response.CompleteListener listener)
+    {
+        ((HttpRequest)request).sendAsync(this, listener);
+    }
+
     protected void send(HttpRequest request, List<Response.ResponseListener> listeners)
     {
-        if (!getScheme().equalsIgnoreCase(request.getScheme()))
-            throw new IllegalArgumentException("Invalid request scheme " + request.getScheme() + " for destination " + this);
-        if (!getHost().equalsIgnoreCase(request.getHost()))
-            throw new IllegalArgumentException("Invalid request host " + request.getHost() + " for destination " + this);
-        int port = request.getPort();
-        if (port >= 0 && getPort() != port)
-            throw new IllegalArgumentException("Invalid request port " + port + " for destination " + this);
         send(new HttpExchange(this, request, listeners));
     }
 
diff --git a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java
index 53750ad0f2a6..2a373e288b02 100644
--- a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java
+++ b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java
@@ -40,6 +40,7 @@
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.TimeoutException;
 import java.util.concurrent.atomic.AtomicReference;
+import java.util.function.BiConsumer;
 import java.util.function.BiFunction;
 import java.util.function.LongConsumer;
 import java.util.function.Supplier;
@@ -722,7 +723,7 @@ public Request timeout(long timeout, TimeUnit unit)
     public ContentResponse send() throws InterruptedException, TimeoutException, ExecutionException
     {
         FutureResponseListener listener = new FutureResponseListener(this);
-        send(this, listener);
+        send(listener);
 
         try
         {
@@ -761,15 +762,20 @@ public ContentResponse send() throws InterruptedException, TimeoutException, Exe
     @Override
     public void send(Response.CompleteListener listener)
     {
-        send(this, listener);
+        sendAsync(client::send, listener);
     }
 
-    private void send(HttpRequest request, Response.CompleteListener listener)
+    void sendAsync(HttpDestination destination, Response.CompleteListener listener)
+    {
+        sendAsync(destination::send, listener);
+    }
+
+    private void sendAsync(BiConsumer<HttpRequest, List<Response.ResponseListener>> sender, Response.CompleteListener listener)
     {
         if (listener != null)
             responseListeners.add(listener);
         sent();
-        client.send(request, responseListeners);
+        sender.accept(this, responseListeners);
     }
 
     void sent()
diff --git a/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/HttpClientTest.java b/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/HttpClientTest.java
index ccc977159cc9..7e58db34ce7e 100644
--- a/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/HttpClientTest.java
+++ b/tests/test-http-client-transport/src/test/java/org/eclipse/jetty/http/client/HttpClientTest.java
@@ -36,6 +36,8 @@
 import javax.servlet.http.HttpServletRequest;
 import javax.servlet.http.HttpServletResponse;
 
+import org.eclipse.jetty.client.HttpDestination;
+import org.eclipse.jetty.client.Origin;
 import org.eclipse.jetty.client.api.ContentResponse;
 import org.eclipse.jetty.client.api.Destination;
 import org.eclipse.jetty.client.api.Response;
@@ -44,7 +46,9 @@
 import org.eclipse.jetty.client.util.InputStreamResponseListener;
 import org.eclipse.jetty.http.HttpHeader;
 import org.eclipse.jetty.http.HttpMethod;
+import org.eclipse.jetty.http.HttpScheme;
 import org.eclipse.jetty.http.HttpStatus;
+import org.eclipse.jetty.http.HttpURI;
 import org.eclipse.jetty.http2.FlowControlStrategy;
 import org.eclipse.jetty.server.Request;
 import org.eclipse.jetty.server.handler.AbstractHandler;
@@ -733,6 +737,46 @@ protected void service(String target, Request jettyRequest, HttpServletRequest r
         assertEquals(1, scenario.client.getDestinations().size());
     }
 
+    @ParameterizedTest
+    @ArgumentsSource(TransportProvider.class)
+    public void testRequestWithDifferentDestination(Transport transport) throws Exception
+    {
+        init(transport);
+
+        String requestScheme = HttpScheme.HTTPS.is(scenario.getScheme()) ? "http" : "https";
+        String requestHost = "otherHost.com";
+        int requestPort = 8888;
+        scenario.start(new EmptyServerHandler()
+        {
+            @Override
+            protected void service(String target, Request jettyRequest, HttpServletRequest request, HttpServletResponse response)
+            {
+                HttpURI uri = jettyRequest.getHttpURI();
+                assertEquals(requestHost, uri.getHost());
+                assertEquals(requestPort, uri.getPort());
+                if (scenario.transport == Transport.H2C || scenario.transport == Transport.H2)
+                    assertEquals(requestScheme, request.getScheme());
+            }
+        });
+
+        Origin origin = new Origin(scenario.getScheme(), "localhost", scenario.getNetworkConnectorLocalPortInt().get());
+        HttpDestination destination = scenario.client.resolveDestination(origin);
+
+        org.eclipse.jetty.client.api.Request request = scenario.client.newRequest(requestHost, requestPort)
+            .scheme(requestScheme)
+            .path("/path");
+
+        CountDownLatch resultLatch = new CountDownLatch(1);
+        destination.send(request, result ->
+        {
+            assertTrue(result.isSucceeded());
+            assertEquals(HttpStatus.OK_200, result.getResponse().getStatus());
+            resultLatch.countDown();
+        });
+
+        assertTrue(resultLatch.await(5, TimeUnit.SECONDS));
+    }
+
     private void sleep(long time) throws IOException
     {
         try