diff --git a/tests/test_question_cmd.py b/tests/test_question_cmd.py
index 89c72c7..c51d5fd 100644
--- a/tests/test_question_cmd.py
+++ b/tests/test_question_cmd.py
@@ -282,6 +282,9 @@ class TestQuestionCmd(TestQuestionCmdBase):
         # exclude '.next'
         return sorted([f for f in Path(tmp_dir.name).glob('*.[ty]*')])
 
+
+class TestQuestionCmdAsk(TestQuestionCmd):
+
     @mock.patch('chatmastermind.commands.question.create_ai')
     def test_ask_single_answer(self, mock_create_ai: MagicMock) -> None:
         """
@@ -370,6 +373,9 @@ class TestQuestionCmd(TestQuestionCmdBase):
         self.assertEqual(len(self.message_list(self.cache_dir)), 1)
         self.assert_messages_equal(cached_msg, [expected_question])
 
+
+class TestQuestionCmdRepeat(TestQuestionCmd):
+
     @mock.patch('chatmastermind.commands.question.create_ai')
     def test_repeat_single_question(self, mock_create_ai: MagicMock) -> None:
         """
@@ -511,3 +517,44 @@ class TestQuestionCmd(TestQuestionCmdBase):
         cached_msg = chat.msg_gather(loc='cache')
         self.assertEqual(len(self.message_list(self.cache_dir)), 2)
         self.assert_messages_equal(cached_msg, expected_responses)
+
+    @mock.patch('chatmastermind.commands.question.create_ai')
+    def test_repeat_multiple_questions(self, mock_create_ai: MagicMock) -> None:
+        """
+        Repeat multiple  questions.
+        """
+        # 1. create some questions / messages
+        # cached message without an answer
+        message1 = Message(Question('Question 1'),
+                           ai='foo',
+                           model='bla',
+                           file_path=Path(self.cache_dir.name) / '0001.txt')
+        # cached message with an answer
+        message2 = Message(Question('Question 2'),
+                           Answer('Answer 2'),
+                           ai='openai',
+                           model='gpt-3.5-turbo',
+                           file_path=Path(self.cache_dir.name) / '0002.txt')
+        # DB message without an answer
+        message3 = Message(Question('Question 3'),
+                           ai='openai',
+                           model='gpt-3.5-turbo',
+                           file_path=Path(self.db_dir.name) / '0003.txt')
+        message1.to_file()
+        message2.to_file()
+        message3.to_file()
+        # chat = ChatDB.from_dir(Path(self.cache_dir.name),
+        #                        Path(self.db_dir.name))
+
+        # 2. repeat all three questions (without overwriting)
+        self.args.ask = None
+        self.args.repeat = ['0001', '0002', '0003']
+        self.args.overwrite = False
+        question_cmd(self.args, self.config)
+        # two new files should be in the cache directory
+        # * the repeated cached message with answer
+        # * the repeated DB message
+        # -> the cached message wihtout answer should be overwritten
+        self.assertEqual(len(self.message_list(self.cache_dir)), 4)
+        self.assertEqual(len(self.message_list(self.db_dir)), 1)
+        # FIXME: also compare actual content!