diff --git a/docs-requirements.txt b/docs-requirements.txt
index 1bf42a9239..a6f9148063 100644
--- a/docs-requirements.txt
+++ b/docs-requirements.txt
@@ -10,7 +10,7 @@ attrs==23.1.0
     # via
     #   -r docs-requirements.in
     #   outcome
-babel==2.12.1
+babel==2.13.0
     # via sphinx
 certifi==2023.7.22
     # via requests
@@ -53,9 +53,9 @@ jinja2==3.1.2
     #   towncrier
 markupsafe==2.1.3
     # via jinja2
-outcome==1.2.0
+outcome==1.3.0
     # via -r docs-requirements.in
-packaging==23.1
+packaging==23.2
     # via sphinx
 pycparser==2.21
     # via cffi
@@ -103,7 +103,7 @@ tomli==2.0.1
     # via towncrier
 towncrier==23.6.0
     # via -r docs-requirements.in
-urllib3==2.0.5
+urllib3==2.0.7
     # via requests
 zipp==3.17.0
     # via
diff --git a/docs/source/conf.py b/docs/source/conf.py
index b85974a901..06b661f126 100755
--- a/docs/source/conf.py
+++ b/docs/source/conf.py
@@ -70,8 +70,6 @@
     # aliasing doesn't actually fix the warning for types.FrameType, but displaying
     # "types.FrameType" is more helpful than just "frame"
     "FrameType": "types.FrameType",
-    # unaliasing these makes intersphinx able to resolve them
-    "Outcome": "outcome.Outcome",
     "Context": "OpenSSL.SSL.Context",
 }
 
@@ -82,8 +80,6 @@ def autodoc_process_signature(
     """Modify found signatures to fix various issues."""
     if signature is not None:
         signature = signature.replace("~_contextvars.Context", "~contextvars.Context")
-        if name == "trio.lowlevel.start_guest_run":
-            signature = signature.replace("Outcome", "~outcome.Outcome")
         if name == "trio.lowlevel.RunVar":  # Typevar is not useful here.
             signature = signature.replace(": ~trio._core._local.T", "")
         if "_NoValue" in signature:
diff --git a/test-requirements.txt b/test-requirements.txt
index dd2caf58dc..b5d2c0a4d5 100644
--- a/test-requirements.txt
+++ b/test-requirements.txt
@@ -6,7 +6,7 @@
 #
 astor==0.8.1
     # via -r test-requirements.in
-astroid==2.15.8
+astroid==3.0.1
     # via pylint
 async-generator==1.10
     # via -r test-requirements.in
@@ -14,7 +14,7 @@ attrs==23.1.0
     # via
     #   -r test-requirements.in
     #   outcome
-black==23.9.1 ; implementation_name == "cpython"
+black==23.10.0 ; implementation_name == "cpython"
     # via -r test-requirements.in
 build==1.0.3
     # via pip-tools
@@ -24,9 +24,9 @@ click==8.1.7
     # via
     #   black
     #   pip-tools
-codespell==2.2.5
+codespell==2.2.6
     # via -r test-requirements.in
-coverage==7.3.1
+coverage==7.3.2
     # via -r test-requirements.in
 cryptography==41.0.4
     # via
@@ -50,13 +50,11 @@ iniconfig==2.0.0
     # via pytest
 isort==5.12.0
     # via pylint
-jedi==0.19.0
+jedi==0.19.1
     # via -r test-requirements.in
-lazy-object-proxy==1.9.0
-    # via astroid
 mccabe==0.7.0
     # via pylint
-mypy==1.5.1 ; implementation_name == "cpython"
+mypy==1.6.0 ; implementation_name == "cpython"
     # via -r test-requirements.in
 mypy-extensions==1.0.0 ; implementation_name == "cpython"
     # via
@@ -65,9 +63,9 @@ mypy-extensions==1.0.0 ; implementation_name == "cpython"
     #   mypy
 nodeenv==1.8.0
     # via pyright
-outcome==1.2.0
+outcome==1.3.0
     # via -r test-requirements.in
-packaging==23.1
+packaging==23.2
     # via
     #   black
     #   build
@@ -78,7 +76,7 @@ pathspec==0.11.2
     # via black
 pip-tools==7.3.0
     # via -r test-requirements.in
-platformdirs==3.10.0
+platformdirs==3.11.0
     # via
     #   black
     #   pylint
@@ -86,17 +84,17 @@ pluggy==1.3.0
     # via pytest
 pycparser==2.21
     # via cffi
-pylint==2.17.7
+pylint==3.0.1
     # via -r test-requirements.in
 pyopenssl==23.2.0
     # via -r test-requirements.in
 pyproject-hooks==1.0.0
     # via build
-pyright==1.1.329
+pyright==1.1.331
     # via -r test-requirements.in
 pytest==7.4.2
     # via -r test-requirements.in
-ruff==0.0.291
+ruff==0.1.0
     # via -r test-requirements.in
 sniffio==1.3.0
     # via -r test-requirements.in
@@ -130,8 +128,6 @@ typing-extensions==4.8.0
     #   pylint
 wheel==0.41.2
     # via pip-tools
-wrapt==1.15.0
-    # via astroid
 zipp==3.17.0
     # via importlib-metadata
 
