diff --git a/.github/workflows/fuzz.yml b/.github/workflows/fuzz.yml
index 1e7c096d2b..e348ecb774 100644
--- a/.github/workflows/fuzz.yml
+++ b/.github/workflows/fuzz.yml
@@ -24,10 +24,10 @@ jobs:
     - uses: actions/checkout@v3
       with:
         fetch-depth: 0
-    - name: Set up Python 3.10
+    - name: Set up Python 3.14
       uses: actions/setup-python@v4
       with:
-        python-version: "3.10.9"
+        python-version: "3.14.2"
     - name: Restore cache
       uses: actions/cache@v3
       with:
@@ -79,7 +79,7 @@ jobs:
       with:
         name: explicit-example-patches
         path: .hypothesis/patches/latest_hypofuzz_*.patch
-    
+
     # Upload the database so it'll be persisted between runs.
     # Note that we can also pull it down to use locally via
     # https://hypothesis.readthedocs.io/en/latest/database.html#hypothesis.database.GitHubArtifactDatabase
diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 178df30cf3..f1f12dfd32 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -33,7 +33,7 @@ jobs:
           - check-format
       fail-fast: false
     env:
-      PYTHON_VERSION: "3.10"
+      PYTHON_VERSION: "3.14"
     steps:
     - uses: actions/checkout@v3
       with:
@@ -88,22 +88,24 @@ jobs:
           - check-py313t-nocover
           - check-py313t-niche
           - check-quality
-          - check-pytest62
-          - check-pytest62
+          - check-pytest9
+          - check-pytest84
+          - check-pytest74
+          - check-py311-pytest62
           - check-django60
           - check-django42
-          - check-pandas22
-          - check-pandas21
-          - check-pandas20
-          - check-pandas15
-          - check-pandas14
-          - check-pandas13
+          - check-py313-pandas22
+          - check-py312-pandas21
+          - check-py311-pandas20
+          - check-py311-pandas15
+          - check-py310-pandas14
+          - check-py310-pandas13
           ## FIXME: actions update means Python builds without eg _bz2, which was required
           # - check-py310-pandas12
           # - check-py310-pandas11
       fail-fast: false
     env:
-      PYTHON_VERSION: "3.10"
+      PYTHON_VERSION: "3.14"
     steps:
     - uses: actions/checkout@v3
       with:
@@ -172,7 +174,7 @@ jobs:
           - check-numpy-nightly
       fail-fast: false
     env:
-      PYTHON_VERSION: "3.10"
+      PYTHON_VERSION: "3.14"
     steps:
     - uses: actions/checkout@v3
       with:
@@ -201,7 +203,7 @@ jobs:
           - macos-latest
         python-version:
           - "3.11"
-          - "3.13"
+          - "3.14"
         python-architecture:
           - null
           - "x86"
@@ -213,11 +215,11 @@ jobs:
           - alt-rest
         exclude:
           - { os: macos-latest, python-architecture: "x86" }
-          - { python-version: "3.13", python-architecture: "x86" }
+          - { python-version: "3.14", python-architecture: "x86" }
           - { python-version: "3.11", task: nocover }
           - { python-version: "3.11", task: rest }
-          - { python-version: "3.13", task: alt-nocover }
-          - { python-version: "3.13", task: alt-rest }
+          - { python-version: "3.14", task: alt-nocover }
+          - { python-version: "3.14", task: alt-rest }
       fail-fast: false
     runs-on: ${{ matrix.os }}
     env:
@@ -253,6 +255,7 @@ jobs:
       # The versions of pyodide-build and the Pyodide runtime may differ.
       PYODIDE_VERSION: 0.29.1
       PYODIDE_BUILD_VERSION: 0.31.1
+      # pyodide 0.29.0 (latest at time of writing) doesn't yet support 3.14
       PYTHON_VERSION: 3.13.2
     steps:
     - uses: actions/checkout@v3
@@ -316,7 +319,7 @@ jobs:
         token: ${{ secrets.GH_TOKEN }}
     - uses: ./.github/actions/install-base
       with:
-        python-version: "3.10"
+        python-version: "3.14"
     - name: Deploy package
       env:
         GH_TOKEN: ${{ secrets.GH_TOKEN }}
diff --git a/.github/workflows/update-deps.yml b/.github/workflows/update-deps.yml
index 685cdf63db..674f5f6b89 100644
--- a/.github/workflows/update-deps.yml
+++ b/.github/workflows/update-deps.yml
@@ -11,10 +11,10 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - uses: actions/checkout@v3
-      - name: Set up Python 3.10
+      - name: Set up Python 3.14
         uses: actions/setup-python@v4
         with:
-          python-version: '3.10'
+          python-version: '3.14'
       - name: Update pinned dependencies
         run: ./build.sh upgrade-requirements
       - name: Open pull request
diff --git a/.readthedocs.yml b/.readthedocs.yml
index 0ca2e8060c..68422c0ead 100644
--- a/.readthedocs.yml
+++ b/.readthedocs.yml
@@ -14,7 +14,7 @@ formats:
 build:
    os: ubuntu-22.04
    tools:
-      python: "3.10"
+      python: "3.14"
 python:
    install:
       - requirements: requirements/tools.txt
diff --git a/build.sh b/build.sh
index c3043c58f7..9d2a129745 100755
--- a/build.sh
+++ b/build.sh
@@ -19,14 +19,16 @@ SCRIPTS="$ROOT/tooling/scripts"
 # shellcheck source=tooling/scripts/common.sh
 source "$SCRIPTS/common.sh"
 
+PYTHON_VERSION="3.14.2"
+
 if [ -n "${GITHUB_ACTIONS-}" ] || [ -n "${CODESPACES-}" ] || [ -n "${CLAUDECODE-}" ] ; then
     # We're on GitHub Actions, Codespaces, or Claude Code and already have a suitable Python
     PYTHON=$(command -v python3 || command -v python)
 else
     # Otherwise, we install it from scratch
     # NOTE: tooling keeps this version in sync with ci_version in tooling
-    "$SCRIPTS/ensure-python.sh" 3.10.19
-    PYTHON=$(pythonloc 3.10.19)/bin/python
+    "$SCRIPTS/ensure-python.sh" "$PYTHON_VERSION"
+    PYTHON=$(pythonloc "$PYTHON_VERSION")/bin/python
 fi
 
 TOOL_REQUIREMENTS="$ROOT/requirements/tools.txt"
diff --git a/hypothesis-python/RELEASE.rst b/hypothesis-python/RELEASE.rst
new file mode 100644
index 0000000000..3d24d900f6
--- /dev/null
+++ b/hypothesis-python/RELEASE.rst
@@ -0,0 +1,3 @@
+RELEASE_TYPE: patch
+
+Update some internal type hints.
diff --git a/hypothesis-python/src/hypothesis/database.py b/hypothesis-python/src/hypothesis/database.py
index 68568675f3..4fbddd2902 100644
--- a/hypothesis-python/src/hypothesis/database.py
+++ b/hypothesis-python/src/hypothesis/database.py
@@ -76,7 +76,9 @@ def _usable_dir(path: StrPathT) -> bool:
             # Loop terminates because the root dir ('/' on unix) always exists.
             path = path.parent
         return path.is_dir() and os.access(path, os.R_OK | os.W_OK | os.X_OK)
-    except PermissionError:
+    except PermissionError:  # pragma: no cover
+        # path.exists() returns False on 3.14+ instead of raising. See
+        # https://docs.python.org/3.14/library/pathlib.html#querying-file-type-and-status
         return False
 
