diff --git a/modmail/extensions/debug.py b/modmail/extensions/debug.py
new file mode 100644
index 00000000..8459c6bd
--- /dev/null
+++ b/modmail/extensions/debug.py
@@ -0,0 +1,143 @@
+"""
+Useful commands for debugging built in bot issues.
+
+Often a problem is a configuration issue, this cog will help determine issues.
+"""
+
+import logging
+import typing
+
+import discord
+from discord.ext import commands
+from discord.ext.commands import Context
+
+import modmail
+from modmail.bot import ModmailBot
+from modmail.log import ModmailLogger
+from modmail.utils.cogs import BotModes, ExtMetadata, ModmailCog
+from modmail.utils.extensions import BOT_MODE
+from modmail.utils.pagination import ButtonPaginator
+
+
+logger: ModmailLogger = logging.getLogger(__name__)
+
+EXT_METADATA = ExtMetadata()
+
+EXTRAS_DEBUG_KEY = "only_if_cog_debug"
+
+
+class AlreadyInModeError(Exception):
+    """Raised if the cog is already in a mode."""
+
+    pass
+
+
+class DebugCog(ModmailCog, name="Debugger"):
+    """Debug commands."""
+
+    def __init__(self, bot: ModmailBot):
+        self.bot = bot
+        self.enable_debug_commands = bool(BOT_MODE & BotModes.DEVELOP.value)
+        self.enable_or_disable_commands(self.enable_debug_commands, force=True)
+
+    def enable_or_disable_commands(self, new_status: bool = None, *, force: bool = False) -> bool:
+        """Enable or disable debug only commands."""
+        if not force and (new_status == self.enable_debug_commands):
+            raise AlreadyInModeError(new_status)
+        elif new_status is not None:
+            self.enable_debug_commands = new_status
+        else:
+            self.enable_debug_commands = not self.enable_debug_commands
+
+        for com in self.walk_commands():
+            if com.extras.get(EXTRAS_DEBUG_KEY, False):
+                com.enabled = self.enable_debug_commands
+        return self.enable_debug_commands
+
+    @commands.group(invoke_without_command=True)
+    async def debug(self, ctx: Context, enable_or_disable: bool = None) -> None:
+        """Commands to show logs and debug portions of the bot."""
+        if enable_or_disable is not None:
+            print(enable_or_disable)
+            if enable_or_disable:
+                self.enable_or_disable_commands(True)
+                msg = "Enabled the debugger commands."
+            else:
+                self.enable_or_disable_commands(False)
+                msg = "Disabled the debugger commands."
+            await ctx.send(msg)
+            return
+
+        await ctx.send(self.enable_debug_commands)
+
+    @staticmethod
+    def get_logs(tail_lines: int = 200, lines_per_page: int = 10) -> typing.List[str]:
+        """Get a list of the tail logs."""
+        logs = []
+
+        pages = tail_lines // lines_per_page
+        if tail_lines < lines_per_page:
+            pages = 1
+
+        try:
+            f = open(modmail.log_file)
+            all_logs = f.read()
+        finally:
+            f.close()
+        # get the last lines on the code
+        pos = len(all_logs)
+        for _ in range(tail_lines):
+            if (nl_pos := all_logs.rfind("\n", None, pos)) == -1:
+                break
+            pos = nl_pos
+
+        # split away the useless section
+        all_logs = all_logs[pos:]
+        for _ in range(pages):
+            slice_pos = -1
+            for _ in range(lines_per_page):
+                if (
+                    (inital_slice_pos := all_logs.find("\n", slice_pos + 1)) == -1
+                ) or slice_pos == inital_slice_pos:
+                    break
+                slice_pos = inital_slice_pos
+            if not len(to_append := all_logs[:slice_pos]) > 0:
+                continue
+            logs.append(to_append)
+            all_logs = all_logs[slice_pos:]
+
+        print(len(logs))
+        return logs
+
+    @debug.command(name="logs", aliases=("log",), extras={EXTRAS_DEBUG_KEY: True})
+    async def logs(self, ctx: Context) -> None:
+        """Paginate through the last 10 pages of logs."""
+        logs = self.get_logs()
+        await ButtonPaginator.paginate(
+            logs,
+            ctx.message,
+            title="**Modmail Logs**",
+            prefix="```prolog\n",
+            suffix="```",
+            embed=None,
+            max_size=2000,
+        )
+
+    @debug.command(name="dump", extras={EXTRAS_DEBUG_KEY: True})
+    async def dump_logs(self, ctx: Context) -> None:
+        """Dump the log file in the chat."""
+        logger.info(f"{ctx.author!s} requested the logs")
+        async with ctx.typing():
+            with open(modmail.log_file, "rb") as f:
+                file = discord.File(f, filename="modmail-logs.prolog")
+
+        await ctx.send(
+            "Please share this file with the developers. Do not share this with anyone else, "
+            "as there may be sensitive information in this file.",
+            file=file,
+        )
+
+
+def setup(bot: ModmailBot) -> None:
+    """Add the debug cog to the bot."""
+    bot.add_cog(DebugCog(bot))