diff --git a/README.md b/README.md
index 12f68e98d8..5083341408 100644
--- a/README.md
+++ b/README.md
@@ -171,6 +171,9 @@ # To install nightly with pip:
 python3 -m pip install -U --pre "yt-dlp[default]"
 ```
 
+When running a yt-dlp version that is older than 90 days, you will see a warning message suggesting to update to the latest version.
+You can suppress this warning by adding `--no-update` to your command or configuration file.
+
 ## DEPENDENCIES
 Python versions 3.9+ (CPython) and 3.11+ (PyPy) are supported. Other versions and implementations may or may not work correctly.
 
diff --git a/devscripts/cli_to_api.py b/devscripts/cli_to_api.py
index 9c2710e09f..cc86b413f4 100755
--- a/devscripts/cli_to_api.py
+++ b/devscripts/cli_to_api.py
@@ -20,6 +20,7 @@ def parse_patched_options(opts):
         'fragment_retries': 0,
         'extract_flat': False,
         'concat_playlist': 'never',
+        'update_self': False,
     })
     yt_dlp.options.create_parser = lambda: patched_parser
     try:
diff --git a/yt_dlp/YoutubeDL.py b/yt_dlp/YoutubeDL.py
index a9f347bf4a..5985d2ec76 100644
--- a/yt_dlp/YoutubeDL.py
+++ b/yt_dlp/YoutubeDL.py
@@ -73,6 +73,7 @@
 from .update import (
     REPOSITORY,
     _get_system_deprecation,
+    _get_outdated_warning,
     _make_label,
     current_git_head,
     detect_variant,
@@ -504,6 +505,7 @@ class YoutubeDL:
     force_keyframes_at_cuts: Re-encode the video when downloading ranges to get precise cuts
     noprogress:        Do not print the progress bar
     live_from_start:   Whether to download livestreams videos from the start
+    warn_when_outdated: Emit a warning if the yt-dlp version is older than 90 days
 
     The following parameters are not used by YoutubeDL itself, they are used by
     the downloader (see yt_dlp/downloader/common.py):
@@ -703,6 +705,9 @@ def process_color_policy(stream):
         system_deprecation = _get_system_deprecation()
         if system_deprecation:
             self.deprecated_feature(system_deprecation.replace('\n', '\n                    '))
+        elif self.params.get('warn_when_outdated'):
+            if outdated_warning := _get_outdated_warning():
+                self.report_warning(outdated_warning)
 
         if self.params.get('allow_unplayable_formats'):
             self.report_warning(
diff --git a/yt_dlp/__init__.py b/yt_dlp/__init__.py
index 2e7646b7ec..f705bed1bf 100644
--- a/yt_dlp/__init__.py
+++ b/yt_dlp/__init__.py
@@ -971,6 +971,7 @@ def parse_options(argv=None):
         'geo_bypass': opts.geo_bypass,
         'geo_bypass_country': opts.geo_bypass_country,
         'geo_bypass_ip_block': opts.geo_bypass_ip_block,
+        'warn_when_outdated': opts.update_self is None,
         '_warnings': warnings,
         '_deprecation_warnings': deprecation_warnings,
         'compat_opts': opts.compat_opts,
diff --git a/yt_dlp/update.py b/yt_dlp/update.py
index 30cbf538e9..045f7ec7f3 100644
--- a/yt_dlp/update.py
+++ b/yt_dlp/update.py
@@ -2,6 +2,7 @@
 
 import atexit
 import contextlib
+import datetime as dt
 import functools
 import hashlib
 import json
@@ -171,6 +172,22 @@ def _get_system_deprecation():
     return f'Support for Python version {major}.{minor} has been deprecated. {PYTHON_MSG}'
 
 
+def _get_outdated_warning():
+    # Only yt-dlp guarantees a stable release at least every 90 days
+    if not ORIGIN.startswith('yt-dlp/'):
+        return None
+
+    with contextlib.suppress(Exception):
+        last_updated = dt.date(*version_tuple(__version__)[:3])
+        if last_updated < dt.datetime.now(dt.timezone.utc).date() - dt.timedelta(days=90):
+            return ('\n         '.join((
+                f'Your yt-dlp version ({__version__}) is older than 90 days!',
+                'It is strongly recommended to always use the latest version.',
+                f'{is_non_updateable() or """Run "yt-dlp --update" or "yt-dlp -U" to update"""}.',
+                'To suppress this warning, add --no-update to your command/config.')))
+    return None
+
+
 def _sha256_file(path):
     h = hashlib.sha256()
     mv = memoryview(bytearray(128 * 1024))