 
@@ -132,18 +134,36 @@ def __call__(self, *args: Any, **kwargs: Any) -> "ExampleDatabase":
 # This code only runs if Sphinx has already been imported; and it would live in our
 # docs/conf.py except that we would also like it to work for anyone documenting
 # downstream ExampleDatabase subclasses too.
-if "sphinx" in sys.modules:
+#
+# We avoid type-checking this block due to this combination facts:
+# * our check-types-api CI job runs under 3.14
+# * tools.txt therefore pins to a newer version of sphinx which uses 3.12+ `type`
+#   syntax
+# * in test_mypy.py, mypy sees this block, sees sphinx is installed, tries parsing
+#   sphinx code, and errors
+#
+# Putting `and not TYPE_CHECKING` here is just a convenience for our testing setup
+# (because we don't split mypy tests by running CI version, eg), not for runtime
+#  behavior.
+if "sphinx" in sys.modules and not TYPE_CHECKING:  # pragma: no cover
     try:
         import sphinx.ext.autodoc
 
         signature = "hypothesis.database._EDMeta.__call__"
+
+        # _METACLASS_CALL_BLACKLIST moved in newer sphinx versions
+        try:
+            import sphinx.ext.autodoc._dynamic._signatures as _module
+        except ImportError:
+            _module = sphinx.ext.autodoc
+
         # _METACLASS_CALL_BLACKLIST is a frozenset in later sphinx versions
-        if isinstance(sphinx.ext.autodoc._METACLASS_CALL_BLACKLIST, frozenset):
-            sphinx.ext.autodoc._METACLASS_CALL_BLACKLIST = (
-                sphinx.ext.autodoc._METACLASS_CALL_BLACKLIST | {signature}
-            )
+        if isinstance(_module._METACLASS_CALL_BLACKLIST, frozenset):
+            _module._METACLASS_CALL_BLACKLIST = _module._METACLASS_CALL_BLACKLIST | {
+                signature
+            }
         else:
-            sphinx.ext.autodoc._METACLASS_CALL_BLACKLIST.append(signature)
+            _module._METACLASS_CALL_BLACKLIST.append(signature)
     except Exception:
         pass
 
diff --git a/hypothesis-python/src/hypothesis/entry_points.py b/hypothesis-python/src/hypothesis/entry_points.py
index 4a68af7c43..98933265c2 100644
--- a/hypothesis-python/src/hypothesis/entry_points.py
+++ b/hypothesis-python/src/hypothesis/entry_points.py
@@ -17,23 +17,15 @@
 
 import importlib.metadata
 import os
-from collections.abc import Generator, Sequence
-from importlib.metadata import EntryPoint
-
-
-def get_entry_points() -> Generator[EntryPoint, None, None]:
-    try:
-        eps: Sequence[EntryPoint] = importlib.metadata.entry_points(group="hypothesis")
-    except TypeError:  # pragma: no cover
-        # Load-time selection requires Python >= 3.10.  See also
-        # https://importlib-metadata.readthedocs.io/en/latest/using.html
-        eps = importlib.metadata.entry_points().get("hypothesis", [])
-    yield from eps
 
 
 def run() -> None:
-    if not os.environ.get("HYPOTHESIS_NO_PLUGINS"):
-        for entry in get_entry_points():  # pragma: no cover
-            hook = entry.load()
-            if callable(hook):
-                hook()
+    if os.environ.get("HYPOTHESIS_NO_PLUGINS"):
+        return
+
+    for entry in importlib.metadata.entry_points(
+        group="hypothesis"
+    ):  # pragma: no cover
+        hook = entry.load()
+        if callable(hook):
+            hook()
diff --git a/hypothesis-python/src/hypothesis/extra/_array_helpers.py b/hypothesis-python/src/hypothesis/extra/_array_helpers.py
index c688bc5508..802f571f24 100644
--- a/hypothesis-python/src/hypothesis/extra/_array_helpers.py
+++ b/hypothesis-python/src/hypothesis/extra/_array_helpers.py
@@ -134,7 +134,8 @@ def valid_tuple_axes(
     min_size: int = 0,
     max_size: int | None = None,
 ) -> st.SearchStrategy[tuple[int, ...]]:
-    """All tuples will have a length >= ``min_size`` and <= ``max_size``. The default
+    """
+    All tuples will have a length >= ``min_size`` and <= ``max_size``. The default
     value for ``max_size`` is ``ndim``.
 
     Examples from this strategy shrink towards an empty tuple, which render most
@@ -153,7 +154,6 @@ def valid_tuple_axes(
     .. code-block:: python
 
       any_axis_strategy = none() | integers(-ndim, ndim - 1) | valid_tuple_axes(ndim)
-
     """
     check_type(int, ndim, "ndim")
     check_type(int, min_size, "min_size")
@@ -364,7 +364,8 @@ def mutually_broadcastable_shapes(
     min_side: int = 1,
     max_side: int | None = None,
 ) -> st.SearchStrategy[BroadcastableShapes]:
-    """Return a strategy for a specified number of shapes N that are
+    """
+    Return a strategy for a specified number of shapes N that are
     mutually-broadcastable with one another and with the provided base shape.
 
     * ``num_shapes`` is the number of mutually broadcast-compatible shapes to generate.
@@ -397,7 +398,6 @@ def mutually_broadcastable_shapes(
         BroadcastableShapes(input_shapes=((), (), ()), result_shape=())
         BroadcastableShapes(input_shapes=((3,), (), (3,)), result_shape=(3,))
         BroadcastableShapes(input_shapes=((1, 2, 3), (3,), ()), result_shape=(1, 2, 3))
-
     """
     arg_msg = "Pass either the `num_shapes` or the `signature` argument, but not both."
     if num_shapes is not not_set:
diff --git a/hypothesis-python/src/hypothesis/internal/compat.py b/hypothesis-python/src/hypothesis/internal/compat.py
index 0c82a53e30..23ccc42815 100644
--- a/hypothesis-python/src/hypothesis/internal/compat.py
+++ b/hypothesis-python/src/hypothesis/internal/compat.py
@@ -27,10 +27,10 @@
     get_args,
 )
 
