diff --git a/Doc/library/os.rst b/Doc/library/os.rst
index c74d687..6cbfb74 100644
--- a/Doc/library/os.rst
+++ b/Doc/library/os.rst
@@ -1858,6 +1858,12 @@
    .. versionchanged:: 3.6
       Accepts a :term:`path-like object` for *src* and *dst*.
 
+   .. versionchanged:: 3.8
+      On Windows, now opens reparse points that represent another path
+      (name surrogates), including symbolic links and directory junctions.
+      Other kinds of reparse points are resolved by the operating system as
+      for :func:`~os.stat`.
+
 
 .. function:: mkdir(path, mode=0o777, *, dir_fd=None)
 
@@ -2039,6 +2045,10 @@
    This function can also support :ref:`paths relative to directory descriptors
    <dir_fd>`.
 
+   When trying to resolve a path that may contain links, use
+   :func:`~os.path.realpath` to properly handle recursion and platform
+   differences.
+
    .. availability:: Unix, Windows.
 
    .. versionchanged:: 3.2
@@ -2053,6 +2063,11 @@
    .. versionchanged:: 3.8
       Accepts a :term:`path-like object` and a bytes object on Windows.
 
+   .. versionchanged:: 3.8
+      Added support for directory junctions, and changed to return the
+      substitution path (which typically includes ``\\?\`` prefix) rather
+      than the optional "print name" field that was previously returned.
+
 .. function:: remove(path, *, dir_fd=None)
 
    Remove (delete) the file *path*.  If *path* is a directory, an
@@ -2366,7 +2381,8 @@
 
       On Unix, this method always requires a system call. On Windows, it
       only requires a system call if *follow_symlinks* is ``True`` and the
-      entry is a symbolic link.
+      entry is a reparse point (for example, a symbolic link or directory
+      junction).
 
       On Windows, the ``st_ino``, ``st_dev`` and ``st_nlink`` attributes of the
       :class:`stat_result` are always set to zero. Call :func:`os.stat` to
@@ -2403,6 +2419,17 @@
    This function can support :ref:`specifying a file descriptor <path_fd>` and
    :ref:`not following symlinks <follow_symlinks>`.
 
+   On Windows, passing ``follow_symlinks=False`` will disable following all
+   name-surrogate reparse points, which includes symlinks and directory
+   junctions. Other types of reparse points that do not resemble links or that
+   the operating system is unable to follow will be opened directly. When
+   following a chain of multiple links, this may result in the original link
+   being returned instead of the non-link that prevented full traversal. To
+   obtain stat results for the final path in this case, use the
+   :func:`os.path.realpath` function to resolve the path name as far as
+   possible and call :func:`lstat` on the result. This does not apply to
+   dangling symlinks or junction points, which will raise the usual exceptions.
+
    .. index:: module: stat
 
    Example::
@@ -2427,6 +2454,14 @@
    .. versionchanged:: 3.6
       Accepts a :term:`path-like object`.
 
+   .. versionchanged:: 3.8
+      On Windows, all reparse points that can be resolved by the operating
+      system are now followed, and passing ``follow_symlinks=False``
+      disables following all name surrogate reparse points. If the operating
+      system reaches a reparse point that it is not able to follow, *stat* now
+      returns the information for the original path as if
+      ``follow_symlinks=False`` had been specified instead of raising an error.
+
 
 .. class:: stat_result
 
@@ -2578,7 +2613,7 @@
 
       File type.
 
-   On Windows systems, the following attribute is also available:
+   On Windows systems, the following attributes are also available:
 
    .. attribute:: st_file_attributes
 
@@ -2587,6 +2622,12 @@
       :c:func:`GetFileInformationByHandle`. See the ``FILE_ATTRIBUTE_*``
       constants in the :mod:`stat` module.
 
+   .. attribute:: st_reparse_tag
+
+      When :attr:`st_file_attributes` has the ``FILE_ATTRIBUTE_REPARSE_POINT``
+      set, this field contains the tag identifying the type of reparse point.
+      See the ``IO_REPARSE_TAG_*`` constants in the :mod:`stat` module.
+
    The standard module :mod:`stat` defines functions and constants that are
    useful for extracting information from a :c:type:`stat` structure. (On
    Windows, some items are filled with dummy values.)
@@ -2614,6 +2655,14 @@
    .. versionadded:: 3.7
       Added the :attr:`st_fstype` member to Solaris/derivatives.
 
+   .. versionadded:: 3.8
+      Added the :attr:`st_reparse_tag` member on Windows.
+
+   .. versionchanged:: 3.8
+      On Windows, the :attr:`st_mode` member now identifies special
+      files as :const:`S_IFCHR`, :const:`S_IFIFO` or :const:`S_IFBLK`
+      as appropriate.
+
 .. function:: statvfs(path)
 
    Perform a :c:func:`statvfs` system call on the given path.  The return value is
diff --git a/Doc/library/shutil.rst b/Doc/library/shutil.rst
index eaeee8d..a51e068 100644
--- a/Doc/library/shutil.rst
+++ b/Doc/library/shutil.rst
@@ -304,6 +304,10 @@
       Added a symlink attack resistant version that is used automatically
       if platform supports fd-based functions.
 
+   .. versionchanged:: 3.8
+      On Windows, will no longer delete the contents of a directory junction
+      before removing the junction.
+
    .. attribute:: rmtree.avoids_symlink_attacks
 
       Indicates whether the current platform and implementation provides a
diff --git a/Doc/library/stat.rst b/Doc/library/stat.rst
index c8f6904..f48a0a9 100644
--- a/Doc/library/stat.rst
+++ b/Doc/library/stat.rst
@@ -425,3 +425,13 @@
           FILE_ATTRIBUTE_VIRTUAL
 
    .. versionadded:: 3.5
+
+On Windows, the following constants are available for comparing against the
+``st_reparse_tag`` member returned by :func:`os.lstat`. These are well-known
+constants, but are not an exhaustive list.
+
+.. data:: IO_REPARSE_TAG_SYMLINK
+          IO_REPARSE_TAG_MOUNT_POINT
+          IO_REPARSE_TAG_APPEXECLINK
+
+   .. versionadded:: 3.8
diff --git a/Doc/whatsnew/3.8.rst b/Doc/whatsnew/3.8.rst
index 93758e9..0294e9a 100644
--- a/Doc/whatsnew/3.8.rst
+++ b/Doc/whatsnew/3.8.rst
@@ -808,6 +808,21 @@
 ``memfd_create()`` syscall.
 (Contributed by Zackery Spytz and Christian Heimes in :issue:`26836`.)
 
