diff --git a/.github/workflows/test.yaml b/.github/workflows/test.yaml
index 22080c95b3..09092d2e58 100644
--- a/.github/workflows/test.yaml
+++ b/.github/workflows/test.yaml
@@ -3,7 +3,7 @@ name: test
 on:
   push: # any branch
   pull_request:
-    branches: [master]
+    branches: [main]
 
 env:
   FORCE_COLOR: 1
@@ -14,41 +14,35 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        python-version: ["3.8", "3.9", "3.10", "3.11", "3.12", "3.13"]
+        python-version:
+          ["3.10", "3.11", "3.12", "3.13", "3.14", "3.14t"]
 
     steps:
-      - uses: actions/checkout@v4
-      - uses: astral-sh/setup-uv@v5
+      - uses: actions/checkout@v6.0.2
+      - uses: astral-sh/setup-uv@v7
         with:
           python-version: ${{ matrix.python-version }}
       - name: Code formatting
-        if: ${{ matrix.python-version == '3.13' }}
+        if: ${{ matrix.python-version == '3.14' }}
         run: |
-          uvx ruff check .
-          uvx ruff format --check .
+          uv run ruff check .
+          uv run ruff format --check .
       - name: Typos
-        if: ${{ matrix.python-version == '3.13' }}
+        if: ${{ matrix.python-version == '3.14' }}
         run: |
-          uvx typos .
+          uv run typos .
       - name: Unit test
         run: |
-          uvx --with . --with pytest coverage run -m pytest tests/
+          uv run coverage run -m pytest tests/
       - name: Type Checking
-        if: ${{ matrix.python-version != '3.8' }}
         run: |
-          uvx --with . --with asyncssh mypy --strict src/ --platform win32
-          uvx --with . --with asyncssh mypy --strict src/ --platform linux
-          uvx --with . --with asyncssh mypy --strict src/ --platform darwin
-      - name: Validate README.md
-        if: ${{ matrix.python-version == '3.13' }}
-        # Ensure that the README renders correctly (required for uploading to PyPI).
-        run: |
-          uv pip install readme_renderer
-          python -m readme_renderer README.rst > /dev/null
+          uv run mypy --strict src/ --platform win32
+          uv run mypy --strict src/ --platform linux
+          uv run mypy --strict src/ --platform darwin
       - name: Run codecov
         run: |
-          uvx codecov
+          uv run codecov
       - name: Upload coverage to Codecov
-        uses: codecov/codecov-action@v4
+        uses: codecov/codecov-action@v5
         env:
           CODECOV_TOKEN: ${{ secrets.CODECOV_TOKEN }}
diff --git a/.gitignore b/.gitignore
index 337ddba0f5..8bf050dc42 100644
--- a/.gitignore
+++ b/.gitignore
@@ -30,10 +30,14 @@ pip-log.txt
 .tox
 nosetests.xml
 .pytest_cache
+coverage.xml
 
 # Translations
 *.mo
 
+# Makefile - for those who like that workflow
+Makefile
+
 # Mr Developer
 .mr.developer.cfg
 .project
@@ -45,6 +49,9 @@ docs/_build
 # pycharm metadata
 .idea
 
+# uv
+uv.lock
+
 # vscode metadata
 .vscode
 
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
new file mode 100644
index 0000000000..ab2291c8be
--- /dev/null
+++ b/.pre-commit-config.yaml
@@ -0,0 +1,30 @@
+repos:
+  - repo: https://github.com/pre-commit/pre-commit-hooks
+    rev: "v6.0.0"
+    hooks:
+      - id: check-case-conflict
+      - id: check-executables-have-shebangs
+      - id: check-merge-conflict
+      - id: check-toml
+      - id: detect-private-key
+      - id: end-of-file-fixer
+      - id: fix-byte-order-marker
+      - id: mixed-line-ending
+      - id: trailing-whitespace
+
+  - repo: https://github.com/astral-sh/ruff-pre-commit
+    rev: "v0.15.6"
+    hooks:
+      - id: ruff-format
+        args: [--config=pyproject.toml]
+      - id: ruff-check
+        args: [--config=pyproject.toml, --fix, --exit-non-zero-on-fix]
+
+  - repo: https://github.com/crate-ci/typos
+    rev: v1.44.0
+    hooks:
+      - id: typos
+        exclude: |
+          (?x)^(
+            tests/.*
+          )$
diff --git a/PROJECTS.rst b/PROJECTS.rst
index 5f862b3d4f..fb3a966739 100644
--- a/PROJECTS.rst
+++ b/PROJECTS.rst
@@ -37,7 +37,7 @@ Shells:
 - `athenacli <https://github.com/dbcli/athenacli>`_: A CLI for AWS Athena.
 - `vulcano <https://github.com/dgarana/vulcano>`_: A framework for creating command-line applications that also runs in REPL mode.
 - `kafka-shell <https://github.com/devshawn/kafka-shell>`_: A supercharged shell for Apache Kafka.
-- `starterTree <https://github.com/thomas10-10/starterTree>`_: A command launcher organized in a tree structure with fuzzy autocompletion 
+- `starterTree <https://github.com/thomas10-10/starterTree>`_: A command launcher organized in a tree structure with fuzzy autocompletion
 - `git-delete-merged-branches <https://github.com/hartwork/git-delete-merged-branches>`_: Command-line tool to delete merged Git branches
 - `radian <https://github.com/randy3k/radian>`_: A 21 century R console
 
diff --git a/README.rst b/README.rst
index 7d02a53bb0..686fa254c9 100644
--- a/README.rst
+++ b/README.rst
@@ -141,4 +141,3 @@ Special thanks to
 
 .. |Codecov| image:: https://codecov.io/gh/prompt-toolkit/python-prompt-toolkit/branch/master/graphs/badge.svg?style=flat
     :target: https://codecov.io/gh/prompt-toolkit/python-prompt-toolkit/
-
diff --git a/docs/index.rst b/docs/index.rst
index 5f0e8a3d2b..802abf6be2 100644
--- a/docs/index.rst
+++ b/docs/index.rst
@@ -42,7 +42,7 @@ Have a look at :ref:`the gallery <gallery>` to get an idea of what is possible.
 Getting started
 ---------------
 
-Go to :ref:`getting started <getting_started>` and build your first prompt. 
+Go to :ref:`getting started <getting_started>` and build your first prompt.
 Issues are tracked `on the Github project
 <https://github.com/prompt-toolkit/python-prompt-toolkit>`_.
 