-try:
-    BaseExceptionGroup = BaseExceptionGroup
-    ExceptionGroup = ExceptionGroup  # pragma: no cover
-except NameError:
+if sys.version_info >= (3, 11):
+    BaseExceptionGroup = BaseExceptionGroup  # noqa: F821
+    ExceptionGroup = ExceptionGroup  # noqa: F821
+else:  # pragma: no cover
     from exceptiongroup import (
         BaseExceptionGroup as BaseExceptionGroup,
         ExceptionGroup as ExceptionGroup,
@@ -47,7 +47,7 @@
     # In order to use NotRequired, we need the version of TypedDict included in Python 3.11+.
     if sys.version_info[:2] >= (3, 11):
         from typing import NotRequired as NotRequired, TypedDict as TypedDict
-    else:
+    else:  # pragma: no cover
         try:
             from typing_extensions import (
                 NotRequired as NotRequired,
@@ -65,7 +65,7 @@ def __class_getitem__(cls, item):
         from typing import (
             override as override,
         )
-    except ImportError:
+    except ImportError:  # pragma: no cover
         try:
             from typing_extensions import (
                 override as override,
@@ -83,7 +83,7 @@ def __class_getitem__(cls, item):
 def add_note(exc, note):
     try:
         exc.add_note(note)
-    except AttributeError:
+    except AttributeError:  # pragma: no cover
         if not hasattr(exc, "__notes__"):
             try:
                 exc.__notes__ = []
@@ -251,6 +251,31 @@ def bad_django_TestCase(runner: Optional["ConjectureRunner"]) -> bool:
 # see issue #3812
 if sys.version_info[:2] < (3, 12):
 
+    def _asdict_inner(obj, dict_factory):
+        if dataclasses._is_dataclass_instance(obj):
+            return dict_factory(
+                (f.name, _asdict_inner(getattr(obj, f.name), dict_factory))
+                for f in dataclasses.fields(obj)
+            )
+        elif isinstance(obj, tuple) and hasattr(obj, "_fields"):
+            return type(obj)(*[_asdict_inner(v, dict_factory) for v in obj])
+        elif isinstance(obj, (list, tuple)):
+            return type(obj)(_asdict_inner(v, dict_factory) for v in obj)
+        elif isinstance(obj, dict):
+            if hasattr(type(obj), "default_factory"):
+                result = type(obj)(obj.default_factory)
+                for k, v in obj.items():
+                    result[_asdict_inner(k, dict_factory)] = _asdict_inner(
+                        v, dict_factory
+                    )
+                return result
+            return type(obj)(
+                (_asdict_inner(k, dict_factory), _asdict_inner(v, dict_factory))
+                for k, v in obj.items()
+            )
+        else:
+            return copy.deepcopy(obj)
+
     def dataclass_asdict(obj, *, dict_factory=dict):
         """
         A vendored variant of dataclasses.asdict. Includes the bugfix for
@@ -267,30 +292,6 @@ def dataclass_asdict(obj, *, dict_factory=dict):
     dataclass_asdict = dataclasses.asdict
 
 
-def _asdict_inner(obj, dict_factory):
-    if dataclasses._is_dataclass_instance(obj):
-        return dict_factory(
-            (f.name, _asdict_inner(getattr(obj, f.name), dict_factory))
-            for f in dataclasses.fields(obj)
-        )
-    elif isinstance(obj, tuple) and hasattr(obj, "_fields"):
-        return type(obj)(*[_asdict_inner(v, dict_factory) for v in obj])
-    elif isinstance(obj, (list, tuple)):
-        return type(obj)(_asdict_inner(v, dict_factory) for v in obj)
-    elif isinstance(obj, dict):
-        if hasattr(type(obj), "default_factory"):
-            result = type(obj)(obj.default_factory)
-            for k, v in obj.items():
-                result[_asdict_inner(k, dict_factory)] = _asdict_inner(v, dict_factory)
-            return result
-        return type(obj)(
-            (_asdict_inner(k, dict_factory), _asdict_inner(v, dict_factory))
-            for k, v in obj.items()
-        )
-    else:
-        return copy.deepcopy(obj)
-
-
 if sys.version_info[:2] < (3, 13):
     # batched was added in 3.12, strict flag in 3.13
     # copied from 3.13 docs reference implementation
diff --git a/hypothesis-python/src/hypothesis/internal/conjecture/provider_conformance.py b/hypothesis-python/src/hypothesis/internal/conjecture/provider_conformance.py
index 558bb68642..55ced851b5 100644
--- a/hypothesis-python/src/hypothesis/internal/conjecture/provider_conformance.py
+++ b/hypothesis-python/src/hypothesis/internal/conjecture/provider_conformance.py
@@ -44,7 +44,8 @@ def build_intervals(intervals: list[int]) -> list[tuple[int, int]]:
     if len(intervals) % 2:
         intervals = intervals[:-1]
     intervals.sort()
-    return list(batched(intervals, 2, strict=True))
+    # help mypy infer tuple[int, ...] -> tuple[int, int]
+    return list(batched(intervals, 2, strict=True))  # type: ignore
 
 
 def interval_lists(
diff --git a/hypothesis-python/src/hypothesis/internal/entropy.py b/hypothesis-python/src/hypothesis/internal/entropy.py
index 0082eb2d88..63477860bf 100644
--- a/hypothesis-python/src/hypothesis/internal/entropy.py
+++ b/hypothesis-python/src/hypothesis/internal/entropy.py
@@ -244,7 +244,7 @@ def restore_all() -> None:
 def deterministic_PRNG(seed: int = 0) -> Generator[None, None, None]:
     """Context manager that handles random.seed without polluting global state.
 
-    See issue #1255 and PR #1295 for details and motivation - in short,
+    See issue #1266 and PR #1295 for details and motivation - in short,
     leaving the global pseudo-random number generator (PRNG) seeded is a very
     bad idea in principle, and breaks all kinds of independence assumptions
     in practice.
diff --git a/hypothesis-python/src/hypothesis/internal/filtering.py b/hypothesis-python/src/hypothesis/internal/filtering.py
index 155e67e74a..cf1f2f4f5d 100644
--- a/hypothesis-python/src/hypothesis/internal/filtering.py
+++ b/hypothesis-python/src/hypothesis/internal/filtering.py
@@ -26,6 +26,7 @@
 import inspect
 import math
 import operator
+import sys
 from collections.abc import Callable, Collection
 from decimal import Decimal
 from fractions import Fraction
@@ -37,10 +38,9 @@
 from hypothesis.internal.lambda_sources import lambda_description
 from hypothesis.internal.reflection import get_pretty_function_description
 
-try:
-    # new in 3.14
-    from functools import Placeholder  # type: ignore
-except ImportError:
+if sys.version_info[:2] >= (3, 14):
+    from functools import Placeholder
+else:  # pragma: no cover
     Placeholder = object()
 
 Ex = TypeVar("Ex")
diff --git a/hypothesis-python/src/hypothesis/internal/lambda_sources.py b/hypothesis-python/src/hypothesis/internal/lambda_sources.py
index 596b4c8810..0803c3010f 100644
--- a/hypothesis-python/src/hypothesis/internal/lambda_sources.py
+++ b/hypothesis-python/src/hypothesis/internal/lambda_sources.py
@@ -301,7 +301,7 @@ def _lambda_code_matches_node(f, node):
     return _function_key(f) == _function_key(compiled)
 
 
-def _check_unknown_perfectly_aligned_lambda(candidate):
+def _check_unknown_perfectly_aligned_lambda(candidate):  # pragma: no cover
     # This is a monkeypatch point for our self-tests, to make unknown
     # lambdas raise.
     pass
diff --git a/hypothesis-python/src/hypothesis/internal/reflection.py b/hypothesis-python/src/hypothesis/internal/reflection.py
index 87bf67a3e7..f462b10fcf 100644
--- a/hypothesis-python/src/hypothesis/internal/reflection.py
+++ b/hypothesis-python/src/hypothesis/internal/reflection.py
@@ -116,7 +116,7 @@ def function_digest(function: Any) -> bytes:
     return hasher.digest()
 
