diff --git a/sphinx/config.py b/sphinx/config.py
index ef1eaa848e3..9e49423d5cc 100644
--- a/sphinx/config.py
+++ b/sphinx/config.py
@@ -51,17 +51,30 @@ class ConfigValue(NamedTuple):
     rebuild: _ConfigRebuild
 
 
-def is_serializable(obj: Any) -> bool:
+def is_serializable(obj: object, *, _recursive_guard: frozenset[int] = frozenset()) -> bool:
     """Check if object is serializable or not."""
     if isinstance(obj, UNSERIALIZABLE_TYPES):
         return False
-    elif isinstance(obj, dict):
+
+    # use id() to handle un-hashable objects
+    if id(obj) in _recursive_guard:
+        return True
+
+    if isinstance(obj, dict):
+        guard = _recursive_guard | {id(obj)}
         for key, value in obj.items():
-            if not is_serializable(key) or not is_serializable(value):
+            if (
+                not is_serializable(key, _recursive_guard=guard)
+                or not is_serializable(value, _recursive_guard=guard)
+            ):
                 return False
-    elif isinstance(obj, (list, tuple, set)):
-        return all(map(is_serializable, obj))
+    elif isinstance(obj, (list, tuple, set, frozenset)):
+        guard = _recursive_guard | {id(obj)}
+        return all(is_serializable(item, _recursive_guard=guard) for item in obj)
 
+    # if an issue occurs for a non-serializable type, pickle will complain
+    # since the object is likely coming from a third-party extension (we
+    # natively expect 'simple' types and not weird ones)
     return True
 
 
diff --git a/tests/test_config/test_config.py b/tests/test_config/test_config.py
index ee305274ecf..d269b7169b0 100644
--- a/tests/test_config/test_config.py
+++ b/tests/test_config/test_config.py
@@ -1,7 +1,11 @@
 """Test the sphinx.config.Config class."""
+from __future__ import annotations
+
 import pickle
 import time
+from collections import Counter
 from pathlib import Path
+from typing import TYPE_CHECKING
 from unittest import mock
 
 import pytest
@@ -14,10 +18,51 @@
     _Opt,
     check_confval_types,
     correct_copyright_year,
+    is_serializable,
 )
 from sphinx.deprecation import RemovedInSphinx90Warning
 from sphinx.errors import ConfigError, ExtensionError, VersionRequirementError
 
+if TYPE_CHECKING:
+    from collections.abc import Iterable
+    from typing import Union
+
+    CircularList = list[Union[int, 'CircularList']]
+    CircularDict = dict[str, Union[int, 'CircularDict']]
+
+
+def check_is_serializable(subject: object, *, circular: bool) -> None:
+    assert is_serializable(subject)
+
+    if circular:
+        class UselessGuard(frozenset[int]):
+            def __or__(self, other: object, /) -> UselessGuard:
+                # do nothing
+                return self
+
+            def union(self, *args: Iterable[object]) -> UselessGuard:
+                # do nothing
+                return self
+
+        # check that without recursive guards, a recursion error occurs
+        with pytest.raises(RecursionError):
+            assert is_serializable(subject, _recursive_guard=UselessGuard())
+
+
+def test_is_serializable() -> None:
+    subject = [1, [2, {3, 'a'}], {'x': {'y': frozenset((4, 5))}}]
+    check_is_serializable(subject, circular=False)
+
+    a, b = [1], [2]  # type: (CircularList, CircularList)
+    a.append(b)
+    b.append(a)
+    check_is_serializable(a, circular=True)
+    check_is_serializable(b, circular=True)
+
+    x: CircularDict = {'a': 1, 'b': {'c': 1}}
+    x['b'] = x
+    check_is_serializable(x, circular=True)
+
 
 def test_config_opt_deprecated(recwarn):
     opt = _Opt('default', '', ())
@@ -102,6 +147,151 @@ def test_config_pickle_protocol(tmp_path, protocol: int):
     assert repr(config) == repr(pickled_config)
 
