Index: magnolia-core/src/main/java/info/magnolia/cms/beans/config/PropertiesInitializer.java
===================================================================
--- magnolia-core/src/main/java/info/magnolia/cms/beans/config/PropertiesInitializer.java	(revision 32016)
+++ magnolia-core/src/main/java/info/magnolia/cms/beans/config/PropertiesInitializer.java	(working copy)
@@ -106,8 +106,10 @@
      * Default value for the MAGNOLIA_INITIALIZATION_FILE parameter.
      */
     public static final String DEFAULT_INITIALIZATION_PARAMETER = //
-    "WEB-INF/config/${servername}/${webapp}/magnolia.properties," //$NON-NLS-1$
+    "WEB-INF/config/${servername}/${contextPath}/magnolia.properties," //$NON-NLS-1$
+        + "WEB-INF/config/${servername}/${webapp}/magnolia.properties," //$NON-NLS-1$
         + "WEB-INF/config/${servername}/magnolia.properties," //$NON-NLS-1$
+        + "WEB-INF/config/${contextPath}/magnolia.properties," //$NON-NLS-1$
         + "WEB-INF/config/${webapp}/magnolia.properties," //$NON-NLS-1$
         + "WEB-INF/config/default/magnolia.properties," //$NON-NLS-1$
         + "WEB-INF/config/magnolia.properties"; //$NON-NLS-1$
@@ -300,6 +302,10 @@
         propertiesFilesString = StringUtils.replace(propertiesFilesString, "${servername}", servername); //$NON-NLS-1$
         propertiesFilesString = StringUtils.replace(propertiesFilesString, "${webapp}", webapp); //$NON-NLS-1$
 
+        if (atLeastServlet25(context)) {
+            propertiesFilesString = StringUtils.replace(propertiesFilesString, "${contextPath}", context.getContextPath()); //$NON-NLS-1$
+        }
+
         // Replacing servlet context attributes (${contextAttribute/something})
         final String contextAttributePlaceHolder = PLACEHOLDER_PREFIX + CONTEXT_ATTRIBUTE_PLACEHOLDER_PREFIX;
         String[] contextAttributes = StringUtils.stripAll(StringUtils.substringsBetween(
@@ -404,4 +410,13 @@
         return buf.toString();
     }
 
+    public static boolean atLeastServlet25(ServletContext context) {
+        final int major = context.getMajorVersion();
+        if (major == 2) {
+            return context.getMinorVersion() >= 5;
+        } else {
+            return major > 2;
+        }
+    }
+
 }