diff --git a/src/Umbraco.Core/Services/ContentService.cs b/src/Umbraco.Core/Services/ContentService.cs
index 376024a3ae..036a40f240 100644
--- a/src/Umbraco.Core/Services/ContentService.cs
+++ b/src/Umbraco.Core/Services/ContentService.cs
@@ -683,7 +683,7 @@ namespace Umbraco.Core.Services
                 }
 
                 //Unpublish descendents of the content item that is being moved to trash
-                var descendants = GetDescendants(content).ToList();
+                var descendants = GetDescendants(content).OrderBy(x => x.Level).ToList();
                 foreach (var descendant in descendants)
                 {
                     UnPublish(descendant, userId);
@@ -819,8 +819,8 @@ namespace Umbraco.Core.Services
 			var uow = _uowProvider.GetUnitOfWork();
 			using (var repository = _repositoryFactory.CreateContentRepository(uow))
 			{
-				var query = Query<IContent>.Builder.Where(x => x.Path.Contains("-20"));
-				var contents = repository.GetByQuery(query).OrderByDescending(x => x.ParentId);
+				var query = Query<IContent>.Builder.Where(x => x.Trashed == true);
+				var contents = repository.GetByQuery(query).OrderByDescending(x => x.Level);
 
 				foreach (var content in contents)
 				{
diff --git a/src/Umbraco.Core/Services/MediaService.cs b/src/Umbraco.Core/Services/MediaService.cs
index 26e0ac15c7..ced8372720 100644
--- a/src/Umbraco.Core/Services/MediaService.cs
+++ b/src/Umbraco.Core/Services/MediaService.cs
@@ -393,7 +393,7 @@ namespace Umbraco.Core.Services
 				return;
 
             //Find Descendants, which will be moved to the recycle bin along with the parent/grandparent.
-            var descendants = GetDescendants(media).ToList();
+            var descendants = GetDescendants(media).OrderBy(x => x.Level).ToList();
 
 			var uow = _uowProvider.GetUnitOfWork();
 			using (var repository = _repositoryFactory.CreateMediaRepository(uow))
@@ -426,8 +426,8 @@ namespace Umbraco.Core.Services
 			var uow = _uowProvider.GetUnitOfWork();
 			using (var repository = _repositoryFactory.CreateMediaRepository(uow))
 			{
-				var query = Query<IMedia>.Builder.Where(x => x.Path.Contains("-21"));
-				var contents = repository.GetByQuery(query).OrderByDescending(x => x.ParentId);
+				var query = Query<IMedia>.Builder.Where(x => x.Trashed == true);
+				var contents = repository.GetByQuery(query).OrderByDescending(x => x.Level);
 
 				foreach (var content in contents)
 				{
diff --git a/src/Umbraco.Tests/Services/ContentServiceTests.cs b/src/Umbraco.Tests/Services/ContentServiceTests.cs
index 29ca90473c..ba94145af2 100644
--- a/src/Umbraco.Tests/Services/ContentServiceTests.cs
+++ b/src/Umbraco.Tests/Services/ContentServiceTests.cs
@@ -567,6 +567,34 @@ namespace Umbraco.Tests.Services
             Assert.That(content.Trashed, Is.True);
         }
 
+        [Test]
+        public void Can_Move_Content_Structure_To_RecycleBin_And_Empty_RecycleBin()
+        {
+            // Arrange
+            var contentService = ServiceContext.ContentService;
+            var contentType = ServiceContext.ContentTypeService.GetContentType("umbTextpage");
+            Content subsubpage = MockedContent.CreateSimpleContent(contentType, "Text Page 3", 1047);
+            contentService.Save(subsubpage, 0);
+
+            var content = contentService.GetById(1046);
+
+            // Act
+            contentService.MoveToRecycleBin(content, 0);
+            var descendants = contentService.GetDescendants(content);
+
+            // Assert
+            Assert.That(content.ParentId, Is.EqualTo(-20));
+            Assert.That(content.Trashed, Is.True);
+            Assert.That(descendants.Count(), Is.EqualTo(3));
+            Assert.That(descendants.Any(x => x.Path.Contains("-20") == false), Is.False);
+
+            //Empty Recycle Bin
+            contentService.EmptyRecycleBin();
+            var trashed = contentService.GetContentInRecycleBin();
+
+            Assert.That(trashed.Any(), Is.False);
+        }
+
         [Test]
         public void Can_Empty_RecycleBin()
         {