diff --git a/src/Umbraco.Core/Configuration/GlobalSettings.cs b/src/Umbraco.Core/Configuration/GlobalSettings.cs
index d2fca6eb36..10446c7f5c 100644
--- a/src/Umbraco.Core/Configuration/GlobalSettings.cs
+++ b/src/Umbraco.Core/Configuration/GlobalSettings.cs
@@ -154,6 +154,9 @@ namespace Umbraco.Core.Configuration
         /// This will return the MVC area that we will route all custom routes through like surface controllers, etc...
         /// We will use the 'Path' (default ~/umbraco) to create it but since it cannot contain '/' and people may specify a path of ~/asdf/asdf/admin
         /// we will convert the '/' to '-' and use that as the path. its a bit lame but will work.
+		/// 
+        /// We also make sure that the virtual directory (SystemDirectories.Root) is stripped off first, otherwise we'd end up with something
+        /// like "MyVirtualDirectory-Umbraco" instead of just "Umbraco".
         /// </remarks>
         internal static string UmbracoMvcArea
         {
@@ -163,7 +166,7 @@ namespace Umbraco.Core.Configuration
                 {
                     throw new InvalidOperationException("Cannot create an MVC Area path without the umbracoPath specified");
                 }
-                return Path.TrimStart('~').TrimStart('/').Replace('/', '-').Trim();
+			    return Path.TrimStart(SystemDirectories.Root).TrimStart('~').TrimStart('/').Replace('/', '-').Trim().ToLower();
             }
         }
 
diff --git a/src/Umbraco.Core/IO/SystemDirectories.cs b/src/Umbraco.Core/IO/SystemDirectories.cs
index e70046c90e..433d01c206 100644
--- a/src/Umbraco.Core/IO/SystemDirectories.cs
+++ b/src/Umbraco.Core/IO/SystemDirectories.cs
@@ -183,16 +183,26 @@ namespace Umbraco.Core.IO
             }
         }
 
+	    private static string _root;
+        /// <summary>
+        /// Gets the root path of the application
+        /// </summary>
         public static string Root
         {
             get
             {
-                string appPath = HttpRuntime.AppDomainAppVirtualPath ?? string.Empty;
-                if (appPath == "/")
-                    appPath = string.Empty;
+                if (_root == null)
+                {
+                    string appPath = HttpRuntime.AppDomainAppVirtualPath ?? string.Empty;
+                    if (appPath == "/")
+                        appPath = string.Empty;
 
-                return appPath;
+                    _root = appPath;    
+                }
+                return _root;
             }
+            //Only required for unit tests
+            internal set { _root = value; }
         }
     }
 
diff --git a/src/Umbraco.Tests/GlobalSettingsTests.cs b/src/Umbraco.Tests/GlobalSettingsTests.cs
index e8d5fc0628..6ea6b93e38 100644
--- a/src/Umbraco.Tests/GlobalSettingsTests.cs
+++ b/src/Umbraco.Tests/GlobalSettingsTests.cs
@@ -2,6 +2,7 @@ using System.Configuration;
 using System.Web.Routing;
 using NUnit.Framework;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.IO;
 using Umbraco.Tests.TestHelpers;
 using System.Web.Mvc;
 
@@ -23,6 +24,9 @@ namespace Umbraco.Tests
 
 		public override void TearDown()
 		{
+            //ensure this is reset
+		    SystemDirectories.Root = null;
+            SettingsForTests.UmbracoPath = "~/umbraco";
             //reset the app config		            
 			base.TearDown();
 			
@@ -35,7 +39,19 @@ namespace Umbraco.Tests
             Assert.That(UmbracoVersion.Current.ToString(3), Is.EqualTo("6.0.0"));
         }
 
-		[TestCase("/umbraco/umbraco.aspx")]
+        [TestCase("~/umbraco", "/", "umbraco")]
+        [TestCase("~/umbraco", "/MyVirtualDir", "umbraco")]
+        [TestCase("~/customPath", "/MyVirtualDir/", "custompath")]
+        [TestCase("~/some-wacky/nestedPath", "/MyVirtualDir", "some-wacky-nestedpath")]
+        [TestCase("~/some-wacky/nestedPath", "/MyVirtualDir/NestedVDir/", "some-wacky-nestedpath")]
+	    public void Umbraco_Mvc_Area(string path, string rootPath, string outcome)
+        {
+            SettingsForTests.UmbracoPath = path;
+            SystemDirectories.Root = rootPath;
+            Assert.AreEqual(outcome, Umbraco.Core.Configuration.GlobalSettings.UmbracoMvcArea);
+        }
+
+	    [TestCase("/umbraco/umbraco.aspx")]
 		[TestCase("/umbraco/editContent.aspx")]
 		[TestCase("/install/default.aspx")]
 		[TestCase("/install/")]
diff --git a/src/Umbraco.Web.UI/Umbraco.Web.UI.csproj b/src/Umbraco.Web.UI/Umbraco.Web.UI.csproj
index 7b61fcdea8..93e7035e83 100644
--- a/src/Umbraco.Web.UI/Umbraco.Web.UI.csproj
+++ b/src/Umbraco.Web.UI/Umbraco.Web.UI.csproj
@@ -2469,7 +2469,7 @@ xcopy "$(ProjectDir)"..\packages\SqlServerCE.4.0.0.0\x86\*.* "$(TargetDir)x86\"
           <AutoAssignPort>True</AutoAssignPort>
           <DevelopmentServerPort>61637</DevelopmentServerPort>
           <DevelopmentServerVPath>/</DevelopmentServerVPath>
-          <IISUrl>http://localhost:61638/</IISUrl>
+          <IISUrl>http://localhost:61639/VirtualDir</IISUrl>
           <NTLMAuthentication>False</NTLMAuthentication>
           <UseCustomServer>False</UseCustomServer>
           <CustomServerUrl>
diff --git a/src/Umbraco.Web/UriUtility.cs b/src/Umbraco.Web/UriUtility.cs
index cd6601ec6c..ee58adf327 100644
--- a/src/Umbraco.Web/UriUtility.cs
+++ b/src/Umbraco.Web/UriUtility.cs
@@ -51,7 +51,7 @@ namespace Umbraco.Web
 		// see also VirtualPathUtility.ToAppRelative
         public static string ToAppRelative(string virtualPath)
         {
-            if (virtualPath.StartsWith(_appPathPrefix))
+            if (virtualPath.InvariantStartsWith(_appPathPrefix))
                 virtualPath = virtualPath.Substring(_appPathPrefix.Length);
 			if (virtualPath.Length == 0)
 				virtualPath = "/";