 
+def test_config_pickle_circular_reference_in_list():
+    a, b = [1], [2]  # type: (CircularList, CircularList)
+    a.append(b)
+    b.append(a)
+
+    check_is_serializable(a, circular=True)
+    check_is_serializable(b, circular=True)
+
+    config = Config()
+    config.add('a', [], '', types=list)
+    config.add('b', [], '', types=list)
+    config.a, config.b = a, b
+
+    actual = pickle.loads(pickle.dumps(config))
+    assert isinstance(actual.a, list)
+    check_is_serializable(actual.a, circular=True)
+
+    assert isinstance(actual.b, list)
+    check_is_serializable(actual.b, circular=True)
+
+    assert actual.a[0] == 1
+    assert actual.a[1][0] == 2
+    assert actual.a[1][1][0] == 1
+    assert actual.a[1][1][1][0] == 2
+
+    assert actual.b[0] == 2
+    assert actual.b[1][0] == 1
+    assert actual.b[1][1][0] == 2
+    assert actual.b[1][1][1][0] == 1
+
+    assert len(actual.a) == 2
+    assert len(actual.a[1]) == 2
+    assert len(actual.a[1][1]) == 2
+    assert len(actual.a[1][1][1]) == 2
+    assert len(actual.a[1][1][1][1]) == 2
+
+    assert len(actual.b) == 2
+    assert len(actual.b[1]) == 2
+    assert len(actual.b[1][1]) == 2
+    assert len(actual.b[1][1][1]) == 2
+    assert len(actual.b[1][1][1][1]) == 2
+
+    def check(
+        u: list[list[object] | int],
+        v: list[list[object] | int],
+        *,
+        counter: Counter[type, int] | None = None,
+        guard: frozenset[int] = frozenset(),
+    ) -> Counter[type, int]:
+        counter = Counter() if counter is None else counter
+
+        if id(u) in guard and id(v) in guard:
+            return counter
+
+        if isinstance(u, int):
+            assert v.__class__ is u.__class__
+            assert u == v
+            counter[type(u)] += 1
+            return counter
+
+        assert isinstance(u, list)
+        assert v.__class__ is u.__class__
+        assert len(u) == len(v)
+
+        for u_i, v_i in zip(u, v):
+            counter[type(u)] += 1
+            check(u_i, v_i, counter=counter, guard=guard | {id(u), id(v)})
+
+        return counter
+
+    counter = check(actual.a, a)
+    # check(actual.a, a)
+    #   check(actual.a[0], a[0]) -> ++counter[dict]
+    #       ++counter[int] (a[0] is an int)
+    #   check(actual.a[1], a[1]) -> ++counter[dict]
+    #       check(actual.a[1][0], a[1][0]) -> ++counter[dict]
+    #           ++counter[int] (a[1][0] is an int)
+    #       check(actual.a[1][1], a[1][1]) -> ++counter[dict]
+    #           recursive guard since a[1][1] == a
+    assert counter[type(a[0])] == 2
+    assert counter[type(a[1])] == 4
+
+    # same logic as above
+    counter = check(actual.b, b)
+    assert counter[type(b[0])] == 2
+    assert counter[type(b[1])] == 4
+
+
+def test_config_pickle_circular_reference_in_dict():
+    x: CircularDict = {'a': 1, 'b': {'c': 1}}
+    x['b'] = x
+    check_is_serializable(x, circular=True)
+
+    config = Config()
+    config.add('x', [], '', types=dict)
+    config.x = x
+
+    actual = pickle.loads(pickle.dumps(config))
+    check_is_serializable(actual.x, circular=True)
+    assert isinstance(actual.x, dict)
+
+    assert actual.x['a'] == 1
+    assert actual.x['b']['a'] == 1
+
+    assert len(actual.x) == 2
+    assert len(actual.x['b']) == 2
+    assert len(actual.x['b']['b']) == 2
+
+    def check(
+        u: dict[str, dict[str, object] | int],
+        v: dict[str, dict[str, object] | int],
+        *,
+        counter: Counter[type, int] | None = None,
+        guard: frozenset[int] = frozenset(),
+    ) -> Counter:
+        counter = Counter() if counter is None else counter
+
+        if id(u) in guard and id(v) in guard:
+            return counter
+
+        if isinstance(u, int):
+            assert v.__class__ is u.__class__
+            assert u == v
+            counter[type(u)] += 1
+            return counter
+
+        assert isinstance(u, dict)
+        assert v.__class__ is u.__class__
+        assert len(u) == len(v)
+
+        for u_i, v_i in zip(u, v):
+            counter[type(u)] += 1
+            check(u[u_i], v[v_i], counter=counter, guard=guard | {id(u), id(v)})
+        return counter
+
+    counters = check(actual.x, x, counter=Counter())
+    # check(actual.x, x)
+    #   check(actual.x['a'], x['a']) -> ++counter[dict]
+    #       ++counter[int] (x['a'] is an int)
+    #   check(actual.x['b'], x['b']) -> ++counter[dict]
+    #       recursive guard since x['b'] == x
+    assert counters[type(x['a'])] == 1
+    assert counters[type(x['b'])] == 2
+
+
 def test_extension_values():
     config = Config()