+On Windows, much of the manual logic for handling reparse points (including
+symlinks and directory junctions) has been delegated to the operating system.
+Specifically, :func:`os.stat` will now traverse anything supported by the
+operating system, while :func:`os.lstat` will only open reparse points that
+identify as "name surrogates" while others are opened as for :func:`os.stat`.
+In all cases, :attr:`stat_result.st_mode` will only have ``S_IFLNK`` set for
+symbolic links and not other kinds of reparse points. To identify other kinds
+of reparse point, check the new :attr:`stat_result.st_reparse_tag` attribute.
+
+On Windows, :func:`os.readlink` is now able to read directory junctions. Note
+that :func:`~os.path.islink` will return ``False`` for directory junctions,
+and so code that checks ``islink`` first will continue to treat junctions as
+directories, while code that handles errors from :func:`os.readlink` may now
+treat junctions as links.
+
 
 os.path
 -------
@@ -824,6 +839,9 @@
 environment variable and does not use :envvar:`HOME`, which is not normally set
 for regular user accounts.
 
+:func:`~os.path.isdir` on Windows no longer returns true for a link to a
+non-existent directory.
+
 :func:`~os.path.realpath` on Windows now resolves reparse points, including
 symlinks and directory junctions.
 
@@ -912,6 +930,9 @@
 inherited from the corresponding change to the :mod:`tarfile` module.
 (Contributed by C.A.M. Gerlach in :issue:`30661`.)
 
+:func:`shutil.rmtree` on Windows now removes directory junctions without
+recursively removing their contents first.
+
 
 ssl
 ---
diff --git a/Include/fileutils.h b/Include/fileutils.h
index f081779..a9655bb 100644
--- a/Include/fileutils.h
+++ b/Include/fileutils.h
@@ -84,6 +84,7 @@
     time_t st_ctime;
     int st_ctime_nsec;
     unsigned long st_file_attributes;
+    unsigned long st_reparse_tag;
 };
 #else
 #  define _Py_stat_struct stat
diff --git a/Lib/shutil.py b/Lib/shutil.py
index ab1a7d6..39f793b 100644
--- a/Lib/shutil.py
+++ b/Lib/shutil.py
@@ -452,7 +452,14 @@
         dstname = os.path.join(dst, srcentry.name)
         srcobj = srcentry if use_srcentry else srcname
         try:
-            if srcentry.is_symlink():
+            is_symlink = srcentry.is_symlink()
+            if is_symlink and os.name == 'nt':
+                # Special check for directory junctions, which appear as
+                # symlinks but we want to recurse.
+                lstat = srcentry.stat(follow_symlinks=False)
+                if lstat.st_reparse_tag == stat.IO_REPARSE_TAG_MOUNT_POINT:
+                    is_symlink = False
+            if is_symlink:
                 linkto = os.readlink(srcname)
                 if symlinks:
                     # We can't just leave it to `copy_function` because legacy
@@ -537,6 +544,37 @@
                          ignore_dangling_symlinks=ignore_dangling_symlinks,
                          dirs_exist_ok=dirs_exist_ok)
 
+if hasattr(stat, 'FILE_ATTRIBUTE_REPARSE_POINT'):
+    # Special handling for directory junctions to make them behave like
+    # symlinks for shutil.rmtree, since in general they do not appear as
+    # regular links.
+    def _rmtree_isdir(entry):
+        try:
+            st = entry.stat(follow_symlinks=False)
+            return (stat.S_ISDIR(st.st_mode) and not
+                (st.st_file_attributes & stat.FILE_ATTRIBUTE_REPARSE_POINT
+                 and st.st_reparse_tag == stat.IO_REPARSE_TAG_MOUNT_POINT))
+        except OSError:
+            return False
+
+    def _rmtree_islink(path):
+        try:
+            st = os.lstat(path)
+            return (stat.S_ISLNK(st.st_mode) or
+                (st.st_file_attributes & stat.FILE_ATTRIBUTE_REPARSE_POINT
+                 and st.st_reparse_tag == stat.IO_REPARSE_TAG_MOUNT_POINT))
+        except OSError:
+            return False
+else:
+    def _rmtree_isdir(entry):
+        try:
+            return entry.is_dir(follow_symlinks=False)
+        except OSError:
+            return False
+
+    def _rmtree_islink(path):
+        return os.path.islink(path)
+
 # version vulnerable to race conditions
 def _rmtree_unsafe(path, onerror):
     try:
@@ -547,11 +585,7 @@
         entries = []
     for entry in entries:
         fullname = entry.path
-        try:
-            is_dir = entry.is_dir(follow_symlinks=False)
-        except OSError:
-            is_dir = False
-        if is_dir:
+        if _rmtree_isdir(entry):
             try:
                 if entry.is_symlink():
                     # This can only happen if someone replaces
@@ -681,7 +715,7 @@
             os.close(fd)
     else:
         try:
-            if os.path.islink(path):
+            if _rmtree_islink(path):
                 # symlinks to directories are forbidden, see bug #1669
                 raise OSError("Cannot call rmtree on a symbolic link")
         except OSError:
diff --git a/Lib/test/test_os.py b/Lib/test/test_os.py
index 15fd65b..ba9f5c3 100644
--- a/Lib/test/test_os.py
+++ b/Lib/test/test_os.py
@@ -8,6 +8,7 @@
 import contextlib
 import decimal
 import errno
+import fnmatch
 import fractions
 import itertools
 import locale
@@ -2253,6 +2254,20 @@
     filelinkb = os.fsencode(filelink)
     filelinkb_target = os.fsencode(filelink_target)
 
+    def assertPathEqual(self, left, right):
+        left = os.path.normcase(left)
+        right = os.path.normcase(right)
+        if sys.platform == 'win32':
+            # Bad practice to blindly strip the prefix as it may be required to
+            # correctly refer to the file, but we're only comparing paths here.
+            has_prefix = lambda p: p.startswith(
+                b'\\\\?\\' if isinstance(p, bytes) else '\\\\?\\')
+            if has_prefix(left):
+                left = left[4:]
+            if has_prefix(right):
+                right = right[4:]
+        self.assertEqual(left, right)
+
     def setUp(self):
         self.assertTrue(os.path.exists(self.filelink_target))
         self.assertTrue(os.path.exists(self.filelinkb_target))
@@ -2274,14 +2289,14 @@
         os.symlink(self.filelink_target, self.filelink)
         self.addCleanup(support.unlink, self.filelink)
         filelink = FakePath(self.filelink)
-        self.assertEqual(os.readlink(filelink), self.filelink_target)
+        self.assertPathEqual(os.readlink(filelink), self.filelink_target)
 
