diff --git a/fjerkroa_bot/ai_responder.py b/fjerkroa_bot/ai_responder.py
index e665752..e64f378 100644
--- a/fjerkroa_bot/ai_responder.py
+++ b/fjerkroa_bot/ai_responder.py
@@ -156,8 +156,8 @@ class AIResponder(object):
             user_ma = re.match(user_re, message.user)
             if chan_ma and user_ma:
                 self.history.append({"role": "user", "content": str(message)})
-                if len(self.history) > limit:
-                    self.history = self.history[-limit:]
+                while len(self.history) > limit:
+                    self.shrink_history_by_one()
                 if self.history_file is not None:
                     with open(self.history_file, 'wb') as fd:
                         pickle.dump(self.history, fd)