diff --git a/jetty-server/src/main/java/org/eclipse/jetty/server/session/SessionHandler.java b/jetty-server/src/main/java/org/eclipse/jetty/server/session/SessionHandler.java
index 0165eda509c..c8397ee7570 100644
--- a/jetty-server/src/main/java/org/eclipse/jetty/server/session/SessionHandler.java
+++ b/jetty-server/src/main/java/org/eclipse/jetty/server/session/SessionHandler.java
@@ -370,11 +370,22 @@ public class SessionHandler extends ScopedHandler
         
         if (_sessionListeners!=null)
         {
-            HttpSessionEvent event=new HttpSessionEvent(session);      
-            for (int i = _sessionListeners.size()-1; i>=0; i--)
+            //We annoint the calling thread with
+            //the webapp's classloader because the calling thread may
+            //come from the scavenger, rather than a request thread
+            Runnable r = new Runnable()
             {
-                _sessionListeners.get(i).sessionDestroyed(event);
-            }
+                @Override
+                public void run ()
+                {
+                    HttpSessionEvent event=new HttpSessionEvent(session);
+                    for (int i = _sessionListeners.size()-1; i>=0; i--)
+                    {
+                        _sessionListeners.get(i).sessionDestroyed(event);
+                    }
+                }
+            };
+            _sessionContext.run(r);
         }
     }
     
diff --git a/tests/test-sessions/test-sessions-common/src/main/java/org/eclipse/jetty/server/session/TestHttpSessionListenerWithWebappClasses.java b/tests/test-sessions/test-sessions-common/src/main/java/org/eclipse/jetty/server/session/TestHttpSessionListenerWithWebappClasses.java
new file mode 100644
index 00000000000..9884a214161
--- /dev/null
+++ b/tests/test-sessions/test-sessions-common/src/main/java/org/eclipse/jetty/server/session/TestHttpSessionListenerWithWebappClasses.java
@@ -0,0 +1,61 @@
+//
+//  ========================================================================
+//  Copyright (c) 1995-2019 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.server.session;
+
+import javax.servlet.http.HttpSessionEvent;
+
+/**
+ * TestHttpSessionListenerWithWebappClasses
+ * 
+ * A session listener class that checks that sessionDestroyed
+ * events can reference classes known only to the webapp, ie
+ * that the calling thread has been correctly annointed with 
+ * the webapp loader.
+ *
+ */
+public class TestHttpSessionListenerWithWebappClasses extends TestHttpSessionListener
+{
+    public TestHttpSessionListenerWithWebappClasses()
+    {
+        super();
+    }
+
+    public TestHttpSessionListenerWithWebappClasses(boolean access)
+    {
+        super(access);
+    }
+
+    @Override
+    public void sessionDestroyed(HttpSessionEvent se)
+    {
+        //try loading a class that is known only to the webapp
+        //to test that the calling thread has been properly
+        //annointed with the webapp's classloader
+        try
+        {
+            Class<?> clazz = Thread.currentThread().getContextClassLoader().loadClass("Foo");
+        }
+        catch (Exception cnfe)
+        {
+            ex=cnfe;
+        }
+        super.sessionDestroyed(se);
+    }
+
+}
diff --git a/tests/test-sessions/test-sessions-common/src/test/java/org/eclipse/jetty/server/session/SessionListenerTest.java b/tests/test-sessions/test-sessions-common/src/test/java/org/eclipse/jetty/server/session/SessionListenerTest.java
index 7769ff0b3d6..11f8155bdda 100644
--- a/tests/test-sessions/test-sessions-common/src/test/java/org/eclipse/jetty/server/session/SessionListenerTest.java
+++ b/tests/test-sessions/test-sessions-common/src/test/java/org/eclipse/jetty/server/session/SessionListenerTest.java
@@ -18,9 +18,14 @@
 
 package org.eclipse.jetty.server.session;
 
+import java.io.File;
+import java.io.FileOutputStream;
 import java.io.IOException;
+import java.io.InputStream;
 import java.io.Serializable;
 import java.net.HttpCookie;
+import java.net.URL;
+import java.net.URLClassLoader;
 import java.util.concurrent.TimeUnit;
 import javax.servlet.ServletException;
 import javax.servlet.http.HttpServlet;
@@ -35,6 +40,8 @@ import org.eclipse.jetty.client.api.ContentResponse;
 import org.eclipse.jetty.client.api.Request;
 import org.eclipse.jetty.servlet.ServletContextHandler;
 import org.eclipse.jetty.servlet.ServletHolder;
+import org.eclipse.jetty.toolchain.test.IO;
+import org.eclipse.jetty.toolchain.test.MavenTestingUtils;
 import org.junit.jupiter.api.Test;
 
 import static org.hamcrest.MatcherAssert.assertThat;
@@ -121,13 +128,27 @@ public class SessionListenerTest
 
     
     /**
-     * Test that listeners are called when a session expires.
+     * Test that listeners are called when a session expires
+     * and that the listener is able to access webapp classes.
      * 
      * @throws Exception
      */
     @Test
     public void testSessionExpiresWithListener() throws Exception
     {
+      //Use a class that would only be known to the webapp classloader
+        InputStream foostream = Thread.currentThread().getContextClassLoader().getResourceAsStream("Foo.clazz");
+        File foodir = new File (MavenTestingUtils.getTargetDir(), "foo");
+        foodir.mkdirs();
+        File fooclass = new File (foodir, "Foo.class");
+        IO.copy(foostream, new FileOutputStream(fooclass));
+        
+        assertTrue(fooclass.exists());
+        assertTrue(fooclass.length() != 0);
+        
+        URL[] foodirUrls = new URL[]{foodir.toURI().toURL()};
+        URLClassLoader contextClassLoader = new URLClassLoader(foodirUrls, Thread.currentThread().getContextClassLoader());
+        
         String contextPath = "/";
         String servletMapping = "/server";
         int inactivePeriod = 3;
@@ -143,8 +164,9 @@ public class SessionListenerTest
         TestServlet servlet = new TestServlet();
         ServletHolder holder = new ServletHolder(servlet);
         ServletContextHandler context = server1.addContext(contextPath);
+        context.setClassLoader(contextClassLoader);
         context.addServlet(holder, servletMapping);
-        TestHttpSessionListener listener = new TestHttpSessionListener(true);
+        TestHttpSessionListener listener = new TestHttpSessionListenerWithWebappClasses(true);
         context.getSessionHandler().addEventListener(listener);
         
         server1.start();