     @support.skip_unless_symlink
     def test_pathlike_bytes(self):
         os.symlink(self.filelinkb_target, self.filelinkb)
         self.addCleanup(support.unlink, self.filelinkb)
         path = os.readlink(FakePath(self.filelinkb))
-        self.assertEqual(path, self.filelinkb_target)
+        self.assertPathEqual(path, self.filelinkb_target)
         self.assertIsInstance(path, bytes)
 
     @support.skip_unless_symlink
@@ -2289,7 +2304,7 @@
         os.symlink(self.filelinkb_target, self.filelinkb)
         self.addCleanup(support.unlink, self.filelinkb)
         path = os.readlink(self.filelinkb)
-        self.assertEqual(path, self.filelinkb_target)
+        self.assertPathEqual(path, self.filelinkb_target)
         self.assertIsInstance(path, bytes)
 
 
@@ -2348,16 +2363,12 @@
         #  was created with target_is_dir==True.
         os.remove(self.missing_link)
 
-    @unittest.skip("currently fails; consider for improvement")
     def test_isdir_on_directory_link_to_missing_target(self):
         self._create_missing_dir_link()
-        # consider having isdir return true for directory links
-        self.assertTrue(os.path.isdir(self.missing_link))
+        self.assertFalse(os.path.isdir(self.missing_link))
 
-    @unittest.skip("currently fails; consider for improvement")
     def test_rmdir_on_directory_link_to_missing_target(self):
         self._create_missing_dir_link()
-        # consider allowing rmdir to remove directory links
         os.rmdir(self.missing_link)
 
     def check_stat(self, link, target):
@@ -2453,6 +2464,24 @@
                 except OSError:
                     pass
 
+    def test_appexeclink(self):
+        root = os.path.expandvars(r'%LOCALAPPDATA%\Microsoft\WindowsApps')
+        aliases = [os.path.join(root, a)
+                   for a in fnmatch.filter(os.listdir(root), '*.exe')]
+
+        for alias in aliases:
+            if support.verbose:
+                print()
+                print("Testing with", alias)
+            st = os.lstat(alias)
+            self.assertEqual(st, os.stat(alias))
+            self.assertFalse(stat.S_ISLNK(st.st_mode))
+            self.assertEqual(st.st_reparse_tag, stat.IO_REPARSE_TAG_APPEXECLINK)
+            # testing the first one we see is sufficient
+            break
+        else:
+            self.skipTest("test requires an app execution alias")
+
 @unittest.skipUnless(sys.platform == "win32", "Win32 specific tests")
 class Win32JunctionTests(unittest.TestCase):
     junction = 'junctiontest'
@@ -2460,25 +2489,29 @@
 
     def setUp(self):
         assert os.path.exists(self.junction_target)
-        assert not os.path.exists(self.junction)
+        assert not os.path.lexists(self.junction)
 
     def tearDown(self):
-        if os.path.exists(self.junction):
-            # os.rmdir delegates to Windows' RemoveDirectoryW,
-            # which removes junction points safely.
-            os.rmdir(self.junction)
+        if os.path.lexists(self.junction):
+            os.unlink(self.junction)
 
     def test_create_junction(self):
         _winapi.CreateJunction(self.junction_target, self.junction)
+        self.assertTrue(os.path.lexists(self.junction))
         self.assertTrue(os.path.exists(self.junction))
         self.assertTrue(os.path.isdir(self.junction))
+        self.assertNotEqual(os.stat(self.junction), os.lstat(self.junction))
+        self.assertEqual(os.stat(self.junction), os.stat(self.junction_target))
 
-        # Junctions are not recognized as links.
+        # bpo-37834: Junctions are not recognized as links.
         self.assertFalse(os.path.islink(self.junction))
+        self.assertEqual(os.path.normcase("\\\\?\\" + self.junction_target),
+                         os.path.normcase(os.readlink(self.junction)))
 
     def test_unlink_removes_junction(self):
         _winapi.CreateJunction(self.junction_target, self.junction)
         self.assertTrue(os.path.exists(self.junction))
+        self.assertTrue(os.path.lexists(self.junction))
 
         os.unlink(self.junction)
         self.assertFalse(os.path.exists(self.junction))
diff --git a/Lib/test/test_shutil.py b/Lib/test/test_shutil.py
index 88dc4d9..636e3bd 100644
--- a/Lib/test/test_shutil.py
+++ b/Lib/test/test_shutil.py
@@ -42,6 +42,11 @@
 except ImportError:
     UID_GID_SUPPORT = False
 
+try:
+    import _winapi
+except ImportError:
+    _winapi = None
+
 def _fake_rename(*args, **kwargs):
     # Pretend the destination path is on a different filesystem.
     raise OSError(getattr(errno, 'EXDEV', 18), "Invalid cross-device link")
@@ -226,6 +231,47 @@
         self.assertTrue(os.path.exists(dir3))
         self.assertTrue(os.path.exists(file1))
 
