diff --git a/redbot/__init__.py b/redbot/__init__.py
index 236ca418e..567d88fc9 100644
--- a/redbot/__init__.py
+++ b/redbot/__init__.py
@@ -1,5 +1,7 @@
 import asyncio as _asyncio
+import logging as _logging
 import os as _os
+import re
 import re as _re
 import sys as _sys
 import warnings as _warnings
@@ -14,6 +16,7 @@ from typing import (
     Union as _Union,
 )
 
+from redbot._log import RedTraceLogger
 
 MIN_PYTHON_VERSION = (3, 8, 1)
 
@@ -209,9 +212,14 @@ def _ensure_no_colorama():
         colorama.initialise.wrap_stream = _colorama_wrap_stream
 
 
+def _update_logger_class():
+    _logging.setLoggerClass(RedTraceLogger)
+
+
 def _early_init():
     _update_event_loop_policy()
     _ensure_no_colorama()
+    _update_logger_class()
 
 
 __version__ = "3.5.0.dev1"
@@ -222,7 +230,8 @@ _warnings.filterwarnings("ignore", module=r"fuzzywuzzy.*")
 # Show DeprecationWarning
 _warnings.filterwarnings("default", category=DeprecationWarning)
 
-if "--debug" not in _sys.argv:
+# TODO: Rearrange cli flags here and use the value instead of this monkeypatch
+if not any(re.match("^-(-debug|d+|-verbose|v+)$", i) for i in _sys.argv):
     # DEP-WARN
     # Individual warnings - tracked in https://github.com/Cog-Creators/Red-DiscordBot/issues/3529
     # DeprecationWarning: an integer is required (got type float).  Implicit conversion to integers using __int__ is deprecated, and may be removed in a future version of Python.
diff --git a/redbot/_log.py b/redbot/_log.py
new file mode 100644
index 000000000..62afdcce5
--- /dev/null
+++ b/redbot/_log.py
@@ -0,0 +1,22 @@
+import logging as _logging
+
+__ALL__ = ["VERBOSE", "TRACE", "RedTraceLogger"]
+
+VERBOSE = _logging.DEBUG - 3
+TRACE = _logging.DEBUG - 5
+
+
+class RedTraceLogger(_logging.getLoggerClass()):
+    def __init__(self, name, level=_logging.NOTSET):
+        super().__init__(name, level)
+
+        _logging.addLevelName(VERBOSE, "VERBOSE")
+        _logging.addLevelName(TRACE, "TRACE")
+
+    def verbose(self, msg, *args, **kwargs):
+        if self.isEnabledFor(VERBOSE):
+            self._log(VERBOSE, msg, args, **kwargs)
+
+    def trace(self, msg, *args, **kwargs):
+        if self.isEnabledFor(TRACE):
+            self._log(TRACE, msg, args, **kwargs)
diff --git a/redbot/core/cli.py b/redbot/core/cli.py
index dcc1378ff..adbf311f9 100644
--- a/redbot/core/cli.py
+++ b/redbot/core/cli.py
@@ -7,6 +7,8 @@ from typing import Optional
 import discord
 from discord import __version__ as discord_version
 
+from redbot.core.utils._internal_utils import cli_level_to_log_level
+
 
 def confirm(text: str, default: Optional[bool] = None) -> bool:
     if default is None:
@@ -186,12 +188,13 @@ def parse_cli_flags(args):
         "process.",
     )
     parser.add_argument(
+        "-v",
+        "--verbose",
         "--debug",
-        action="store_const",
+        action="count",
+        default=0,
         dest="logging_level",
-        const=logging.DEBUG,
-        default=logging.INFO,
-        help="Sets the loggers level as debug",
+        help="Increase the verbosity of the logs, each usage of this flag increases the verbosity level by 1.",
     )
     parser.add_argument("--dev", action="store_true", help="Enables developer mode")
     parser.add_argument(
@@ -291,5 +294,6 @@ def parse_cli_flags(args):
         args.prefix = sorted(args.prefix, reverse=True)
     else:
         args.prefix = []
+    args.logging_level = cli_level_to_log_level(args.logging_level)
 