 
-def check_signature(sig: Signature) -> None:
+def check_signature(sig: Signature) -> None:  # pragma: no cover  # 3.10 only
     # Backport from Python 3.11; see https://github.com/python/cpython/pull/92065
     for p in sig.parameters.values():
         if iskeyword(p.name) and p.kind is not p.POSITIONAL_ONLY:
diff --git a/hypothesis-python/src/hypothesis/strategies/_internal/core.py b/hypothesis-python/src/hypothesis/strategies/_internal/core.py
index 1006fc792d..cfcb1f58bc 100644
--- a/hypothesis-python/src/hypothesis/strategies/_internal/core.py
+++ b/hypothesis-python/src/hypothesis/strategies/_internal/core.py
@@ -1067,6 +1067,7 @@ def do_draw(self, data: ConjectureData) -> Ex:
             with context.track_arg_label(k) as arg_label:
                 kwargs[k] = data.draw(v)
             arg_labels |= arg_label
+
         try:
             obj = self.target(*args, **kwargs)
         except TypeError as err:
@@ -2499,6 +2500,7 @@ def register_type_strategy(
         )
     if (
         "pydantic.generics" in sys.modules
+        and isinstance(custom_type, type)
         and issubclass(custom_type, sys.modules["pydantic.generics"].GenericModel)
         and not re.search(r"[A-Za-z_]+\[.+\]", repr(custom_type))
         and callable(strategy)
diff --git a/hypothesis-python/src/hypothesis/strategies/_internal/types.py b/hypothesis-python/src/hypothesis/strategies/_internal/types.py
index dae1691d15..84d73a2d20 100644
--- a/hypothesis-python/src/hypothesis/strategies/_internal/types.py
+++ b/hypothesis-python/src/hypothesis/strategies/_internal/types.py
@@ -104,7 +104,7 @@
 except AttributeError:  # pragma: no cover
     pass  # Is missing for `python<3.10`
 try:
-    TypeGuardTypes += (typing.TypeIs,)  # type: ignore
+    TypeGuardTypes += (typing.TypeIs,)
 except AttributeError:  # pragma: no cover
     pass  # Is missing for `python<3.13`
 try:
@@ -115,7 +115,7 @@
 
 RequiredTypes: tuple = ()
 try:
-    RequiredTypes += (typing.Required,)  # type: ignore
+    RequiredTypes += (typing.Required,)
 except AttributeError:  # pragma: no cover
     pass  # Is missing for `python<3.11`
 try:
@@ -126,7 +126,7 @@
 
 NotRequiredTypes: tuple = ()
 try:
-    NotRequiredTypes += (typing.NotRequired,)  # type: ignore
+    NotRequiredTypes += (typing.NotRequired,)
 except AttributeError:  # pragma: no cover
     pass  # Is missing for `python<3.11`
 try:
@@ -137,7 +137,7 @@
 
 ReadOnlyTypes: tuple = ()
 try:
-    ReadOnlyTypes += (typing.ReadOnly,)  # type: ignore
+    ReadOnlyTypes += (typing.ReadOnly,)
 except AttributeError:  # pragma: no cover
     pass  # Is missing for `python<3.13`
 try:
@@ -148,7 +148,7 @@
 
 LiteralStringTypes: tuple = ()
 try:
-    LiteralStringTypes += (typing.LiteralString,)  # type: ignore
+    LiteralStringTypes += (typing.LiteralString,)
 except AttributeError:  # pragma: no cover
     pass  # Is missing for `python<3.11`
 try:
@@ -202,7 +202,7 @@
 ):
     try:
         NON_RUNTIME_TYPES += (getattr(typing, name),)
-    except AttributeError:
+    except AttributeError:  # pragma: no cover
         pass
     try:
         NON_RUNTIME_TYPES += (getattr(typing_extensions, name),)
@@ -717,8 +717,13 @@ def _networks(bits):
 # exposed for it, and NotImplemented itself is typed as Any so that it can be
 # returned without being listed in a function signature:
 # https://github.com/python/mypy/issues/6710#issuecomment-485580032
+if sys.version_info < (3, 12):
+    _RegistryKeyT: typing.TypeAlias = type
+else:  # pragma: no cover
+    _RegistryKeyT: typing.TypeAlias = type | typing.TypeAliasType
+
 _global_type_lookup: dict[
-    type, st.SearchStrategy | typing.Callable[[type], st.SearchStrategy]
+    _RegistryKeyT, st.SearchStrategy | typing.Callable[[type], st.SearchStrategy]
 ] = {
     type(None): st.none(),
     bool: st.booleans(),
@@ -976,8 +981,11 @@ def resolve_Tuple(thing):
     elem_types = getattr(thing, "__args__", None) or ()
     if len(elem_types) == 2 and elem_types[-1] is Ellipsis:
         return st.lists(st.from_type(elem_types[0])).map(tuple)
-    elif len(elem_types) == 1 and elem_types[0] == ():
-        return st.tuples()  # Empty tuple; see issue #1583
+    elif len(elem_types) == 1 and elem_types[0] == ():  # pragma: no cover
+        # Empty tuple; see issue #1583.
+        # Only possible on 3.10. `from typing import Tuple; Tuple[()].__args__`
+        # is ((),) on 3.10, and () on 3.11+.
+        return st.tuples()
     return st.tuples(*map(st.from_type, elem_types))
 
 
diff --git a/hypothesis-python/tests/common/utils.py b/hypothesis-python/tests/common/utils.py
index d84c1946d8..dcb3f73be9 100644
--- a/hypothesis-python/tests/common/utils.py
+++ b/hypothesis-python/tests/common/utils.py
@@ -258,14 +258,14 @@ class Why(enum.Enum):
 
 def xfail_on_crosshair(why: Why, /, *, strict=True, as_marks=False):
     # run `pytest -m xf_crosshair` to select these tests!
-    kw = {
-        "strict": strict and why != Why.undiscovered,
-        "reason": f"Expected failure due to: {why.value}",
-        "condition": settings().backend == "crosshair",
-    }
+    mark = pytest.mark.xfail(
+        strict=strict and why != Why.undiscovered,
+        reason=f"Expected failure due to: {why.value}",
+        condition=settings().backend == "crosshair",
+    )
     if as_marks:  # for use with pytest.param(..., marks=xfail_on_crosshair())
-        return (pytest.mark.xf_crosshair, pytest.mark.xfail(**kw))
-    return lambda fn: pytest.mark.xf_crosshair(pytest.mark.xfail(**kw)(fn))
+        return (pytest.mark.xf_crosshair, mark)
+    return lambda fn: pytest.mark.xf_crosshair(mark(fn))
 
 
 def skipif_threading(f):
diff --git a/hypothesis-python/tests/conjecture/test_provider.py b/hypothesis-python/tests/conjecture/test_provider.py
index 75f2bbec36..0349119b30 100644
--- a/hypothesis-python/tests/conjecture/test_provider.py
+++ b/hypothesis-python/tests/conjecture/test_provider.py
@@ -13,6 +13,7 @@
 import math
 import sys
 import time
+import warnings
 from contextlib import contextmanager, nullcontext
 from random import Random
 from threading import RLock
@@ -790,9 +791,15 @@ def f(n):
 