+    @unittest.skipUnless(_winapi, 'only relevant on Windows')
+    def test_rmtree_fails_on_junctions(self):
+        tmp = self.mkdtemp()
+        dir_ = os.path.join(tmp, 'dir')
+        os.mkdir(dir_)
+        link = os.path.join(tmp, 'link')
+        _winapi.CreateJunction(dir_, link)
+        self.assertRaises(OSError, shutil.rmtree, link)
+        self.assertTrue(os.path.exists(dir_))
+        self.assertTrue(os.path.lexists(link))
+        errors = []
+        def onerror(*args):
+            errors.append(args)
+        shutil.rmtree(link, onerror=onerror)
+        self.assertEqual(len(errors), 1)
+        self.assertIs(errors[0][0], os.path.islink)
+        self.assertEqual(errors[0][1], link)
+        self.assertIsInstance(errors[0][2][1], OSError)
+
+    @unittest.skipUnless(_winapi, 'only relevant on Windows')
+    def test_rmtree_works_on_junctions(self):
+        tmp = self.mkdtemp()
+        dir1 = os.path.join(tmp, 'dir1')
+        dir2 = os.path.join(dir1, 'dir2')
+        dir3 = os.path.join(tmp, 'dir3')
+        for d in dir1, dir2, dir3:
+            os.mkdir(d)
+        file1 = os.path.join(tmp, 'file1')
+        write_file(file1, 'foo')
+        link1 = os.path.join(dir1, 'link1')
+        _winapi.CreateJunction(dir2, link1)
+        link2 = os.path.join(dir1, 'link2')
+        _winapi.CreateJunction(dir3, link2)
+        link3 = os.path.join(dir1, 'link3')
+        _winapi.CreateJunction(file1, link3)
+        # make sure junctions are removed but not followed
+        shutil.rmtree(dir1)
+        self.assertFalse(os.path.exists(dir1))
+        self.assertTrue(os.path.exists(dir3))
+        self.assertTrue(os.path.exists(file1))
+
     def test_rmtree_errors(self):
         # filename is guaranteed not to exist
         filename = tempfile.mktemp()
@@ -754,8 +800,12 @@
         src_stat = os.lstat(src_link)
         shutil.copytree(src_dir, dst_dir, symlinks=True)
         self.assertTrue(os.path.islink(os.path.join(dst_dir, 'sub', 'link')))
-        self.assertEqual(os.readlink(os.path.join(dst_dir, 'sub', 'link')),
-                         os.path.join(src_dir, 'file.txt'))
+        actual = os.readlink(os.path.join(dst_dir, 'sub', 'link'))
+        # Bad practice to blindly strip the prefix as it may be required to
+        # correctly refer to the file, but we're only comparing paths here.
+        if os.name == 'nt' and actual.startswith('\\\\?\\'):
+            actual = actual[4:]
+        self.assertEqual(actual, os.path.join(src_dir, 'file.txt'))
         dst_stat = os.lstat(dst_link)
         if hasattr(os, 'lchmod'):
             self.assertEqual(dst_stat.st_mode, src_stat.st_mode)
@@ -886,7 +936,6 @@
         shutil.copytree(src, dst, copy_function=custom_cpfun)
         self.assertEqual(len(flag), 1)
 
-    @unittest.skipIf(os.name == 'nt', 'temporarily disabled on Windows')
     @unittest.skipUnless(hasattr(os, 'link'), 'requires os.link')
     def test_dont_copy_file_onto_link_to_itself(self):
         # bug 851123.
@@ -941,6 +990,20 @@
         finally:
             shutil.rmtree(TESTFN, ignore_errors=True)
 
+    @unittest.skipUnless(_winapi, 'only relevant on Windows')
+    def test_rmtree_on_junction(self):
+        os.mkdir(TESTFN)
+        try:
+            src = os.path.join(TESTFN, 'cheese')
+            dst = os.path.join(TESTFN, 'shop')
+            os.mkdir(src)
+            open(os.path.join(src, 'spam'), 'wb').close()
+            _winapi.CreateJunction(src, dst)
+            self.assertRaises(OSError, shutil.rmtree, dst)
+            shutil.rmtree(dst, ignore_errors=True)
+        finally:
+            shutil.rmtree(TESTFN, ignore_errors=True)
+
     # Issue #3002: copyfile and copytree block indefinitely on named pipes
     @unittest.skipUnless(hasattr(os, "mkfifo"), 'requires os.mkfifo()')
     def test_copyfile_named_pipe(self):
diff --git a/Lib/test/test_tools/test_lll.py b/Lib/test/test_tools/test_lll.py
index f3fbe96..b01e218 100644
--- a/Lib/test/test_tools/test_lll.py
+++ b/Lib/test/test_tools/test_lll.py
@@ -1,6 +1,7 @@
 """Tests for the lll script in the Tools/script directory."""
 
 import os
+import sys
 import tempfile
 from test import support
 from test.test_tools import skip_if_missing, import_tool
@@ -26,12 +27,13 @@
 
             with support.captured_stdout() as output:
                 self.lll.main([dir1, dir2])
+            prefix = '\\\\?\\' if os.name == 'nt' else ''
             self.assertEqual(output.getvalue(),
                 f'{dir1}:\n'
-                f'symlink -> {fn1}\n'
+                f'symlink -> {prefix}{fn1}\n'
                 f'\n'
                 f'{dir2}:\n'
-                f'symlink -> {fn2}\n'
+                f'symlink -> {prefix}{fn2}\n'
             )
 
 
diff --git a/Lib/test/test_venv.py b/Lib/test/test_venv.py
index 9724d9e..de93d95 100644
--- a/Lib/test/test_venv.py
+++ b/Lib/test/test_venv.py
@@ -394,11 +394,7 @@
         with open(os.devnull, "rb") as f:
             self.assertEqual(f.read(), b"")
 
-        # Issue #20541: os.path.exists('nul') is False on Windows
-        if os.devnull.lower() == 'nul':
-            self.assertFalse(os.path.exists(os.devnull))
-        else:
-            self.assertTrue(os.path.exists(os.devnull))
+        self.assertTrue(os.path.exists(os.devnull))
 