diff --git a/trio/_core/_tests/test_run.py b/trio/_core/_tests/test_run.py
index f67f83a4b8..25e1f65e0a 100644
--- a/trio/_core/_tests/test_run.py
+++ b/trio/_core/_tests/test_run.py
@@ -17,7 +17,7 @@
 )
 from contextlib import ExitStack, contextmanager
 from math import inf
-from typing import NoReturn, TypeVar
+from typing import Any, NoReturn, TypeVar, cast
 
 import outcome
 import pytest
@@ -2121,12 +2121,13 @@ async def detachable_coroutine(
         nursery.start_soon(detachable_coroutine, outcome.Value(None), "I'm free!")
 
     # If we get here then Trio thinks the task has exited... but the coroutine
-    # is still iterable
+    # is still iterable. At that point anything can be sent into the coroutine, so the .coro type
+    # is wrong.
     assert pdco_outcome is None
-    assert not_none(task).coro.send("be free!") == "I'm free!"
+    assert not_none(task).coro.send(cast(Any, "be free!")) == "I'm free!"
     assert pdco_outcome == outcome.Value("be free!")
     with pytest.raises(StopIteration):
-        not_none(task).coro.send(None)
+        not_none(task).coro.send(cast(Any, None))
 
     # Check the exception paths too
     task = None
@@ -2139,7 +2140,7 @@ async def detachable_coroutine(
     assert not_none(task).coro.throw(throw_in) == "uh oh"
     assert pdco_outcome == outcome.Error(throw_in)
     with pytest.raises(StopIteration):
-        task.coro.send(None)
+        task.coro.send(cast(Any, None))
 
     async def bad_detach() -> None:
         async with _core.open_nursery():
@@ -2190,9 +2191,9 @@ def abort_fn(_: _core.RaiseCancelT) -> _core.Abort:  # pragma: no cover
         await wait_all_tasks_blocked()
 
         # Okay, it's detached. Here's our coroutine runner:
-        assert not_none(task).coro.send("not trio!") == 1
-        assert not_none(task).coro.send(None) == 2
-        assert not_none(task).coro.send(None) == "byebye"
+        assert not_none(task).coro.send(cast(Any, "not trio!")) == 1
+        assert not_none(task).coro.send(cast(Any, None)) == 2
+        assert not_none(task).coro.send(cast(Any, None)) == "byebye"
 
         # Now it's been reattached, and we can leave the nursery
 
@@ -2222,7 +2223,7 @@ def abort_fn(_: _core.RaiseCancelT) -> _core.Abort:
         await wait_all_tasks_blocked()
         assert task is not None
         nursery.cancel_scope.cancel()
-        task.coro.send(None)
+        task.coro.send(cast(Any, None))
 
     assert abort_fn_called
 
diff --git a/trio/_core/_traps.py b/trio/_core/_traps.py
index 760c46bc51..f08fd69090 100644
--- a/trio/_core/_traps.py
+++ b/trio/_core/_traps.py
@@ -11,7 +11,6 @@
 from . import _run
 
 if TYPE_CHECKING:
-    from outcome import Outcome
     from typing_extensions import TypeAlias
 
     from ._run import Task
@@ -182,10 +181,12 @@ def abort(inner_raise_cancel):
 # Not exported in the trio._core namespace, but imported directly by _run.
 @attr.s(frozen=True)
 class PermanentlyDetachCoroutineObject:
-    final_outcome: Outcome = attr.ib()
+    final_outcome: outcome.Outcome[Any] = attr.ib()
 
 
-async def permanently_detach_coroutine_object(final_outcome: Outcome) -> Any:
+async def permanently_detach_coroutine_object(
+    final_outcome: outcome.Outcome[Any],
+) -> Any:
     """Permanently detach the current task from the Trio scheduler.
 
