diff --git a/fjerkroa_bot/ai_responder.py b/fjerkroa_bot/ai_responder.py
index 7e46eeb..74b5c81 100644
--- a/fjerkroa_bot/ai_responder.py
+++ b/fjerkroa_bot/ai_responder.py
@@ -4,6 +4,8 @@ import aiohttp
 import logging
 import time
 import re
+import pickle
+from pathlib import Path
 from io import BytesIO
 from pprint import pformat
 from typing import Optional, List, Dict, Any, Tuple
@@ -39,6 +41,12 @@ class AIResponder(object):
         self.history: List[Dict[str, Any]] = []
         self.channel = channel if channel is not None else 'system'
         openai.api_key = self.config['openai-token']
+        self.history_file: Optional[Path] = None
+        if 'history-directory' in self.config:
+            self.history_file = Path(self.config['history-directory']).expanduser() / f'{self.channel}.dat'
+            if self.history_file.exists():
+                with open(self.history_file, 'rb') as fd:
+                    self.history = pickle.load(fd)
 
     def _message(self, message: AIMessage, limit: Optional[int] = None) -> List[Dict[str, Any]]:
         messages = []
@@ -133,6 +141,15 @@ class AIResponder(object):
                 logging.warning(f"failed to execute a fix for the answer: {repr(err)}")
         return answer
 
+    def update_history(self, question: Dict[str, Any], answer: Dict[str, Any], limit: int) -> None:
+        self.history.append(question)
+        self.history.append(answer)
+        if len(self.history) > limit:
+            self.history = self.history[-limit:]
+            if self.history_file is not None:
+                with open(self.history_file, 'wb') as fd:
+                    pickle.dump(self.history, fd)
+
     async def send(self, message: AIMessage) -> AIResponse:
         limit = self.config["history-limit"]
         if self.short_path(message, limit):
@@ -156,9 +173,6 @@ class AIResponder(object):
             if 'hack' not in response or type(response.get('picture', None)) not in (type(None), str):
                 continue
             logging.info(f"got this answer:\n{pformat(response)}")
-            self.history.append(messages[-1])
-            self.history.append(answer)
-            if len(self.history) > limit:
-                self.history = self.history[-limit:]
+            self.update_history(messages[-1], answer, limit)
             return await self.post_process(response)
         raise RuntimeError("Failed to generate answer after multiple retries")
diff --git a/tests/test_main.py b/tests/test_main.py
index 62fe0f8..9057ce2 100644
--- a/tests/test_main.py
+++ b/tests/test_main.py
@@ -111,12 +111,8 @@ class TestFunctionality(TestBotBase):
     async def test_on_message_event3(self) -> None:
         async def acreate(*a, **kw):
             return {'choices': [{'message': {'content': '{ "test": 3 ]'}}]}
-
-        def logging_warning(msg):
-            raise RuntimeError(msg)
         message = self.create_message("Hello there! How are you?")
-        with patch.object(openai.ChatCompletion, 'acreate', new=acreate), \
-             patch.object(logging, 'warning', logging_warning):
+        with patch.object(openai.ChatCompletion, 'acreate', new=acreate):
             await self.bot.on_message(message)
         self.bot.staff_channel.send.assert_called_once_with("ERROR: I could not parse this answer: '{ \"test\": 3 ]'", suppress_embeds=True)