     def do_test_with_pip(self, system_site_packages):
         rmtree(self.env_dir)
diff --git a/Misc/NEWS.d/next/Windows/2019-08-12-12-00-24.bpo-37834.VB2QVj.rst b/Misc/NEWS.d/next/Windows/2019-08-12-12-00-24.bpo-37834.VB2QVj.rst
new file mode 100644
index 0000000..f2a654c
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2019-08-12-12-00-24.bpo-37834.VB2QVj.rst
@@ -0,0 +1,2 @@
+Treat all name surrogate reparse points on Windows in :func:`os.lstat` and
+other reparse points as regular files in :func:`os.stat`.
diff --git a/Misc/NEWS.d/next/Windows/2019-08-21-12-58-18.bpo-1311.BoW1wU.rst b/Misc/NEWS.d/next/Windows/2019-08-21-12-58-18.bpo-1311.BoW1wU.rst
new file mode 100644
index 0000000..2ee98e4
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2019-08-21-12-58-18.bpo-1311.BoW1wU.rst
@@ -0,0 +1,2 @@
+The ``nul`` file on Windows now returns True from :func:`~os.path.exists`
+and a valid result from :func:`os.stat` with ``S_IFCHR`` set.
diff --git a/Modules/_stat.c b/Modules/_stat.c
index f6cb303..6a3020a 100644
--- a/Modules/_stat.c
+++ b/Modules/_stat.c
@@ -589,6 +589,13 @@
     if (PyModule_AddIntMacro(m, FILE_ATTRIBUTE_SYSTEM)) return NULL;
     if (PyModule_AddIntMacro(m, FILE_ATTRIBUTE_TEMPORARY)) return NULL;
     if (PyModule_AddIntMacro(m, FILE_ATTRIBUTE_VIRTUAL)) return NULL;
+
+    if (PyModule_AddObject(m, "IO_REPARSE_TAG_SYMLINK",
+        PyLong_FromUnsignedLong(IO_REPARSE_TAG_SYMLINK))) return NULL;
+    if (PyModule_AddObject(m, "IO_REPARSE_TAG_MOUNT_POINT",
+        PyLong_FromUnsignedLong(IO_REPARSE_TAG_MOUNT_POINT))) return NULL;
+    if (PyModule_AddObject(m, "IO_REPARSE_TAG_APPEXECLINK",
+        PyLong_FromUnsignedLong(IO_REPARSE_TAG_APPEXECLINK))) return NULL;
 #endif
 
     return m;
diff --git a/Modules/clinic/posixmodule.c.h b/Modules/clinic/posixmodule.c.h
index aa1ab79..c4ebe39 100644
--- a/Modules/clinic/posixmodule.c.h
+++ b/Modules/clinic/posixmodule.c.h
@@ -1272,19 +1272,6 @@
 
 #if defined(MS_WINDOWS)
 
-PyDoc_STRVAR(os__isdir__doc__,
-"_isdir($module, path, /)\n"
-"--\n"
-"\n"
-"Return true if the pathname refers to an existing directory.");
-
-#define OS__ISDIR_METHODDEF    \
-    {"_isdir", (PyCFunction)os__isdir, METH_O, os__isdir__doc__},
-
-#endif /* defined(MS_WINDOWS) */
-
-#if defined(MS_WINDOWS)
-
 PyDoc_STRVAR(os__getvolumepathname__doc__,
 "_getvolumepathname($module, /, path)\n"
 "--\n"
@@ -8274,10 +8261,6 @@
     #define OS__GETFINALPATHNAME_METHODDEF
 #endif /* !defined(OS__GETFINALPATHNAME_METHODDEF) */
 
-#ifndef OS__ISDIR_METHODDEF
-    #define OS__ISDIR_METHODDEF
-#endif /* !defined(OS__ISDIR_METHODDEF) */
-
 #ifndef OS__GETVOLUMEPATHNAME_METHODDEF
     #define OS__GETVOLUMEPATHNAME_METHODDEF
 #endif /* !defined(OS__GETVOLUMEPATHNAME_METHODDEF) */
@@ -8741,4 +8724,4 @@
 #ifndef OS__REMOVE_DLL_DIRECTORY_METHODDEF
     #define OS__REMOVE_DLL_DIRECTORY_METHODDEF
 #endif /* !defined(OS__REMOVE_DLL_DIRECTORY_METHODDEF) */
-/*[clinic end generated code: output=1e001c855e011720 input=a9049054013a1b77]*/
+/*[clinic end generated code: output=b71eff00b91f5e43 input=a9049054013a1b77]*/
diff --git a/Modules/posixmodule.c b/Modules/posixmodule.c
index 4f8c074..2302678 100644
--- a/Modules/posixmodule.c
+++ b/Modules/posixmodule.c
@@ -1625,6 +1625,7 @@
 */
 #define HAVE_STAT_NSEC 1
 #define HAVE_STRUCT_STAT_ST_FILE_ATTRIBUTES 1
+#define HAVE_STRUCT_STAT_ST_REPARSE_TAG 1
 
 static void
 find_data_to_file_info(WIN32_FIND_DATAW *pFileData,
@@ -1658,136 +1659,178 @@
     return TRUE;
 }
 
-static BOOL
-get_target_path(HANDLE hdl, wchar_t **target_path)
-{
-    int buf_size, result_length;
-    wchar_t *buf;
-
-    /* We have a good handle to the target, use it to determine
-       the target path name (then we'll call lstat on it). */
-    buf_size = GetFinalPathNameByHandleW(hdl, 0, 0,
-                                         VOLUME_NAME_DOS);
-    if(!buf_size)
-        return FALSE;
-
-    buf = (wchar_t *)PyMem_RawMalloc((buf_size + 1) * sizeof(wchar_t));
-    if (!buf) {
-        SetLastError(ERROR_OUTOFMEMORY);
-        return FALSE;
-    }
-
-    result_length = GetFinalPathNameByHandleW(hdl,
-                       buf, buf_size, VOLUME_NAME_DOS);
-
-    if(!result_length) {
-        PyMem_RawFree(buf);
-        return FALSE;
-    }
-
-    buf[result_length] = 0;
-
-    *target_path = buf;
-    return TRUE;
-}
-
 static int
 win32_xstat_impl(const wchar_t *path, struct _Py_stat_struct *result,
                  BOOL traverse)
 {
-    int code;
-    HANDLE hFile, hFile2;
-    BY_HANDLE_FILE_INFORMATION info;
-    ULONG reparse_tag = 0;
-    wchar_t *target_path;
-    const wchar_t *dot;
+    HANDLE hFile;
+    BY_HANDLE_FILE_INFORMATION fileInfo;
+    FILE_ATTRIBUTE_TAG_INFO tagInfo = { 0 };
+    DWORD fileType, error;
+    BOOL isUnhandledTag = FALSE;
+    int retval = 0;
 
-    hFile = CreateFileW(
-        path,
-        FILE_READ_ATTRIBUTES, /* desired access */
-        0, /* share mode */
-        NULL, /* security attributes */
-        OPEN_EXISTING,
-        /* FILE_FLAG_BACKUP_SEMANTICS is required to open a directory */
-        /* FILE_FLAG_OPEN_REPARSE_POINT does not follow the symlink.
-           Because of this, calls like GetFinalPathNameByHandle will return
-           the symlink path again and not the actual final path. */
-        FILE_ATTRIBUTE_NORMAL|FILE_FLAG_BACKUP_SEMANTICS|
-            FILE_FLAG_OPEN_REPARSE_POINT,
-        NULL);
+    DWORD access = FILE_READ_ATTRIBUTES;
+    DWORD flags = FILE_FLAG_BACKUP_SEMANTICS; /* Allow opening directories. */
+    if (!traverse) {
+        flags |= FILE_FLAG_OPEN_REPARSE_POINT;
+    }
 
