diff --git a/stdlib/@tests/test_cases/check_json.py b/stdlib/@tests/test_cases/check_json.py
new file mode 100644
index 000000000000..15fc78a8ca48
--- /dev/null
+++ b/stdlib/@tests/test_cases/check_json.py
@@ -0,0 +1,97 @@
+from __future__ import annotations
+
+import json
+from decimal import Decimal
+from typing import TypedDict
+
+
+class _File:
+    def write(self, s: str) -> int: ...
+
+
+fp = _File()
+
+
+# By default, json.dumps() will not accept any non JSON-serializable objects.
+class CustomClass: ...
+
+
+json.dumps(CustomClass())  # type: ignore
+json.dump(CustomClass(), fp)  # type: ignore
+json.dumps(object())  # type: ignore
+json.dump(object(), fp)  # type: ignore
+json.dumps(Decimal(1))  # type: ignore
+json.dump(Decimal(1), fp)  # type: ignore
+
+# Serializable types are supported, included nested JSON.
+json.dumps({"a": 34, "b": [1, 2, 3], "c": {"d": "hello", "e": False}})
+json.dump({"a": 34, "b": [1, 2, 3], "c": {"d": "hello", "e": False}}, fp)
+json.dumps(
+    {
+        "numbers": [1, 2, 3, 4, 5],
+        "strings": ["hello", "world"],
+        "booleans": [True, False],
+        "null": None,
+        "nested": {"array": [[1, 2], [3, 4.34]], "object": {"x": 1, "y": 2}},
+    }
+)
+json.dump(
+    {
+        "numbers": [1, 2, 3, 4, 5],
+        "strings": ["hello", "world"],
+        "booleans": [True, False],
+        "null": None,
+        "nested": {"array": [[1, 2], [3, 4.34]], "object": {"x": 1, "y": 2}},
+    },
+    fp,
+)
+json.dumps(1)
+json.dump(1, fp)
+json.dumps(1.23)
+json.dump(1.23, fp)
+json.dumps(True)
+json.dump(True, fp)
+
+# Test explicit nested types that might cause variance issues.
+x: dict[str, float | int] = {"a": 1, "b": 2.0}
+json.dumps(x)
+json.dump(x, fp)
+
+z: dict[str, dict[str, dict[str, list[int]]]] = {"a": {"b": {"c": [1, 2, 3]}}}
+json.dumps(z)
+json.dump(z, fp)
+
+
+# Custom types are supported when a custom encoder is provided.
+def decimal_encoder(obj: Decimal) -> float:
+    return float(obj)
+
+
+json.dumps(Decimal(1), default=decimal_encoder)
+json.dump(Decimal(1), fp, default=decimal_encoder)
+
+
+# If the custom encoder doesn't return JSON, it will lead a typing error..
+def custom_encoder(obj: Decimal) -> Decimal:
+    return obj
+
+
+json.dumps(Decimal(1), default=custom_encoder)  #  type: ignore
+json.dump(Decimal(1), fp, default=custom_encoder)  #  type: ignore
+
+
+class MyTypedDict(TypedDict):
+    a: str
+    b: str
+
+
+json.dumps(MyTypedDict(a="hello", b="world"))
+
+
+# We should allow anything for subclasses of json.JSONEncoder.
+# Type-checking custom encoders is not practical without generics.
+class MyJSONEncoder(json.JSONEncoder): ...
+
+
+json.dumps(Decimal(1), cls=MyJSONEncoder)
+json.dump(Decimal(1), fp, cls=MyJSONEncoder)
diff --git a/stdlib/json/__init__.pyi b/stdlib/json/__init__.pyi
index 63e9718ee151..45b89da8260e 100644
--- a/stdlib/json/__init__.pyi
+++ b/stdlib/json/__init__.pyi
@@ -1,28 +1,85 @@
 from _typeshed import SupportsRead, SupportsWrite
-from collections.abc import Callable
-from typing import Any
+from collections.abc import Callable, Mapping, Sequence
+from typing import Any, TypeVar, overload
+from typing_extensions import TypeAlias
 
 from .decoder import JSONDecodeError as JSONDecodeError, JSONDecoder as JSONDecoder
 from .encoder import JSONEncoder as JSONEncoder
 
 __all__ = ["dump", "dumps", "load", "loads", "JSONDecoder", "JSONDecodeError", "JSONEncoder"]
 
+_T = TypeVar("_T")
+
+# Mapping[str, object] is used to maintain compatibility with typed dictionaries
+# despite it being very loose it's preferrable to using Any.
+_JSON: TypeAlias = Mapping[str, object] | Sequence[_JSON] | str | float | bool | None
+
+@overload
 def dumps(
-    obj: Any,
+    obj: _JSON,
     *,
     skipkeys: bool = False,
     ensure_ascii: bool = True,
     check_circular: bool = True,
     allow_nan: bool = True,
-    cls: type[JSONEncoder] | None = None,
+    cls: None = None,
+    indent: None | int | str = None,
+    separators: tuple[str, str] | None = None,
+    default: None = None,
+    sort_keys: bool = False,
+    **kwds: Any,
+) -> str: ...
+@overload
+def dumps(
+    obj: _JSON | _T,
+    *,
+    skipkeys: bool = False,
+    ensure_ascii: bool = True,
+    check_circular: bool = True,
+    allow_nan: bool = True,
+    cls: None = None,
+    indent: None | int | str = None,
+    separators: tuple[str, str] | None = None,
+    default: Callable[[_T], _JSON],
+    sort_keys: bool = False,
+    **kwds: Any,
+) -> str: ...
+
+# Type-checking subclasses without generics isn't practical.
+@overload
+def dumps(
+    obj: object,
+    *,
+    skipkeys: bool = False,
+    ensure_ascii: bool = True,
+    check_circular: bool = True,
+    allow_nan: bool = True,
+    cls: type[JSONEncoder],
     indent: None | int | str = None,
     separators: tuple[str, str] | None = None,
     default: Callable[[Any], Any] | None = None,
     sort_keys: bool = False,
     **kwds: Any,
 ) -> str: ...
+@overload
 def dump(
-    obj: Any,
+    obj: _JSON,
+    fp: SupportsWrite[str],
+    *,
+    skipkeys: bool = False,
+    ensure_ascii: bool = True,
+    check_circular: bool = True,
+    allow_nan: bool = True,
+    cls: None = None,
+    indent: None | int | str = None,
+    separators: tuple[str, str] | None = None,
+    default: None = None,
+    sort_keys: bool = False,
+    **kwds: Any,
+) -> None: ...
+@overload
+def dump(
+    obj: _JSON | _T,
     fp: SupportsWrite[str],
     *,
     skipkeys: bool = False,
@@ -32,6 +89,24 @@ def dump(
     cls: type[JSONEncoder] | None = None,
     indent: None | int | str = None,
     separators: tuple[str, str] | None = None,
+    default: Callable[[_T], _JSON],
+    sort_keys: bool = False,
+    **kwds: Any,
+) -> None: ...
+
+# Type-checking subclasses without generics isn't practical.
+@overload
+def dump(
+    obj: object,
+    fp: SupportsWrite[str],
+    *,
+    skipkeys: bool = False,
+    ensure_ascii: bool = True,
+    check_circular: bool = True,
+    allow_nan: bool = True,
+    cls: type[JSONEncoder],
+    indent: None | int | str = None,
+    separators: tuple[str, str] | None = None,
     default: Callable[[Any], Any] | None = None,
     sort_keys: bool = False,
     **kwds: Any,