diff --git a/uSync.Core/Serialization/Serializers/ContentSerializer.cs b/uSync.Core/Serialization/Serializers/ContentSerializer.cs
index 7f44d2a2..6ace158c 100644
--- a/uSync.Core/Serialization/Serializers/ContentSerializer.cs
+++ b/uSync.Core/Serialization/Serializers/ContentSerializer.cs
@@ -402,6 +402,9 @@ protected override uSyncChange HandleTrashedState(IContent item, bool trashed)
                 // if the item is trashed, then the change of it's parent 
                 // should restore it (as long as we do a move!)
 
+                // if this item is new but in the bin, we can't move it to the bin. 
+                
+
                 contentService.Move(item, item.ParentId);
 
                 // clean out any relations for this item (some versions of Umbraco don't do this on a Move)
@@ -412,12 +415,16 @@ protected override uSyncChange HandleTrashedState(IContent item, bool trashed)
             }
             else if (trashed && !item.Trashed)
             {
+                // not already in the recycle bin?
+                if (item.ParentId > Constants.System.RecycleBinContent)
+                {
+                    // clean any relations that may be there (stops an error)
+                    CleanRelations(item, "relateParentDocumentOnDelete");
 
-                // clean any relations that may be there (stops an error)
-                CleanRelations(item, "relateParentDocumentOnDelete");
+                    // move to the recycle bin    
+                    contentService.MoveToRecycleBin(item);
+                }
 
-                // move to the recycle bin
-                contentService.MoveToRecycleBin(item);
                 return uSyncChange.Update("Moved to Bin", item.Name, "", "Recycle Bin");
             }
 
@@ -432,8 +439,9 @@ protected virtual Attempt<string> DoSaveOrPublish(IContent item, XElement node,
                 return Attempt.Succeed("No Changes");
             }
 
+            var trashed = item.Trashed || (node.Element("Info")?.Element("Trashed").ValueOrDefault(false) ?? false);
             var publishedNode = node.Element("Info")?.Element("Published");
-            if (!item.Trashed && publishedNode != null)
+            if (!trashed && publishedNode != null)
             {
                 var schedules = GetSchedules(node.Element("Info")?.Element("Schedule"));
 
diff --git a/uSync.Core/Serialization/Serializers/ContentSerializerBase.cs b/uSync.Core/Serialization/Serializers/ContentSerializerBase.cs
index 0300a0d9..c6c30615 100644
--- a/uSync.Core/Serialization/Serializers/ContentSerializerBase.cs
+++ b/uSync.Core/Serialization/Serializers/ContentSerializerBase.cs
@@ -394,7 +394,17 @@ protected virtual IEnumerable<uSyncChange> DeserializeBase(TObject item, XElemen
                     item.Level = nodeLevel;
                 }
             }
-
+            else // trashed. 
+            {
+                // we need to set the parent to something,
+                // or the move will fail.
+                if (item.ParentId == -1)
+                {
+                    item.ParentId = item is IContent
+                        ? Constants.System.RecycleBinContent
+                        : Constants.System.RecycleBinMedia;
+                }
+            }
 
             var key = node.GetKey();
             if (key != Guid.Empty && item.Key != key)
@@ -679,13 +689,17 @@ protected override Attempt<TObject> FindOrCreate(XElement node)
 
             var alias = node.GetAlias();
 
-            var parentKey = node.Attribute(uSyncConstants.Xml.Parent).ValueOrDefault(Guid.Empty);
+            var parentKey = node.Element(uSyncConstants.Xml.Info)
+                ?.Element(uSyncConstants.Xml.Parent)
+                ?.Attribute(uSyncConstants.Xml.Key)
+                .ValueOrDefault(Guid.Empty) ?? Guid.Empty;
+
             if (parentKey != Guid.Empty)
             {
                 item = FindItem(alias, parentKey);
                 if (item != null) return Attempt.Succeed(item);
             }
-
+           
             // create
             var parent = default(TObject);