diff --git a/src/Umbraco.Core/Persistence/Repositories/Implement/ContentTypeRepositoryBase.cs b/src/Umbraco.Core/Persistence/Repositories/Implement/ContentTypeRepositoryBase.cs
index 19f3623680..7104c9f713 100644
--- a/src/Umbraco.Core/Persistence/Repositories/Implement/ContentTypeRepositoryBase.cs
+++ b/src/Umbraco.Core/Persistence/Repositories/Implement/ContentTypeRepositoryBase.cs
@@ -274,6 +274,8 @@ AND umbracoNode.id <> @id",
             if (compositionBase != null && compositionBase.RemovedContentTypeKeyTracker != null &&
                 compositionBase.RemovedContentTypeKeyTracker.Any())
             {
+                //TODO: Could we do the below with bulk SQL statements instead of looking everything up and then manipulating?
+
                 // find Content based on the current ContentType
                 var sql = Sql()
                     .SelectAll()
@@ -292,6 +294,7 @@ AND umbracoNode.id <> @id",
                     // based on the PropertyTypes that belong to the removed ContentType.
                     foreach (var contentDto in contentDtos)
                     {
+                        //TODO: This could be done with bulk SQL statements
                         foreach (var propertyType in propertyTypes)
                         {
                             var nodeId = contentDto.NodeId;
@@ -408,6 +411,7 @@ AND umbracoNode.id <> @id",
             {
                 //we've already looked up the previous version of the content type so we know it's previous variation state
                 MoveVariantData(entity, (ContentVariation)dtoPk.Variations, entity.Variations);
+                Clear301Redirects(entity);
             }   
 
             //track any property types that are changing variation
@@ -492,6 +496,23 @@ AND umbracoNode.id <> @id",
                     DeletePropertyType(entity.Id, id);
         }
 
+        /// <summary>
+        /// Clear any redirects associated with content for a content type
+        /// </summary>
+        private void Clear301Redirects(IContentTypeComposition contentType)
+        {
+            //first clear out any existing property data that might already exists under the default lang
+            var sqlSelect = Sql().Select<NodeDto>(x => x.UniqueId)
+                .From<NodeDto>()
+                .InnerJoin<ContentDto>().On<ContentDto, NodeDto>(x => x.NodeId, x => x.NodeId)
+                .Where<ContentDto>(x => x.ContentTypeId == contentType.Id);
+            var sqlDelete = Sql()
+                .Delete<RedirectUrlDto>()
+                .WhereIn((System.Linq.Expressions.Expression<Func<RedirectUrlDto, object>>)(x => x.ContentKey), sqlSelect);
+            
+            Database.Execute(sqlDelete);
+        }
+
         /// <summary>
         /// Moves variant data for property type changes
         /// </summary>
diff --git a/src/Umbraco.Tests/Services/ContentTypeServiceTests.cs b/src/Umbraco.Tests/Services/ContentTypeServiceTests.cs
index 892166e566..2d0471b9bd 100644
--- a/src/Umbraco.Tests/Services/ContentTypeServiceTests.cs
+++ b/src/Umbraco.Tests/Services/ContentTypeServiceTests.cs
@@ -24,6 +24,50 @@ namespace Umbraco.Tests.Services
     [UmbracoTest(Database = UmbracoTestOptions.Database.NewSchemaPerTest, PublishedRepositoryEvents = true)]
     public class ContentTypeServiceTests : TestWithSomeContentBase
     {
+        [Test]
+        public void Change_Content_Type_Variation_Clears_Redirects()
+        {
+            //create content type with a property type that varies by culture
+            var contentType = MockedContentTypes.CreateBasicContentType();
+            contentType.Variations = ContentVariation.Nothing;
+            var contentCollection = new PropertyTypeCollection(true);
+            contentCollection.Add(new PropertyType("test", ValueStorageType.Ntext)
+            {
+                Alias = "title",
+                Name = "Title",
+                Description = "",
+                Mandatory = false,
+                SortOrder = 1,
+                DataTypeId = -88,
+                Variations = ContentVariation.Nothing
+            });
+            contentType.PropertyGroups.Add(new PropertyGroup(contentCollection) { Name = "Content", SortOrder = 1 });
+            ServiceContext.ContentTypeService.Save(contentType);
+            var contentType2 = MockedContentTypes.CreateBasicContentType("test");
+            ServiceContext.ContentTypeService.Save(contentType2);
+
+            //create some content of this content type
+            IContent doc = MockedContent.CreateBasicContent(contentType);
+            doc.Name = "Hello1";
+            ServiceContext.ContentService.Save(doc);
+
+            IContent doc2 = MockedContent.CreateBasicContent(contentType2);
+            ServiceContext.ContentService.Save(doc2);
+
+            ServiceContext.RedirectUrlService.Register("hello/world", doc.Key);
+            ServiceContext.RedirectUrlService.Register("hello2/world2", doc2.Key);
+
+            Assert.AreEqual(1, ServiceContext.RedirectUrlService.GetContentRedirectUrls(doc.Key).Count());
+            Assert.AreEqual(1, ServiceContext.RedirectUrlService.GetContentRedirectUrls(doc2.Key).Count());
+
+            //change variation
+            contentType.Variations = ContentVariation.Culture;
+            ServiceContext.ContentTypeService.Save(contentType);
+
+            Assert.AreEqual(0, ServiceContext.RedirectUrlService.GetContentRedirectUrls(doc.Key).Count());
+            Assert.AreEqual(1, ServiceContext.RedirectUrlService.GetContentRedirectUrls(doc2.Key).Count());
+
+        }
 
         [Test]
         public void Change_Content_Type_From_Invariant_Variant()