 @pytest.mark.parametrize("provider", [HypothesisProvider, PrngProvider])
 def test_provider_conformance(provider):
-    run_conformance_test(
-        provider, settings=settings(max_examples=20, stateful_step_count=20)
-    )
+    with warnings.catch_warnings():
+        # emitted by available_timezones() from st.timezone_keys() on 3.11+
+        # with tzdata installed. see https://github.com/python/cpython/issues/137841.
+        # Once cpython fixes this, we can remove this.
+        if sys.version_info >= (3, 11):
+            warnings.simplefilter("ignore", EncodingWarning)
+        run_conformance_test(
+            provider, settings=settings(max_examples=20, stateful_step_count=20)
+        )
 
 
 # see https://github.com/HypothesisWorks/hypothesis/issues/4462 and discussion
diff --git a/hypothesis-python/tests/cover/test_cache_implementation.py b/hypothesis-python/tests/cover/test_cache_implementation.py
index a664555dc7..bf9732037e 100644
--- a/hypothesis-python/tests/cover/test_cache_implementation.py
+++ b/hypothesis-python/tests/cover/test_cache_implementation.py
@@ -116,7 +116,7 @@ def test_behaves_like_a_dict_with_losses(implementation, writes, size):
         assert len(target) <= min(len(model), size)
 
 
-@xfail_on_crosshair(Why.symbolic_outside_context)
+@xfail_on_crosshair(Why.symbolic_outside_context, strict=False)
 @settings(
     suppress_health_check={HealthCheck.too_slow}
     | set(settings().suppress_health_check),
diff --git a/hypothesis-python/tests/cover/test_core.py b/hypothesis-python/tests/cover/test_core.py
index 2112134bc0..ac4cb0d89b 100644
--- a/hypothesis-python/tests/cover/test_core.py
+++ b/hypothesis-python/tests/cover/test_core.py
@@ -17,6 +17,8 @@
 from hypothesis.database import InMemoryExampleDatabase
 from hypothesis.errors import InvalidArgument, NoSuchExample, Unsatisfiable
 
+from tests.common.utils import Why, xfail_on_crosshair
+
 
 def test_stops_after_max_examples_if_satisfying():
     count = 0
@@ -162,6 +164,9 @@ def test_non_executed_tests_raise_skipped(test_fn):
     ],
 )
 @given(st.data())
+@xfail_on_crosshair(
+    Why.other, strict=False
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/48
 def test_characters_codec(codec, max_codepoint, exclude_categories, categories, data):
     strategy = st.characters(
         codec=codec,
diff --git a/hypothesis-python/tests/cover/test_lookup.py b/hypothesis-python/tests/cover/test_lookup.py
index a00fdf04c6..83b37dd451 100644
--- a/hypothesis-python/tests/cover/test_lookup.py
+++ b/hypothesis-python/tests/cover/test_lookup.py
@@ -52,7 +52,7 @@
     find_any,
     minimal,
 )
-from tests.common.utils import fails_with, temp_registered
+from tests.common.utils import Why, fails_with, temp_registered, xfail_on_crosshair
 
 # we'll continue testing the typing variants until their removal from the stdlib
 # ruff: noqa: UP006, UP035, UP045, UP007
@@ -665,38 +665,44 @@ def test_recursive_type_with_defaults_minimizes_to_defaults():
     assert minimal(from_type(MyList), lambda ex: True) == MyList()
 
 
-class A:
-    def __init__(self, nxt: typing.Optional["B"]):
+class MutualA:
+    def __init__(self, nxt: typing.Optional["MutualB"]):
         self.nxt = nxt
 
     def __repr__(self):
         return f"A({self.nxt})"
 
 
-class B:
-    def __init__(self, nxt: typing.Optional["A"]):
+class MutualB:
+    def __init__(self, nxt: typing.Optional["MutualA"]):
         self.nxt = nxt
 
     def __repr__(self):
         return f"B({self.nxt})"
 
 
-@given(nxt=st.from_type(A))
+@given(nxt=st.from_type(MutualA))
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/49
 def test_resolving_mutually_recursive_types(nxt):
     i = 0
     while nxt:
-        assert isinstance(nxt, [A, B][i % 2])
+        assert isinstance(nxt, [MutualA, MutualB][i % 2])
         nxt = nxt.nxt
         i += 1
 
 
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/49
 def test_resolving_mutually_recursive_types_with_limited_stack():
     orig_recursionlimit = sys.getrecursionlimit()
     current_stack_depth = stack_depth_of_caller()
     sys.setrecursionlimit(current_stack_depth + 100)
     try:
 
-        @given(nxt=st.from_type(A))
+        @given(nxt=st.from_type(MutualA))
         def test(nxt):
             pass
 
@@ -979,6 +985,9 @@ def test_timezone_lookup(type_):
 )
 @settings(suppress_health_check=[HealthCheck.data_too_large])
 @given(data=st.data())
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/49
 def test_generic_collections_only_use_hashable_elements(typ, data):
     data.draw(from_type(typ))
 
@@ -1101,6 +1110,9 @@ def __init__(self, value: int) -> None:
 
 
 @given(st.data())
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/49
 def test_constructor_is_more_important(data):
     """Constructor types should take precedence over all other annotations."""
     data.draw(st.builds(AnnotatedConstructor))
diff --git a/hypothesis-python/tests/cover/test_regex.py b/hypothesis-python/tests/cover/test_regex.py
index 3e26d97d2a..ade39911c6 100644
--- a/hypothesis-python/tests/cover/test_regex.py
+++ b/hypothesis-python/tests/cover/test_regex.py
@@ -33,6 +33,7 @@
     check_can_generate_examples,
     find_any,
 )
+from tests.common.utils import Why, xfail_on_crosshair
 
 
 def is_ascii(s):
@@ -409,6 +410,9 @@ def test_shared_union():
 
 
 @given(st.data())
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/48
 def test_issue_992_regression(data):
     strat = st.from_regex(
         re.compile(
diff --git a/hypothesis-python/tests/nocover/test_drypython_returns.py b/hypothesis-python/tests/nocover/test_drypython_returns.py
index e3767bfcd2..635a6e6b63 100644
--- a/hypothesis-python/tests/nocover/test_drypython_returns.py
+++ b/hypothesis-python/tests/nocover/test_drypython_returns.py
@@ -16,7 +16,7 @@
 from hypothesis.errors import ResolutionFailed
 
 from tests.common.debug import check_can_generate_examples, find_any
-from tests.common.utils import temp_registered
+from tests.common.utils import Why, temp_registered, xfail_on_crosshair
 
 # Primitives:
 # ===========
@@ -59,6 +59,9 @@ def target_func(mappable: "MappableN[_FirstType]") -> bool:
 
 
 @given(st.data())
+@xfail_on_crosshair(
+    Why.other, strict=False
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/49
 def test_my_mappable(source: st.DataObject) -> None:
     """
     Checks that complex types with multiple inheritance levels and strings are fine.
diff --git a/hypothesis-python/tests/nocover/test_regex.py b/hypothesis-python/tests/nocover/test_regex.py
index b4f49165de..f30582ee8b 100644
--- a/hypothesis-python/tests/nocover/test_regex.py
+++ b/hypothesis-python/tests/nocover/test_regex.py
@@ -21,6 +21,8 @@
     base_regex_strategy,
 )
 
