diff --git a/doc/index.rst b/doc/index.rst
index 21d6fa60..d3d96315 100644
--- a/doc/index.rst
+++ b/doc/index.rst
@@ -1030,13 +1030,25 @@ Capsule objects
 Sentinel objects
 ~~~~~~~~~~~~~~~~
 
-.. class:: Sentinel(name, repr=None)
+.. class:: Sentinel(name, module_name=None, *, repr=None)
 
-   A type used to define sentinel values. The *name* argument should be the
-   name of the variable to which the return value shall be assigned.
+   A type used to define custom sentinel values.
+
+   *name* should be the qualified name of the variable to which
+   the return value shall be assigned.
+
+   *module_name* is the module where the sentinel is defined.
+   Defaults to the current modules ``__name__``.
 
    If *repr* is provided, it will be used for the :meth:`~object.__repr__`
-   of the sentinel object. If not provided, ``"<name>"`` will be used.
+   of the sentinel object. If not provided, *name* will be used.
+
+   All sentinels with the same *name* and *module_name* have the same identity.
+   Sentinel identity is preserved across :py:mod:`copy` and :py:mod:`pickle`.
+
+   Sentinel objects are tested using :py:ref:`is`.
+   Sentinels have no truthiness and attempting to convert a sentinel to
+   :py:class:`bool` will raise :py:exc:`TypeError`.
 
    Example::
 
@@ -1050,6 +1062,13 @@ Sentinel objects
       ...
       >>> func(MISSING)
 
+   Sentinels defined in a class scope must use fully qualified names.
+
+   Example::
+
+      >>> class MyClass:
+      ...     MISSING = Sentinel('MyClass.MISSING')
+
    .. versionadded:: 4.14.0
 
       See :pep:`661`
diff --git a/src/test_typing_extensions.py b/src/test_typing_extensions.py
index 5de161f9..34add814 100644
--- a/src/test_typing_extensions.py
+++ b/src/test_typing_extensions.py
@@ -9269,16 +9269,33 @@ def test_invalid_special_forms(self):
 
 
 class TestSentinels(BaseTestCase):
-    def test_sentinel_no_repr(self):
-        sentinel_no_repr = Sentinel('sentinel_no_repr')
+    SENTINEL = Sentinel("TestSentinels.SENTINEL")
 
-        self.assertEqual(sentinel_no_repr._name, 'sentinel_no_repr')
-        self.assertEqual(repr(sentinel_no_repr), '<sentinel_no_repr>')
+    def test_sentinel_repr(self):
+        self.assertEqual(repr(TestSentinels.SENTINEL), "TestSentinels.SENTINEL")
+        self.assertEqual(repr(Sentinel("sentinel")), "sentinel")
 
     def test_sentinel_explicit_repr(self):
-        sentinel_explicit_repr = Sentinel('sentinel_explicit_repr', repr='explicit_repr')
+        sentinel_explicit_repr = Sentinel("sentinel_explicit_repr", repr="explicit_repr")
+        self.assertEqual(repr(sentinel_explicit_repr), "explicit_repr")
+        with self.assertWarnsRegex(
+            DeprecationWarning,
+            r"repr='sentinel_explicit_repr' conflicts with initial definition of repr='explicit_repr'"
+        ):
+            self.assertEqual(repr(Sentinel("sentinel_explicit_repr")), "explicit_repr")
 
-        self.assertEqual(repr(sentinel_explicit_repr), 'explicit_repr')
+    def test_sentinel_explicit_repr_deprecated(self):
+        with self.assertWarnsRegex(
+            DeprecationWarning,
+            r"Use keyword parameter repr='explicit_repr' instead"
+        ):
+            deprecated_repr = Sentinel("deprecated_repr", "explicit_repr")
+        self.assertEqual(repr(deprecated_repr), "explicit_repr")
+        with self.assertWarnsRegex(
+            DeprecationWarning,
+            r"repr='deprecated_repr' conflicts with initial definition of repr='explicit_repr'"
+        ):
+            self.assertEqual(repr(Sentinel("deprecated_repr")), "explicit_repr")
 
     @skipIf(sys.version_info < (3, 10), reason='New unions not available in 3.9')
     def test_sentinel_type_expression_union(self):
@@ -9298,13 +9315,33 @@ def test_sentinel_not_callable(self):
         ):
             sentinel()
 
-    def test_sentinel_not_picklable(self):
-        sentinel = Sentinel('sentinel')
+    def test_sentinel_identity(self):
+        self.assertIs(TestSentinels.SENTINEL, Sentinel("TestSentinels.SENTINEL"))
+        self.assertIs(Sentinel("SENTINEL"), Sentinel("SENTINEL", __name__))
+        self.assertIsNot(TestSentinels.SENTINEL, Sentinel("SENTINEL"))
+
+    def test_sentinel_copy(self):
+        self.assertIs(self.SENTINEL, copy.copy(self.SENTINEL))
+        self.assertIs(self.SENTINEL, copy.deepcopy(self.SENTINEL))
+
+    def test_sentinel_picklable_qualified(self):
+        for proto in range(pickle.HIGHEST_PROTOCOL + 1):
+            self.assertIs(self.SENTINEL, pickle.loads(pickle.dumps(self.SENTINEL, protocol=proto)))
+
+    def test_sentinel_picklable_anonymous(self):
+        anonymous_sentinel = Sentinel("anonymous_sentinel")  # Anonymous sentinel can not be pickled
+        for proto in range(pickle.HIGHEST_PROTOCOL + 1):
