diff --git a/Doc/library/pathlib.rst b/Doc/library/pathlib.rst
index 4b48880d6d9a18..4e386241114c35 100644
--- a/Doc/library/pathlib.rst
+++ b/Doc/library/pathlib.rst
@@ -1654,15 +1654,19 @@ Copying, moving and deleting
    Remove this file or symbolic link.  If the path points to a directory,
    use :func:`Path.rmdir` instead.
 
-   If *missing_ok* is false (the default), :exc:`FileNotFoundError` is
-   raised if the path does not exist.
+   If *missing_ok* is false (the default), this method propagates any
+   :exc:`OSError` from the operating system.
 
-   If *missing_ok* is true, :exc:`FileNotFoundError` exceptions will be
-   ignored (same behavior as the POSIX ``rm -f`` command).
+   If *missing_ok* is true, :exc:`FileNotFoundError` and
+   :exc:`NotADirectoryError` exceptions will be ignored. This behavior is
+   similar to the POSIX ``rm -f`` command.
 
    .. versionchanged:: 3.8
       The *missing_ok* parameter was added.
 
+   .. versionchanged:: 3.14
+      Suppresses :exc:`NotADirectoryError` exceptions when *missing_ok* is
+      true.
 
 .. method:: Path.rmdir()
 
diff --git a/Lib/pathlib/_local.py b/Lib/pathlib/_local.py
index 2b42f3c22254b8..22e59f17588d16 100644
--- a/Lib/pathlib/_local.py
+++ b/Lib/pathlib/_local.py
@@ -1104,7 +1104,7 @@ def unlink(self, missing_ok=False):
         """
         try:
             os.unlink(self)
-        except FileNotFoundError:
+        except (FileNotFoundError, NotADirectoryError):
             if not missing_ok:
                 raise
 
diff --git a/Lib/test/test_pathlib/test_pathlib.py b/Lib/test/test_pathlib/test_pathlib.py
index 866a2d07dd692a..68e73464b1cc96 100644
--- a/Lib/test/test_pathlib/test_pathlib.py
+++ b/Lib/test/test_pathlib/test_pathlib.py
@@ -1882,6 +1882,15 @@ def test_unlink_missing_ok(self):
         self.assertFileNotFound(p.unlink)
         p.unlink(missing_ok=True)
 
+    #Windows will raise FileNotFoundError - handling already tested above.
+    @needs_posix
+    def test_unlink_missing_ok_intermediate_file(self):
+        p = self.cls(self.base) / 'fileAAA'
+        p.touch()
+        p = p / 'fileBBB'
+        self.assertNotADirectory(p.unlink)
+        p.unlink(missing_ok=True)
+
     def test_rmdir(self):
         p = self.cls(self.base) / 'dirA'
         for q in p.iterdir():
diff --git a/Lib/test/test_pathlib/test_pathlib_abc.py b/Lib/test/test_pathlib/test_pathlib_abc.py
index d60bb147b72971..21bcfc884dc4a2 100644
--- a/Lib/test/test_pathlib/test_pathlib_abc.py
+++ b/Lib/test/test_pathlib/test_pathlib_abc.py
@@ -1067,6 +1067,11 @@ def assertFileNotFound(self, func, *args, **kwargs):
             func(*args, **kwargs)
         self.assertEqual(cm.exception.errno, errno.ENOENT)
 
+    def assertNotADirectory(self, func, *args, **kwargs):
+        with self.assertRaises(NotADirectoryError) as cm:
+            func(*args, **kwargs)
+        self.assertEqual(cm.exception.errno, errno.ENOTDIR)
+
     def assertEqualNormCase(self, path_a, path_b):
         normcase = self.parser.normcase
         self.assertEqual(normcase(path_a), normcase(path_b))
diff --git a/Misc/NEWS.d/next/Library/2024-07-04-11-55-15.gh-issue-119993._IXsOb.rst b/Misc/NEWS.d/next/Library/2024-07-04-11-55-15.gh-issue-119993._IXsOb.rst
new file mode 100644
index 00000000000000..4199422ccabca8
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2024-07-04-11-55-15.gh-issue-119993._IXsOb.rst
@@ -0,0 +1,2 @@
+:meth:`pathlib.Path.unlink` will also ignore any :exc:`NotADirectoryError`
+if *missing_ok* is true.