diff --git a/demos/demo-proxy-webapp/src/test/java/org/eclipse/jetty/demos/ProxyWebAppTest.java b/demos/demo-proxy-webapp/src/test/java/org/eclipse/jetty/demos/ProxyWebAppTest.java
new file mode 100644
index 00000000000..a9156382f1b
--- /dev/null
+++ b/demos/demo-proxy-webapp/src/test/java/org/eclipse/jetty/demos/ProxyWebAppTest.java
@@ -0,0 +1,96 @@
+//
+//  ========================================================================
+//  Copyright (c) 1995-2020 Mort Bay Consulting Pty Ltd and others.
+//  ------------------------------------------------------------------------
+//  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.demos;
+
+import java.util.concurrent.ExecutionException;
+import java.util.concurrent.TimeoutException;
+
+import org.eclipse.jetty.client.HttpClient;
+import org.eclipse.jetty.client.api.ContentResponse;
+import org.eclipse.jetty.http.HttpStatus;
+import org.eclipse.jetty.server.Server;
+import org.eclipse.jetty.server.ServerConnector;
+import org.eclipse.jetty.toolchain.test.MavenTestingUtils;
+import org.eclipse.jetty.util.component.LifeCycle;
+import org.eclipse.jetty.webapp.WebAppContext;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Tag;
+import org.junit.jupiter.api.Test;
+
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.hamcrest.Matchers.containsString;
+import static org.hamcrest.Matchers.is;
+
+/**
+ * Test the configuration found in WEB-INF/web.xml for purposes of the demo-base
+ */
+public class ProxyWebAppTest
+{
+    private Server server;
+    private HttpClient client;
+
+    @BeforeEach
+    public void setup() throws Exception
+    {
+        server = new Server();
+
+        ServerConnector connector = new ServerConnector(server);
+        connector.setPort(0);
+        server.addConnector(connector);
+
+        WebAppContext webapp = new WebAppContext();
+        // This is a pieced together WebApp.
+        // We don't have a valid WEB-INF/lib to rely on at this point.
+        // So, open up server classes here, for purposes of this testcase.
+        webapp.getServerClassMatcher().add("-org.eclipse.jetty.proxy.");
+        webapp.setWar(MavenTestingUtils.getProjectDirPath("src/main/webapp").toString());
+        webapp.setExtraClasspath(MavenTestingUtils.getTargetPath().resolve("classes").toString());
+        server.setHandler(webapp);
+
+        server.start();
+
+        client = new HttpClient();
+        client.start();
+    }
+
+    @AfterEach
+    public void teardown()
+    {
+        LifeCycle.stop(client);
+        LifeCycle.stop(server);
+    }
+
+    @Test
+    @Tag("external")
+    public void testProxyRequest() throws InterruptedException, ExecutionException, TimeoutException
+    {
+        ContentResponse response = client.newRequest(server.getURI().resolve("/proxy/current/"))
+            .followRedirects(false)
+            .send();
+
+        // Expecting a 200 OK (not a 302 redirect or other error)
+        // If we got an error here, that means our configuration in web.xml is bad / out of date.
+        // Such as the redirect from the eclipse website, we want all of the requests to go through
+        // this proxy configuration, not redirected to the actual website.
+        assertThat("response status", response.getStatus(), is(HttpStatus.OK_200));
+        // Expecting a Javadoc / APIDoc response - look for something unique for APIdoc.
+        assertThat("response", response.getContentAsString(), containsString("All Classes"));
+    }
+}
diff --git a/demos/demo-proxy-webapp/src/test/resources/jetty-logging.properties b/demos/demo-proxy-webapp/src/test/resources/jetty-logging.properties
new file mode 100644
index 00000000000..bf725104bbd
--- /dev/null
+++ b/demos/demo-proxy-webapp/src/test/resources/jetty-logging.properties
@@ -0,0 +1,5 @@
+org.eclipse.jetty.util.log.class=org.eclipse.jetty.util.log.StdErrLog
+#org.eclipse.jetty.LEVEL=WARN
+#org.eclipse.jetty.client.LEVEL=DEBUG
+#org.eclipse.jetty.http.LEVEL=DEBUG
+#org.eclipse.jetty.proxy.LEVEL=DEBUG