diff --git a/bot/exts/levels/_cog.py b/bot/exts/levels/_cog.py
index abdd3b1..9f934de 100644
--- a/bot/exts/levels/_cog.py
+++ b/bot/exts/levels/_cog.py
@@ -132,6 +132,10 @@ async def _cycle_rules_task(self) -> None:
             rule_trigger for rule in self.rules_active
             for rule_trigger in rule.rule_triggers if rule_trigger.interaction_type=="reaction"
         ]
+        self.all_message_rule_triggers = [
+            rule_trigger for rule in self.rules_all
+            for rule_trigger in rule.rule_triggers if rule_trigger.interaction_type=="message"
+        ]
         # [rule for rule in self.rules_active if rule.interaction_type=="reaction"]
         # self.active_message_rule_triggers = [rule for rule in self.rules_active if rule.interaction_type=="message"]
 
@@ -194,6 +198,9 @@ async def _update_role_assignment(self, user_id: int) -> None:
         user = await members.get_or_fetch_member(guild, user_id)
         if role in user.roles:
             return
+        for user_role in user.roles:
+            if user_role in LEVEL_ROLES:
+                await members.handle_role_change(user, user.remove_roles, user_role)
         logger.debug(f"Assigning {role.name} to {user.name}")
         await members.handle_role_change(user, user.add_roles, role)
 
@@ -224,6 +231,15 @@ async def on_message(self, msg: discord.Message) -> None:
             user_id = msg.author.id
             await self._update_points(user_id, total_points)
 
+        total_rule_matches = 0
+        for rule_trigger in self.all_message_rule_triggers:
+            re_pattern = rule_trigger.message_content
+            match = re.search(re_pattern, msg.content)
+            if match:
+                total_rule_matches += 1
+        if total_rule_matches >= 3:
+            await self._update_points(user_id, -5)
+
 
     @commands.Cog.listener()
     async def on_reaction_add(self, reaction: discord.Reaction, user: discord.Member) -> None:
diff --git a/bot/exts/levels/rules/monty_python.toml b/bot/exts/levels/rules/monty_python.toml
index 721fb4b..ec74112 100644
--- a/bot/exts/levels/rules/monty_python.toml
+++ b/bot/exts/levels/rules/monty_python.toml
@@ -17,3 +17,13 @@ points = 3
 interaction_type = "message"
 message_content = '''\b(IDLE|Idle|Cleese|Gilliam|Jones|Chapman|Palin)\b'''
 points = 1
+
+[[rule]]
+interaction_type = "message"
+message_content = '''\b(\'[Tt]is but a scratch)\b'''
+points = 1
+
+[[rule]]
+interaction_type = "message"
+message_content = '''\b([Ff]light [Ss]peed|[Uu]nladen [Ss]wallow|[Aa]frican or [Ee]uropean)\b'''
+points = 2