diff --git a/redbot/core/events.py b/redbot/core/events.py
index 7bd8dd14a..ecb50f31c 100644
--- a/redbot/core/events.py
+++ b/redbot/core/events.py
@@ -1,5 +1,6 @@
 import asyncio
 import contextlib
+import platform
 import sys
 import codecs
 import datetime
@@ -19,7 +20,7 @@ from .utils import AsyncIter
 from .. import __version__ as red_version, version_info as red_version_info, VersionInfo
 from . import commands
 from .config import get_latest_confs
-from .utils._internal_utils import fuzzy_command_search, format_fuzzy_results
+from .utils._internal_utils import fuzzy_command_search, format_fuzzy_results, expected_version
 from .utils.chat_formatting import inline, bordered, format_perms_list, humanize_timedelta
 
 log = logging.getLogger("red")
@@ -99,10 +100,59 @@ def init_events(bot, cli_flags):
                     "Outdated version! {} is available "
                     "but you're using {}".format(data["info"]["version"], red_version)
                 )
-                outdated_red_message = (
+                outdated_red_message = _(
                     "Your Red instance is out of date! {} is the current "
                     "version, however you are using {}!"
                 ).format(data["info"]["version"], red_version)
+                requires_python = data["info"]["requires_python"]
+                current_python = platform.python_version()
+                extra_update = _(
+                    "\n\nWhile the following command should work in most scenarios as it is "
+                    "based on your current OS, environment, and Python version, "
+                    "**we highly recommend you to read the update docs at <{docs}> and "
+                    "make sure there is nothing else that "
+                    "needs to be done during the update.**"
+                ).format(docs="https://docs.discord.red/en/stable/update_red.html",)
+                if expected_version(current_python, requires_python):
+                    installed_extras = []
+                    for extra, reqs in red_pkg._dep_map.items():
+                        if extra is None:
+                            continue
+                        try:
+                            pkg_resources.require(req.name for req in reqs)
+                        except pkg_resources.DistributionNotFound:
+                            pass
+                        else:
+                            installed_extras.append(extra)
+
+                    if installed_extras:
+                        package_extras = f"[{','.join(installed_extras)}]"
+                    else:
+                        package_extras = ""
+
+                    extra_update += _(
+                        "\n\nTo update your bot, first shutdown your "
+                        "bot then open a window of {console} (Not as admin) and "
+                        "run the following:\n\n"
+                    ).format(
+                        console=_("Command Prompt")
+                        if platform.system() == "Windows"
+                        else _("Terminal")
+                    )
+                    extra_update += '```"{python}" -m pip install -U Red-DiscordBot{package_extras}```'.format(
+                        python=sys.executable, package_extras=package_extras
+                    )
+
+                else:
+                    extra_update += _(
+                        "\n\nYou have Python `{py_version}` and this update "
+                        "requires `{req_py}`; you cannot simply run the update command.\n\n"
+                        "You will need to follow the update instructions in our docs above, "
+                        "if you still need help updating after following the docs go to our "
+                        "#support channel in <https://discord.gg/red>"
+                    ).format(py_version=current_python, req_py=requires_python)
+                outdated_red_message += extra_update
+
         INFO2 = []
 
         reqs_installed = {"docs": None, "test": None}
diff --git a/redbot/core/utils/_internal_utils.py b/redbot/core/utils/_internal_utils.py
index 238aca44c..05957a0f9 100644
--- a/redbot/core/utils/_internal_utils.py
+++ b/redbot/core/utils/_internal_utils.py
@@ -22,6 +22,7 @@ from typing import (
 )
 
 import discord
+import pkg_resources
 from fuzzywuzzy import fuzz, process
 
 from redbot.core import data_manager
@@ -33,7 +34,15 @@ if TYPE_CHECKING:
 
 main_log = logging.getLogger("red")
 
-__all__ = ("safe_delete", "fuzzy_command_search", "format_fuzzy_results", "create_backup")
+__all__ = (
+    "safe_delete",
+    "fuzzy_command_search",
+    "format_fuzzy_results",
+    "create_backup",
+    "send_to_owners_with_preprocessor",
+    "send_to_owners_with_prefix_replaced",
+    "expected_version",
+)
 
 
 def safe_delete(pth: Path):
@@ -282,3 +291,8 @@ async def send_to_owners_with_prefix_replaced(bot: Red, content: str, **kwargs):
         return content.replace("[p]", prefix)
 
     await send_to_owners_with_preprocessor(bot, content, content_preprocessor=preprocessor)
+
+
+def expected_version(current: str, expected: str) -> bool:
+    # `pkg_resources` needs a regular requirement string, so "x" serves as requirement's name here
+    return current in pkg_resources.Requirement.parse(f"x{expected}")