diff --git a/docs/pages/advanced_topics/styling.rst b/docs/pages/advanced_topics/styling.rst
index 55cf6ee0ea..846f3aff87 100644
--- a/docs/pages/advanced_topics/styling.rst
+++ b/docs/pages/advanced_topics/styling.rst
@@ -185,7 +185,7 @@ The style is determined as follows:
 
 - Then we go through this style from left to right, starting from the default
   style. Inline styling is applied directly.
-  
+
   If we come across a class name, then we generate all combinations of the
   class names that we collected so far (this one and all class names to the
   left), and for each combination which includes the new class name, we look
diff --git a/docs/pages/advanced_topics/unit_testing.rst b/docs/pages/advanced_topics/unit_testing.rst
index 02ca82d46f..b3ccdc4362 100644
--- a/docs/pages/advanced_topics/unit_testing.rst
+++ b/docs/pages/advanced_topics/unit_testing.rst
@@ -36,7 +36,7 @@ these.
     structures (like text buffers) change over time.
 
 So we programmatically feed some input to the input pipe, have the key
-bindings process the input and then test what comes out of it. 
+bindings process the input and then test what comes out of it.
 
 In the following example we use a
 :class:`~prompt_toolkit.shortcuts.PromptSession`, but the same works for any
diff --git a/docs/pages/asking_for_input.rst b/docs/pages/asking_for_input.rst
index f960aeb61d..83da97aea2 100644
--- a/docs/pages/asking_for_input.rst
+++ b/docs/pages/asking_for_input.rst
@@ -178,7 +178,7 @@ Suppose we'd like to use a Pygments style, for instance
     tango_style = style_from_pygments_cls(TangoStyle)
 
     text = prompt(
-        "Enter HTML: ", 
+        "Enter HTML: ",
         lexer=PygmentsLexer(HtmlLexer),
         style=tango_style
     )
diff --git a/docs/pages/dialogs.rst b/docs/pages/dialogs.rst
index e171995181..86d3fdddb3 100644
--- a/docs/pages/dialogs.rst
+++ b/docs/pages/dialogs.rst
@@ -98,14 +98,14 @@ each providing the return value (first element) and the displayed value (second
 
     from prompt_toolkit.shortcuts import radiolist_dialog
 
-    result = radiolist_dialog( 
-        title="RadioList dialog", 
-        text="Which breakfast would you like ?", 
-        values=[ 
-            ("breakfast1", "Eggs and beacon"), 
-            ("breakfast2", "French breakfast"), 
-            ("breakfast3", "Equestrian breakfast") 
-        ] 
+    result = radiolist_dialog(
+        title="RadioList dialog",
+        text="Which breakfast would you like ?",
+        values=[
+            ("breakfast1", "Eggs and beacon"),
+            ("breakfast2", "French breakfast"),
+            ("breakfast3", "Equestrian breakfast")
+        ]
     ).run()
 
 
@@ -118,15 +118,15 @@ The :func:`~prompt_toolkit.shortcuts.checkboxlist_dialog` has the same usage and
 
     from prompt_toolkit.shortcuts import checkboxlist_dialog
 
-    results_array = checkboxlist_dialog( 
-        title="CheckboxList dialog", 
+    results_array = checkboxlist_dialog(
+        title="CheckboxList dialog",
         text="What would you like in your breakfast ?",
-        values=[ 
+        values=[
             ("eggs", "Eggs"),
             ("bacon", "Bacon"),
             ("croissants", "20 Croissants"),
             ("daily", "The breakfast of the day")
-        ] 
+        ]
     ).run()
 
 
diff --git a/docs/pages/full_screen_apps.rst b/docs/pages/full_screen_apps.rst
index 9123c20cfa..2e24a268be 100644
--- a/docs/pages/full_screen_apps.rst
+++ b/docs/pages/full_screen_apps.rst
@@ -84,7 +84,7 @@ a key press), it will send that to the the appropriate handler, like for
 instance, a key binding.
 
 When :func:`~prompt_toolkit.application.Application.run()` is called, the event
-loop will run until the application is done. An application will quit when 
+loop will run until the application is done. An application will quit when
 :func:`~prompt_toolkit.application.Application.exit()` is called.
 
 
@@ -311,7 +311,7 @@ the key handler:
         Pressing Ctrl-Q will exit the user interface.
 
         Setting a return value means: quit the event loop that drives the user
-        interface and return this value from the `Application.run()` call. 
+        interface and return this value from the `Application.run()` call.
         """
         event.app.exit()
 
diff --git a/docs/pages/progress_bars.rst b/docs/pages/progress_bars.rst
index 5248f98436..99ee693b90 100644
--- a/docs/pages/progress_bars.rst
+++ b/docs/pages/progress_bars.rst
@@ -4,7 +4,7 @@ Progress bars
 =============
 
 Prompt_toolkit ships with a high level API for displaying progress bars,
-inspired by `tqdm <https://github.com/tqdm/tqdm>`_ 
+inspired by `tqdm <https://github.com/tqdm/tqdm>`_
 
 .. warning::
 