     return args
diff --git a/redbot/core/utils/_internal_utils.py b/redbot/core/utils/_internal_utils.py
index 3a7ff1e77..d23be45a3 100644
--- a/redbot/core/utils/_internal_utils.py
+++ b/redbot/core/utils/_internal_utils.py
@@ -36,7 +36,7 @@ from fuzzywuzzy import fuzz, process
 from rich.progress import ProgressColumn
 from rich.progress_bar import ProgressBar
 
-from redbot import VersionInfo
+from redbot import VersionInfo, _log
 from redbot.core import data_manager
 from redbot.core.utils.chat_formatting import box
 
@@ -57,6 +57,7 @@ __all__ = (
     "fetch_latest_red_version_info",
     "deprecated_removed",
     "RichIndefiniteBarColumn",
+    "cli_level_to_log_level",
 )
 
 _T = TypeVar("_T")
@@ -357,3 +358,15 @@ class RichIndefiniteBarColumn(ProgressColumn):
             total=task.total,
             completed=task.completed,
         )
+
+
+def cli_level_to_log_level(level: int) -> int:
+    if level == 0:
+        log_level = logging.INFO
+    elif level == 1:
+        log_level = logging.DEBUG
+    elif level == 2:
+        log_level = _log.VERBOSE
+    else:
+        log_level = _log.TRACE
+    return log_level
diff --git a/redbot/logging.py b/redbot/logging.py
index ec1af3114..e52c18b4f 100644
--- a/redbot/logging.py
+++ b/redbot/logging.py
@@ -282,7 +282,6 @@ class RedRichHandler(RichHandler):
 
 def init_logging(level: int, location: pathlib.Path, cli_flags: argparse.Namespace) -> None:
     root_logger = logging.getLogger()
-
     base_logger = logging.getLogger("red")
     base_logger.setLevel(level)
     dpy_logger = logging.getLogger("discord")
@@ -298,6 +297,8 @@ def init_logging(level: int, location: pathlib.Path, cli_flags: argparse.Namespa
                 "log.time": Style(dim=True),
                 "logging.level.warning": Style(color="yellow"),
                 "logging.level.critical": Style(color="white", bgcolor="red"),
+                "logging.level.verbose": Style(color="magenta", italic=True, dim=True),
+                "logging.level.trace": Style(color="white", italic=True, dim=True),
                 "repr.number": Style(color="cyan"),
                 "repr.url": Style(underline=True, italic=True, bold=False, color="cyan"),
             }
diff --git a/redbot/setup.py b/redbot/setup.py
index f3363d4d1..89b4f2993 100644
--- a/redbot/setup.py
+++ b/redbot/setup.py
@@ -17,7 +17,11 @@ import appdirs
 import click
 
 from redbot.core.cli import confirm
-from redbot.core.utils._internal_utils import safe_delete, create_backup as red_create_backup
+from redbot.core.utils._internal_utils import (
+    safe_delete,
+    create_backup as red_create_backup,
+    cli_level_to_log_level,
+)
 from redbot.core import config, data_manager, drivers
 from redbot.core.drivers import BackendType, IdentifierData
 
@@ -352,7 +356,7 @@ async def remove_instance_interaction() -> None:
 
 
 @click.group(invoke_without_command=True)
-@click.option("--debug", type=bool)
+@click.option("--debug", "--verbose", "-v", count=True)
 @click.option(
     "--no-prompt",
     "interactive",
@@ -402,7 +406,7 @@ def cli(
     overwrite_existing_instance: bool,
 ) -> None:
     """Create a new instance."""
-    level = logging.DEBUG if debug else logging.INFO
+    level = cli_level_to_log_level(debug)
     base_logger = logging.getLogger("red")
     base_logger.setLevel(level)
     formatter = logging.Formatter(