+    hFile = CreateFileW(path, access, 0, NULL, OPEN_EXISTING, flags, NULL);
     if (hFile == INVALID_HANDLE_VALUE) {
-        /* Either the target doesn't exist, or we don't have access to
-           get a handle to it. If the former, we need to return an error.
-           If the latter, we can use attributes_from_dir. */
-        DWORD lastError = GetLastError();
-        if (lastError != ERROR_ACCESS_DENIED &&
-            lastError != ERROR_SHARING_VIOLATION)
-            return -1;
-        /* Could not get attributes on open file. Fall back to
-           reading the directory. */
-        if (!attributes_from_dir(path, &info, &reparse_tag))
-            /* Very strange. This should not fail now */
-            return -1;
-        if (info.dwFileAttributes & FILE_ATTRIBUTE_REPARSE_POINT) {
-            if (traverse) {
-                /* Should traverse, but could not open reparse point handle */
-                SetLastError(lastError);
+        /* Either the path doesn't exist, or the caller lacks access. */
+        error = GetLastError();
+        switch (error) {
+        case ERROR_ACCESS_DENIED:     /* Cannot sync or read attributes. */
+        case ERROR_SHARING_VIOLATION: /* It's a paging file. */
+            /* Try reading the parent directory. */
+            if (!attributes_from_dir(path, &fileInfo, &tagInfo.ReparseTag)) {
+                /* Cannot read the parent directory. */
+                SetLastError(error);
                 return -1;
             }
-        }
-    } else {
-        if (!GetFileInformationByHandle(hFile, &info)) {
-            CloseHandle(hFile);
-            return -1;
-        }
-        if (info.dwFileAttributes & FILE_ATTRIBUTE_REPARSE_POINT) {
-            if (!win32_get_reparse_tag(hFile, &reparse_tag)) {
-                CloseHandle(hFile);
-                return -1;
-            }
-            /* Close the outer open file handle now that we're about to
-               reopen it with different flags. */
-            if (!CloseHandle(hFile))
-                return -1;
-
-            if (traverse) {
-                /* In order to call GetFinalPathNameByHandle we need to open
-                   the file without the reparse handling flag set. */
-                hFile2 = CreateFileW(
-                           path, FILE_READ_ATTRIBUTES, FILE_SHARE_READ,
-                           NULL, OPEN_EXISTING,
-                           FILE_ATTRIBUTE_NORMAL|FILE_FLAG_BACKUP_SEMANTICS,
-                           NULL);
-                if (hFile2 == INVALID_HANDLE_VALUE)
-                    return -1;
-
-                if (!get_target_path(hFile2, &target_path)) {
-                    CloseHandle(hFile2);
+            if (fileInfo.dwFileAttributes & FILE_ATTRIBUTE_REPARSE_POINT) {
+                if (traverse ||
+                    !IsReparseTagNameSurrogate(tagInfo.ReparseTag)) {
+                    /* The stat call has to traverse but cannot, so fail. */
+                    SetLastError(error);
                     return -1;
                 }
-
-                if (!CloseHandle(hFile2)) {
-                    return -1;
-                }
-
-                code = win32_xstat_impl(target_path, result, FALSE);
-                PyMem_RawFree(target_path);
-                return code;
             }
-        } else
-            CloseHandle(hFile);
-    }
-    _Py_attribute_data_to_stat(&info, reparse_tag, result);
+            break;
 