+            with self.assertRaisesRegex(
+                pickle.PicklingError,
+                r"attribute lookup anonymous_sentinel on \w+ failed|not found as \w+.anonymous_sentinel"
+            ):
+                self.assertIs(anonymous_sentinel, pickle.loads(pickle.dumps(anonymous_sentinel, protocol=proto)))
+
+    def test_sentinel_bool(self):
         with self.assertRaisesRegex(
-            TypeError,
-            "Cannot pickle 'Sentinel' object"
+            TypeError, rf"{self.SENTINEL!r} is not convertable to bool",
         ):
-            pickle.dumps(sentinel)
+            bool(self.SENTINEL)
 
 
 if __name__ == '__main__':
diff --git a/src/typing_extensions.py b/src/typing_extensions.py
index efa09d55..74d5ffcd 100644
--- a/src/typing_extensions.py
+++ b/src/typing_extensions.py
@@ -5,6 +5,7 @@
 import contextlib
 import enum
 import functools
+import importlib
 import inspect
 import io
 import keyword
@@ -4155,24 +4156,78 @@ def evaluate_forward_ref(
             )
 
 
+_sentinel_registry = {}
+
 class Sentinel:
-    """Create a unique sentinel object.
+    """A sentinel object.
+
+    *name* should be the qualified name of the variable to which
+    the return value shall be assigned.
 
-    *name* should be the name of the variable to which the return value shall be assigned.
+    *module_name* is the module where the sentinel is defined.
+    Defaults to the current modules ``__name__``.
 
     *repr*, if supplied, will be used for the repr of the sentinel object.
-    If not provided, "<name>" will be used.
+    If not provided, *name* will be used.
+
+    All sentinels with the same *name* and *module_name* have the same identity.
+    The ``is`` operator is used to test if an object is a sentinel.
+    Sentinel identity is preserved across copy and pickle.
     """
 
-    def __init__(
-        self,
+    def __new__(
+        cls,
         name: str,
+        module_name: typing.Optional[str] = None,
+        *,
         repr: typing.Optional[str] = None,
     ):
-        self._name = name
-        self._repr = repr if repr is not None else f'<{name}>'
+        """Return an object with a consistent identity."""
+        if module_name is not None and repr is None:
+            # 'repr' used to be the 2nd positional argument but is now 'module_name'
+            # Test if 'module_name' is a module or is the old 'repr' argument
+            # Use 'repr=name' to suppress this check
+            try:
+                importlib.import_module(module_name)
+            except Exception:
+                repr = module_name
+                module_name = None
+                warnings.warn(
+                    "'repr' as a positional argument could be mistaken for the sentinels"
+                    " 'module_name'."
+                    f" Use keyword parameter repr={repr!r} instead.",
+                    category=DeprecationWarning,
+                    stacklevel=2,
+                )
 
-    def __repr__(self):
+        if module_name is None:
+            module_name = _caller(default="")
+
+        registry_key = f"{module_name}-{name}"
+
+        repr = repr if repr is not None else name
+
+        # Check registered sentinels
+        sentinel = _sentinel_registry.get(registry_key, None)
+        if sentinel is not None:
+            if sentinel._repr != repr:
+                warnings.warn(
+                    f"repr={repr!r} conflicts with initial definition of "
+                    f"repr={sentinel._repr!r} and will be ignored"
+                    "\nUsage of repr should be consistent across definitions",
+                    DeprecationWarning,
+                    stacklevel=2,
+                )
+            return sentinel
+
+        # Create initial or anonymous sentinel
+        sentinel = super().__new__(cls)
+        sentinel._name = name
+        sentinel.__module__ = module_name  # Assign which module defined this instance
+        sentinel._repr = repr
+        return _sentinel_registry.setdefault(registry_key, sentinel)
+
+    def __repr__(self) -> str:
         return self._repr
 
     if sys.version_info < (3, 11):
@@ -4188,8 +4243,13 @@ def __or__(self, other):
         def __ror__(self, other):
             return typing.Union[other, self]
 
-    def __getstate__(self):
-        raise TypeError(f"Cannot pickle {type(self).__name__!r} object")
+    def __reduce__(self) -> str:
+        """Reduce this sentinel to a singleton."""
+        return self._name  # Module is set from __module__ attribute
+
+    def __bool__(self) -> Never:
+        """Raise TypeError."""
+        raise TypeError(f"Sentinel {self!r} is not convertable to bool.")
 
 
 # Aliases for items that are in typing in all supported versions.

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