diff --git a/jetty-policy/src/main/java/org/eclipse/jetty/policy/JettyPolicy.java b/jetty-policy/src/main/java/org/eclipse/jetty/policy/JettyPolicy.java
index cb513935f07..9f0b18678d7 100644
--- a/jetty-policy/src/main/java/org/eclipse/jetty/policy/JettyPolicy.java
+++ b/jetty-policy/src/main/java/org/eclipse/jetty/policy/JettyPolicy.java
@@ -179,6 +179,11 @@ public class JettyPolicy extends Policy
                 File policyFile = new File( i.next() );              
                 pdMapping.putAll( DefaultPolicyLoader.load( new FileInputStream( policyFile ), _context ) );
             }
+            
+            //for ( Iterator<ProtectionDomain> i = pdMapping.keySet().iterator(); i.hasNext();)
+            //{
+            //    System.out.println(i.next().toString());
+            //}
         }
         catch ( Exception e )
         {
diff --git a/jetty-policy/src/main/java/org/eclipse/jetty/policy/PolicyContext.java b/jetty-policy/src/main/java/org/eclipse/jetty/policy/PolicyContext.java
index 88d35c5eda9..2f01c4099f1 100644
--- a/jetty-policy/src/main/java/org/eclipse/jetty/policy/PolicyContext.java
+++ b/jetty-policy/src/main/java/org/eclipse/jetty/policy/PolicyContext.java
@@ -15,6 +15,7 @@ package org.eclipse.jetty.policy;
 //You may elect to redistribute this code under either of these licenses.
 //========================================================================
 
+import java.io.File;
 import java.security.KeyStore;
 import java.security.Principal;
 import java.security.cert.Certificate;
@@ -29,6 +30,12 @@ public class PolicyContext
     private Principal[] principals;
     private KeyStore keystore;
     
+    public PolicyContext()
+    {
+        // special property case for resolving ${/} to native separator
+        properties.put( "/", File.separator );
+    }
+    
     public void addProperty( String name, String value )
     {
         this.properties.put( name, value );
@@ -68,13 +75,17 @@ public class PolicyContext
 
         while (s!=null)
         {
-            i1=s.indexOf("${",i2);
+            System.out.println("Reviewing: " + s );
+            //i1=s.indexOf("${",i2);
+            i1=s.indexOf("${");
+            System.out.println("i1:" + i1);
             if (i1<0)
             {
                 break;
             }
             
             i2=s.indexOf("}",i1+2);
+            System.out.println("i2:" + i2);
             if (i2<0)
             {
                 break;
@@ -83,6 +94,8 @@ public class PolicyContext
             String property=getProperty(s.substring(i1+2,i2));
        
             s=s.substring(0,i1)+property+s.substring(i2+1);
+            
+            System.out.println("expanded to: " + s);
         }
         
         return s;
@@ -95,7 +108,7 @@ public class PolicyContext
 
         while (s!=null)
         {
-            i1=s.indexOf("${{",i2);
+            i1=s.indexOf("${{");
             if (i1<0)
             {
                 break;
diff --git a/jetty-policy/src/test/java/org/eclipse/jetty/policy/TestPolicyContext.java b/jetty-policy/src/test/java/org/eclipse/jetty/policy/TestPolicyContext.java
index 265e588bb7c..1846b5e9ee8 100644
--- a/jetty-policy/src/test/java/org/eclipse/jetty/policy/TestPolicyContext.java
+++ b/jetty-policy/src/test/java/org/eclipse/jetty/policy/TestPolicyContext.java
@@ -103,6 +103,19 @@ public class TestPolicyContext
         assertEquals( __PRINCIPAL, perm.getName() );
     }
     
+    public void testFileSeparatorExpansion() throws Exception
+    {
+        PolicyContext context = new PolicyContext();  
+        context.addProperty( "foo", "bar" );
+        
+        assertEquals(File.separator, context.evaluate( "${/}" ) );
+
+        assertEquals(File.separator + "bar" + File.separator, context.evaluate( "${/}${foo}${/}" ) );
+        
+
+        assertEquals(File.separator + File.separator, context.evaluate( "${/}${/}" ) );
+    }
+    
     private String getWorkingDirectory()
     {
         String cwd = System.getProperty( "basedir" );