-    /* Set S_IEXEC if it is an .exe, .bat, ... */
-    dot = wcsrchr(path, '.');
-    if (dot) {
-        if (_wcsicmp(dot, L".bat") == 0 || _wcsicmp(dot, L".cmd") == 0 ||
-            _wcsicmp(dot, L".exe") == 0 || _wcsicmp(dot, L".com") == 0)
-            result->st_mode |= 0111;
+        case ERROR_INVALID_PARAMETER:
+            /* \\.\con requires read or write access. */
+            hFile = CreateFileW(path, access | GENERIC_READ,
+                        FILE_SHARE_READ | FILE_SHARE_WRITE, NULL,
+                        OPEN_EXISTING, flags, NULL);
+            if (hFile == INVALID_HANDLE_VALUE) {
+                SetLastError(error);
+                return -1;
+            }
+            break;
+
+        case ERROR_CANT_ACCESS_FILE:
+            /* bpo37834: open unhandled reparse points if traverse fails. */
+            if (traverse) {
+                traverse = FALSE;
+                isUnhandledTag = TRUE;
+                hFile = CreateFileW(path, access, 0, NULL, OPEN_EXISTING,
+                            flags | FILE_FLAG_OPEN_REPARSE_POINT, NULL);
+            }
+            if (hFile == INVALID_HANDLE_VALUE) {
+                SetLastError(error);
+                return -1;
+            }
+            break;
+
+        default:
+            return -1;
+        }
     }
-    return 0;
+
+    if (hFile != INVALID_HANDLE_VALUE) {
+        /* Handle types other than files on disk. */
+        fileType = GetFileType(hFile);
+        if (fileType != FILE_TYPE_DISK) {
+            if (fileType == FILE_TYPE_UNKNOWN && GetLastError() != 0) {
+                retval = -1;
+                goto cleanup;
+            }
+            DWORD fileAttributes = GetFileAttributesW(path);
+            memset(result, 0, sizeof(*result));
+            if (fileAttributes != INVALID_FILE_ATTRIBUTES &&
+                fileAttributes & FILE_ATTRIBUTE_DIRECTORY) {
+                /* \\.\pipe\ or \\.\mailslot\ */
+                result->st_mode = _S_IFDIR;
+            } else if (fileType == FILE_TYPE_CHAR) {
+                /* \\.\nul */
+                result->st_mode = _S_IFCHR;
+            } else if (fileType == FILE_TYPE_PIPE) {
+                /* \\.\pipe\spam */
+                result->st_mode = _S_IFIFO;
+            }
+            /* FILE_TYPE_UNKNOWN, e.g. \\.\mailslot\waitfor.exe\spam */
+            goto cleanup;
+        }
+
+        /* Query the reparse tag, and traverse a non-link. */
+        if (!traverse) {
+            if (!GetFileInformationByHandleEx(hFile, FileAttributeTagInfo,
+                    &tagInfo, sizeof(tagInfo))) {
+                /* Allow devices that do not support FileAttributeTagInfo. */
+                switch (GetLastError()) {
+                case ERROR_INVALID_PARAMETER:
+                case ERROR_INVALID_FUNCTION:
+                case ERROR_NOT_SUPPORTED:
+                    tagInfo.FileAttributes = FILE_ATTRIBUTE_NORMAL;
+                    tagInfo.ReparseTag = 0;
+                    break;
+                default:
+                    retval = -1;
+                    goto cleanup;
+                }
+            } else if (tagInfo.FileAttributes &
+                         FILE_ATTRIBUTE_REPARSE_POINT) {
+                if (IsReparseTagNameSurrogate(tagInfo.ReparseTag)) {
+                    if (isUnhandledTag) {
+                        /* Traversing previously failed for either this link
+                           or its target. */
+                        SetLastError(ERROR_CANT_ACCESS_FILE);
+                        retval = -1;
+                        goto cleanup;
+                    }
+                /* Traverse a non-link, but not if traversing already failed
+                   for an unhandled tag. */
+                } else if (!isUnhandledTag) {
+                    CloseHandle(hFile);
+                    return win32_xstat_impl(path, result, TRUE);
+                }
+            }
+        }
+
+        if (!GetFileInformationByHandle(hFile, &fileInfo)) {
+            switch (GetLastError()) {
+            case ERROR_INVALID_PARAMETER:
+            case ERROR_INVALID_FUNCTION:
+            case ERROR_NOT_SUPPORTED:
+                retval = -1;
+                goto cleanup;
+            }
+            /* Volumes and physical disks are block devices, e.g.
+               \\.\C: and \\.\PhysicalDrive0. */
+            memset(result, 0, sizeof(*result));
+            result->st_mode = 0x6000; /* S_IFBLK */
+            goto cleanup;
+        }
+    }
+
+    _Py_attribute_data_to_stat(&fileInfo, tagInfo.ReparseTag, result);
+
+    if (!(fileInfo.dwFileAttributes & FILE_ATTRIBUTE_DIRECTORY)) {
+        /* Fix the file execute permissions. This hack sets S_IEXEC if
+           the filename has an extension that is commonly used by files
+           that CreateProcessW can execute. A real implementation calls
+           GetSecurityInfo, OpenThreadToken/OpenProcessToken, and
+           AccessCheck to check for generic read, write, and execute
+           access. */
+        const wchar_t *fileExtension = wcsrchr(path, '.');
+        if (fileExtension) {
+            if (_wcsicmp(fileExtension, L".exe") == 0 ||
+                _wcsicmp(fileExtension, L".bat") == 0 ||
+                _wcsicmp(fileExtension, L".cmd") == 0 ||
+                _wcsicmp(fileExtension, L".com") == 0) {
+                result->st_mode |= 0111;
+            }
+        }
+    }
+
+cleanup:
+    if (hFile != INVALID_HANDLE_VALUE) {
+        CloseHandle(hFile);
+    }
+
+    return retval;
 }
 
 static int
@@ -1806,9 +1849,8 @@
    default does not traverse symlinks and instead returns attributes for
    the symlink.
 
-   Therefore, win32_lstat will get the attributes traditionally, and
-   win32_stat will first explicitly resolve the symlink target and then will
-   call win32_lstat on that result. */
+   Instead, we will open the file (which *does* traverse symlinks by default)
+   and GetFileInformationByHandle(). */
 
 static int
 win32_lstat(const wchar_t* path, struct _Py_stat_struct *result)
@@ -1877,6 +1919,9 @@
 #ifdef HAVE_STRUCT_STAT_ST_FSTYPE
     {"st_fstype",  "Type of filesystem"},
 #endif
+#ifdef HAVE_STRUCT_STAT_ST_REPARSE_TAG
+    {"st_reparse_tag", "Windows reparse tag"},
+#endif
     {0}
 };
 
@@ -1928,6 +1973,12 @@
 #define ST_FSTYPE_IDX ST_FILE_ATTRIBUTES_IDX
 #endif
 
+#ifdef HAVE_STRUCT_STAT_ST_REPARSE_TAG
+#define ST_REPARSE_TAG_IDX (ST_FSTYPE_IDX+1)
+#else
+#define ST_REPARSE_TAG_IDX ST_FSTYPE_IDX
+#endif
+
 static PyStructSequence_Desc stat_result_desc = {
     "stat_result", /* name */
     stat_result__doc__, /* doc */
@@ -2155,6 +2206,10 @@
    PyStructSequence_SET_ITEM(v, ST_FSTYPE_IDX,
                               PyUnicode_FromString(st->st_fstype));
 #endif
+#ifdef HAVE_STRUCT_STAT_ST_REPARSE_TAG
+    PyStructSequence_SET_ITEM(v, ST_REPARSE_TAG_IDX,
+                              PyLong_FromUnsignedLong(st->st_reparse_tag));
+#endif
 
     if (PyErr_Occurred()) {
         Py_DECREF(v);
@@ -3877,8 +3932,9 @@
     }
 
     result = PyUnicode_FromWideChar(target_path, result_length);
-    if (path->narrow)
+    if (result && path->narrow) {
         Py_SETREF(result, PyUnicode_EncodeFSDefault(result));
+    }
 
 cleanup:
     if (target_path != buf) {
@@ -3888,44 +3944,6 @@
     return result;
 }
 
-/*[clinic input]
-os._isdir
-
-    path as arg: object
-    /
-
-Return true if the pathname refers to an existing directory.
-[clinic start generated code]*/
-
-static PyObject *
-os__isdir(PyObject *module, PyObject *arg)
-/*[clinic end generated code: output=404f334d85d4bf25 input=36cb6785874d479e]*/
-{
-    DWORD attributes;
-    path_t path = PATH_T_INITIALIZE("_isdir", "path", 0, 0);
-
-    if (!path_converter(arg, &path)) {
-        if (PyErr_ExceptionMatches(PyExc_ValueError)) {
-            PyErr_Clear();
-            Py_RETURN_FALSE;
-        }
-        return NULL;
-    }
-
-    Py_BEGIN_ALLOW_THREADS
-    attributes = GetFileAttributesW(path.wide);
-    Py_END_ALLOW_THREADS
-
-    path_cleanup(&path);
-    if (attributes == INVALID_FILE_ATTRIBUTES)
-        Py_RETURN_FALSE;
-
-    if (attributes & FILE_ATTRIBUTE_DIRECTORY)
-        Py_RETURN_TRUE;
-    else
-        Py_RETURN_FALSE;
-}
-
 