diff --git a/docs/pages/upgrading/2.0.rst b/docs/pages/upgrading/2.0.rst
index 60670578fc..e16d2f6277 100644
--- a/docs/pages/upgrading/2.0.rst
+++ b/docs/pages/upgrading/2.0.rst
@@ -218,4 +218,3 @@ rather then inheriting from `Filter`. For instance:
     @Condition
     def my_filter();
         return True  # Or False
-
diff --git a/examples/tutorial/README.md b/examples/tutorial/README.md
old mode 100755
new mode 100644
index 3aa5f70d69..37b0138011
--- a/examples/tutorial/README.md
+++ b/examples/tutorial/README.md
@@ -1 +1 @@
-See http://python-prompt-toolkit.readthedocs.io/en/stable/pages/tutorials/repl.html
+See http://python-prompt-toolkit.readthedocs.io/en/stable/pages/tutorials/repl.html
diff --git a/pyproject.toml b/pyproject.toml
index 1d4e169b0e..cd89b96d6c 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,7 +1,7 @@
 [project]
 name = "prompt_toolkit"
-version = "3.0.52"  # Also update in `docs/conf.py`.
-description="Library for building powerful interactive command lines in Python"
+version = "3.0.52" # Also update in `docs/conf.py`.
+description = "Library for building powerful interactive command lines in Python"
 readme = "README.rst"
 authors = [{ name = "Jonathan Slenders" }]
 classifiers = [
@@ -10,19 +10,40 @@ classifiers = [
     "License :: OSI Approved :: BSD License",
     "Operating System :: OS Independent",
     "Programming Language :: Python :: 3",
-    "Programming Language :: Python :: 3.8",
-    "Programming Language :: Python :: 3.9",
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
     "Programming Language :: Python :: 3.13",
+    "Programming Language :: Python :: 3.14",
     "Programming Language :: Python :: 3 :: Only",
+    "Programming Language :: Python :: Free Threading :: 3 - Stable",
     "Programming Language :: Python",
     "Topic :: Software Development",
 ]
-requires-python = ">=3.8"
-dependencies = [
-    "wcwidth>=0.1.4",
+requires-python = ">=3.10"
+dependencies = ["wcwidth>=0.1.4"]
+
+[dependency-groups]
+build = ["build>=1", "setuptools>=68"]
+docs = [
+    "sphinx>=8,<9",
+    "wcwidth",
+    "pyperclip",
+    "sphinx_copybutton>=0.5.2,<1.0.0",
+    "sphinx-nefertiti>=0.8.8",
+]
+dev = [
+    "asyncssh",
+    "codecov>=2.1",
+    "coverage>=7.11",
+    "ipython>=8.23",
+    "mypy>=1.13",
+    "prek>=0.3.5",
+    "pytest>=8.1.1",
+    "pytest-cov>=5",
+    "pytest-mock>=3.14.1",
+    "ruff>=0.14.10",
+    "typos",
 ]
 
 [project.urls]
@@ -30,38 +51,52 @@ Homepage = "https://github.com/prompt-toolkit/python-prompt-toolkit"
 Documentation = "https://python-prompt-toolkit.readthedocs.io/en/stable/"
 
 [tool.ruff]
-target-version = "py37"
+target-version = "py310"
 lint.select = [
-    "E",  # pycodestyle errors
-    "W",  # pycodestyle warnings
-    "F",  # pyflakes
-    "C",  # flake8-comprehensions
-    "T",  # Print.
-    "I",  # isort
+    "E", # pycodestyle errors
+    "W", # pycodestyle warnings
+    "F", # pyflakes
+    "C", # flake8-comprehensions
+    "T", # Print.
+    "I", # isort
     # "B",  # flake8-bugbear
-    "UP",  # pyupgrade
-    "RUF100",  # unused-noqa
-    "Q", # quotes
+    "UP",     # pyupgrade
+    "RUF100", # unused-noqa
+    "Q",      # quotes
 ]
 lint.ignore = [
-    "E501",  # Line too long, handled by black
-    "C901",  # Too complex
-    "E731",  # Assign lambda.
+    "E501", # Line too long, handled by black
+    "C901", # Too complex
+    "E731", # Assign lambda.
     "E402", # Module level import not at the top.
     "E741", # Ambiguous variable name.
 ]
 
 [tool.ruff.lint.per-file-ignores]
-"examples/*" = ["UP031", "T201"]  # Print allowed in examples.
-"src/prompt_toolkit/application/application.py" = ["T100", "T201", "F821"]  # pdb and print allowed.
-"src/prompt_toolkit/contrib/telnet/server.py" = ["T201"]  # Print allowed.
-"src/prompt_toolkit/key_binding/bindings/named_commands.py" = ["T201"]  # Print allowed.
-"src/prompt_toolkit/shortcuts/progress_bar/base.py" = ["T201"]  # Print allowed.
-"tools/*" = ["T201"]  # Print allowed.
-"src/prompt_toolkit/filters/__init__.py" = ["F403", "F405"]  # Possibly undefined due to star import.
-"src/prompt_toolkit/filters/cli.py" = ["F403", "F405"]  # Possibly undefined due to star import.
-"src/prompt_toolkit/shortcuts/progress_bar/formatters.py" = ["UP031"] # %-style formatting.
-"src/*" = ["UP031", "UP032"]  # f-strings instead of format calls.
+"examples/*" = ["UP031", "T201"] # Print allowed in examples.
+"src/prompt_toolkit/application/application.py" = [
+    "T100",
+    "T201",
+    "F821",
+] # pdb and print allowed.
+"src/prompt_toolkit/contrib/telnet/server.py" = ["T201"] # Print allowed.
+"src/prompt_toolkit/key_binding/bindings/named_commands.py" = [
+    "T201",
+] # Print allowed.
+"src/prompt_toolkit/shortcuts/progress_bar/base.py" = ["T201"] # Print allowed.
+"tools/*" = ["T201"] # Print allowed.
+"src/prompt_toolkit/filters/__init__.py" = [
+    "F403",
+    "F405",
+] # Possibly undefined due to star import.
+"src/prompt_toolkit/filters/cli.py" = [
+    "F403",
+    "F405",
+] # Possibly undefined due to star import.
+"src/prompt_toolkit/shortcuts/progress_bar/formatters.py" = [
+    "UP031",
+] # %-style formatting.
+"src/*" = ["UP031", "UP032"] # f-strings instead of format calls.
 
 [tool.ruff.lint.isort]
 known-first-party = ["prompt_toolkit"]
@@ -79,7 +114,7 @@ extend-ignore-re = [
     "ret",
     "rouble",
     "x1b\\[4m",
-    "Vertica",  # Database.
+    "Vertica",    # Database.
     # Deliberate spelling mistakes in autocorrection.py
     "wolrd",
     "impotr",
@@ -88,7 +123,7 @@ extend-ignore-re = [
     "varius",
 ]
 
-locale = 'en-us'  # US English.
+locale = 'en-us' # US English.
 
