diff --git a/src/Site/Site.py b/src/Site/Site.py
index ce31695a..a48d2818 100644
--- a/src/Site/Site.py
+++ b/src/Site/Site.py
@@ -681,13 +681,13 @@ class Site(object):
                             delete_removed_files=False, load_includes=False
                         )
                         if privatekey:
-                            new_site.content_manager.sign(file_inner_path.replace("-default", ""), privatekey)
+                            new_site.content_manager.sign(file_inner_path.replace("-default", ""), privatekey, remove_missing_optional=True)
                             new_site.content_manager.loadContent(
                                 file_inner_path, add_bad_files=False, delete_removed_files=False, load_includes=False
                             )
 
         if privatekey:
-            new_site.content_manager.sign("content.json", privatekey)
+            new_site.content_manager.sign("content.json", privatekey, remove_missing_optional=True)
             new_site.content_manager.loadContent(
                 "content.json", add_bad_files=False, delete_removed_files=False, load_includes=False
             )
diff --git a/src/Test/TestSite.py b/src/Test/TestSite.py
index 368c6529..92f20081 100644
--- a/src/Test/TestSite.py
+++ b/src/Test/TestSite.py
@@ -29,6 +29,10 @@ class TestSite:
         assert new_site.storage.verifyFiles()["bad_files"] == []  # No bad files allowed
         assert new_site.storage.query("SELECT * FROM keyvalue WHERE key = 'title'").fetchone()["value"] == "MyZeroBlog"
 
+        # Optional files should be removed
+
+        assert len(new_site.storage.loadJson("content.json").get("files_optional", {})) == 0
+
         # Test re-cloning (updating)
 
         # Changes in non-data files should be overwritten