diff --git a/src/Umbraco.Web/UriUtility.cs b/src/Umbraco.Web/UriUtility.cs
index 86a97e2857..8a1c55e758 100644
--- a/src/Umbraco.Web/UriUtility.cs
+++ b/src/Umbraco.Web/UriUtility.cs
@@ -51,7 +51,8 @@ namespace Umbraco.Web
 		// see also VirtualPathUtility.ToAppRelative
         public static string ToAppRelative(string virtualPath)
         {
-            if (virtualPath.InvariantStartsWith(_appPathPrefix))
+            if (virtualPath.InvariantStartsWith(_appPathPrefix)
+                    && (virtualPath.Length == _appPathPrefix.Length || virtualPath[_appPathPrefix.Length] == '/'))
                 virtualPath = virtualPath.Substring(_appPathPrefix.Length);
 			if (virtualPath.Length == 0)
 				virtualPath = "/";