 [tool.typos.files]
 extend-exclude = [
@@ -108,6 +143,16 @@ disallow_subclassing_any = true
 disallow_untyped_calls = true
 disallow_untyped_decorators = true
 disallow_untyped_defs = true
+exclude = [
+    "^.git/",
+    "^.venv/",
+    "^build/",    # .build directory
+    "^docs/",     # docs directory
+    "^dist/",
+    "^examples/", # examples directory
+    "^tests/",    # tests directory
+]
+files = ['.']
 ignore_missing_imports = true
 no_implicit_optional = true
 no_implicit_reexport = true
@@ -121,3 +166,6 @@ warn_unused_ignores = true
 [build-system]
 requires = ["setuptools>=68"]
 build-backend = "setuptools.build_meta"
+
+[tool.uv]
+default-groups = ["build", "dev"]
diff --git a/src/prompt_toolkit/application/application.py b/src/prompt_toolkit/application/application.py
index f27ada1a00..8d7402f6cb 100644
--- a/src/prompt_toolkit/application/application.py
+++ b/src/prompt_toolkit/application/application.py
@@ -16,18 +16,13 @@
     get_running_loop,
     sleep,
 )
+from collections.abc import Callable, Coroutine, Generator, Hashable, Iterable, Iterator
 from contextlib import ExitStack, contextmanager
 from subprocess import Popen
 from traceback import format_tb
 from typing import (
     Any,
-    Callable,
-    Coroutine,
-    Generator,
     Generic,
-    Hashable,
-    Iterable,
-    Iterator,
     TypeVar,
     cast,
     overload,
@@ -731,9 +726,11 @@ def flush_input() -> None:
                         f.set_exception(EOFError)
 
             # Enter raw mode, attach input and attach WINCH event handler.
-            with self.input.raw_mode(), self.input.attach(
-                read_from_input_in_context
-            ), attach_winch_signal_handler(self._on_resize):
+            with (
+                self.input.raw_mode(),
+                self.input.attach(read_from_input_in_context),
+                attach_winch_signal_handler(self._on_resize),
+            ):
                 # Draw UI.
                 self._request_absolute_cursor_position()
                 self._redraw()
diff --git a/src/prompt_toolkit/application/current.py b/src/prompt_toolkit/application/current.py
index f7032fe72a..2b4681be9f 100644
--- a/src/prompt_toolkit/application/current.py
+++ b/src/prompt_toolkit/application/current.py
@@ -1,8 +1,9 @@
 from __future__ import annotations
 
+from collections.abc import Generator
 from contextlib import contextmanager
 from contextvars import ContextVar
-from typing import TYPE_CHECKING, Any, Generator
+from typing import TYPE_CHECKING, Any
 
 if TYPE_CHECKING:
     from prompt_toolkit.input.base import Input
diff --git a/src/prompt_toolkit/application/dummy.py b/src/prompt_toolkit/application/dummy.py
index 43819e1e71..c134c33fe7 100644
--- a/src/prompt_toolkit/application/dummy.py
+++ b/src/prompt_toolkit/application/dummy.py
@@ -1,6 +1,6 @@
 from __future__ import annotations
 
-from typing import Callable
+from collections.abc import Callable
 
 from prompt_toolkit.eventloop import InputHook
 from prompt_toolkit.formatted_text import AnyFormattedText
diff --git a/src/prompt_toolkit/application/run_in_terminal.py b/src/prompt_toolkit/application/run_in_terminal.py
index 1f5e18ea78..24bae836be 100644
--- a/src/prompt_toolkit/application/run_in_terminal.py
+++ b/src/prompt_toolkit/application/run_in_terminal.py
@@ -5,8 +5,9 @@
 from __future__ import annotations
 
 from asyncio import Future, ensure_future
+from collections.abc import AsyncGenerator, Awaitable, Callable
 from contextlib import asynccontextmanager
-from typing import AsyncGenerator, Awaitable, Callable, TypeVar
+from typing import TypeVar
 
 from prompt_toolkit.eventloop import run_in_executor_with_context
 
diff --git a/src/prompt_toolkit/auto_suggest.py b/src/prompt_toolkit/auto_suggest.py
index 73213ba690..198c5cadd6 100644
--- a/src/prompt_toolkit/auto_suggest.py
+++ b/src/prompt_toolkit/auto_suggest.py
@@ -15,7 +15,8 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import TYPE_CHECKING, Callable
+from collections.abc import Callable
+from typing import TYPE_CHECKING
 
 from prompt_toolkit.eventloop import run_in_executor_with_context
 
diff --git a/src/prompt_toolkit/buffer.py b/src/prompt_toolkit/buffer.py
index f5847d4ab9..ae1198f114 100644
--- a/src/prompt_toolkit/buffer.py
+++ b/src/prompt_toolkit/buffer.py
@@ -14,9 +14,10 @@
 import subprocess
 import tempfile
 from collections import deque
+from collections.abc import Callable, Coroutine, Iterable
 from enum import Enum
 from functools import wraps
-from typing import Any, Callable, Coroutine, Iterable, TypeVar, cast
+from typing import Any, TypeVar, cast
 
 from .application.current import get_app
 from .application.run_in_terminal import run_in_terminal
diff --git a/src/prompt_toolkit/cache.py b/src/prompt_toolkit/cache.py
index 01dd1f79d6..5ca170a7c4 100644
--- a/src/prompt_toolkit/cache.py
+++ b/src/prompt_toolkit/cache.py
@@ -1,8 +1,9 @@
 from __future__ import annotations
 
 from collections import deque
+from collections.abc import Callable, Hashable
 from functools import wraps
-from typing import Any, Callable, Dict, Generic, Hashable, Tuple, TypeVar, cast
+from typing import Any, Generic, TypeVar, cast
 
 __all__ = [
     "SimpleCache",
@@ -58,11 +59,11 @@ def clear(self) -> None:
         self._keys = deque()
 
 
-_K = TypeVar("_K", bound=Tuple[Hashable, ...])
+_K = TypeVar("_K", bound=tuple[Hashable, ...])
 _V = TypeVar("_V")
 
 
-class FastDictCache(Dict[_K, _V]):
+class FastDictCache(dict[_K, _V]):
     """
     Fast, lightweight cache which keeps at most `size` items.
     It will discard the oldest items in the cache first.
diff --git a/src/prompt_toolkit/clipboard/base.py b/src/prompt_toolkit/clipboard/base.py
index 28cfdcd766..be1a606e36 100644
--- a/src/prompt_toolkit/clipboard/base.py
+++ b/src/prompt_toolkit/clipboard/base.py
@@ -5,7 +5,7 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import Callable
+from collections.abc import Callable
 
 from prompt_toolkit.selection import SelectionType
 
diff --git a/src/prompt_toolkit/completion/base.py b/src/prompt_toolkit/completion/base.py
index 3846ef7562..6e73290ec0 100644
--- a/src/prompt_toolkit/completion/base.py
+++ b/src/prompt_toolkit/completion/base.py
@@ -3,7 +3,7 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import AsyncGenerator, Callable, Iterable, Sequence
+from collections.abc import AsyncGenerator, Callable, Iterable, Sequence
 
 from prompt_toolkit.document import Document
 from prompt_toolkit.eventloop import aclosing, generator_to_async_generator
diff --git a/src/prompt_toolkit/completion/deduplicate.py b/src/prompt_toolkit/completion/deduplicate.py
index c3d525669d..0bb82ea064 100644
--- a/src/prompt_toolkit/completion/deduplicate.py
+++ b/src/prompt_toolkit/completion/deduplicate.py
@@ -1,6 +1,6 @@
 from __future__ import annotations
 
