diff --git a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebAppClassLoader.java b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebAppClassLoader.java
index 13770b2f15d..50704352c5f 100644
--- a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebAppClassLoader.java
+++ b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebAppClassLoader.java
@@ -279,12 +279,20 @@ public class WebAppClassLoader extends URLClassLoader
         StringTokenizer tokenizer= new StringTokenizer(classPath, ",;");
         while (tokenizer.hasMoreTokens())
         {
-            Resource resource= _context.newResource(tokenizer.nextToken().trim());
+            String token = tokenizer.nextToken().trim();
+            Resource resource= _context.newResource(token);
             if (LOG.isDebugEnabled())
                 LOG.debug("Path resource=" + resource);
 
-            // Add the resource
-            if (resource.isDirectory() && resource instanceof ResourceCollection)
+            if(token.endsWith("*"))
+            {
+                if(token.length() > 1)
+                {
+                    token = token.substring(0, token.length() - 1);
+                    resource= _context.newResource(token);
+                    addJars(resource);
+                }
+            } else if (resource.isDirectory() && resource instanceof ResourceCollection)
                 addClassPath(resource);
             else
             {
diff --git a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebAppClassLoaderTest.java b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebAppClassLoaderTest.java
index 2dd052775ce..ea56302f0f0 100644
--- a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebAppClassLoaderTest.java
+++ b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebAppClassLoaderTest.java
@@ -65,6 +65,7 @@ public class WebAppClassLoaderTest
         _context = new WebAppContext();
         _context.setBaseResource(webapp);
         _context.setContextPath("/test");
+        _context.setExtraClasspath("src/test/resources/ext/*");
 
         _loader = new WebAppClassLoader(_context);
         _loader.addJars(webapp.addPath("WEB-INF/lib"));
@@ -105,6 +106,10 @@ public class WebAppClassLoaderTest
         assertCanLoadClass("org.acme.webapp.ClassInJarB");
         assertCanLoadClass("org.acme.other.ClassInClassesC");
 
+        assertCanLoadClass("org.acme.extone.Main");
+        assertCanLoadClass("org.acme.exttwo.Main");
+        assertCantLoadClass("org.acme.extthree.Main");
+
         assertCantLoadClass("org.eclipse.jetty.webapp.Configuration");
 
         Class<?> clazzA = _loader.loadClass("org.acme.webapp.ClassInJarA");
@@ -119,6 +124,10 @@ public class WebAppClassLoaderTest
         assertCanLoadClass("org.acme.webapp.ClassInJarB");
         assertCanLoadClass("org.acme.other.ClassInClassesC");
 
+        assertCanLoadClass("org.acme.extone.Main");
+        assertCanLoadClass("org.acme.exttwo.Main");
+        assertCantLoadClass("org.acme.extthree.Main");
+
         assertCantLoadClass("org.eclipse.jetty.webapp.Configuration");
 
         Class<?> clazzA = _loader.loadClass("org.acme.webapp.ClassInJarA");
diff --git a/jetty-webapp/src/test/resources/ext/org-acme-ext-one.jar b/jetty-webapp/src/test/resources/ext/org-acme-ext-one.jar
new file mode 100644
index 00000000000..e52c47a83d8
Binary files /dev/null and b/jetty-webapp/src/test/resources/ext/org-acme-ext-one.jar differ
diff --git a/jetty-webapp/src/test/resources/ext/org-acme-ext-two.jar b/jetty-webapp/src/test/resources/ext/org-acme-ext-two.jar
new file mode 100644
index 00000000000..f46fb20ad35
Binary files /dev/null and b/jetty-webapp/src/test/resources/ext/org-acme-ext-two.jar differ
diff --git a/jetty-webapp/src/test/resources/ext/sub/org-acme-ext-three.jar b/jetty-webapp/src/test/resources/ext/sub/org-acme-ext-three.jar
new file mode 100644
index 00000000000..11a24abab72
Binary files /dev/null and b/jetty-webapp/src/test/resources/ext/sub/org-acme-ext-three.jar differ