diff --git a/src/Umbraco.Core/Services/ContentService.cs b/src/Umbraco.Core/Services/ContentService.cs
index d2bdb6d785..af06c7e0ba 100644
--- a/src/Umbraco.Core/Services/ContentService.cs
+++ b/src/Umbraco.Core/Services/ContentService.cs
@@ -1039,7 +1039,8 @@ namespace Umbraco.Core.Services
                     };
 
                     //get descendents to process of the content item that is being moved to trash - must be done before changing the state below
-                    var descendants = ignoreDescendants ? Enumerable.Empty<IContent>() : GetDescendants(content).OrderByDescending(x => x.Level);
+                    //must be processed with shallowest levels first
+                    var descendants = ignoreDescendants ? Enumerable.Empty<IContent>() : GetDescendants(content).OrderBy(x => x.Level);
 
                     //Do the updates for this item
                     var repository = RepositoryFactory.CreateContentRepository(uow);
diff --git a/src/Umbraco.Core/Services/MediaService.cs b/src/Umbraco.Core/Services/MediaService.cs
index fb2a410cc8..9f5ec811c9 100644
--- a/src/Umbraco.Core/Services/MediaService.cs
+++ b/src/Umbraco.Core/Services/MediaService.cs
@@ -1072,8 +1072,9 @@ namespace Umbraco.Core.Services
                         new MoveEventInfo<IMedia>(media, originalPath, Constants.System.RecycleBinMedia)
                     };
 
-                    //get descendents to process of the content item that is being moved to trash - must be done before changing the state below
-                    var descendants = ignoreDescendants ? Enumerable.Empty<IMedia>() : GetDescendants(media).OrderByDescending(x => x.Level);
+                    //get descendents to process of the content item that is being moved to trash - must be done before changing the state below, 
+                    //must be processed with shallowest levels first
+                    var descendants = ignoreDescendants ? Enumerable.Empty<IMedia>() : GetDescendants(media).OrderBy(x => x.Level);
 
                     //Do the updates for this item
                     var repository = RepositoryFactory.CreateMediaRepository(uow);
diff --git a/src/Umbraco.Tests/Services/ContentServiceTests.cs b/src/Umbraco.Tests/Services/ContentServiceTests.cs
index d8c26e1abb..e360018104 100644
--- a/src/Umbraco.Tests/Services/ContentServiceTests.cs
+++ b/src/Umbraco.Tests/Services/ContentServiceTests.cs
@@ -1319,7 +1319,7 @@ namespace Umbraco.Tests.Services
             // Assert
             Assert.That(content.ParentId, Is.EqualTo(-20));
             Assert.That(content.Trashed, Is.True);
-            Assert.That(descendants.Count(), Is.EqualTo(3));
+            Assert.That(descendants.Count, Is.EqualTo(3));
             Assert.That(descendants.Any(x => x.Path.Contains("-20") == false), Is.False);
 
             //Empty Recycle Bin