test_question_cmd: added more testcases for '--repeat'

chatmastermind/commands/question.py

@@ -1,3 +1,4 @@
+import sys
 import argparse
 from pathlib import Path
 from itertools import zip_longest
@@ -51,7 +52,7 @@ def add_file_as_code(question_parts: list[str], file: str) -> None:
 
 def create_message(chat: ChatDB, args: argparse.Namespace) -> Message:
     """
-    Creates a new message from the given arguments and writes it
+    Create a new message from the given arguments and write it
     to the cache directory.
     """
     question_parts = []
@@ -73,10 +74,37 @@ def create_message(chat: ChatDB, args: argparse.Namespace) -> Message:
                       tags=args.output_tags,  # FIXME
                       ai=args.AI,
                       model=args.model)
-    chat.cache_add([message])
+    # only write the new message to the cache,
+    # don't add it to the internal list
+    chat.cache_write([message])
     return message
 
 
+def make_request(ai: AI, chat: ChatDB, message: Message, args: argparse.Namespace) -> None:
+    """
+    Make an AI request with the given AI, chat history, message and arguments.
+    Write the response(s) to the cache directory, without appending it to the
+    given chat history. Then print the response(s).
+    """
+    # print history and message question before making the request
+    ai.print()
+    chat.print(paged=False)
+    print(message.to_str())
+    response: AIResponse = ai.request(message,
+                                      chat,
+                                      args.num_answers,  # FIXME
+                                      args.output_tags)  # FIXME
+    # only write the response messages to the cache,
+    # don't add them to the internal list
+    chat.cache_write(response.messages)
+    for idx, msg in enumerate(response.messages):
+        print(f"=== ANSWER {idx+1} ===")
+        print(msg.answer)
+    if response.tokens:
+        print("===============")
+        print(response.tokens)
+
+
 def question_cmd(args: argparse.Namespace, config: Config) -> None:
     """
     Handler for the 'question' command.
@@ -95,28 +123,29 @@ def question_cmd(args: argparse.Namespace, config: Config) -> None:
 
     # create the correct AI instance
     ai: AI = create_ai(args, config)
+
+    # === ASK ===
     if args.ask:
-        ai.print()
+        make_request(ai, chat, message, args)
-        chat.print(paged=False)
+    # === REPEAT ===
-        response: AIResponse = ai.request(message,
-                                          chat,
-                                          args.num_answers,  # FIXME
-                                          args.output_tags)  # FIXME
-        chat.msg_update([response.messages[0]])
-        chat.cache_add(response.messages[1:])
-        for idx, msg in enumerate(response.messages):
-            print(f"=== ANSWER {idx+1} ===")
-            print(msg.answer)
-        if response.tokens:
-            print("===============")
-            print(response.tokens)
     elif args.repeat is not None:
-        lmessage = chat.msg_latest()
+        lmessage = chat.msg_latest(loc='cache')
-        assert lmessage
+        if lmessage is None:
-        # TODO: repeat either the last question or the
+            print("No message found to repeat!")
-        # one(s) given in 'args.repeat' (overwrite
+            sys.exit(1)
-        # existing ones if 'args.overwrite' is True)
+        else:
-        pass
+            print(f"Repeating message '{lmessage.msg_id()}':")
+        # overwrite the latest message if requested or empty
+        if lmessage.answer is None or args.overwrite is True:
+            lmessage.clear_answer()
+            make_request(ai, chat, lmessage, args)
+        # otherwise create a new one
+        else:
+            args.ask = [lmessage.question]
+            message = create_message(chat, args)
+            make_request(ai, chat, message, args)
+
+    # === PROCESS ===
     elif args.process is not None:
         # TODO: process either all questions without an
         # answer or the one(s) given in 'args.process'

chatmastermind/message.py

@@ -222,12 +222,36 @@ class Message():
     ai_yaml_key: ClassVar[str] = 'ai'
     model_yaml_key: ClassVar[str] = 'model'
 
+    def __post_init__(self) -> None:
+        # convert some types that are often set wrong
+        if self.tags is not None and not isinstance(self.tags, set):
+            self.tags = set(self.tags)
+        if self.file_path is not None and not isinstance(self.file_path, pathlib.Path):
+            self.file_path = pathlib.Path(self.file_path)
+
     def __hash__(self) -> int:
         """
         The hash value is computed based on immutable members.
         """
         return hash((self.question, self.answer))
 
