diff --git a/jetty-util/src/main/java/org/eclipse/jetty/util/ArrayTernaryTrie.java b/jetty-util/src/main/java/org/eclipse/jetty/util/ArrayTernaryTrie.java
index db4ea9909c5..f1d86de3783 100644
--- a/jetty-util/src/main/java/org/eclipse/jetty/util/ArrayTernaryTrie.java
+++ b/jetty-util/src/main/java/org/eclipse/jetty/util/ArrayTernaryTrie.java
@@ -630,15 +630,16 @@ public class ArrayTernaryTrie<V> extends AbstractTrie<V>
         public boolean put(String s, V v)
         {
             boolean added = _trie.put(s,v);
-            while (!added)
+            while (!added && _growby>0)
             {
                 ArrayTernaryTrie<V> bigger = new ArrayTernaryTrie<>(_trie._key.length+_growby);
                 for (Map.Entry<String,V> entry : _trie.entrySet())
                     bigger.put(entry.getKey(),entry.getValue());
+                _trie = bigger;
                 added = _trie.put(s,v);
             }
             
-            return true;
+            return added;
         }
 
         public V get(String s, int offset, int len)
diff --git a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/ClasspathPattern.java b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/ClasspathPattern.java
index 6385a310934..9e7fd968456 100644
--- a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/ClasspathPattern.java
+++ b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/ClasspathPattern.java
@@ -180,8 +180,7 @@ public class ClasspathPattern extends AbstractSet<String>
             if (_entries.get(name)!=null)
                 return false;
             
-            _entries.put(name,entry);
-            return true;
+            return _entries.put(name,entry);
         }
         
         @Override
diff --git a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/ClasspathPatternTest.java b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/ClasspathPatternTest.java
index 9ccf88c935e..47c195dffe0 100644
--- a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/ClasspathPatternTest.java
+++ b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/ClasspathPatternTest.java
@@ -228,4 +228,21 @@ public class ClasspathPatternTest
         assertThat(pattern.match(JDK.class),is(true));
         assertThat(pattern.match(ClasspathPatternTest.class),is(false));
     }
+    
+
+    
+    @Test
+    public void testLarge()
+    {
+        ClasspathPattern pattern = new ClasspathPattern();
+        for (int i=0; i<500; i++)
+        {
+            assertTrue(pattern.add("n"+i+"."+Integer.toHexString(100+i)+".Name"));
+        }
+        
+        for (int i=0; i<500; i++)
+        {
+            assertTrue(pattern.match("n"+i+"."+Integer.toHexString(100+i)+".Name"));
+        }
+    }
 }