diff --git a/src/Umbraco.Core/CustomBooleanTypeConverter.cs b/src/Umbraco.Core/CustomBooleanTypeConverter.cs
index e528b9638d..6246b04bd1 100644
--- a/src/Umbraco.Core/CustomBooleanTypeConverter.cs
+++ b/src/Umbraco.Core/CustomBooleanTypeConverter.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.ComponentModel;
 
 namespace Umbraco.Cms.Core
@@ -24,6 +24,8 @@ namespace Umbraco.Cms.Core
                 var str = (string)value;
                 if (str == null || str.Length == 0 || str == "0") return false;
                 if (str == "1") return true;
+                if (str.Equals("Yes", StringComparison.OrdinalIgnoreCase)) return true;
+                if (str.Equals("No", StringComparison.OrdinalIgnoreCase)) return false;
             }
 
             return base.ConvertFrom(context, culture, value);
diff --git a/src/Umbraco.Tests.UnitTests/Umbraco.Core/CoreThings/TryConvertToTests.cs b/src/Umbraco.Tests.UnitTests/Umbraco.Core/CoreThings/TryConvertToTests.cs
index 6857a055bb..0525a24173 100644
--- a/src/Umbraco.Tests.UnitTests/Umbraco.Core/CoreThings/TryConvertToTests.cs
+++ b/src/Umbraco.Tests.UnitTests/Umbraco.Core/CoreThings/TryConvertToTests.cs
@@ -1,4 +1,4 @@
-// Copyright (c) Umbraco.
+// Copyright (c) Umbraco.
 // See LICENSE for more details.
 
 using System;
@@ -10,6 +10,42 @@ namespace Umbraco.Cms.Tests.UnitTests.Umbraco.Core.CoreThings
     [TestFixture]
     public class TryConvertToTests
     {
+        [Test]
+        public void ConvertToBoolTest()
+        {
+            var conv = 1.TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(true, conv.Result);
+
+            conv = "1".TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(true, conv.Result);
+
+            conv = 0.TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(false, conv.Result);
+
+            conv = "0".TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(false, conv.Result);
+
+            conv = "Yes".TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(true, conv.Result);
+
+            conv = "yes".TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(true, conv.Result);
+
+            conv = "No".TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(false, conv.Result);
+
+            conv = "no".TryConvertTo<bool>();
+            Assert.IsTrue(conv);
+            Assert.AreEqual(false, conv.Result);
+        }
+
         [Test]
         public void ConvertToIntegerTest()
         {