+    def equals(self, other: MessageInst, tags: bool = True, ai: bool = True,
+               model: bool = True, file_path: bool = True, verbose: bool = False) -> bool:
+        """
+        Compare this message with another one, including the metadata.
+        Return True if everything is identical, False otherwise.
+        """
+        equal: bool = ((not tags or (self.tags == other.tags))
+                       and (not ai or (self.ai == other.ai))  # noqa: W503
+                       and (not model or (self.model == other.model))  # noqa: W503
+                       and (not file_path or (self.file_path == other.file_path))  # noqa: W503
+                       and (self == other))  # noqa: W503
+        if not equal and verbose:
+            print("Messages not equal:")
+            print(self)
+            print(other)
+        return equal
+
     @classmethod
     def from_dict(cls: Type[MessageInst], data: dict[str, Any]) -> MessageInst:
         """
@@ -418,9 +442,6 @@ class Message():
             output.append(self.answer)
         return '\n'.join(output)
 
-    def __str__(self) -> str:
-        return self.to_str(True, True, False)
-
     def to_file(self, file_path: Optional[pathlib.Path]=None) -> None:  # noqa: 11
         """
         Write a Message to the given file. Type is determined based on the suffix.
@@ -540,6 +561,9 @@ class Message():
         if self.tags:
             self.tags = rename_tags(self.tags, tags_rename)
 
+    def clear_answer(self) -> None:
+        self.answer = None
+
     def msg_id(self) -> str:
         """
         Returns an ID that is unique throughout all messages in the same (DB) directory.

tests/test_chat.py

@@ -10,7 +10,18 @@ from chatmastermind.message import Message, Question, Answer, Tag, MessageFilter
 from chatmastermind.chat import Chat, ChatDB, ChatError
 
 
-class TestChat(unittest.TestCase):
+class TestChatBase(unittest.TestCase):
+    def assert_messages_equal(self, msg1: list[Message], msg2: list[Message]) -> None:
+        """
+        Compare messages using more than just Question and Answer.
+        """
+        self.assertEqual(len(msg1), len(msg2))
+        for m1, m2 in zip(msg1, msg2):
+            # exclude the file_path, compare only Q, A and metadata
+            self.assertTrue(m1.equals(m2, file_path=False, verbose=True))
+
+
+class TestChat(TestChatBase):
     def setUp(self) -> None:
         self.chat = Chat([])
         self.message1 = Message(Question('Question 1'),
@@ -26,24 +37,24 @@ class TestChat(unittest.TestCase):
     def test_unique_id(self) -> None:
         # test with two identical messages
         self.chat.msg_add([self.message1, self.message1])
-        self.assertSequenceEqual(self.chat.messages, [self.message1, self.message1])
+        self.assert_messages_equal(self.chat.messages, [self.message1, self.message1])
         self.chat.msg_unique_id()
-        self.assertSequenceEqual(self.chat.messages, [self.message1])
+        self.assert_messages_equal(self.chat.messages, [self.message1])
         # test with two different messages
         self.chat.msg_add([self.message2])
         self.chat.msg_unique_id()
-        self.assertSequenceEqual(self.chat.messages, [self.message1, self.message2])
+        self.assert_messages_equal(self.chat.messages, [self.message1, self.message2])
 
     def test_unique_content(self) -> None:
         # test with two identical messages
         self.chat.msg_add([self.message1, self.message1])
-        self.assertSequenceEqual(self.chat.messages, [self.message1, self.message1])
+        self.assert_messages_equal(self.chat.messages, [self.message1, self.message1])
         self.chat.msg_unique_content()
-        self.assertSequenceEqual(self.chat.messages, [self.message1])
+        self.assert_messages_equal(self.chat.messages, [self.message1])
         # test with two different messages
         self.chat.msg_add([self.message2])
         self.chat.msg_unique_content()
-        self.assertSequenceEqual(self.chat.messages, [self.message1, self.message2])
+        self.assert_messages_equal(self.chat.messages, [self.message1, self.message2])
 
     def test_filter(self) -> None:
         self.chat.msg_add([self.message1, self.message2])
@@ -150,7 +161,7 @@ Answer 2
         self.assertEqual(mock_stdout.getvalue(), expected_output)
 
