diff --git a/http/base/src/main/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistry.java b/http/base/src/main/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistry.java
index c6b1f4d..6221f47 100644
--- a/http/base/src/main/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistry.java
+++ b/http/base/src/main/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistry.java
@@ -46,7 +46,7 @@
     private final int ranking;
 
     private final String path;
-    
+
     private final String prefix;
 
     public PerContextHandlerRegistry() {
@@ -61,7 +61,7 @@
         this.serviceId = info.getServiceId();
         this.ranking = info.getRanking();
         this.path = info.getPath();
-        if ( this.path.equals("/") ) 
+        if ( this.path.equals("/") )
         {
         	prefix = null;
         }
@@ -87,7 +87,7 @@
     @Override
     public int compareTo(final PerContextHandlerRegistry other)
     {
-        final int result = other.path.compareTo(this.path);
+        final int result = ((Integer)other.path.length()).compareTo(this.path.length());
         if ( result == 0 ) {
             if (other.ranking == this.ranking)
             {
diff --git a/http/base/src/test/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistryTest.java b/http/base/src/test/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistryTest.java
new file mode 100644
index 0000000..2cad3ba
--- /dev/null
+++ b/http/base/src/test/java/org/apache/felix/http/base/internal/handler/PerContextHandlerRegistryTest.java
@@ -0,0 +1,83 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one or more
+ * contributor license agreements.  See the NOTICE file distributed with
+ * this work for additional information regarding copyright ownership.
+ * The ASF licenses this file to You under the Apache License, Version 2.0
+ * (the "License"); you may not use this file except in compliance with
+ * the License.  You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.apache.felix.http.base.internal.handler;
+
+import static org.junit.Assert.assertEquals;
+import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.when;
+
+import java.util.ArrayList;
+import java.util.Collections;
+import java.util.List;
+
+import org.apache.felix.http.base.internal.runtime.ServletContextHelperInfo;
+import org.junit.Test;
+import org.osgi.framework.Constants;
+import org.osgi.framework.ServiceReference;
+import org.osgi.service.http.context.ServletContextHelper;
+import org.osgi.service.http.whiteboard.HttpWhiteboardConstants;
+
+/**
+ * Test for the ordering of servlet contexts
+ */
+public class PerContextHandlerRegistryTest
+{
+
+    @Test public void testPathOrdering()
+    {
+        final List<PerContextHandlerRegistry> list = new ArrayList<PerContextHandlerRegistry>();
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/", 1L, 0)));
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/foo", 2L, 0)));
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/", 3L, 0)));
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/bar", 4L, 0)));
+
+        Collections.sort(list);
+
+        assertEquals(2L, list.get(0).getContextServiceId());
+        assertEquals(4L, list.get(1).getContextServiceId());
+        assertEquals(1L, list.get(2).getContextServiceId());
+        assertEquals(3L, list.get(3).getContextServiceId());
+    }
+
+    @Test public void testRankingOrdering()
+    {
+        final List<PerContextHandlerRegistry> list = new ArrayList<PerContextHandlerRegistry>();
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/", 1L, 0)));
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/", 2L, 0)));
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/", 3L, -30)));
+        list.add(new PerContextHandlerRegistry(createServletContextHelperInfo("/", 4L, 50)));
+
+        Collections.sort(list);
+
+        assertEquals(4L, list.get(0).getContextServiceId());
+        assertEquals(1L, list.get(1).getContextServiceId());
+        assertEquals(2L, list.get(2).getContextServiceId());
+        assertEquals(3L, list.get(3).getContextServiceId());
+    }
+
+    private ServletContextHelperInfo createServletContextHelperInfo(final String path,
+            final long serviceId,
+            final int ranking)
+    {
+        final ServiceReference<ServletContextHelper> ref = mock(ServiceReference.class);
+        when(ref.getProperty(Constants.SERVICE_ID)).thenReturn(serviceId);
+        when(ref.getProperty(Constants.SERVICE_RANKING)).thenReturn(ranking);
+        when(ref.getProperty(HttpWhiteboardConstants.HTTP_WHITEBOARD_CONTEXT_PATH)).thenReturn(path);
+        when(ref.getPropertyKeys()).thenReturn(new String[0]);
+        return new ServletContextHelperInfo(ref);
+    }
+}