-from typing import Iterable
+from collections.abc import Iterable
 
 from prompt_toolkit.document import Document
 
diff --git a/src/prompt_toolkit/completion/filesystem.py b/src/prompt_toolkit/completion/filesystem.py
index 8e7f87e00b..5da254d8e3 100644
--- a/src/prompt_toolkit/completion/filesystem.py
+++ b/src/prompt_toolkit/completion/filesystem.py
@@ -1,7 +1,7 @@
 from __future__ import annotations
 
 import os
-from typing import Callable, Iterable
+from collections.abc import Callable, Iterable
 
 from prompt_toolkit.completion import CompleteEvent, Completer, Completion
 from prompt_toolkit.document import Document
diff --git a/src/prompt_toolkit/completion/fuzzy_completer.py b/src/prompt_toolkit/completion/fuzzy_completer.py
index 82625ab63f..adaa763e11 100644
--- a/src/prompt_toolkit/completion/fuzzy_completer.py
+++ b/src/prompt_toolkit/completion/fuzzy_completer.py
@@ -1,7 +1,8 @@
 from __future__ import annotations
 
 import re
-from typing import Callable, Iterable, NamedTuple, Sequence
+from collections.abc import Callable, Iterable, Sequence
+from typing import NamedTuple
 
 from prompt_toolkit.document import Document
 from prompt_toolkit.filters import FilterOrBool, to_filter
diff --git a/src/prompt_toolkit/completion/nested.py b/src/prompt_toolkit/completion/nested.py
index b72b69ee21..5c18114efa 100644
--- a/src/prompt_toolkit/completion/nested.py
+++ b/src/prompt_toolkit/completion/nested.py
@@ -4,7 +4,8 @@
 
 from __future__ import annotations
 
-from typing import Any, Iterable, Mapping, Set, Union
+from collections.abc import Iterable, Mapping
+from typing import Any
 
 from prompt_toolkit.completion import CompleteEvent, Completer, Completion
 from prompt_toolkit.completion.word_completer import WordCompleter
@@ -13,7 +14,7 @@
 __all__ = ["NestedCompleter"]
 
 # NestedDict = Mapping[str, Union['NestedDict', Set[str], None, Completer]]
-NestedDict = Mapping[str, Union[Any, Set[str], None, Completer]]
+NestedDict = Mapping[str, Any | set[str] | None | Completer]
 
 
 class NestedCompleter(Completer):
diff --git a/src/prompt_toolkit/completion/word_completer.py b/src/prompt_toolkit/completion/word_completer.py
index 2e124056ba..563fdadcb6 100644
--- a/src/prompt_toolkit/completion/word_completer.py
+++ b/src/prompt_toolkit/completion/word_completer.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
-from typing import Callable, Iterable, Mapping, Pattern, Sequence
+from collections.abc import Callable, Iterable, Mapping, Sequence
+from re import Pattern
 
 from prompt_toolkit.completion import CompleteEvent, Completer, Completion
 from prompt_toolkit.document import Document
diff --git a/src/prompt_toolkit/contrib/regular_languages/compiler.py b/src/prompt_toolkit/contrib/regular_languages/compiler.py
index 4009d54f2d..9416291096 100644
--- a/src/prompt_toolkit/contrib/regular_languages/compiler.py
+++ b/src/prompt_toolkit/contrib/regular_languages/compiler.py
@@ -42,8 +42,10 @@
 from __future__ import annotations
 
 import re
-from typing import Callable, Dict, Iterable, Iterator, Pattern, TypeVar, overload
-from typing import Match as RegexMatch
+from collections.abc import Callable, Iterable, Iterator
+from re import Match as RegexMatch
+from re import Pattern
+from typing import TypeVar, overload
 
 from .regex_parser import (
     AnyNode,
@@ -65,7 +67,7 @@
 # expression has been matched.)
 _INVALID_TRAILING_INPUT = "invalid_trailing"
 
-EscapeFuncDict = Dict[str, Callable[[str], str]]
+EscapeFuncDict = dict[str, Callable[[str], str]]
 
 
 class _CompiledGrammar:
diff --git a/src/prompt_toolkit/contrib/regular_languages/completion.py b/src/prompt_toolkit/contrib/regular_languages/completion.py
index 19ebaad938..2181a42ccf 100644
--- a/src/prompt_toolkit/contrib/regular_languages/completion.py
+++ b/src/prompt_toolkit/contrib/regular_languages/completion.py
@@ -4,7 +4,7 @@
 
 from __future__ import annotations
 
-from typing import Iterable
+from collections.abc import Iterable
 
 from prompt_toolkit.completion import CompleteEvent, Completer, Completion
 from prompt_toolkit.document import Document
diff --git a/src/prompt_toolkit/contrib/regular_languages/lexer.py b/src/prompt_toolkit/contrib/regular_languages/lexer.py
index c5434cfdee..774df2869a 100644
--- a/src/prompt_toolkit/contrib/regular_languages/lexer.py
+++ b/src/prompt_toolkit/contrib/regular_languages/lexer.py
@@ -5,7 +5,7 @@
 
 from __future__ import annotations
 
-from typing import Callable
+from collections.abc import Callable
 
 from prompt_toolkit.document import Document
 from prompt_toolkit.formatted_text.base import StyleAndTextTuples
diff --git a/src/prompt_toolkit/contrib/ssh/server.py b/src/prompt_toolkit/contrib/ssh/server.py
index 4badc6cad0..7ce70f7812 100644
--- a/src/prompt_toolkit/contrib/ssh/server.py
+++ b/src/prompt_toolkit/contrib/ssh/server.py
@@ -7,7 +7,8 @@
 import asyncio
 import traceback
 from asyncio import get_running_loop
-from typing import Any, Callable, Coroutine, TextIO, cast
+from collections.abc import Callable, Coroutine
+from typing import Any, TextIO, cast
 