 
-class TestChatDB(unittest.TestCase):
+class TestChatDB(TestChatBase):
     def setUp(self) -> None:
         self.db_path = tempfile.TemporaryDirectory()
         self.cache_path = tempfile.TemporaryDirectory()
@@ -569,7 +580,7 @@ class TestChatDB(unittest.TestCase):
         search_names = ['0001', '0002.yaml', self.message3.msg_id(), str(self.message3.file_path)]
         expected_result = [self.message1, self.message2, self.message3]
         result = chat_db.msg_find(search_names, loc='all')
-        self.assertSequenceEqual(result, expected_result)
+        self.assert_messages_equal(result, expected_result)
 
     def test_msg_latest(self) -> None:
         chat_db = ChatDB.from_dir(pathlib.Path(self.cache_path.name),
@@ -595,47 +606,47 @@ class TestChatDB(unittest.TestCase):
         chat_db = ChatDB.from_dir(pathlib.Path(self.cache_path.name),
                                   pathlib.Path(self.db_path.name))
         all_messages = [self.message1, self.message2, self.message3, self.message4]
-        self.assertSequenceEqual(chat_db.msg_gather(loc='all'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='all'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='db'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='db'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='mem'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='mem'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='disk'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='disk'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='cache'), [])
+        self.assert_messages_equal(chat_db.msg_gather(loc='cache'), [])
         # add a new message, but only to the internal list
         new_message = Message(Question("What?"))
         all_messages_mem = all_messages + [new_message]
         chat_db.msg_add([new_message])
-        self.assertSequenceEqual(chat_db.msg_gather(loc='mem'), all_messages_mem)
+        self.assert_messages_equal(chat_db.msg_gather(loc='mem'), all_messages_mem)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='all'), all_messages_mem)
+        self.assert_messages_equal(chat_db.msg_gather(loc='all'), all_messages_mem)
         # the nr. of messages on disk did not change -> expect old result
-        self.assertSequenceEqual(chat_db.msg_gather(loc='db'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='db'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='disk'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='disk'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='cache'), [])
+        self.assert_messages_equal(chat_db.msg_gather(loc='cache'), [])
         # test with MessageFilter
-        self.assertSequenceEqual(chat_db.msg_gather(loc='all', mfilter=MessageFilter(tags_or={Tag('tag1')})),
+        self.assert_messages_equal(chat_db.msg_gather(loc='all', mfilter=MessageFilter(tags_or={Tag('tag1')})),
                                    [self.message1])
-        self.assertSequenceEqual(chat_db.msg_gather(loc='disk', mfilter=MessageFilter(tags_or={Tag('tag2')})),
+        self.assert_messages_equal(chat_db.msg_gather(loc='disk', mfilter=MessageFilter(tags_or={Tag('tag2')})),
                                    [self.message2])
-        self.assertSequenceEqual(chat_db.msg_gather(loc='cache', mfilter=MessageFilter(tags_or={Tag('tag3')})),
+        self.assert_messages_equal(chat_db.msg_gather(loc='cache', mfilter=MessageFilter(tags_or={Tag('tag3')})),
                                    [])
-        self.assertSequenceEqual(chat_db.msg_gather(loc='mem', mfilter=MessageFilter(question_contains="What")),
+        self.assert_messages_equal(chat_db.msg_gather(loc='mem', mfilter=MessageFilter(question_contains="What")),
                                    [new_message])
 
     def test_msg_move_and_gather(self) -> None:
         chat_db = ChatDB.from_dir(pathlib.Path(self.cache_path.name),
                                   pathlib.Path(self.db_path.name))
         all_messages = [self.message1, self.message2, self.message3, self.message4]
-        self.assertSequenceEqual(chat_db.msg_gather(loc='db'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='db'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='cache'), [])
+        self.assert_messages_equal(chat_db.msg_gather(loc='cache'), [])
         # move first message to the cache
         chat_db.cache_move(self.message1)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='cache'), [self.message1])
+        self.assert_messages_equal(chat_db.msg_gather(loc='cache'), [self.message1])
         self.assertEqual(self.message1.file_path.parent, pathlib.Path(self.cache_path.name))  # type: ignore [union-attr]
-        self.assertSequenceEqual(chat_db.msg_gather(loc='db'), [self.message2, self.message3, self.message4])
+        self.assert_messages_equal(chat_db.msg_gather(loc='db'), [self.message2, self.message3, self.message4])
-        self.assertSequenceEqual(chat_db.msg_gather(loc='all'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='all'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='disk'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='disk'), all_messages)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='mem'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='mem'), all_messages)
         # now move first message back to the DB
         chat_db.db_move(self.message1)
-        self.assertSequenceEqual(chat_db.msg_gather(loc='cache'), [])
+        self.assert_messages_equal(chat_db.msg_gather(loc='cache'), [])
         self.assertEqual(self.message1.file_path.parent, pathlib.Path(self.db_path.name))  # type: ignore [union-attr]
-        self.assertSequenceEqual(chat_db.msg_gather(loc='db'), all_messages)
+        self.assert_messages_equal(chat_db.msg_gather(loc='db'), all_messages)

