From a89239a391c4843101a28919ec7c00bff453e503 Mon Sep 17 00:00:00 2001
From: VanshAgarwal24036 <148854295+VanshAgarwal24036@users.noreply.github.com>
Date: Tue, 20 Jan 2026 17:35:42 +0530
Subject: [PATCH] gh-144050: Fix stat.filemode pure Python file type detection
 (GH-144059) (cherry picked from commit
 fe629262c0db7aa18bad8bf3ac524acd8695739b)

Co-authored-by: VanshAgarwal24036 <148854295+VanshAgarwal24036@users.noreply.github.com>
---
 Lib/stat.py                                           | 11 ++++++++---
 Lib/test/test_stat.py                                 |  5 +++++
 .../2026-01-20-16-35-55.gh-issue-144050.0kKFbF.rst    |  2 ++
 3 files changed, 15 insertions(+), 3 deletions(-)
 create mode 100644 Misc/NEWS.d/next/Library/2026-01-20-16-35-55.gh-issue-144050.0kKFbF.rst

diff --git a/Lib/stat.py b/Lib/stat.py
index 1b4ed1ebc940ef..81f694329bf4ff 100644
--- a/Lib/stat.py
+++ b/Lib/stat.py
@@ -166,9 +166,14 @@ def filemode(mode):
     perm = []
     for index, table in enumerate(_filemode_table):
         for bit, char in table:
-            if mode & bit == bit:
-                perm.append(char)
-                break
+            if index == 0:
+                if S_IFMT(mode) == bit:
+                    perm.append(char)
+                    break
+            else:
+                if mode & bit == bit:
+                    perm.append(char)
+                    break
         else:
             if index == 0:
                 # Unknown filetype
diff --git a/Lib/test/test_stat.py b/Lib/test/test_stat.py
index 5fd25d5012c425..a83f7d076f027e 100644
--- a/Lib/test/test_stat.py
+++ b/Lib/test/test_stat.py
@@ -163,6 +163,11 @@ def test_mode(self):
                              self.statmod.S_IFREG)
             self.assertEqual(self.statmod.S_IMODE(st_mode), 0o666)
 
+    def test_filemode_does_not_misclassify_random_bits(self):
+        # gh-144050 regression test
+        self.assertEqual(self.statmod.filemode(0o77777)[0], "?")
+        self.assertEqual(self.statmod.filemode(0o177777)[0], "?")
+
     @os_helper.skip_unless_working_chmod
     def test_directory(self):
         os.mkdir(TESTFN)
diff --git a/Misc/NEWS.d/next/Library/2026-01-20-16-35-55.gh-issue-144050.0kKFbF.rst b/Misc/NEWS.d/next/Library/2026-01-20-16-35-55.gh-issue-144050.0kKFbF.rst
new file mode 100644
index 00000000000000..dfc062d023c8f1
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-01-20-16-35-55.gh-issue-144050.0kKFbF.rst
@@ -0,0 +1,2 @@
+Fix :func:`stat.filemode` in the pure-Python implementation to avoid misclassifying
+invalid mode values as block devices.