diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 0b87fec53767..3f269d5aa3fb 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -191,9 +191,9 @@ supported:
 * `partial_stub` (optional): This field marks the type stub package as
   [partial](https://peps.python.org/pep-0561/#partial-stub-packages). This is for
   3rd-party stubs that don't cover the entirety of the package's public API.
-* `requires_python` (optional): The minimum version of Python required to install
-  the type stub package. It must be in the form `>=3.*`. If omitted, the oldest
-  Python version supported by typeshed is used.
+* `requires_python` (optional): The Python version required to install the
+  the type stub package. It must be in the form `>=3.*`, `<3.*` or `>=3.*,<3.*`.
+  If omitted, the oldest Python version supported by typeshed is used.
 
 In addition, we specify configuration for stubtest in the `tool.stubtest` table.
 This has the following keys:
diff --git a/lib/ts_utils/metadata.py b/lib/ts_utils/metadata.py
index 1b700021640c..af81a8210d87 100644
--- a/lib/ts_utils/metadata.py
+++ b/lib/ts_utils/metadata.py
@@ -23,7 +23,8 @@
 
 import tomlkit
 from packaging.requirements import Requirement
-from packaging.specifiers import Specifier
+from packaging.specifiers import Specifier, SpecifierSet
+from packaging.version import Version
 from tomlkit.items import String
 
 from .paths import PYPROJECT_PATH, STUBS_PATH, distribution_path
@@ -33,6 +34,7 @@
     "PackageDependencies",
     "StubMetadata",
     "StubtestSettings",
+    "get_newest_supported_python",
     "get_oldest_supported_python",
     "get_recursive_requirements",
     "read_dependencies",
@@ -55,6 +57,51 @@ def _is_nested_dict(obj: object) -> TypeGuard[dict[str, dict[str, Any]]]:
     return isinstance(obj, dict) and all(isinstance(k, str) and isinstance(v, dict) for k, v in obj.items())
 
 
+def _bump_minor_version(version: str) -> str:
+    v = Version(version)
+    major, minor, *_ = v.release
+    minor += 1
+    return str(Version(f"{major}.{minor}"))
+
+
+def _is_specifier_subset(base: SpecifierSet, other: SpecifierSet) -> bool:
+    """
+    Check `other` does not extend beyond `base`.
+    `other` is allowed to have only one bound (>= or <).
+    """
+    base_lower = None
+    base_upper = None
+    for spec in base:
+        if spec.operator.startswith(">"):
+            base_lower = Version(spec.version)
+        elif spec.operator.startswith("<"):
+            base_upper = Version(spec.version)
+    assert isinstance(base_lower, Version)
+    assert isinstance(base_upper, Version)
+
+    other_lower = None
+    other_upper = None
+    for spec in other:
+        if spec.operator.startswith(">"):
+            other_lower = Version(spec.version)
+        elif spec.operator.startswith("<"):
+            other_upper = Version(spec.version)
+
+    # Check lower bound
+    if other_lower and other_lower < base_lower:
+        return False
+    # Check upper bound
+    return not (other_upper and other_upper > base_upper)
+
+
+@functools.cache
+def get_newest_supported_python() -> str:
+    with PYPROJECT_PATH.open("rb") as config:
+        val = tomllib.load(config)["tool"]["typeshed"]["newest_supported_python"]
+    assert type(val) is str
+    return val
+
+
 @functools.cache
 def get_oldest_supported_python() -> str:
     with PYPROJECT_PATH.open("rb") as config:
@@ -183,7 +230,7 @@ class StubMetadata:
     uploaded_to_pypi: Annotated[bool, "Whether or not a distribution is uploaded to PyPI"]
     partial_stub: Annotated[bool, "Whether this is a partial type stub package as per PEP 561."]
     stubtest_settings: StubtestSettings
-    requires_python: Annotated[Specifier, "Versions of Python supported by the stub package"]
+    requires_python: Annotated[SpecifierSet, "Versions of Python supported by the stub package"]
 
     @property
     def is_obsolete(self) -> bool:
@@ -310,18 +357,22 @@ def read_metadata(distribution: str) -> StubMetadata:
     assert type(partial_stub) is bool
     requires_python_str: object = data.get("requires_python")  # pyright: ignore[reportUnknownMemberType]
     oldest_supported_python = get_oldest_supported_python()
-    oldest_supported_python_specifier = Specifier(f">={oldest_supported_python}")
+    newest_supported_python = get_newest_supported_python()
+    newest_supported_python = _bump_minor_version(newest_supported_python)
+    supported_python_specifier = SpecifierSet(f">={oldest_supported_python},<{newest_supported_python}")
     if requires_python_str is None:
-        requires_python = oldest_supported_python_specifier
+        requires_python = supported_python_specifier
     else:
         assert isinstance(requires_python_str, str)
-        requires_python = Specifier(requires_python_str)
-        assert requires_python != oldest_supported_python_specifier, f'requires_python="{requires_python}" is redundant'
-        # Check minimum Python version is not less than the oldest version of Python supported by typeshed
-        assert oldest_supported_python_specifier.contains(
-            requires_python.version
-        ), f"'requires_python' contains versions lower than typeshed's oldest supported Python ({oldest_supported_python})"
-        assert requires_python.operator == ">=", "'requires_python' should be a minimum version specifier, use '>=3.x'"
+        requires_python = SpecifierSet(requires_python_str)
+
+        base_specs = {str(spec) for spec in supported_python_specifier}
+        metadata_specs = {str(spec) for spec in requires_python}
+        duplicates = base_specs & metadata_specs
+        assert not duplicates, f"'requires_python' contains redundant specifier(s): {','.join(duplicates)}"
+        assert _is_specifier_subset(
+            supported_python_specifier, requires_python
+        ), f"'requires_python' contains versions beyond the typeshed's supported Python ({supported_python_specifier})"
 
     empty_tools: dict[object, object] = {}
     tools_settings: object = data.get("tool", empty_tools)  # pyright: ignore[reportUnknownMemberType]
diff --git a/pyproject.toml b/pyproject.toml
index c523ec07b934..6ba1fdd1191f 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -254,3 +254,4 @@ known-first-party = ["_utils", "ts_utils"]
 
 [tool.typeshed]
 oldest_supported_python = "3.9"
+newest_supported_python = "3.14"
diff --git a/tests/runtests.py b/tests/runtests.py
index 296cb8ccd068..f62d9f8bbcb2 100755
--- a/tests/runtests.py
+++ b/tests/runtests.py
@@ -71,7 +71,11 @@ def main() -> None:
     if args.python_version:
         python_version: str = args.python_version
     elif folder in "stubs":
-        python_version = read_metadata(stub).requires_python.version
+        python_version = get_oldest_supported_python()
+        metadata_python_version = read_metadata(stub).requires_python
+        for spec in metadata_python_version:
+            if spec.operator.startswith(">"):
+                python_version = spec.version
     else:
         python_version = get_oldest_supported_python()