diff --git a/Lib/stat.py b/Lib/stat.py
index 1b4ed1ebc..81f694329 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 49013a4bc..a83f7d076 100644
--- a/Lib/test/test_stat.py
+++ b/Lib/test/test_stat.py
@@ -157,12 +157,17 @@ class TestFilemode:
 
             os.chmod(TESTFN, 0o700)
             st_mode, modestr = self.get_mode()
-            self.assertEqual(modestr[:3], '-rw')
+            self.assertStartsWith(modestr, '-rw')
             self.assertS_IS("REG", st_mode)
             self.assertEqual(self.statmod.S_IFMT(st_mode),
                              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)
@@ -256,7 +261,7 @@ class TestFilemode:
                          "FILE_ATTRIBUTE_* constants are Win32 specific")
     def test_file_attribute_constants(self):
         for key, value in sorted(self.file_attributes.items()):
-            self.assertTrue(hasattr(self.statmod, key), key)
+            self.assertHasAttr(self.statmod, key)
             modvalue = getattr(self.statmod, key)
             self.assertEqual(value, modvalue, key)
 
@@ -314,7 +319,7 @@ class TestFilemode:
         self.assertEqual(self.statmod.S_ISGID, 0o002000)
         self.assertEqual(self.statmod.S_ISVTX, 0o001000)
 
-        self.assertFalse(hasattr(self.statmod, "S_ISTXT"))
+        self.assertNotHasAttr(self.statmod, "S_ISTXT")
         self.assertEqual(self.statmod.S_IREAD, self.statmod.S_IRUSR)
         self.assertEqual(self.statmod.S_IWRITE, self.statmod.S_IWUSR)
         self.assertEqual(self.statmod.S_IEXEC, self.statmod.S_IXUSR)