diff --git a/src/Umbraco.Core/CoreBootManager.cs b/src/Umbraco.Core/CoreBootManager.cs
index 11ee5b4eab..877928957a 100644
--- a/src/Umbraco.Core/CoreBootManager.cs
+++ b/src/Umbraco.Core/CoreBootManager.cs
@@ -239,8 +239,15 @@ namespace Umbraco.Core
 			PropertyEditorValueConvertersResolver.Current.AddType<TinyMcePropertyEditorValueConverter>();
 			PropertyEditorValueConvertersResolver.Current.AddType<YesNoPropertyEditorValueConverter>();
 
-		    ShortStringHelperResolver.Current = new ShortStringHelperResolver(
+            // this is how we'd switch over to DefaultShortStringHelper _and_ still use
+            // UmbracoSettings UrlReplaceCharacters...
+            //ShortStringHelperResolver.Current = new ShortStringHelperResolver(
+            //    new DefaultShortStringHelper().WithConfig(DefaultShortStringHelper.ApplyUrlReplaceCharacters));
+
+            // use the Legacy one for now
+            ShortStringHelperResolver.Current = new ShortStringHelperResolver(
 		        new LegacyShortStringHelper());
+
 		    UrlSegmentProviderResolver.Current = new UrlSegmentProviderResolver(
 		        typeof (DefaultUrlSegmentProvider));
 		}
diff --git a/src/Umbraco.Core/Strings/DefaultShortStringHelper.cs b/src/Umbraco.Core/Strings/DefaultShortStringHelper.cs
index af0bcbbaf3..f60265940d 100644
--- a/src/Umbraco.Core/Strings/DefaultShortStringHelper.cs
+++ b/src/Umbraco.Core/Strings/DefaultShortStringHelper.cs
@@ -20,6 +20,11 @@ namespace Umbraco.Core.Strings
     {
         #region Ctor and vars
 
+        static DefaultShortStringHelper()
+        {
+            InitializeLegacyUrlReplaceCharacters();
+        }
+
         /// <summary>
         /// Freezes the helper so it can prevents its configuration from being modified.
         /// </summary>
@@ -46,6 +51,33 @@ namespace Umbraco.Core.Strings
 
         #endregion
 
+        #region Legacy UrlReplaceCharacters
+
+        static readonly Dictionary<string, string> UrlReplaceCharacters = new Dictionary<string, string>();
+
+        static void InitializeLegacyUrlReplaceCharacters()
+        {
+            var replaceChars = UmbracoSettings.UrlReplaceCharacters;
+            foreach (var node in replaceChars.SelectNodes("char").Cast<System.Xml.XmlNode>())
+            {
+                var org = node.Attributes.GetNamedItem("org");
+                if (org != null && org.Value != "")
+                    UrlReplaceCharacters[org.Value] = XmlHelper.GetNodeValue(node);
+            }
+        }
+
+        /// <summary>
+        /// Returns a new string in which characters have been replaced according to the Umbraco settings UrlReplaceCharacters.
+        /// </summary>
+        /// <param name="s">The string to filter.</param>
+        /// <returns>The filtered string.</returns>
+        public static string ApplyUrlReplaceCharacters(string s)
+        {
+            return s.ReplaceMany(UrlReplaceCharacters);
+        }
+
+        #endregion
+
         #region Configuration
 
         private void EnsureNotFrozen()
diff --git a/src/Umbraco.Core/Strings/ShortStringHelperResolver.cs b/src/Umbraco.Core/Strings/ShortStringHelperResolver.cs
index 2ad40342a6..25be58b102 100644
--- a/src/Umbraco.Core/Strings/ShortStringHelperResolver.cs
+++ b/src/Umbraco.Core/Strings/ShortStringHelperResolver.cs
@@ -15,7 +15,7 @@ namespace Umbraco.Core.Strings
         internal ShortStringHelperResolver(IShortStringHelper helper)
             : base(helper)
         {
-            Resolution.Frozen += (sender, args) => helper.Freeze();
+            Resolution.Frozen += (sender, args) => Value.Freeze();
         }
         
         /// <summary>