diff --git a/uSync8.ContentEdition/Serializers/ContentSerializer.cs b/uSync8.ContentEdition/Serializers/ContentSerializer.cs
index 4b793155..f3deee37 100644
--- a/uSync8.ContentEdition/Serializers/ContentSerializer.cs
+++ b/uSync8.ContentEdition/Serializers/ContentSerializer.cs
@@ -333,9 +333,11 @@ protected override uSyncChange HandleTrashedState(IContent item, bool trashed)
             else if (trashed && !item.Trashed)
             {
                 // move to the recycle bin
-
                 logger.Debug<ContentSerializer>("Moving content into Recycle bin {id}", item.Id);
 
+                // clean any relations that may be there (stops an error)
+                CleanRelations(item, "relateParentDocumentOnDelete");
+
                 contentService.MoveToRecycleBin(item);
                 return uSyncChange.Update("Moved to Bin", item.Name, "", "Recycle Bin");
             }
diff --git a/uSync8.ContentEdition/Serializers/MediaSerializer.cs b/uSync8.ContentEdition/Serializers/MediaSerializer.cs
index 76729648..942fb948 100644
--- a/uSync8.ContentEdition/Serializers/MediaSerializer.cs
+++ b/uSync8.ContentEdition/Serializers/MediaSerializer.cs
@@ -110,6 +110,10 @@ protected override uSyncChange HandleTrashedState(IMedia item, bool trashed)
             }
             else if (trashed && !item.Trashed)
             {
+
+                // clean any rouge relations 
+                CleanRelations(item, "relateParentMediaFolderOnDelete");
+
                 // move to the recycle bin
                 mediaService.MoveToRecycleBin(item);
                 return uSyncChange.Update("Moved to Bin", item.Name, "", "Recycle Bin");