tests/test_question_cmd.py

@@ -3,23 +3,39 @@ import unittest
 import argparse
 import tempfile
 from pathlib import Path
-from unittest.mock import MagicMock
+from unittest import mock
-from chatmastermind.commands.question import create_message
+from unittest.mock import MagicMock, call, ANY
+from typing import Optional
+from chatmastermind.configuration import Config
+from chatmastermind.commands.question import create_message, question_cmd
+from chatmastermind.tags import Tag
 from chatmastermind.message import Message, Question, Answer
-from chatmastermind.chat import ChatDB
+from chatmastermind.chat import Chat, ChatDB
+from chatmastermind.ai import AI, AIResponse, Tokens, AIError
 
 
-class TestMessageCreate(unittest.TestCase):
+class TestQuestionCmdBase(unittest.TestCase):
+    def assert_messages_equal(self, msg1: list[Message], msg2: list[Message]) -> None:
+        """
+        Compare messages using more than just Question and Answer.
+        """
+        self.assertEqual(len(msg1), len(msg2))
+        for m1, m2 in zip(msg1, msg2):
+            # exclude the file_path, compare only Q, A and metadata
+            self.assertTrue(m1.equals(m2, file_path=False, verbose=True))
+
+
+class TestMessageCreate(TestQuestionCmdBase):
     """
     Test if messages created by the 'question' command have
     the correct format.
     """
     def setUp(self) -> None:
         # create ChatDB structure
-        self.db_path = tempfile.TemporaryDirectory()
+        self.db_dir = tempfile.TemporaryDirectory()
-        self.cache_path = tempfile.TemporaryDirectory()
+        self.cache_dir = tempfile.TemporaryDirectory()
-        self.chat = ChatDB.from_dir(cache_path=Path(self.cache_path.name),
+        self.chat = ChatDB.from_dir(cache_path=Path(self.cache_dir.name),
-                                    db_path=Path(self.db_path.name))
+                                    db_path=Path(self.db_dir.name))
         # create some messages
         self.message_text = Message(Question("What is this?"),
                                     Answer("It is pure text"))
@@ -74,6 +90,7 @@ Aaaand again some text."""
         os.remove(self.source_file1.name)
         os.remove(self.source_file2.name)
         os.remove(self.source_file3.name)
+        os.remove(self.source_file4.name)
 
     def message_list(self, tmp_dir: tempfile.TemporaryDirectory) -> list[Path]:
         # exclude '.next'
@@ -81,10 +98,10 @@ Aaaand again some text."""
 
