diff --git a/src/Umbraco.Tests/Configurations/UmbracoSettings/ContentElementTests.cs b/src/Umbraco.Tests/Configurations/UmbracoSettings/ContentElementTests.cs
index 5ad7f9cc51..b41b0d2683 100644
--- a/src/Umbraco.Tests/Configurations/UmbracoSettings/ContentElementTests.cs
+++ b/src/Umbraco.Tests/Configurations/UmbracoSettings/ContentElementTests.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Diagnostics;
 using System.Linq;
 using NUnit.Framework;
 using Umbraco.Core;
@@ -183,15 +184,28 @@ namespace Umbraco.Tests.Configurations.UmbracoSettings
         public void AllowedUploadFiles()
         {
             Assert.IsTrue(SettingsSection.Content.AllowedUploadFiles.All(x => "jpg,gif,png".Split(',').Contains(x)));
-        }
-
+        }
+
         [Test]
-        public void IsFileAllowedForUpload_WithWhitelist()
+        [TestCase("png", true)]
+        [TestCase("jpg", true)]
+        [TestCase("gif", true)]
+        [TestCase("bmp", false)]
+        [TestCase("php", false)]
+        [TestCase("ashx", false)]
+        [TestCase("config", false)]
+        public void IsFileAllowedForUpload_WithWhitelist(string extension, bool expected)
         {
-            Assert.IsTrue(SettingsSection.Content.IsFileAllowedForUpload("png"));
-            // TODO: why does this fail on the build server but not locally?
-            //Assert.IsFalse(SettingsSection.Content.IsFileAllowedForUpload("bmp"));
-            Assert.IsFalse(SettingsSection.Content.IsFileAllowedForUpload("php"));
+            Debug.WriteLine("AllowedUploadFiles: {0}", SettingsSection.Content.AllowedUploadFiles);
+            Debug.WriteLine("DisallowedUploadFiles: {0}", SettingsSection.Content.DisallowedUploadFiles);
+
+            var allowedContainsExtension = SettingsSection.Content.AllowedUploadFiles.Any(x => x.InvariantEquals(extension));
+            var disallowedContainsExtension = SettingsSection.Content.DisallowedUploadFiles.Any(x => x.InvariantEquals(extension));
+
+            Debug.WriteLine("AllowedContainsBmp: {0}", allowedContainsExtension);
+            Debug.WriteLine("DisallowedContainsBmp: {0}", disallowedContainsExtension);
+
+            Assert.AreEqual(SettingsSection.Content.IsFileAllowedForUpload(extension), expected);
         }
     }
 }