Index: magnolia-core/pom.xml
===================================================================
--- magnolia-core/pom.xml	(revision Local version)
+++ magnolia-core/pom.xml	(revision Shelved version)
@@ -141,6 +141,7 @@
     <dependency>
       <groupId>javax.servlet</groupId>
       <artifactId>servlet-api</artifactId>
+      <version>2.5</version>
       <scope>provided</scope>
     </dependency>
     <dependency>
Index: magnolia-core/src/test/java/info/magnolia/cms/beans/config/PropertiesInitializerTest.java
===================================================================
--- magnolia-core/src/test/java/info/magnolia/cms/beans/config/PropertiesInitializerTest.java	(revision Local version)
+++ magnolia-core/src/test/java/info/magnolia/cms/beans/config/PropertiesInitializerTest.java	(revision Shelved version)
@@ -39,8 +39,9 @@
 import java.io.File;
 import java.net.URL;
 
-import com.mockrunner.mock.web.MockServletContext;
+import javax.servlet.ServletContext;
 
+import static org.easymock.EasyMock.*;
 
 /**
  * @author fgiust
@@ -89,27 +90,79 @@
     }
 
     public void testFileResolution() {
+        ServletContext ctx = createMock(ServletContext.class);
+        expect(ctx.getMajorVersion()).andReturn(2);
+        expect(ctx.getMinorVersion()).andReturn(4);
+        replay(ctx);
+        String replaced = PropertiesInitializer.processPropertyFilesString(
+            ctx,
+            "xserver",
+            "xwebapp",
+            PropertiesInitializer.DEFAULT_INITIALIZATION_PARAMETER);
 
-        MockServletContext ctx = new MockServletContext();
+        assertEquals("WEB-INF/config/xserver/${contextPath}/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/xserver/xwebapp/magnolia.properties,"
+            + "WEB-INF/config/xserver/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/${contextPath}/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/xwebapp/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/default/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/magnolia.properties", replaced);
+        verify(ctx);
+    }
+
+    public void testFileResolutionWithServlet25() {
+        ServletContext ctx = createMock(ServletContext.class);
+        expect(ctx.getMajorVersion()).andReturn(2);
+        expect(ctx.getMinorVersion()).andReturn(5);
+        expect(ctx.getContextPath()).andReturn("myContextPath");
+        replay(ctx);
         String replaced = PropertiesInitializer.processPropertyFilesString(
             ctx,
             "xserver",
             "xwebapp",
             PropertiesInitializer.DEFAULT_INITIALIZATION_PARAMETER);
 
-        assertEquals("WEB-INF/config/xserver/xwebapp/magnolia.properties," //$NON-NLS-1$
+        assertEquals("WEB-INF/config/xserver/myContextPath/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/xserver/xwebapp/magnolia.properties,"
             + "WEB-INF/config/xserver/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/myContextPath/magnolia.properties," //$NON-NLS-1$
             + "WEB-INF/config/xwebapp/magnolia.properties," //$NON-NLS-1$
             + "WEB-INF/config/default/magnolia.properties," //$NON-NLS-1$
             + "WEB-INF/config/magnolia.properties", replaced);
+        verify(ctx);
     }
 
-    public void testFileResolutionCtxAttributes() {
+    public void testFileResolutionWithServlet25AndRootContextPath() {
+        ServletContext ctx = createMock(ServletContext.class);
+        expect(ctx.getMajorVersion()).andReturn(2);
+        expect(ctx.getMinorVersion()).andReturn(5);
+        expect(ctx.getContextPath()).andReturn("");
+        replay(ctx);
+        String replaced = PropertiesInitializer.processPropertyFilesString(
+            ctx,
+            "xserver",
+            "xwebapp",
+            PropertiesInitializer.DEFAULT_INITIALIZATION_PARAMETER);
 
-        MockServletContext ctx = new MockServletContext();
-        ctx.setAttribute("attribute", "attributevalue");
-        ctx.setInitParameter("param", "paramvalue");
+        // TODO - this is ugly: double-slash
+        assertEquals("WEB-INF/config/xserver//magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/xserver/xwebapp/magnolia.properties,"
+            + "WEB-INF/config/xserver/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config//magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/xwebapp/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/default/magnolia.properties," //$NON-NLS-1$
+            + "WEB-INF/config/magnolia.properties", replaced);
+        verify(ctx);
+    }
 
+    public void testFileResolutionCtxAttributes() {
+        ServletContext ctx = createMock(ServletContext.class);
+        expect(ctx.getInitParameter("param")).andReturn("paramvalue");
+        expect(ctx.getAttribute("attribute")).andReturn("attributevalue");
+        expect(ctx.getMajorVersion()).andReturn(2);
+        expect(ctx.getMinorVersion()).andReturn(4);
+        replay(ctx);
+
         String replaced = PropertiesInitializer.processPropertyFilesString(
             ctx,
             "xserver",
@@ -117,5 +170,31 @@
             "WEB-INF/${contextParam/param}/${contextAttribute/attribute}");
 
         assertEquals("WEB-INF/paramvalue/attributevalue", replaced);
+        verify(ctx);
     }
+
+    // TODO - test to ensure properties are indeed loaded in the correct order, i.e no accidental override
+
+    public void testAtLeast25() {
+        doTestAtLeast25(true, 3, 3);
+        doTestAtLeast25(true, 3, 0);
+        doTestAtLeast25(true, 2, 6);
+        doTestAtLeast25(true, 2, 5);
+        doTestAtLeast25(false, 2, 4);
+        doTestAtLeast25(false, 2, 2);
+        doTestAtLeast25(false, 2, 0);
+        doTestAtLeast25(false, 1, 7);
+        doTestAtLeast25(false, 1, 0);
+        doTestAtLeast25(false, 0, 1);
+        doTestAtLeast25(false, 0, 0);
-}
+    }
+
+    private void doTestAtLeast25(boolean expected, int major, int minor) {
+        final ServletContext sc = createMock(ServletContext.class);
+        expect(sc.getMajorVersion()).andReturn(major).anyTimes();
+        expect(sc.getMinorVersion()).andReturn(minor).anyTimes();
+        replay(sc);
+        assertEquals(expected, PropertiesInitializer.atLeastServlet25(sc));
+        verify(sc);
+    }
+}
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 Local version)
+++ magnolia-core/src/main/java/info/magnolia/cms/beans/config/PropertiesInitializer.java	(revision Shelved version)
@@ -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;
-}
+        }
+    }
+
+}
Index: magnolia-empty-webapp/src/main/webapp/WEB-INF/web.xml
===================================================================
--- magnolia-empty-webapp/src/main/webapp/WEB-INF/web.xml	(revision Local version)
+++ magnolia-empty-webapp/src/main/webapp/WEB-INF/web.xml	(revision Shelved version)
@@ -27,8 +27,12 @@
   <context-param>
     <param-name>magnolia.initialization.file</param-name>
     <param-value>
-      WEB-INF/config/${servername}/${webapp}/magnolia.properties, WEB-INF/config/${servername}/magnolia.properties,
-      WEB-INF/config/${webapp}/magnolia.properties, WEB-INF/config/default/magnolia.properties,
+      WEB-INF/config/${servername}/${contextPath}/magnolia.properties,
+      WEB-INF/config/${servername}/${webapp}/magnolia.properties,
+      WEB-INF/config/${servername}/magnolia.properties,
+      WEB-INF/config/${contextPath}/magnolia.properties,
+      WEB-INF/config/${webapp}/magnolia.properties,
+      WEB-INF/config/default/magnolia.properties,
       WEB-INF/config/magnolia.properties
     </param-value>
   </context-param>