+from tests.common.utils import Why, xfail_on_crosshair
+
 
 @st.composite
 def charset(draw):
@@ -73,6 +75,9 @@ def test_conservative_regex_are_correct_by_construction(data):
     assert pattern.search(result) is not None
 
 
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/48
 @given(st.data())
 def test_fuzz_stuff(data):
     pattern = data.draw(
@@ -102,6 +107,9 @@ def test_fuzz_stuff(data):
     assert regex.search(ex)
 
 
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/48
 @pytest.mark.skipif(sys.version_info[:2] < (3, 11), reason="new syntax")
 @given(st.data())
 def test_regex_atomic_group(data):
@@ -110,6 +118,9 @@ def test_regex_atomic_group(data):
     assert re.search(pattern, ex)
 
 
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/48
 @pytest.mark.skipif(sys.version_info[:2] < (3, 11), reason="new syntax")
 @given(st.data())
 def test_regex_possessive(data):
@@ -124,6 +135,9 @@ def test_regex_possessive(data):
 assert re.compile(I_WITH_DOT, flags=re.IGNORECASE).match(I_WITH_DOT.swapcase())
 
 
+@xfail_on_crosshair(
+    Why.other
+)  # https://github.com/pschanely/hypothesis-crosshair/issues/48
 @given(st.data())
 def test_case_insensitive_not_literal_never_constructs_multichar_match(data):
     # So our goal is to confirm that we can never accidentally create a non-matching
diff --git a/hypothesis-python/tox.ini b/hypothesis-python/tox.ini
index 8066e7f401..f0b84b5081 100644
--- a/hypothesis-python/tox.ini
+++ b/hypothesis-python/tox.ini
@@ -97,7 +97,7 @@ deps =
 commands =
     python -bb -X dev -m pytest tests/pandas -n auto
 
-[testenv:pandas13]
+[testenv:py310-pandas13]
 deps =
     -r../requirements/test.txt
     numpy~=1.26.4
@@ -105,7 +105,7 @@ deps =
 commands =
     python -bb -X dev -m pytest tests/pandas -n auto
 
-[testenv:pandas14]
+[testenv:py310-pandas14]
 deps =
     -r../requirements/test.txt
     numpy~=1.26.4
@@ -113,7 +113,7 @@ deps =
 commands =
     python -bb -X dev -m pytest tests/pandas -n auto
 
-[testenv:pandas15]
+[testenv:py311-pandas15]
 deps =
     -r../requirements/test.txt
     numpy~=1.26.4
@@ -121,7 +121,7 @@ deps =
 commands =
     python -bb -X dev -m pytest tests/pandas -n auto
 
-[testenv:pandas20]
+[testenv:py311-pandas20]
 deps =
     -r../requirements/test.txt
     numpy~=1.26.4
@@ -129,7 +129,7 @@ deps =
 commands =
     python -bb -X dev -m pytest tests/pandas -n auto
 
-[testenv:pandas21]
+[testenv:py312-pandas21]
 deps =
     -r../requirements/test.txt
     numpy~=1.26.4
@@ -139,7 +139,7 @@ setenv=
 commands =
     python -bb -X dev -m pytest tests/pandas -n auto
 
-[testenv:pandas22]
+[testenv:py313-pandas22]
 deps =
     -r../requirements/test.txt
     pandas~=2.2.2
@@ -223,11 +223,19 @@ commands_pre =
 commands =
     python -bb -X dev -m pytest tests/pytest tests/cover/test_testdecorators.py
 
-[testenv:pytest8]
+[testenv:pytest84]
 deps =
     -r../requirements/test.txt
 commands_pre =
-    pip install pytest==8.* pytest-xdist
+    pip install pytest==8.4.2 pytest-xdist
+commands =
+    python -bb -X dev -m pytest tests/pytest tests/cover/test_testdecorators.py
+
+[testenv:pytest9]
+deps =
+    -r../requirements/test.txt
+commands_pre =
+    pip install pytest==9.* pytest-xdist
 commands =
     python -bb -X dev -m pytest tests/pytest tests/cover/test_testdecorators.py
 
diff --git a/pyproject.toml b/pyproject.toml
index 7c387fdce0..4e634a5a2c 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -91,7 +91,7 @@ ignore = [
 "hypothesis-python/tests/conjecture/test_data_tree.py" = ["B023"]
 
 [tool.mypy]
-python_version = "3.10"
+python_version = "3.14"
 platform = "linux"
 
