diff --git a/src/Umbraco.Core/Configuration/GlobalSettings.cs b/src/Umbraco.Core/Configuration/GlobalSettings.cs
index ac4f7647ae..290f252db3 100644
--- a/src/Umbraco.Core/Configuration/GlobalSettings.cs
+++ b/src/Umbraco.Core/Configuration/GlobalSettings.cs
@@ -834,12 +834,12 @@ namespace Umbraco.Core.Configuration
 				public int Compare(string part, string whole)
 				{
 					// let the default string comparer deal with null or when part is not smaller then whole
-					if (part == null || whole == null)
+					if (part == null || whole == null || part.Length >= whole.Length)
 						return _stringComparer.Compare(part, whole);
 
-					//trim the end '/' of each
-					part = part.TrimEnd('/');
-					whole = whole.TrimEnd('/');
+					//ensure both have a / on the end
+					part = part.EndsWith("/") ? part : part + "/"; 
+					whole = whole.EndsWith("/") ? whole : whole + "/";
 					if (part.Length >= whole.Length)
 						return _stringComparer.Compare(part, whole);
 
diff --git a/src/Umbraco.Tests/ActionsResolverTests.cs b/src/Umbraco.Tests/ActionsResolverTests.cs
index 45eab01c35..3885d74808 100644
--- a/src/Umbraco.Tests/ActionsResolverTests.cs
+++ b/src/Umbraco.Tests/ActionsResolverTests.cs
@@ -8,6 +8,13 @@ using umbraco.interfaces;
 
 namespace Umbraco.Tests
 {
+
+	[TestFixture]
+	public class GlobalSettingsTests
+	{
+
+	}
+
 	[TestFixture]
 	public class ActionsResolverTests
 	{
diff --git a/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs b/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs
index 8c95076684..c855a82a46 100644
--- a/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs
+++ b/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs
@@ -65,6 +65,8 @@ namespace Umbraco.Tests.Routing
 		[TestCase("/base/somebasehandler", false)]
 		[TestCase("/", true)]
 		[TestCase("/home.aspx", true)]
+		[TestCase("/umbraco-test", true)]
+		[TestCase("/install-test", true)]
 		public void Ensure_Request_Routable(string url, bool assert)
 		{
 			var httpContextFactory = new FakeHttpContextFactory(url);