     def test_message_file_created(self) -> None:
         self.args.ask = ["What is this?"]
-        cache_dir_files = self.message_list(self.cache_path)
+        cache_dir_files = self.message_list(self.cache_dir)
         self.assertEqual(len(cache_dir_files), 0)
         create_message(self.chat, self.args)
-        cache_dir_files = self.message_list(self.cache_path)
+        cache_dir_files = self.message_list(self.cache_dir)
         self.assertEqual(len(cache_dir_files), 1)
         message = Message.from_file(cache_dir_files[0])
         self.assertIsInstance(message, Message)
@@ -193,3 +210,267 @@ This is embedded source code.
 It is embedded code
 ```
 """))
+
+
+class TestQuestionCmd(TestQuestionCmdBase):
+
+    def setUp(self) -> None:
+        # create DB and cache
+        self.db_dir = tempfile.TemporaryDirectory()
+        self.cache_dir = tempfile.TemporaryDirectory()
+        # create configuration
+        self.config = Config()
+        self.config.cache = self.cache_dir.name
+        self.config.db = self.db_dir.name
+        # create a mock argparse.Namespace
+        self.args = argparse.Namespace(
+            ask=['What is the meaning of life?'],
+            num_answers=1,
+            output_tags=['science'],
+            AI='openai',
+            model='gpt-3.5-turbo',
+            or_tags=None,
+            and_tags=None,
+            exclude_tags=None,
+            source_text=None,
+            source_code=None,
+            create=None,
+            repeat=None,
+            process=None,
+            overwrite=None
+        )
+        # create a mock AI instance
+        self.ai = MagicMock(spec=AI)
+        self.ai.request.side_effect = self.mock_request
+
+    def input_message(self, args: argparse.Namespace) -> Message:
+        """
+        Create the expected input message for a question using the
+        given arguments.
+        """
+        # NOTE: we only use the first question from the "ask" list
+        # -> message creation using "question.create_message()" is
+        #    tested above
+        # the answer is always empty for the input message
+        return Message(Question(args.ask[0]),
+                       tags=args.output_tags,
+                       ai=args.AI,
+                       model=args.model)
+
+    def mock_request(self,
+                     question: Message,
+                     chat: Chat,
+                     num_answers: int = 1,
+                     otags: Optional[set[Tag]] = None) -> AIResponse:
+        """
+        Mock the 'ai.request()' function
+        """
+        question.answer = Answer("Answer 0")
+        question.tags = set(otags) if otags else None
+        question.ai = 'FakeAI'
+        question.model = 'FakeModel'
+        answers: list[Message] = [question]
+        for n in range(1, num_answers):
+            answers.append(Message(question=question.question,
+                                   answer=Answer(f"Answer {n}"),
+                                   tags=otags,
+                                   ai='FakeAI',
+                                   model='FakeModel'))
+        return AIResponse(answers, Tokens(10, 10, 20))
+
+    def message_list(self, tmp_dir: tempfile.TemporaryDirectory) -> list[Path]:
+        # exclude '.next'
+        return sorted([f for f in Path(tmp_dir.name).glob('*.[ty]*')])
+
+    @mock.patch('chatmastermind.commands.question.create_ai')
+    def test_ask_single_answer(self, mock_create_ai: MagicMock) -> None:
+        """
+        Test single answer with no errors.
+        """
+        mock_create_ai.return_value = self.ai
+        expected_question = self.input_message(self.args)
+        expected_responses = self.mock_request(expected_question,
+                                               Chat([]),
+                                               self.args.num_answers,
+                                               self.args.output_tags).messages
+
+        # execute the command
+        question_cmd(self.args, self.config)
+
+        # check for correct request call
+        self.ai.request.assert_called_once_with(expected_question,
+                                                ANY,
+                                                self.args.num_answers,
+                                                self.args.output_tags)
+        # check for the expected message files
+        chat = ChatDB.from_dir(Path(self.cache_dir.name),
+                               Path(self.db_dir.name))
+        cached_msg = chat.msg_gather(loc='cache')
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, expected_responses)
+
+    @mock.patch('chatmastermind.commands.question.ChatDB.from_dir')
+    @mock.patch('chatmastermind.commands.question.create_ai')
+    def test_ask_single_answer_mocked(self, mock_create_ai: MagicMock, mock_from_dir: MagicMock) -> None:
+        """
+        Test single answer with no errors (mocked ChatDB version).
+        """
+        chat = MagicMock(spec=ChatDB)
+        mock_from_dir.return_value = chat
+
+        mock_create_ai.return_value = self.ai
+        expected_question = self.input_message(self.args)
+        expected_responses = self.mock_request(expected_question,
+                                               Chat([]),
+                                               self.args.num_answers,
+                                               self.args.output_tags).messages
+
+        # execute the command
+        question_cmd(self.args, self.config)
+
+        # check for correct request call
+        self.ai.request.assert_called_once_with(expected_question,
+                                                chat,
+                                                self.args.num_answers,
+                                                self.args.output_tags)
+
+        # check for the correct ChatDB calls:
+        # - initial question has been written (prior to the actual request)
+        # - responses have been written (after the request)
+        chat.cache_write.assert_has_calls([call([expected_question]),