 import asyncssh
 
diff --git a/src/prompt_toolkit/contrib/telnet/protocol.py b/src/prompt_toolkit/contrib/telnet/protocol.py
index 58286e23e7..e56edd1ca3 100644
--- a/src/prompt_toolkit/contrib/telnet/protocol.py
+++ b/src/prompt_toolkit/contrib/telnet/protocol.py
@@ -8,7 +8,7 @@
 from __future__ import annotations
 
 import struct
-from typing import Callable, Generator
+from collections.abc import Callable, Generator
 
 from .log import logger
 
diff --git a/src/prompt_toolkit/contrib/telnet/server.py b/src/prompt_toolkit/contrib/telnet/server.py
index bc2ad53064..5347a3f98a 100644
--- a/src/prompt_toolkit/contrib/telnet/server.py
+++ b/src/prompt_toolkit/contrib/telnet/server.py
@@ -8,7 +8,8 @@
 import contextvars
 import socket
 from asyncio import get_running_loop
-from typing import Any, Callable, Coroutine, TextIO, cast
+from collections.abc import Callable, Coroutine
+from typing import Any, TextIO, cast
 
 from prompt_toolkit.application.current import create_app_session, get_app
 from prompt_toolkit.application.run_in_terminal import run_in_terminal
diff --git a/src/prompt_toolkit/cursor_shapes.py b/src/prompt_toolkit/cursor_shapes.py
index 01d10926a2..04a42ccf54 100644
--- a/src/prompt_toolkit/cursor_shapes.py
+++ b/src/prompt_toolkit/cursor_shapes.py
@@ -1,8 +1,9 @@
 from __future__ import annotations
 
 from abc import ABC, abstractmethod
+from collections.abc import Callable
 from enum import Enum
-from typing import TYPE_CHECKING, Any, Callable, Union
+from typing import TYPE_CHECKING, Any
 
 from prompt_toolkit.enums import EditingMode
 from prompt_toolkit.key_binding.vi_state import InputMode
@@ -47,7 +48,7 @@ def get_cursor_shape(self, application: Application[Any]) -> CursorShape:
         """
 
 
-AnyCursorShapeConfig = Union[CursorShape, CursorShapeConfig, None]
+AnyCursorShapeConfig = CursorShape | CursorShapeConfig | None
 
 
 class SimpleCursorShapeConfig(CursorShapeConfig):
diff --git a/src/prompt_toolkit/document.py b/src/prompt_toolkit/document.py
index d2657a50ef..003a7852e4 100644
--- a/src/prompt_toolkit/document.py
+++ b/src/prompt_toolkit/document.py
@@ -8,7 +8,9 @@
 import re
 import string
 import weakref
-from typing import Callable, Dict, Iterable, List, NoReturn, Pattern, cast
+from collections.abc import Callable, Iterable
+from re import Pattern
+from typing import NoReturn, cast
 
 from .clipboard import ClipboardData
 from .filters import vi_mode
@@ -40,12 +42,12 @@
 # `Document` is constructed with the same text, it should have the same
 # `_DocumentCache`.)
 _text_to_document_cache: dict[str, _DocumentCache] = cast(
-    Dict[str, "_DocumentCache"],
+    dict[str, "_DocumentCache"],
     weakref.WeakValueDictionary(),  # Maps document.text to DocumentCache instance.
 )
 
 
-class _ImmutableLineList(List[str]):
+class _ImmutableLineList(list[str]):
     """
     Some protection for our 'lines' list, which is assumed to be immutable in the cache.
     (Useful for detecting obvious bugs.)
diff --git a/src/prompt_toolkit/eventloop/async_generator.py b/src/prompt_toolkit/eventloop/async_generator.py
index 32e5f88247..6b92d06ce9 100644
--- a/src/prompt_toolkit/eventloop/async_generator.py
+++ b/src/prompt_toolkit/eventloop/async_generator.py
@@ -5,9 +5,10 @@
 from __future__ import annotations
 
 from asyncio import get_running_loop
+from collections.abc import AsyncGenerator, Callable, Iterable
 from contextlib import asynccontextmanager
 from queue import Empty, Full, Queue
-from typing import Any, AsyncGenerator, Callable, Iterable, TypeVar
+from typing import Any, TypeVar
 
 from .utils import run_in_executor_with_context
 
diff --git a/src/prompt_toolkit/eventloop/inputhook.py b/src/prompt_toolkit/eventloop/inputhook.py
index 40016e87f6..60c2da4d54 100644
--- a/src/prompt_toolkit/eventloop/inputhook.py
+++ b/src/prompt_toolkit/eventloop/inputhook.py
@@ -32,8 +32,9 @@
 import sys
 import threading
 from asyncio import AbstractEventLoop, get_running_loop
+from collections.abc import Callable, Mapping
 from selectors import BaseSelector, SelectorKey
-from typing import TYPE_CHECKING, Any, Callable, Mapping
+from typing import TYPE_CHECKING, Any
 
 __all__ = [
     "new_eventloop_with_inputhook",
@@ -44,8 +45,9 @@
 ]
 
 if TYPE_CHECKING:
+    from typing import TypeAlias
+
     from _typeshed import FileDescriptorLike
-    from typing_extensions import TypeAlias
 
     _EventMask = int
 
diff --git a/src/prompt_toolkit/eventloop/utils.py b/src/prompt_toolkit/eventloop/utils.py
index 313836137c..69b797a32d 100644
--- a/src/prompt_toolkit/eventloop/utils.py
+++ b/src/prompt_toolkit/eventloop/utils.py
@@ -5,8 +5,9 @@
 import sys
 import time
 from asyncio import get_running_loop
+from collections.abc import Awaitable, Callable
 from types import TracebackType
-from typing import Any, Awaitable, Callable, TypeVar, cast
+from typing import Any, TypeVar, cast
 
 __all__ = [
     "run_in_executor_with_context",
diff --git a/src/prompt_toolkit/filters/base.py b/src/prompt_toolkit/filters/base.py
index cd95424dc3..4a513eccd4 100644
--- a/src/prompt_toolkit/filters/base.py
+++ b/src/prompt_toolkit/filters/base.py
@@ -1,7 +1,7 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import Callable, Iterable, Union
+from collections.abc import Callable, Iterable
 
