diff --git a/Lib/ntpath.py b/Lib/ntpath.py
index d4ecff9..6f77177 100644
--- a/Lib/ntpath.py
+++ b/Lib/ntpath.py
@@ -61,6 +61,14 @@
 def isabs(s):
     """Test whether a path is absolute"""
     s = os.fspath(s)
+    # Paths beginning with \\?\ are always absolute, but do not
+    # necessarily contain a drive.
+    if isinstance(s, bytes):
+        if s.replace(b'/', b'\\').startswith(b'\\\\?\\'):
+            return True
+    else:
+        if s.replace('/', '\\').startswith('\\\\?\\'):
+            return True
     s = splitdrive(s)[1]
     return len(s) > 0 and s[0] in _get_bothseps(s)
 
@@ -526,10 +534,7 @@
     # realpath is a no-op on systems without _getfinalpathname support.
     realpath = abspath
 else:
-    def _readlink_deep(path, seen=None):
-        if seen is None:
-            seen = set()
-
+    def _readlink_deep(path):
         # These error codes indicate that we should stop reading links and
         # return the path we currently have.
         # 1: ERROR_INVALID_FUNCTION
@@ -546,10 +551,22 @@
         # 4393: ERROR_REPARSE_TAG_INVALID
         allowed_winerror = 1, 2, 3, 5, 21, 32, 50, 67, 87, 4390, 4392, 4393
 
+        seen = set()
         while normcase(path) not in seen:
             seen.add(normcase(path))
             try:
+                old_path = path
                 path = _nt_readlink(path)
+                # Links may be relative, so resolve them against their
+                # own location
+                if not isabs(path):
+                    # If it's something other than a symlink, we don't know
+                    # what it's actually going to be resolved against, so
+                    # just return the old path.
+                    if not islink(old_path):
+                        path = old_path
+                        break
+                    path = normpath(join(dirname(old_path), path))
             except OSError as ex:
                 if ex.winerror in allowed_winerror:
                     break
@@ -579,23 +596,31 @@
         # Non-strict algorithm is to find as much of the target directory
         # as we can and join the rest.
         tail = ''
-        seen = set()
         while path:
             try:
-                path = _readlink_deep(path, seen)
                 path = _getfinalpathname(path)
                 return join(path, tail) if tail else path
             except OSError as ex:
                 if ex.winerror not in allowed_winerror:
                     raise
+                try:
+                    # The OS could not resolve this path fully, so we attempt
+                    # to follow the link ourselves. If we succeed, join the tail
+                    # and return.
+                    new_path = _readlink_deep(path)
+                    if new_path != path:
+                        return join(new_path, tail) if tail else new_path
+                except OSError:
+                    # If we fail to readlink(), let's keep traversing
+                    pass
                 path, name = split(path)
                 # TODO (bpo-38186): Request the real file name from the directory
                 # entry using FindFirstFileW. For now, we will return the path
                 # as best we have it
                 if path and not name:
-                    return abspath(path + tail)
+                    return path + tail
                 tail = join(name, tail) if tail else name
-        return abspath(tail)
+        return tail
 
     def realpath(path):
         path = normpath(path)
@@ -604,12 +629,20 @@
             unc_prefix = b'\\\\?\\UNC\\'
             new_unc_prefix = b'\\\\'
             cwd = os.getcwdb()
+            # bpo-38081: Special case for realpath(b'nul')
+            if normcase(path) == normcase(os.fsencode(devnull)):
+                return b'\\\\.\\NUL'
         else:
             prefix = '\\\\?\\'
             unc_prefix = '\\\\?\\UNC\\'
             new_unc_prefix = '\\\\'
             cwd = os.getcwd()
+            # bpo-38081: Special case for realpath('nul')
+            if normcase(path) == normcase(devnull):
+                return '\\\\.\\NUL'
         had_prefix = path.startswith(prefix)
+        if not had_prefix and not isabs(path):
+            path = join(cwd, path)
         try:
             path = _getfinalpathname(path)
             initial_winerror = 0
diff --git a/Lib/test/test_ntpath.py b/Lib/test/test_ntpath.py
index e0ec441..a84b94c 100644
--- a/Lib/test/test_ntpath.py
+++ b/Lib/test/test_ntpath.py
@@ -286,14 +286,16 @@
                                  ABSTFN + r"\missing")
             self.assertPathEqual(ntpath.realpath(r"broken\foo"),
                                  ABSTFN + r"\missing\foo")
+            # bpo-38453: We no longer recursively resolve segments of relative
+            # symlinks that the OS cannot resolve.
             self.assertPathEqual(ntpath.realpath(r"broken1"),
-                                 ABSTFN + r"\missing\bar")
+                                 ABSTFN + r"\broken\bar")
             self.assertPathEqual(ntpath.realpath(r"broken1\baz"),
-                                 ABSTFN + r"\missing\bar\baz")
+                                 ABSTFN + r"\broken\bar\baz")
             self.assertPathEqual(ntpath.realpath("broken2"),
-                                 ABSTFN + r"\missing")
+                                 ABSTFN + r"\self\self\missing")
             self.assertPathEqual(ntpath.realpath("broken3"),
-                                 ABSTFN + r"\missing")
+                                 ABSTFN + r"\subdir\parent\subdir\parent\missing")
             self.assertPathEqual(ntpath.realpath("broken4"),
                                  ABSTFN + r"\missing")
             self.assertPathEqual(ntpath.realpath("broken5"),
@@ -304,13 +306,13 @@
             self.assertPathEqual(ntpath.realpath(rb"broken\foo"),
                                  os.fsencode(ABSTFN + r"\missing\foo"))
             self.assertPathEqual(ntpath.realpath(rb"broken1"),
-                                 os.fsencode(ABSTFN + r"\missing\bar"))
+                                 os.fsencode(ABSTFN + r"\broken\bar"))
             self.assertPathEqual(ntpath.realpath(rb"broken1\baz"),
-                                 os.fsencode(ABSTFN + r"\missing\bar\baz"))
+                                 os.fsencode(ABSTFN + r"\broken\bar\baz"))
             self.assertPathEqual(ntpath.realpath(b"broken2"),
-                                 os.fsencode(ABSTFN + r"\missing"))
+                                 os.fsencode(ABSTFN + r"\self\self\missing"))
             self.assertPathEqual(ntpath.realpath(rb"broken3"),
-                                 os.fsencode(ABSTFN + r"\missing"))
+                                 os.fsencode(ABSTFN + r"\subdir\parent\subdir\parent\missing"))
             self.assertPathEqual(ntpath.realpath(b"broken4"),
                                  os.fsencode(ABSTFN + r"\missing"))
             self.assertPathEqual(ntpath.realpath(b"broken5"),
@@ -319,8 +321,8 @@
     @support.skip_unless_symlink
     @unittest.skipUnless(HAVE_GETFINALPATHNAME, 'need _getfinalpathname')
     def test_realpath_symlink_loops(self):
-        # Bug #930024, return the path unchanged if we get into an infinite
-        # symlink loop.
+        # Symlink loops are non-deterministic as to which path is returned, but
+        # it will always be the fully resolved path of one member of the cycle
         ABSTFN = ntpath.abspath(support.TESTFN)
         self.addCleanup(support.unlink, ABSTFN)
         self.addCleanup(support.unlink, ABSTFN + "1")
@@ -332,8 +334,6 @@
         os.symlink(ABSTFN, ABSTFN)
         self.assertPathEqual(ntpath.realpath(ABSTFN), ABSTFN)
 