 allow_redefinition = true
diff --git a/requirements/coverage.txt b/requirements/coverage.txt
index ec7403efd6..ac64e679e9 100644
--- a/requirements/coverage.txt
+++ b/requirements/coverage.txt
@@ -1,13 +1,11 @@
 #
-# This file is autogenerated by pip-compile with Python 3.10
+# This file is autogenerated by pip-compile with Python 3.14
 # by the following command:
 #
 #    ./build.sh upgrade-requirements
 #
 annotated-types==0.7.0
     # via -r requirements/coverage.in
-async-timeout==5.0.1
-    # via redis
 black==25.12.0
     # via -r requirements/coverage.in
 click==8.3.1
@@ -18,10 +16,6 @@ coverage[toml]==7.13.1
     # via pytest-cov
 dpcontracts==0.6.0
     # via -r requirements/coverage.in
-exceptiongroup==1.3.1 ; python_version < "3.11"
-    # via
-    #   hypothesis (hypothesis-python/pyproject.toml)
-    #   pytest
 execnet==2.1.2
     # via pytest-xdist
 fakeredis==2.33.0
@@ -34,7 +28,7 @@ libcst==1.8.6
     # via -r requirements/coverage.in
 mypy-extensions==1.1.0
     # via black
-numpy==2.2.6
+numpy==2.4.1
     # via
     #   -r requirements/coverage.in
     #   pandas
@@ -89,17 +83,8 @@ sortedcontainers==2.4.0
     # via
     #   fakeredis
     #   hypothesis (hypothesis-python/pyproject.toml)
-tomli==2.3.0
-    # via
-    #   black
-    #   coverage
-    #   pytest
 typing-extensions==4.15.0
-    # via
-    #   -r requirements/coverage.in
-    #   black
-    #   exceptiongroup
-    #   fakeredis
+    # via -r requirements/coverage.in
 tzdata==2025.3
     # via pandas
 watchdog==6.0.0
diff --git a/requirements/crosshair.txt b/requirements/crosshair.txt
index af5f5cbf56..baa890184c 100644
--- a/requirements/crosshair.txt
+++ b/requirements/crosshair.txt
@@ -1,5 +1,5 @@
 #
-# This file is autogenerated by pip-compile with Python 3.10
+# This file is autogenerated by pip-compile with Python 3.14
 # by the following command:
 #
 #    ./build.sh upgrade-requirements
@@ -17,12 +17,6 @@ crosshair-tool==0.0.101
     # via
     #   -r requirements/crosshair.in
     #   hypothesis-crosshair
-exceptiongroup==1.3.1 ; python_version < "3.11"
-    # via
-    #   cattrs
-    #   hypothesis
-    #   hypothesis (hypothesis-python/pyproject.toml)
-    #   pytest
 execnet==2.1.2
     # via pytest-xdist
 hypothesis==6.150.0
@@ -63,15 +57,12 @@ sortedcontainers==2.4.0
     # via
     #   hypothesis
     #   hypothesis (hypothesis-python/pyproject.toml)
-tomli==2.3.0
-    # via pytest
 typeshed-client==2.8.2
     # via crosshair-tool
 typing-extensions==4.15.0
     # via
     #   cattrs
     #   crosshair-tool
-    #   exceptiongroup
     #   typeshed-client
     #   typing-inspect
 typing-inspect==0.9.0
diff --git a/requirements/fuzzing.txt b/requirements/fuzzing.txt
index 7d9a28a61c..f4838e5cda 100644
--- a/requirements/fuzzing.txt
+++ b/requirements/fuzzing.txt
@@ -1,5 +1,5 @@
 #
-# This file is autogenerated by pip-compile with Python 3.10
+# This file is autogenerated by pip-compile with Python 3.14
 # by the following command:
 #
 #    ./build.sh upgrade-requirements
@@ -8,8 +8,6 @@ annotated-types==0.7.0
     # via -r requirements/coverage.in
 anyio==4.12.1
     # via starlette
-async-timeout==5.0.1
-    # via redis
 attrs==25.4.0
     # via
     #   outcome
@@ -30,15 +28,6 @@ coverage[toml]==7.13.1
     #   pytest-cov
 dpcontracts==0.6.0
     # via -r requirements/coverage.in
-exceptiongroup==1.3.1 ; python_version < "3.11"
-    # via
-    #   anyio
-    #   hypercorn
-    #   hypothesis
-    #   hypothesis (hypothesis-python/pyproject.toml)
-    #   pytest
-    #   taskgroup
-    #   trio
 execnet==2.1.2
     # via pytest-xdist
 fakeredis==2.33.0
@@ -77,7 +66,7 @@ mdurl==0.1.2
     # via markdown-it-py
 mypy-extensions==1.1.0
     # via black
-numpy==2.2.6
+numpy==2.4.1
     # via
     #   -r requirements/coverage.in
     #   pandas
@@ -149,26 +138,10 @@ sortedcontainers==2.4.0
     #   trio
 starlette==0.51.0
     # via hypofuzz
-taskgroup==0.2.2
-    # via hypercorn
-tomli==2.3.0
-    # via
-    #   black
-    #   coverage
-    #   hypercorn
-    #   pytest
 trio==0.32.0
     # via hypofuzz
 typing-extensions==4.15.0
-    # via
-    #   -r requirements/coverage.in
-    #   anyio
-    #   black
-    #   exceptiongroup
-    #   fakeredis
-    #   hypercorn
-    #   starlette
-    #   taskgroup
+    # via -r requirements/coverage.in
 tzdata==2025.3
     # via pandas
 watchdog==6.0.0
diff --git a/requirements/test.txt b/requirements/test.txt
index 60462b2eaa..a6cda8a2fe 100644
--- a/requirements/test.txt
+++ b/requirements/test.txt
@@ -1,13 +1,9 @@
 #
-# This file is autogenerated by pip-compile with Python 3.10
+# This file is autogenerated by pip-compile with Python 3.14
 # by the following command:
 #
 #    ./build.sh upgrade-requirements
 #
-exceptiongroup==1.3.1 ; python_version < "3.11"
-    # via
-    #   hypothesis (hypothesis-python/pyproject.toml)
-    #   pytest
 execnet==2.1.2
     # via pytest-xdist
 iniconfig==2.3.0
@@ -30,7 +26,3 @@ pytest-xdist==3.8.0
     # via -r requirements/test.in
 sortedcontainers==2.4.0
     # via hypothesis (hypothesis-python/pyproject.toml)
-tomli==2.3.0
-    # via pytest
-typing-extensions==4.15.0
-    # via exceptiongroup
diff --git a/requirements/tools.in b/requirements/tools.in
index e9314b5989..4bf4e87e7c 100644
--- a/requirements/tools.in
+++ b/requirements/tools.in
@@ -28,7 +28,8 @@ types-pytz
 types-redis
 typing-extensions
 watchdog # for typing
-attrs # for typing
 build
 sortedcontainers-stubs # for typing
+attrs # for typing
+tomli # for update_pyproject_toml
 -r test.in
diff --git a/requirements/tools.txt b/requirements/tools.txt
index f50e1af140..72d0f6bb3a 100644
--- a/requirements/tools.txt
+++ b/requirements/tools.txt
@@ -1,5 +1,5 @@
 #
-# This file is autogenerated by pip-compile with Python 3.10
+# This file is autogenerated by pip-compile with Python 3.14
 # by the following command:
 #
 #    ./build.sh upgrade-requirements
@@ -22,8 +22,6 @@ autoflake==2.3.1
     # via shed
 babel==2.17.0
     # via sphinx
-backports-tarfile==1.2.0
-    # via jaraco-context
 beautifulsoup4==4.14.3
     # via
     #   furo
@@ -63,16 +61,15 @@ coverage==7.13.1
     # via -r requirements/tools.in
 cryptography==46.0.3
     # via
-    #   secretstorage
     #   types-pyopenssl
     #   types-redis
 decorator==5.2.1
     # via ipython
 distlib==0.4.0
     # via virtualenv
-django==5.2.10
+django==6.0.1
     # via -r requirements/tools.in
-docutils==0.21.2
+docutils==0.22.4
     # via
     #   pelican
     #   readme-renderer
@@ -81,12 +78,6 @@ docutils==0.21.2
     #   sphinx-jsonschema
 dpcontracts==0.6.0
     # via -r requirements/tools.in
-exceptiongroup==1.3.1 ; python_version < "3.11"
-    # via
-    #   anyio
-    #   hypothesis (hypothesis-python/pyproject.toml)
-    #   ipython
-    #   pytest
 execnet==2.1.2
     # via pytest-xdist
 executing==2.2.1
@@ -109,12 +100,12 @@ idna==3.11
     #   requests
 imagesize==1.4.1
     # via sphinx
-importlib-metadata==8.7.1
-    # via keyring
 iniconfig==2.3.0
     # via pytest
-ipython==8.38.0
+ipython==9.9.0
     # via -r requirements/tools.in
+ipython-pygments-lexers==1.1.1
+    # via ipython
 isort==7.0.0
     # via shed
 jaraco-classes==3.4.0
@@ -125,10 +116,6 @@ jaraco-functools==4.4.0
     # via keyring
 jedi==0.19.2
     # via ipython
-jeepney==0.9.0
-    # via
-    #   keyring
-    #   secretstorage
 jinja2==3.1.6
     # via
     #   pelican
@@ -169,7 +156,7 @@ nh3==0.3.2
     # via readme-renderer
 nodeenv==1.10.0
     # via pyright
-numpy==2.2.6
+numpy==2.4.1
     # via -r requirements/tools.in
 ordered-set==4.1.0
     # via pelican
@@ -220,6 +207,7 @@ pygments==2.18.0
     #   accessible-pygments
     #   furo
     #   ipython
+    #   ipython-pygments-lexers
     #   pelican
     #   pytest
     #   readme-renderer
@@ -271,10 +259,10 @@ rich==14.2.0
     # via
     #   pelican
     #   twine
+roman-numerals==4.1.0
+    # via sphinx
 ruff==0.14.11
     # via -r requirements/tools.in
-secretstorage==3.5.0
-    # via keyring
 shed==2024.1.1
     # via -r requirements/tools.in
 six==1.17.0
@@ -289,14 +277,14 @@ sortedcontainers-stubs==2.4.3
     # via -r requirements/tools.in
 soupsieve==2.8.1
     # via beautifulsoup4
-sphinx==8.1.3
+sphinx==9.1.0
     # via
     #   -r requirements/tools.in
     #   furo
     #   sphinx-autobuild
     #   sphinx-basic-ng
     #   sphinx-codeautolink
-sphinx-autobuild==2024.10.3
+sphinx-autobuild==2025.8.25
     # via -r requirements/tools.in
 sphinx-basic-ng==1.0.0b2
     # via furo
@@ -326,17 +314,8 @@ starlette==0.51.0
     # via sphinx-autobuild
 tokenize-rt==6.2.0
     # via pyupgrade
-tomli==2.3.0
-    # via
-    #   autoflake
-    #   black
-    #   build
-    #   mypy
-    #   pip-tools
-    #   pyproject-api
-    #   pytest
-    #   sphinx
-    #   tox
+tomli==2.4.0
+    # via -r requirements/tools.in
 tox==4.34.1
     # via -r requirements/tools.in
 traitlets==5.14.3
@@ -360,20 +339,10 @@ types-setuptools==80.9.0.20251223
 typing-extensions==4.15.0
     # via
     #   -r requirements/tools.in
-    #   anyio
-    #   asgiref
     #   beautifulsoup4
-    #   black
-    #   cryptography
-    #   exceptiongroup
-    #   ipython
     #   mypy
     #   pyright
     #   sortedcontainers-stubs
-    #   starlette
-    #   tox
-    #   uvicorn
-    #   virtualenv
 unidecode==1.4.0
     # via pelican
 urllib3==2.6.3
@@ -396,8 +365,6 @@ websockets==16.0
     # via sphinx-autobuild
 wheel==0.45.1
     # via pip-tools
-zipp==3.23.0
-    # via importlib-metadata
 
