diff --git a/matrix_pygmalion_bot/bot/ai/langchain.py b/matrix_pygmalion_bot/bot/ai/langchain.py
index c596e77..a91afb7 100644
--- a/matrix_pygmalion_bot/bot/ai/langchain.py
+++ b/matrix_pygmalion_bot/bot/ai/langchain.py
@@ -119,6 +119,7 @@ class AI(object):
         room_id = message.additional_kwargs['room_id']
         conversation_memory = self.get_memory(room_id)
         conversation_memory.chat_memory.messages.append(message)
+        conversation_memory.chat_memory_day.messages.append(message)
 
     async def clear(self, room_id):
         conversation_memory = self.get_memory(room_id)
@@ -219,6 +220,8 @@ class AI(object):
 
         if prompt_len+256 > 2000:
             logger.warning(f"Prompt too large. Estimated {prompt_len} tokens")
+            await reply_fn(f"<WARNING> Prompt too large. Estimated {prompt_len} tokens")
+            await conversation_memory.prune_memory(conversation_memory.min_len)
 
 
         #roleplay_chain = RoleplayChain(llm_chain=chain, character_name=self.bot.name, persona=self.bot.persona, scenario=self.bot.scenario, ai_name_chat=chat_ai_name, human_name_chat=chat_human_name)
@@ -370,6 +373,8 @@ class AI(object):
                     "room_id": room_id,
                 }
             )
+            if conversation_memory.chat_memory.messages[-1].content.startswith('~~~~ '):
+                conversation_memory.chat_memory.messages.pop()
             conversation_memory.chat_memory.messages.append(message)
             #conversation_memory.chat_memory.add_system_message(message)
 
@@ -377,6 +382,8 @@ class AI(object):
         yesterday = ( datetime.now() - timedelta(days=1) ).strftime('%Y-%m-%d')
         for room_id in self.rooms.keys():
             if len(conversation_memory.chat_memory_day.messages) > 0:
+                if not "diary" in self.bot.rooms[room_id]:
+                    self.bot.rooms[room_id]['diary'] = {}
                 self.bot.rooms[room_id]["diary"][yesterday] = await self.diary(room_id)
         # Calculate new goals for the character
         # Update stats
diff --git a/matrix_pygmalion_bot/bot/ai/langchain_memory.py b/matrix_pygmalion_bot/bot/ai/langchain_memory.py
index 5161fab..ed3abce 100644
--- a/matrix_pygmalion_bot/bot/ai/langchain_memory.py
+++ b/matrix_pygmalion_bot/bot/ai/langchain_memory.py
@@ -91,22 +91,24 @@ class CustomMemory(BaseMemory):
                 self.predict_new_summary(pruned_memory, self.moving_summary_buffer)
             )
 
-    async def asave_context(self, input_msg: BaseMessage, output_msg: BaseMessage) -> None:
-        """Save context from this conversation to buffer."""
-        self.chat_memory.messages.append(input_msg)
-        self.chat_memory.messages.append(output_msg)
-        self.chat_memory_day.messages.append(input_msg)
-        self.chat_memory_day.messages.append(output_msg)
+    async def prune_memory(self, max_len):
         # Prune buffer if it exceeds max token limit
         buffer = self.chat_memory.messages
         curr_buffer_length = self.llm.get_num_tokens_from_messages(buffer)
-        if curr_buffer_length > self.max_len:
+        if curr_buffer_length > max_len:
             pruned_memory = []
-            while curr_buffer_length > self.min_len:
+            while curr_buffer_length > self.min_len and len(buffer) > 0:
                 pruned_memory.append(buffer.pop(0))
                 curr_buffer_length = self.llm.get_num_tokens_from_messages(buffer)
             self.moving_summary_buffer = await self.apredict_new_summary(pruned_memory, self.moving_summary_buffer)
 
+    async def asave_context(self, input_msg: BaseMessage, output_msg: BaseMessage) -> None:
+        """Save context from this conversation to buffer."""
+        self.chat_memory.messages.append(input_msg)
+        self.chat_memory.messages.append(output_msg)
+        self.chat_memory_day.messages.append(input_msg)
+        self.chat_memory_day.messages.append(output_msg)
+        await self.prune_memory(self.max_len)
 
     def clear(self) -> None:
         """Clear memory contents."""
diff --git a/matrix_pygmalion_bot/bot/utilities/messages.py b/matrix_pygmalion_bot/bot/utilities/messages.py
index 6ef3f28..6166b1b 100644
--- a/matrix_pygmalion_bot/bot/utilities/messages.py
+++ b/matrix_pygmalion_bot/bot/utilities/messages.py
@@ -77,7 +77,12 @@ class Message(object):
         return self.message.startswith('!')
 
     def is_error(self):
-        return self.message.startswith('<ERROR>')
+        if self.message.startswith('<ERROR>'):
+            return True
+        elif self.message.startswith('<WARNING>'):
+            return True
+        else:
+            return False
 
     def __str__(self):
         return str("{}: {}".format(self.user_name, self.message))