 __all__ = ["Filter", "Never", "Always", "Condition", "FilterOrBool"]
 
@@ -257,4 +257,4 @@ def __repr__(self) -> str:
 
 
 # Often used as type annotation.
-FilterOrBool = Union[Filter, bool]
+FilterOrBool = Filter | bool
diff --git a/src/prompt_toolkit/formatted_text/ansi.py b/src/prompt_toolkit/formatted_text/ansi.py
index 8cc37a6363..2f355c2b74 100644
--- a/src/prompt_toolkit/formatted_text/ansi.py
+++ b/src/prompt_toolkit/formatted_text/ansi.py
@@ -1,7 +1,7 @@
 from __future__ import annotations
 
+from collections.abc import Generator
 from string import Formatter
-from typing import Generator
 
 from prompt_toolkit.output.vt100 import BG_ANSI_COLORS, FG_ANSI_COLORS
 from prompt_toolkit.output.vt100 import _256_colors as _256_colors_table
diff --git a/src/prompt_toolkit/formatted_text/base.py b/src/prompt_toolkit/formatted_text/base.py
index 75f47d87ac..5866b46acb 100644
--- a/src/prompt_toolkit/formatted_text/base.py
+++ b/src/prompt_toolkit/formatted_text/base.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Callable, Iterable, List, Tuple, Union, cast
+from collections.abc import Callable, Iterable
+from typing import TYPE_CHECKING, Union, cast
 
 from prompt_toolkit.mouse_events import MouseEvent
 
@@ -21,16 +22,17 @@
     "FormattedText",
 ]
 
-OneStyleAndTextTuple = Union[
-    Tuple[str, str], Tuple[str, str, Callable[[MouseEvent], "NotImplementedOrNone"]]
-]
+OneStyleAndTextTuple = (
+    tuple[str, str] | tuple[str, str, Callable[[MouseEvent], "NotImplementedOrNone"]]
+)
+
 
 # List of (style, text) tuples.
-StyleAndTextTuples = List[OneStyleAndTextTuple]
+StyleAndTextTuples = list[OneStyleAndTextTuple]
 
 
 if TYPE_CHECKING:
-    from typing_extensions import TypeGuard
+    from typing import TypeGuard
 
     class MagicFormattedText(Protocol):
         """
@@ -83,8 +85,7 @@ def to_formatted_text(
         result = [("", f"{value}")]
     else:
         raise ValueError(
-            "No formatted text. Expecting a unicode object, "
-            f"HTML, ANSI or a FormattedText instance. Got {value!r}"
+            f"No formatted text. Expecting a unicode object, HTML, ANSI or a FormattedText instance. Got {value!r}"
         )
 
     # Apply extra style.
diff --git a/src/prompt_toolkit/formatted_text/utils.py b/src/prompt_toolkit/formatted_text/utils.py
index a6f78cb4e0..8aede2b55f 100644
--- a/src/prompt_toolkit/formatted_text/utils.py
+++ b/src/prompt_toolkit/formatted_text/utils.py
@@ -7,7 +7,8 @@
 
 from __future__ import annotations
 
-from typing import Iterable, cast
+from collections.abc import Iterable
+from typing import cast
 
 from prompt_toolkit.utils import get_cwidth
 
diff --git a/src/prompt_toolkit/history.py b/src/prompt_toolkit/history.py
index 2d497a0209..764a8d6578 100644
--- a/src/prompt_toolkit/history.py
+++ b/src/prompt_toolkit/history.py
@@ -15,7 +15,8 @@
 import threading
 from abc import ABCMeta, abstractmethod
 from asyncio import get_running_loop
-from typing import AsyncGenerator, Iterable, Sequence, Union
+from collections.abc import AsyncGenerator, Iterable, Sequence
+from typing import Union
 
 __all__ = [
     "History",
diff --git a/src/prompt_toolkit/input/base.py b/src/prompt_toolkit/input/base.py
index 40ffd9df20..eac80ec9b7 100644
--- a/src/prompt_toolkit/input/base.py
+++ b/src/prompt_toolkit/input/base.py
@@ -5,8 +5,8 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from contextlib import contextmanager
-from typing import Callable, ContextManager, Generator
+from collections.abc import Callable, Generator
+from contextlib import AbstractContextManager, contextmanager
 
 from prompt_toolkit.key_binding import KeyPress
 
@@ -62,26 +62,28 @@ def closed(self) -> bool:
         return False
 
     @abstractmethod
-    def raw_mode(self) -> ContextManager[None]:
+    def raw_mode(self) -> AbstractContextManager[None]:
         """
         Context manager that turns the input into raw mode.
         """
 
     @abstractmethod
-    def cooked_mode(self) -> ContextManager[None]:
+    def cooked_mode(self) -> AbstractContextManager[None]:
         """
         Context manager that turns the input into cooked mode.
         """
 
     @abstractmethod
-    def attach(self, input_ready_callback: Callable[[], None]) -> ContextManager[None]:
+    def attach(
+        self, input_ready_callback: Callable[[], None]
+    ) -> AbstractContextManager[None]:
         """
         Return a context manager that makes this input active in the current
         event loop.
         """
 
     @abstractmethod
-    def detach(self) -> ContextManager[None]:
+    def detach(self) -> AbstractContextManager[None]:
         """
         Return a context manager that makes sure that this input is not active
         in the current event loop.
@@ -129,13 +131,15 @@ def closed(self) -> bool:
         # `EOFError` immediately in the application.
         return True
 
-    def raw_mode(self) -> ContextManager[None]:
+    def raw_mode(self) -> AbstractContextManager[None]:
         return _dummy_context_manager()
 
-    def cooked_mode(self) -> ContextManager[None]:
+    def cooked_mode(self) -> AbstractContextManager[None]:
         return _dummy_context_manager()
 
-    def attach(self, input_ready_callback: Callable[[], None]) -> ContextManager[None]:
+    def attach(
+        self, input_ready_callback: Callable[[], None]
+    ) -> AbstractContextManager[None]:
         # Call the callback immediately once after attaching.
         # This tells the callback to call `read_keys` and check the
         # `input.closed` flag, after which it won't receive any keys, but knows
@@ -145,7 +149,7 @@ def attach(self, input_ready_callback: Callable[[], None]) -> ContextManager[Non
 
         return _dummy_context_manager()
 