 /*[clinic input]
 os._getvolumepathname
@@ -7796,11 +7814,10 @@
         return PyBytes_FromStringAndSize(buffer, length);
 #elif defined(MS_WINDOWS)
     DWORD n_bytes_returned;
-    DWORD io_result;
+    DWORD io_result = 0;
     HANDLE reparse_point_handle;
     char target_buffer[_Py_MAXIMUM_REPARSE_DATA_BUFFER_SIZE];
     _Py_REPARSE_DATA_BUFFER *rdb = (_Py_REPARSE_DATA_BUFFER *)target_buffer;
-    const wchar_t *print_name;
     PyObject *result;
 
     /* First get a handle to the reparse point */
@@ -7813,42 +7830,51 @@
         OPEN_EXISTING,
         FILE_FLAG_OPEN_REPARSE_POINT|FILE_FLAG_BACKUP_SEMANTICS,
         0);
-    Py_END_ALLOW_THREADS
-
-    if (reparse_point_handle == INVALID_HANDLE_VALUE) {
-        return path_error(path);
+    if (reparse_point_handle != INVALID_HANDLE_VALUE) {
+        /* New call DeviceIoControl to read the reparse point */
+        io_result = DeviceIoControl(
+            reparse_point_handle,
+            FSCTL_GET_REPARSE_POINT,
+            0, 0, /* in buffer */
+            target_buffer, sizeof(target_buffer),
+            &n_bytes_returned,
+            0 /* we're not using OVERLAPPED_IO */
+            );
+        CloseHandle(reparse_point_handle);
     }
-
-    Py_BEGIN_ALLOW_THREADS
-    /* New call DeviceIoControl to read the reparse point */
-    io_result = DeviceIoControl(
-        reparse_point_handle,
-        FSCTL_GET_REPARSE_POINT,
-        0, 0, /* in buffer */
-        target_buffer, sizeof(target_buffer),
-        &n_bytes_returned,
-        0 /* we're not using OVERLAPPED_IO */
-        );
-    CloseHandle(reparse_point_handle);
     Py_END_ALLOW_THREADS
 
     if (io_result == 0) {
         return path_error(path);
     }
 
-    if (rdb->ReparseTag != IO_REPARSE_TAG_SYMLINK)
+    wchar_t *name = NULL;
+    Py_ssize_t nameLen = 0;
+    if (rdb->ReparseTag == IO_REPARSE_TAG_SYMLINK)
     {
-        PyErr_SetString(PyExc_ValueError,
-                "not a symbolic link");
-        return NULL;
+        name = (wchar_t *)((char*)rdb->SymbolicLinkReparseBuffer.PathBuffer +
+                           rdb->SymbolicLinkReparseBuffer.SubstituteNameOffset);
+        nameLen = rdb->SymbolicLinkReparseBuffer.SubstituteNameLength / sizeof(wchar_t);
     }
-    print_name = (wchar_t *)((char*)rdb->SymbolicLinkReparseBuffer.PathBuffer +
-                 rdb->SymbolicLinkReparseBuffer.PrintNameOffset);
-
-    result = PyUnicode_FromWideChar(print_name,
-            rdb->SymbolicLinkReparseBuffer.PrintNameLength / sizeof(wchar_t));
-    if (path->narrow) {
-        Py_SETREF(result, PyUnicode_EncodeFSDefault(result));
+    else if (rdb->ReparseTag == IO_REPARSE_TAG_MOUNT_POINT)
+    {
+        name = (wchar_t *)((char*)rdb->MountPointReparseBuffer.PathBuffer +
+                           rdb->MountPointReparseBuffer.SubstituteNameOffset);
+        nameLen = rdb->MountPointReparseBuffer.SubstituteNameLength / sizeof(wchar_t);
+    }
+    else
+    {
+        PyErr_SetString(PyExc_ValueError, "not a symbolic link");
+    }
+    if (name) {
+        if (nameLen > 4 && wcsncmp(name, L"\\??\\", 4) == 0) {
+            /* Our buffer is mutable, so this is okay */
+            name[1] = L'\\';
+        }
+        result = PyUnicode_FromWideChar(name, nameLen);
+        if (path->narrow) {
+            Py_SETREF(result, PyUnicode_EncodeFSDefault(result));
+        }
     }
     return result;
 #endif
@@ -13647,7 +13673,6 @@
     OS_PATHCONF_METHODDEF
     OS_ABORT_METHODDEF
     OS__GETFULLPATHNAME_METHODDEF
-    OS__ISDIR_METHODDEF
     OS__GETDISKUSAGE_METHODDEF
     OS__GETFINALPATHNAME_METHODDEF
     OS__GETVOLUMEPATHNAME_METHODDEF
diff --git a/Python/fileutils.c b/Python/fileutils.c
index 55bc194..36a3c99 100644
--- a/Python/fileutils.c
+++ b/Python/fileutils.c
@@ -878,7 +878,12 @@
     FILE_TIME_to_time_t_nsec(&info->ftLastAccessTime, &result->st_atime, &result->st_atime_nsec);
     result->st_nlink = info->nNumberOfLinks;
     result->st_ino = (((uint64_t)info->nFileIndexHigh) << 32) + info->nFileIndexLow;
-    if (reparse_tag == IO_REPARSE_TAG_SYMLINK) {
+    /* bpo-37834: Only actual symlinks set the S_IFLNK flag. But lstat() will
+       open other name surrogate reparse points without traversing them. To
+       detect/handle these, check st_file_attributes and st_reparse_tag. */
+    result->st_reparse_tag = reparse_tag;
+    if (info->dwFileAttributes & FILE_ATTRIBUTE_REPARSE_POINT &&
+        reparse_tag == IO_REPARSE_TAG_SYMLINK) {
         /* first clear the S_IFMT bits */
         result->st_mode ^= (result->st_mode & S_IFMT);
         /* now set the bits that make this a symlink */