[ENG-7725] CLONE/Recurring - Preprint Emails Not Being Sent as Expected

framework/email/tasks.py

@@ -171,7 +171,12 @@ def _send_with_sendgrid(
     # Personalization to handle To, CC, and BCC sendgrid client concept
     personalization = Personalization()
 
-    personalization.add_to(To(to_addr))
+    to = To(to_addr)
+    if to.email is None:
+        sentry.log_message(f"Receiver email is not valid: {to_addr}. {subject} email won't be sent.")
+        return False
+
+    personalization.add_to(to)
 
     if cc_addr:
         if isinstance(cc_addr, str):
@@ -191,7 +196,8 @@ def _send_with_sendgrid(
     mail.add_personalization(personalization)
 
     if categories:
-        mail.add_category([Category(x) for x in categories])
+        for category in categories:
+            mail.add_category(Category(category))
 
     if attachment_name and attachment_content:
         attachment = Attachment(

tests/framework_tests/test_email.py

@@ -66,13 +66,14 @@ def test_send_with_sendgrid_success(self, mock_mail: MagicMock):
         mock_mail.return_value.add_personalization.assert_called_once()
 
         # Capture the categories added via add_category
-        mock_mail.return_value.add_category.assert_called_once()
-        added_categories = mock_mail.return_value.add_category.call_args.args[0]
+        # mock_mail.return_value.add_category.assert_called_once()
+        assert mock_mail.return_value.add_category.call_count == 2
+        added_categories = mock_mail.return_value.add_category.call_args_list
         assert len(added_categories) == 2
-        assert isinstance(added_categories[0], Category)
-        assert isinstance(added_categories[1], Category)
-        assert added_categories[0].get() == category1
-        assert added_categories[1].get() == category2
+        assert isinstance(added_categories[0].args[0], Category)
+        assert isinstance(added_categories[1].args[0], Category)
+        assert added_categories[0].args[0].get() == category1
+        assert added_categories[1].args[0].get() == category2
 
         mock_client.send.assert_called_once_with(mock_mail.return_value)
 
@@ -103,6 +104,18 @@ def test_send_with_sendgrid_failure_returns_false(self, mock_mail, sentry_mock):
 
         mock_client.send.assert_called_once_with(mock_mail.return_value)
 
+        mock_client.send.return_value = mock.Mock(status_code=200, body='correct')
+        to_addr = 'not-an-email'
+        ret = _send_with_sendgrid(
+            from_addr=from_addr,
+            to_addr=to_addr,
+            subject=subject,
+            message=message,
+            client=mock_client
+        )
+        assert not ret
+        sentry_mock.assert_called()
+
 
 if __name__ == '__main__':
     unittest.main()