+                                           call(expected_responses)],
+                                          any_order=False)
+
+        # check that the messages have not been added to the internal message list
+        chat.cache_add.assert_not_called()
+
+    @mock.patch('chatmastermind.commands.question.create_ai')
+    def test_ask_with_error(self, mock_create_ai: MagicMock) -> None:
+        """
+        Provoke an error during the AI request and verify that the question
+        has been correctly stored in the cache.
+        """
+        mock_create_ai.return_value = self.ai
+        expected_question = self.input_message(self.args)
+        self.ai.request.side_effect = AIError
+
+        # execute the command
+        with self.assertRaises(AIError):
+            question_cmd(self.args, self.config)
+
+        # check for correct request call
+        self.ai.request.assert_called_once_with(expected_question,
+                                                ANY,
+                                                self.args.num_answers,
+                                                self.args.output_tags)
+        # check for the expected message files
+        chat = ChatDB.from_dir(Path(self.cache_dir.name),
+                               Path(self.db_dir.name))
+        cached_msg = chat.msg_gather(loc='cache')
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, [expected_question])
+
+    @mock.patch('chatmastermind.commands.question.create_ai')
+    def test_repeat_single_question(self, mock_create_ai: MagicMock) -> None:
+        """
+        Repeat a single question.
+        """
+        # 1. ask a question
+        mock_create_ai.return_value = self.ai
+        expected_question = self.input_message(self.args)
+        expected_responses = self.mock_request(expected_question,
+                                               Chat([]),
+                                               self.args.num_answers,
+                                               self.args.output_tags).messages
+        question_cmd(self.args, self.config)
+        chat = ChatDB.from_dir(Path(self.cache_dir.name),
+                               Path(self.db_dir.name))
+        cached_msg = chat.msg_gather(loc='cache')
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, expected_responses)
+
+        # 2. repeat the last question (without overwriting)
+        # -> expect two identical messages (except for the file_path)
+        self.args.ask = None
+        self.args.repeat = []
+        self.args.overwrite = False
+        expected_responses += expected_responses
+        question_cmd(self.args, self.config)
+        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_single_question_overwrite(self, mock_create_ai: MagicMock) -> None:
+        """
+        Repeat a single question and overwrite the old one.
+        """
+        # 1. ask a question
+        mock_create_ai.return_value = self.ai
+        expected_question = self.input_message(self.args)
+        expected_responses = self.mock_request(expected_question,
+                                               Chat([]),
+                                               self.args.num_answers,
+                                               self.args.output_tags).messages
+        question_cmd(self.args, self.config)
+        chat = ChatDB.from_dir(Path(self.cache_dir.name),
+                               Path(self.db_dir.name))
+        cached_msg = chat.msg_gather(loc='cache')
+        assert cached_msg[0].file_path
+        cached_msg_file_id = cached_msg[0].file_path.stem
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, expected_responses)
+
+        # 2. repeat the last question (WITH overwriting)
+        # -> expect a single message afterwards
+        self.args.ask = None
+        self.args.repeat = []
+        self.args.overwrite = True
+        question_cmd(self.args, self.config)
+        cached_msg = chat.msg_gather(loc='cache')
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, expected_responses)
+        # also check that the file ID has not been changed
+        assert cached_msg[0].file_path
+        self.assertEqual(cached_msg_file_id, cached_msg[0].file_path.stem)
+
+    @mock.patch('chatmastermind.commands.question.create_ai')
+    def test_repeat_single_question_after_error(self, mock_create_ai: MagicMock) -> None:
+        """
+        Repeat a single question after an error.
+        """
+        # 1. ask a question
+        mock_create_ai.return_value = self.ai
+        expected_question = self.input_message(self.args)
+        self.ai.request.side_effect = AIError
+
+        # execute the command
+        with self.assertRaises(AIError):
+            question_cmd(self.args, self.config)
+
+        chat = ChatDB.from_dir(Path(self.cache_dir.name),
+                               Path(self.db_dir.name))
+        cached_msg = chat.msg_gather(loc='cache')
+        assert cached_msg[0].file_path
+        cached_msg_file_id = cached_msg[0].file_path.stem
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, [expected_question])
+
+        # 2. repeat the last question (without overwriting)
+        # -> expect a single message because if the original has
+        #    no answer, it should be overwritten by default
+        self.args.ask = None
+        self.args.repeat = []
+        self.args.overwrite = False
+        self.ai.request.side_effect = self.mock_request
+        expected_responses = self.mock_request(expected_question,
+                                               Chat([]),
+                                               self.args.num_answers,
+                                               self.args.output_tags).messages
+        question_cmd(self.args, self.config)
+        cached_msg = chat.msg_gather(loc='cache')
+        self.assertEqual(len(self.message_list(self.cache_dir)), 1)
+        self.assert_messages_equal(cached_msg, expected_responses)
+        # also check that the file ID has not been changed
+        assert cached_msg[0].file_path
+        self.assertEqual(cached_msg_file_id, cached_msg[0].file_path.stem)