diff --git a/src/Umbraco.Core/IO/IOHelper.cs b/src/Umbraco.Core/IO/IOHelper.cs
index adaf4280e2..8ecb0c15fe 100644
--- a/src/Umbraco.Core/IO/IOHelper.cs
+++ b/src/Umbraco.Core/IO/IOHelper.cs
@@ -8,6 +8,7 @@ using System.IO;
 using System.Configuration;
 using System.Web;
 using System.Text.RegularExpressions;
+using System.Xml;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Logging;
 
@@ -277,6 +278,20 @@ namespace Umbraco.Core.IO
                 filePath = String.Empty;
             }
 
+            //Break up the file in name and extension before applying the UrlReplaceCharacters
+            var fileNamePart = filePath.Substring(0, filePath.LastIndexOf('.'));
+            var ext = filePath.Substring(filePath.LastIndexOf('.'));
+
+            //Because the file usually is downloadable as well we check characters against 'UmbracoSettings.UrlReplaceCharacters'
+            XmlNode replaceChars = UmbracoSettings.UrlReplaceCharacters;
+            foreach (XmlNode n in replaceChars.SelectNodes("char"))
+            {
+                if (n.Attributes.GetNamedItem("org") != null && n.Attributes.GetNamedItem("org").Value != "")
+                    fileNamePart = fileNamePart.Replace(n.Attributes.GetNamedItem("org").Value, XmlHelper.GetNodeValue(n));
+            }
+
+            filePath = string.Concat(fileNamePart, ext);
+
             // Adapted from: http://stackoverflow.com/a/4827510/5018
             // Combined both Reserved Characters and Character Data 
             // from http://en.wikipedia.org/wiki/Percent-encoding
diff --git a/src/Umbraco.Core/Persistence/Querying/ModelToSqlExpressionHelper.cs b/src/Umbraco.Core/Persistence/Querying/ModelToSqlExpressionHelper.cs
index 3f0495cfd5..dff000acc2 100644
--- a/src/Umbraco.Core/Persistence/Querying/ModelToSqlExpressionHelper.cs
+++ b/src/Umbraco.Core/Persistence/Querying/ModelToSqlExpressionHelper.cs
@@ -523,7 +523,8 @@ namespace Umbraco.Core.Persistence.Querying
 
         protected bool IsFieldName(string quotedExp)
         {
-            return true;
+            //Not entirely sure this is reliable, but its better then simply returning true
+            return quotedExp.LastIndexOf("'", StringComparison.InvariantCultureIgnoreCase) + 1 != quotedExp.Length;
         }
     }
 }
\ No newline at end of file
diff --git a/src/Umbraco.Core/Services/ContentService.cs b/src/Umbraco.Core/Services/ContentService.cs
index f4a3cf6d07..c46dd0d901 100644
--- a/src/Umbraco.Core/Services/ContentService.cs
+++ b/src/Umbraco.Core/Services/ContentService.cs
@@ -198,7 +198,7 @@ namespace Umbraco.Core.Services
 		{
 			using (var repository = _repositoryFactory.CreateContentRepository(_uowProvider.GetUnitOfWork()))
 			{
-                var query = Query<IContent>.Builder.Where(x => x.Level == level && x.Path.Contains("-20") == false);
+                var query = Query<IContent>.Builder.Where(x => x.Level == level && !x.Path.StartsWith("-20"));
 				var contents = repository.GetByQuery(query);
 
 				return contents;
diff --git a/src/Umbraco.Core/Services/MediaService.cs b/src/Umbraco.Core/Services/MediaService.cs
index 0da6a10f13..ebe681259d 100644
--- a/src/Umbraco.Core/Services/MediaService.cs
+++ b/src/Umbraco.Core/Services/MediaService.cs
@@ -156,7 +156,7 @@ namespace Umbraco.Core.Services
         {
             using (var repository = _repositoryFactory.CreateMediaRepository(_uowProvider.GetUnitOfWork()))
             {
-                var query = Query<IMedia>.Builder.Where(x => x.Level == level && x.Path.Contains("-21") == false);
+                var query = Query<IMedia>.Builder.Where(x => x.Level == level && !x.Path.StartsWith("-21"));
                 var contents = repository.GetByQuery(query);
 
                 return contents;