diff --git a/Lib/pathlib.py b/Lib/pathlib.py
index a36ffdd73d8af1..b4a872e2e05feb 100644
--- a/Lib/pathlib.py
+++ b/Lib/pathlib.py
@@ -399,9 +399,6 @@ def __str__(self):
                                                   self._tail) or '.'
             return self._str
 
-    def __fspath__(self):
-        return str(self)
-
     def as_posix(self):
         """Return the string representation of the path with forward (/)
         slashes."""
@@ -411,7 +408,7 @@ def as_posix(self):
     def __bytes__(self):
         """Return the bytes representation of the path.  This is only
         recommended to use under Unix."""
-        return os.fsencode(self)
+        return os.fsencode(str(self))
 
     def __repr__(self):
         return "{}({!r})".format(self.__class__.__name__, self.as_posix())
@@ -743,11 +740,6 @@ def match(self, path_pattern, *, case_sensitive=None):
             raise ValueError("empty pattern")
 
 
-# Subclassing os.PathLike makes isinstance() checks slower,
-# which in turn makes Path construction slower. Register instead!
-os.PathLike.register(PurePath)
-
-
 class PurePosixPath(PurePath):
     """PurePath subclass for non-Windows systems.
 
@@ -757,6 +749,8 @@ class PurePosixPath(PurePath):
     _flavour = posixpath
     __slots__ = ()
 
+    def __fspath__(self):
+        return str(self)
 
 class PureWindowsPath(PurePath):
     """PurePath subclass for Windows systems.
@@ -767,6 +761,13 @@ class PureWindowsPath(PurePath):
     _flavour = ntpath
     __slots__ = ()
 
+    def __fspath__(self):
+        return str(self)
+
+
+# These classes implement os.PathLike for backwards compatibility.
+os.PathLike.register(PurePosixPath)
+os.PathLike.register(PureWindowsPath)
 
 # Filesystem-accessing classes
 
@@ -1174,6 +1175,9 @@ def __new__(cls, *args, **kwargs):
             cls = WindowsPath if os.name == 'nt' else PosixPath
         return object.__new__(cls)
 
+    def __fspath__(self):
+        return str(self)
+
     @classmethod
     def cwd(cls):
         """Return a new path pointing to the current working directory."""
@@ -1398,6 +1402,10 @@ def expanduser(self):
 
         return self
 
+# Subclassing os.PathLike makes isinstance() checks slower,
+# which in turn makes Path construction slower. Register instead!
+os.PathLike.register(Path)
+
 
 class PosixPath(Path, PurePosixPath):
     """Path subclass for non-Windows systems.
diff --git a/Lib/test/test_pathlib.py b/Lib/test/test_pathlib.py
index f9356909cb0982..a3db944364994d 100644
--- a/Lib/test/test_pathlib.py
+++ b/Lib/test/test_pathlib.py
@@ -1545,6 +1545,15 @@ class cls(pathlib.PurePath):
     # repr() roundtripping is not supported in custom subclass.
     test_repr_roundtrips = None
 
+    # PurePath subclass is not automatically path-like
+    def test_fspath_common(self):
+        P = self.cls
+        p = P()
+        self.assertFalse(issubclass(P, os.PathLike))
+        self.assertFalse(isinstance(p, os.PathLike))
+        with self.assertRaises(TypeError):
+            os.fspath(p)
+
 
 @only_posix
 class PosixPathAsPureTest(PurePosixPathTest):
diff --git a/Misc/NEWS.d/next/Library/2023-06-23-18-23-18.gh-issue-106037.hLb-E3.rst b/Misc/NEWS.d/next/Library/2023-06-23-18-23-18.gh-issue-106037.hLb-E3.rst
new file mode 100644
index 00000000000000..69b1a0335eaa95
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2023-06-23-18-23-18.gh-issue-106037.hLb-E3.rst
@@ -0,0 +1,3 @@
+Fix misidentification of :class:`pathlib.PurePath` user subclasses as
+:class:`os.PathLike`. Subclasses are free to define an
+:meth:`~os.PathLike.__fspath__` method, but do not inherit one.