diff --git a/chatmastermind/commands/question.py b/chatmastermind/commands/question.py
index d143792..d582396 100644
--- a/chatmastermind/commands/question.py
+++ b/chatmastermind/commands/question.py
@@ -1,3 +1,4 @@
+import sys
 import argparse
 from pathlib import Path
 from itertools import zip_longest
@@ -72,10 +73,26 @@ def create_message(chat: ChatDB, args: argparse.Namespace) -> Message:
                       tags=args.output_tags,  # FIXME
                       ai=args.AI,
                       model=args.model)
-    chat.add_to_cache([message])
+    chat.write_cache([message])
     return message
 
 
+def make_request(ai: AI, chat: ChatDB, message: Message, args: argparse.Namespace) -> None:
+    ai.print()
+    chat.print(paged=False)
+    response: AIResponse = ai.request(message,
+                                      chat,
+                                      args.num_answers,  # FIXME
+                                      args.output_tags)  # FIXME
+    chat.write_cache(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.
@@ -94,28 +111,29 @@ 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()
-        chat.print(paged=False)
-        response: AIResponse = ai.request(message,
-                                          chat,
-                                          args.num_answers,  # FIXME
-                                          args.output_tags)  # FIXME
-        chat.update_messages([response.messages[0]])
-        chat.add_to_cache(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)
+        make_request(ai, chat, message, args)
+    # === REPEAT ===
     elif args.repeat is not None:
-        lmessage = chat.latest_message()
-        assert lmessage
-        # TODO: repeat either the last question or the
-        # one(s) given in 'args.repeat' (overwrite
-        # existing ones if 'args.overwrite' is True)
-        pass
+        lmessage = chat.latest_message(source='cache')
+        if lmessage is None:
+            print("No message found to repeat!")
+            sys.exit(1)
+        else:
+            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'
diff --git a/chatmastermind/message.py b/chatmastermind/message.py
index 8b32ae9..9d48945 100644
--- a/chatmastermind/message.py
+++ b/chatmastermind/message.py
@@ -540,6 +540,9 @@ 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.