     Normally, a Trio task doesn't exit until its coroutine object exits. When
diff --git a/trio/_file_io.py b/trio/_file_io.py
index 4a5650b453..6f30f89dd8 100644
--- a/trio/_file_io.py
+++ b/trio/_file_io.py
@@ -430,7 +430,7 @@ async def open_file(
 
 
 @overload
-async def open_file(
+async def open_file(  # type: ignore[misc]  # Any usage matches builtins.open().
     file: _OpenFile,
     mode: str,
     buffering: int = -1,
diff --git a/trio/_path.py b/trio/_path.py
index fb01420a75..219f706825 100644
--- a/trio/_path.py
+++ b/trio/_path.py
@@ -311,7 +311,7 @@ async def open(
         ...
 
     @overload
-    async def open(
+    async def open(  # type: ignore[misc]  # Any usage matches builtins.open().
         self,
         mode: str,
         buffering: int = -1,
diff --git a/trio/_socket.py b/trio/_socket.py
index 540641a628..7f6d9b3581 100644
--- a/trio/_socket.py
+++ b/trio/_socket.py
@@ -694,7 +694,7 @@ def send(__self, __bytes: Buffer, __flags: int = 0) -> Awaitable[int]:
 
     @overload
     async def sendto(
-        self, __data: Buffer, __address: tuple[Any, ...] | str | Buffer
+        self, __data: Buffer, __address: tuple[object, ...] | str | Buffer
     ) -> int:
         ...
 
@@ -703,7 +703,7 @@ async def sendto(
         self,
         __data: Buffer,
         __flags: int,
-        __address: tuple[Any, ...] | str | Buffer,
+        __address: tuple[object, ...] | str | Buffer,
     ) -> int:
         ...
 
@@ -1167,13 +1167,13 @@ def send(__self, __bytes: Buffer, __flags: int = 0) -> Awaitable[int]:
 
     @overload
     async def sendto(
-        self, __data: Buffer, __address: tuple[Any, ...] | str | Buffer
+        self, __data: Buffer, __address: tuple[object, ...] | str | Buffer
     ) -> int:
         ...
 
     @overload
     async def sendto(
-        self, __data: Buffer, __flags: int, __address: tuple[Any, ...] | str | Buffer
+        self, __data: Buffer, __flags: int, __address: tuple[object, ...] | str | Buffer
     ) -> int:
         ...
 
@@ -1184,8 +1184,12 @@ async def sendto(self, *args: Any) -> int:
         # and kwargs are not accepted
         args_list = list(args)
         args_list[-1] = await self._resolve_address_nocp(args[-1], local=False)
+        # args_list is Any, which isn't the signature of sendto().
+        # We don't care about invalid types, sendto() will do the checking.
         return await self._nonblocking_helper(
-            _core.wait_writable, _stdlib_socket.socket.sendto, *args_list
+            _core.wait_writable,
+            _stdlib_socket.socket.sendto,  # type: ignore[arg-type]
+            *args_list,
         )
 
     ################################################################
diff --git a/trio/_ssl.py b/trio/_ssl.py
index 21c4deabb3..81c98a2d3d 100644
--- a/trio/_ssl.py
+++ b/trio/_ssl.py
@@ -356,7 +356,7 @@ def __init__(
             self._incoming,
             self._outgoing,
             server_side=server_side,
-            server_hostname=server_hostname,  # type: ignore[arg-type]  # Typeshed bug, does accept bytes as well (typeshed#10590)
+            server_hostname=server_hostname,
         )
         # Tracks whether we've already done the initial handshake
         self._handshook = _Once(self._do_handshake)
diff --git a/trio/_tests/test_exports.py b/trio/_tests/test_exports.py
index e756e8ad69..4838579fc3 100644
--- a/trio/_tests/test_exports.py
+++ b/trio/_tests/test_exports.py
@@ -364,6 +364,10 @@ def lookup_symbol(symbol):
             "__setstate__",
             "__slots__",
             "__weakref__",
+            # ignore errors about dunders inherited from stdlib that tools might
+            # not see
+            "__copy__",
+            "__deepcopy__",
         }
 
         # pypy seems to have some additional dunders that differ
diff --git a/trio/_tests/tools/test_gen_exports.py b/trio/_tests/tools/test_gen_exports.py
index b4e23916a0..ad337cbe20 100644
--- a/trio/_tests/tools/test_gen_exports.py
+++ b/trio/_tests/tools/test_gen_exports.py
@@ -24,7 +24,7 @@
 )
 
