diff --git a/chatmastermind/commands/question.py b/chatmastermind/commands/question.py
index 37b62c4..e35bfe5 100644
--- a/chatmastermind/commands/question.py
+++ b/chatmastermind/commands/question.py
@@ -105,6 +105,25 @@ def make_request(ai: AI, chat: ChatDB, message: Message, args: argparse.Namespac
         print(response.tokens)
 
 
+def repeat_messages(messages: list[Message], ai: AI, chat: ChatDB, args: argparse.Namespace) -> None:
+    """
+    Repeat the given messages using the given arguments.
+    """
+    for msg in messages:
+        print(f"--------- Repeating message '{msg.msg_id()}': ---------")
+        # overwrite the latest message if requested or empty
+        # -> but not if it's in the DB!
+        if ((msg.answer is None or args.overwrite is True)
+           and (not chat.msg_in_db(msg))):  # noqa: W503
+            msg.clear_answer()
+            make_request(ai, chat, msg, args)
+        # otherwise create a new one
+        else:
+            args.ask = [msg.question]
+            message = create_message(chat, args)
+            make_request(ai, chat, message, args)
+
+
 def question_cmd(args: argparse.Namespace, config: Config) -> None:
     """
     Handler for the 'question' command.
@@ -120,7 +139,6 @@ def question_cmd(args: argparse.Namespace, config: Config) -> None:
         message = create_message(chat, args)
     if args.create:
         return
-
     # create the correct AI instance
     ai: AI = create_ai(args, config)
 
@@ -129,22 +147,18 @@ def question_cmd(args: argparse.Namespace, config: Config) -> None:
         make_request(ai, chat, message, args)
     # === REPEAT ===
     elif args.repeat is not None:
-        lmessage = chat.msg_latest(loc='cache')
-        if lmessage is None:
-            print("No message found to repeat!")
-            sys.exit(1)
+        repeat_msgs: list[Message] = []
+        # repeat latest message
+        if len(args.repeat) == 0:
+            lmessage = chat.msg_latest(loc='cache')
+            if lmessage is None:
+                print("No message found to repeat!")
+                sys.exit(1)
+            repeat_msgs.append(lmessage)
+        # repeat given message(s)
         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)
-
+            repeat_msgs = chat.msg_find(args.repeat, loc='disk')
+        repeat_messages(repeat_msgs, ai, chat, args)
     # === PROCESS ===
     elif args.process is not None:
         # TODO: process either all questions without an