-        # cycles are non-deterministic as to which path is returned, but
-        # it will always be the fully resolved path of one member of the cycle
         os.symlink(ABSTFN + "1", ABSTFN + "2")
         os.symlink(ABSTFN + "2", ABSTFN + "1")
         expected = (ABSTFN + "1", ABSTFN + "2")
@@ -402,6 +402,34 @@
     def test_realpath_nul(self):
         tester("ntpath.realpath('NUL')", r'\\.\NUL')
 
+    @unittest.skipUnless(HAVE_GETFINALPATHNAME, 'need _getfinalpathname')
+    def test_realpath_cwd(self):
+        ABSTFN = ntpath.abspath(support.TESTFN)
+
+        support.unlink(ABSTFN)
+        support.rmtree(ABSTFN)
+        os.mkdir(ABSTFN)
+        self.addCleanup(support.rmtree, ABSTFN)
+
+        test_dir_long = ntpath.join(ABSTFN, "MyVeryLongDirectoryName")
+        test_dir_short = ntpath.join(ABSTFN, "MYVERY~1")
+        test_file_long = ntpath.join(test_dir_long, "file.txt")
+        test_file_short = ntpath.join(test_dir_short, "file.txt")
+
+        os.mkdir(test_dir_long)
+
+        with open(test_file_long, "wb") as f:
+            f.write(b"content")
+
+        self.assertPathEqual(test_file_long, ntpath.realpath(test_file_short))
+
+        with support.change_cwd(test_dir_long):
+            self.assertPathEqual(test_file_long, ntpath.realpath("file.txt"))
+        with support.change_cwd(test_dir_long.lower()):
+            self.assertPathEqual(test_file_long, ntpath.realpath("file.txt"))
+        with support.change_cwd(test_dir_short):
+            self.assertPathEqual(test_file_long, ntpath.realpath("file.txt"))
+
     def test_expandvars(self):
         with support.EnvironmentVarGuard() as env:
             env.clear()
diff --git a/Lib/test/test_shutil.py b/Lib/test/test_shutil.py
index 636e3bd..b98e7dc 100644
--- a/Lib/test/test_shutil.py
+++ b/Lib/test/test_shutil.py
@@ -177,7 +177,10 @@
 
         Returns the path of the directory.
         """
-        d = tempfile.mkdtemp()
+        basedir = None
+        if sys.platform == "win32":
+            basedir = os.path.realpath(os.getcwd())
+        d = tempfile.mkdtemp(dir=basedir)
         self.tempdirs.append(d)
         return d
 
@@ -1788,8 +1791,11 @@
 
     def setUp(self):
         filename = "foo"
-        self.src_dir = tempfile.mkdtemp()
-        self.dst_dir = tempfile.mkdtemp()
+        basedir = None
+        if sys.platform == "win32":
+            basedir = os.path.realpath(os.getcwd())
+        self.src_dir = tempfile.mkdtemp(dir=basedir)
+        self.dst_dir = tempfile.mkdtemp(dir=basedir)
         self.src_file = os.path.join(self.src_dir, filename)
         self.dst_file = os.path.join(self.dst_dir, filename)
         with open(self.src_file, "wb") as f:
diff --git a/Misc/NEWS.d/next/Windows/2019-10-28-10-32-43.bpo-38453.NwwatW.rst b/Misc/NEWS.d/next/Windows/2019-10-28-10-32-43.bpo-38453.NwwatW.rst
new file mode 100644
index 0000000..deacb03
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2019-10-28-10-32-43.bpo-38453.NwwatW.rst
@@ -0,0 +1 @@
+Ensure ntpath.realpath() correctly resolves relative paths.