diff --git a/yt_dlp/update.py b/yt_dlp/update.py
index c22843d891..ad0862ab3e 100644
--- a/yt_dlp/update.py
+++ b/yt_dlp/update.py
@@ -165,7 +165,7 @@ def _get_binary_name():
 
 
 def _get_system_deprecation():
-    MIN_SUPPORTED, MIN_RECOMMENDED = (3, 10), (3, 10)
+    MIN_SUPPORTED, MIN_RECOMMENDED = (3, 10), (3, 11)
 
     if sys.version_info > MIN_RECOMMENDED:
         return None
@@ -176,6 +176,19 @@ def _get_system_deprecation():
     if sys.version_info < MIN_SUPPORTED:
         return f'Python version {major}.{minor} is no longer supported! {PYTHON_MSG}'
 
+    # Temporary until Windows builds use 3.14, which will drop support for Win8.x and 2012Server
+    if detect_variant() in ('win_exe', 'win_x86_exe'):
+        # Do not inappropriately warn for unofficial/third-party binaries
+        if not ORIGIN.startswith('yt-dlp/'):
+            return None
+        platform_name = platform.platform()
+        if any(platform_name.startswith(f'Windows-{name}') for name in ('8', '2012Server')):
+            return (
+                'Support for Windows 8.x and Windows Server 2012 has been deprecated. '
+                'See  https://github.com/yt-dlp/yt-dlp/issues/16917  for details.\n'
+                'You may stop receiving updates on this version at any time!')
+        return None
+
     return f'Support for Python version {major}.{minor} has been deprecated. {PYTHON_MSG}'