 SOURCE = '''from _run import _public
-from somewhere import Thing
+from collections import Counter
 
 class Test:
     @_public
@@ -34,7 +34,7 @@ def public_func(self):
     @ignore_this
     @_public
     @another_decorator
-    async def public_async_func(self) -> Thing:
+    async def public_async_func(self) -> Counter:
         pass  # no doc string
 
     def not_public(self):
@@ -45,18 +45,18 @@ async def not_public_async(self):
 '''
 
 IMPORT_1 = """\
-from somewhere import Thing
+from collections import Counter
 """
 
 IMPORT_2 = """\
-from somewhere import Thing
+from collections import Counter
 import os
 """
 
 IMPORT_3 = """\
 from typing import TYPE_CHECKING
 if TYPE_CHECKING:
-    from somewhere import Thing
+    from collections import Counter
 """
 
 
@@ -90,7 +90,7 @@ def test_create_pass_through_args():
 
 
 @skip_lints
-@pytest.mark.parametrize("imports", ["", IMPORT_1, IMPORT_2, IMPORT_3])
+@pytest.mark.parametrize("imports", [IMPORT_1, IMPORT_2, IMPORT_3])
 def test_process(tmp_path, imports):
     try:
         import black  # noqa: F401
@@ -141,7 +141,7 @@ def test_run_black(tmp_path) -> None:
 
 @skip_lints
 def test_run_ruff(tmp_path) -> None:
-    """Test that processing properly fails if black does."""
+    """Test that processing properly fails if ruff does."""
     try:
         import ruff  # noqa: F401
     except ImportError as error:  # pragma: no cover
diff --git a/trio/_threads.py b/trio/_threads.py
index 7649587751..cea1b24fa4 100644
--- a/trio/_threads.py
+++ b/trio/_threads.py
@@ -153,7 +153,9 @@ def unprotected_fn(self) -> RetT:
         return ret
 
     def run_sync(self) -> None:
-        result = outcome.capture(self.context.run, self.unprotected_fn)
+        # Two paramspecs + overload is a bit too hard for mypy to handle. Tell it what to infer.
+        runner: Callable[[Callable[[], RetT]], RetT] = self.context.run
+        result = outcome.capture(runner, self.unprotected_fn)
         self.queue.put_nowait(result)
 
     def run_in_host_task(self, token: TrioToken) -> None:
@@ -285,7 +287,7 @@ def do_release_then_return_result() -> RetT:
             # replace the regular return value, and if the regular return was
             # already an exception then we want them to chain.
             try:
-                return result.unwrap()  # type: ignore[no-any-return]  # Until outcome is typed
+                return result.unwrap()
             finally:
                 limiter.release_on_behalf_of(placeholder)
 
@@ -365,7 +367,7 @@ def abort(raise_cancel: RaiseCancelT) -> trio.lowlevel.Abort:
             object
         ] = await trio.lowlevel.wait_task_rescheduled(abort)
         if isinstance(msg_from_thread, outcome.Outcome):
-            return msg_from_thread.unwrap()  # type: ignore[no-any-return]
+            return msg_from_thread.unwrap()
         elif isinstance(msg_from_thread, Run):
             await msg_from_thread.run()
         elif isinstance(msg_from_thread, RunSync):
@@ -496,7 +498,7 @@ def from_thread_run(
     else:
         message_to_trio.run_in_host_task(trio_token)
 
-    return message_to_trio.queue.get().unwrap()  # type: ignore[no-any-return]
+    return message_to_trio.queue.get().unwrap()
 
 
 def from_thread_run_sync(
@@ -544,4 +546,4 @@ def from_thread_run_sync(
     else:
         message_to_trio.run_in_host_task(trio_token)
 
-    return message_to_trio.queue.get().unwrap()  # type: ignore[no-any-return]
+    return message_to_trio.queue.get().unwrap()
diff --git a/trio/_tools/gen_exports.py b/trio/_tools/gen_exports.py
index 153070bfc9..8ed99c9327 100755
--- a/trio/_tools/gen_exports.py
+++ b/trio/_tools/gen_exports.py
@@ -154,7 +154,8 @@ def run_ruff(file: File, source: str) -> tuple[bool, str]:
             sys.executable,
             "-m",
             "ruff",
-            "--fix-only",
+            "check",
+            "--fix",
             "--output-format=text",
             "--stdin-filename",
             file.path,
@@ -165,7 +166,7 @@ def run_ruff(file: File, source: str) -> tuple[bool, str]:
         encoding="utf8",
     )
 
-    if result.returncode != 0 or result.stderr:
+    if result.returncode != 0:
         return False, f"Failed to run ruff!\n{result.stderr}"
     return True, result.stdout