diff --git a/pterodactyl/pterodactyl.py b/pterodactyl/pterodactyl.py
index 88b9c20..df0b849 100644
--- a/pterodactyl/pterodactyl.py
+++ b/pterodactyl/pterodactyl.py
@@ -111,22 +111,29 @@ class Pterodactyl(commands.Cog):
         return ansi_escape.sub('', text)
 
     def check_if_chat_message(self, text: str) -> Union[bool, dict]:
+        self.logger.debug("Checking if message is a chat message")
         regex = self.config.chat_regex()
         match: Optional[re.Match[str]] = re.match(regex, text)
         if match:
+            self.logger.debug("Message is a chat message")
             return {"time": match.group(1), "username": match.group(2), "message": match.group(3)}
+        self.logger.debug("Message is not a chat message")
         return False
 
     async def get_info(self, username: str) -> Optional[dict]:
+        self.logger.debug("Retrieving player info for %s", username)
         endpoint = await self.config.endpoint()
         async with aiohttp.ClientSession() as session:
             async with session.get(f"https://playerdb.co/api/player/{endpoint}/{username}") as response:
                 if response.status == 200:
+                    self.logger.debug("Player info retrieved for %s", username)
                     return await response.json()
                 else:
+                    self.logger.error("Failed to retrieve player info for %s: %s", username, response.status)
                     return None
 
     async def send_chat_discord(self, username: str, message: str, avatar_url: str) -> None:
+        self.logger.debug("Sending chat message to Discord")
         channel = self.bot.get_channel(await self.config.chat_channel())
         if channel is not None:
             webhooks = await channel.webhooks()
@@ -134,6 +141,8 @@ class Pterodactyl(commands.Cog):
             if webhook is None:
                 webhook = await channel.create_webhook(name="Pterodactyl Chat")
             await webhook.send(content=message, username=username, avatar_url=avatar_url)
+            self.logger.debug("Chat message sent to Discord")
+        self.logger.debug("Chat channel not set. Skipping sending chat message to Discord")
 
     def get_task(self):
         return self.bot.loop.create_task(self.establish_websocket_connection(), name="Pterodactyl Websocket Connection")