Index: java/org/apache/catalina/loader/WebappClassLoader.java
===================================================================
--- java/org/apache/catalina/loader/WebappClassLoader.java	(revision 683845)
+++ java/org/apache/catalina/loader/WebappClassLoader.java	(working copy)
@@ -1617,7 +1617,29 @@
         // Null out any static or final fields from loaded classes,
         // as a workaround for apparent garbage collection bugs
         if (ENABLE_CLEAR_REFERENCES) {
-            Iterator loadedClasses = ((HashMap) resourceEntries.clone()).values().iterator();
+            java.util.Collection values = ((HashMap) resourceEntries.clone()).values();
+            Iterator loadedClasses = values.iterator();
+            //
+            // walk through all loaded class to trigger initialization for
+            //    any uninitialized classes, otherwise initialization of
+            //    one class may call a previously cleared class.
+            while(loadedClasses.hasNext()) {
+                ResourceEntry entry = (ResourceEntry) loadedClasses.next();
+                if (entry.loadedClass != null) {
+                    Class clazz = entry.loadedClass;
+                    try {
+                        Field[] fields = clazz.getDeclaredFields();
+                        for (int i = 0; i < fields.length; i++) {
+                            if(Modifier.isStatic(fields[i].getModifiers())) {
+                                fields[i].get(null);
+                                break;
+                            }
+                        }
+                    } catch(Throwable t) {
+                    }
+                }
+            }
+            loadedClasses = values.iterator();
             while (loadedClasses.hasNext()) {
                 ResourceEntry entry = (ResourceEntry) loadedClasses.next();
                 if (entry.loadedClass != null) {