 # The following packages are considered to be unsafe in a requirements file:
 pip==25.3
diff --git a/tooling/README.rst b/tooling/README.md
similarity index 67%
rename from tooling/README.rst
rename to tooling/README.md
index 7d42af830f..b2c2276d7c 100644
--- a/tooling/README.rst
+++ b/tooling/README.md
@@ -1,6 +1,4 @@
-========================
-Hypothesis Build Tooling
-========================
+# Hypothesis Build Tooling
 
 This is a piece of software for managing Hypothesis's build tasks, releases,
 etc. It's very Hypothesis specific, though it may become less so in the future.
diff --git a/tooling/src/hypothesistooling/__main__.py b/tooling/src/hypothesistooling/__main__.py
index 47fbc324bc..01de77dd5a 100644
--- a/tooling/src/hypothesistooling/__main__.py
+++ b/tooling/src/hypothesistooling/__main__.py
@@ -631,7 +631,7 @@ def run_tox(task, version, *args):
     "pypy3.10": "pypy3.10-7.3.19",
     "pypy3.11": "pypy3.11-7.3.20",
 }
-ci_version = "3.10"  # Keep this in sync with GH Actions main.yml and .readthedocs.yml
+ci_version = "3.14"  # Keep this in sync with GH Actions main.yml and .readthedocs.yml
 
 python_tests = task(
     if_changed=(
@@ -689,8 +689,10 @@ def standard_tox_task(name, py=ci_version):
     )
 
 
-# standard_tox_task("py310-pytest46", py="3.10")
-standard_tox_task("pytest62")
+standard_tox_task("py311-pytest62", py="3.11")  # hits "ast.Str is deprecated" in 3.12+
+standard_tox_task("pytest74")
+standard_tox_task("pytest84")
+standard_tox_task("pytest9")
 
 dj_version = max(ci_version, "3.12")
 for n in DJANGO_VERSIONS:
@@ -698,10 +700,15 @@ def standard_tox_task(name, py=ci_version):
 # we also test no-contrib on the latest django version
 standard_tox_task("django-nocontrib", py=dj_version)
 
-for n in [13, 14, 15, 20, 21, 22]:
-    standard_tox_task(f"pandas{n}")
+# test each pandas version with the latest python version they support
 standard_tox_task("py310-pandas11", py="3.10")
 standard_tox_task("py310-pandas12", py="3.10")
+standard_tox_task("py310-pandas13", py="3.10")
+standard_tox_task("py310-pandas14", py="3.10")
+standard_tox_task("py311-pandas15", py="3.11")
+standard_tox_task("py311-pandas20", py="3.11")
+standard_tox_task("py312-pandas21", py="3.12")
+standard_tox_task("py313-pandas22", py="3.13")
 
 for kind in ("cover", "nocover", "niche", "custom"):
     standard_tox_task(f"crosshair-{kind}")
diff --git a/whole_repo_tests/types/revealed_types.py b/whole_repo_tests/types/revealed_types.py
index 2cc7c22398..fd211c511f 100644
--- a/whole_repo_tests/types/revealed_types.py
+++ b/whole_repo_tests/types/revealed_types.py
@@ -94,7 +94,7 @@ class DifferingRevealedTypes(NamedTuple):
 NUMPY_REVEALED_TYPES = [
     (
         'arrays(dtype=np.dtype("int32"), shape=1)',
-        "ndarray[tuple[int, ...], dtype[signedinteger[_32Bit]]]",
+        "ndarray[tuple[Any, ...], dtype[signedinteger[_32Bit]]]",
     ),
     # (
     #     "arrays(dtype=np.dtype(int), shape=1)",
@@ -199,15 +199,15 @@ class DifferingRevealedTypes(NamedTuple):
     ),
     (
         "integer_array_indices(shape=(2, 3))",
-        "tuple[ndarray[tuple[int, ...], dtype[signedinteger[Any]]], ...]",
+        "tuple[ndarray[tuple[Any, ...], dtype[signedinteger[Any]]], ...]",
     ),
     (
         'integer_array_indices(shape=(2, 3), dtype=np.dtype("int32"))',
-        "tuple[ndarray[tuple[int, ...], dtype[signedinteger[_32Bit]]], ...]",
+        "tuple[ndarray[tuple[Any, ...], dtype[signedinteger[_32Bit]]], ...]",
     ),
     (
         'integer_array_indices(shape=(2, 3), dtype=np.dtype("uint8"))',
-        "tuple[ndarray[tuple[int, ...], dtype[unsignedinteger[_8Bit]]], ...]",
+        "tuple[ndarray[tuple[Any, ...], dtype[unsignedinteger[_8Bit]]], ...]",
     ),
     # basic_indices with allow_ellipsis=False (no EllipsisType differences)
     (