-    def detach(self) -> ContextManager[None]:
+    def detach(self) -> AbstractContextManager[None]:
         return _dummy_context_manager()
 
 
diff --git a/src/prompt_toolkit/input/defaults.py b/src/prompt_toolkit/input/defaults.py
index 483eeb2092..ac375a13c0 100644
--- a/src/prompt_toolkit/input/defaults.py
+++ b/src/prompt_toolkit/input/defaults.py
@@ -2,7 +2,8 @@
 
 import io
 import sys
-from typing import ContextManager, TextIO
+from contextlib import AbstractContextManager
+from typing import TextIO
 
 from .base import DummyInput, Input, PipeInput
 
@@ -56,7 +57,7 @@ def create_input(stdin: TextIO | None = None, always_prefer_tty: bool = False) -
         return Vt100Input(stdin)
 
 
-def create_pipe_input() -> ContextManager[PipeInput]:
+def create_pipe_input() -> AbstractContextManager[PipeInput]:
     """
     Create an input pipe.
     This is mostly useful for unit testing.
diff --git a/src/prompt_toolkit/input/posix_pipe.py b/src/prompt_toolkit/input/posix_pipe.py
index c131fb816e..61410f60ab 100644
--- a/src/prompt_toolkit/input/posix_pipe.py
+++ b/src/prompt_toolkit/input/posix_pipe.py
@@ -5,8 +5,9 @@
 assert sys.platform != "win32"
 
 import os
-from contextlib import contextmanager
-from typing import ContextManager, Iterator, TextIO, cast
+from collections.abc import Iterator
+from contextlib import AbstractContextManager, contextmanager
+from typing import TextIO, cast
 
 from ..utils import DummyContext
 from .base import PipeInput
@@ -97,10 +98,10 @@ def send_text(self, data: str) -> None:
         "Send text to the input."
         os.write(self.pipe.write_fd, data.encode("utf-8"))
 
-    def raw_mode(self) -> ContextManager[None]:
+    def raw_mode(self) -> AbstractContextManager[None]:
         return DummyContext()
 
-    def cooked_mode(self) -> ContextManager[None]:
+    def cooked_mode(self) -> AbstractContextManager[None]:
         return DummyContext()
 
     def close(self) -> None:
diff --git a/src/prompt_toolkit/input/vt100.py b/src/prompt_toolkit/input/vt100.py
index c1660de956..60a049b35f 100644
--- a/src/prompt_toolkit/input/vt100.py
+++ b/src/prompt_toolkit/input/vt100.py
@@ -9,7 +9,9 @@
 import termios
 import tty
 from asyncio import AbstractEventLoop, get_running_loop
-from typing import Callable, ContextManager, Generator, TextIO
+from collections.abc import Callable, Generator
+from contextlib import AbstractContextManager
+from typing import TextIO
 
 from ..key_binding import KeyPress
 from .base import Input
@@ -74,14 +76,16 @@ def __init__(self, stdin: TextIO) -> None:
             lambda key_press: self._buffer.append(key_press)
         )
 
-    def attach(self, input_ready_callback: Callable[[], None]) -> ContextManager[None]:
+    def attach(
+        self, input_ready_callback: Callable[[], None]
+    ) -> AbstractContextManager[None]:
         """
         Return a context manager that makes this input active in the current
         event loop.
         """
         return _attached_input(self, input_ready_callback)
 
-    def detach(self) -> ContextManager[None]:
+    def detach(self) -> AbstractContextManager[None]:
         """
         Return a context manager that makes sure that this input is not active
         in the current event loop.
@@ -119,10 +123,10 @@ def flush_keys(self) -> list[KeyPress]:
     def closed(self) -> bool:
         return self.stdin_reader.closed
 
-    def raw_mode(self) -> ContextManager[None]:
+    def raw_mode(self) -> AbstractContextManager[None]:
         return raw_mode(self.stdin.fileno())
 
-    def cooked_mode(self) -> ContextManager[None]:
+    def cooked_mode(self) -> AbstractContextManager[None]:
         return cooked_mode(self.stdin.fileno())
 
     def fileno(self) -> int:
diff --git a/src/prompt_toolkit/input/vt100_parser.py b/src/prompt_toolkit/input/vt100_parser.py
index 73dbce3d83..34ea110575 100644
--- a/src/prompt_toolkit/input/vt100_parser.py
+++ b/src/prompt_toolkit/input/vt100_parser.py
@@ -5,7 +5,7 @@
 from __future__ import annotations
 
 import re
-from typing import Callable, Dict, Generator
+from collections.abc import Callable, Generator
 
 from ..key_binding.key_processor import KeyPress
 from ..keys import Keys
@@ -39,7 +39,7 @@ class _Flush:
     pass
 
 
-class _IsPrefixOfLongerMatchCache(Dict[str, bool]):
+class _IsPrefixOfLongerMatchCache(dict[str, bool]):
     """
     Dictionary that maps input sequences to a boolean indicating whether there is
     any key that start with this characters.
diff --git a/src/prompt_toolkit/input/win32.py b/src/prompt_toolkit/input/win32.py
index 616df8e78d..25a97e1a15 100644
--- a/src/prompt_toolkit/input/win32.py
+++ b/src/prompt_toolkit/input/win32.py
@@ -4,7 +4,7 @@
 import sys
 from abc import abstractmethod
 from asyncio import get_running_loop
-from contextlib import contextmanager
+from contextlib import AbstractContextManager, contextmanager
 
 from ..utils import SPHINX_AUTODOC_RUNNING
 
@@ -16,9 +16,10 @@
     import msvcrt
     from ctypes import windll
 
+from collections.abc import Callable, Iterable, Iterator
 from ctypes import Array, byref, pointer
 from ctypes.wintypes import DWORD, HANDLE
-from typing import Callable, ContextManager, Iterable, Iterator, TextIO
+from typing import TextIO
 
 from prompt_toolkit.eventloop import run_in_executor_with_context
 from prompt_toolkit.eventloop.win32 import create_win32_event, wait_for_handles
@@ -87,14 +88,16 @@ def __init__(self, stdin: TextIO | None = None) -> None:
         else:
             self.console_input_reader = ConsoleInputReader()
 
-    def attach(self, input_ready_callback: Callable[[], None]) -> ContextManager[None]:
+    def attach(
+        self, input_ready_callback: Callable[[], None]
+    ) -> AbstractContextManager[None]:
         """
         Return a context manager that makes this input active in the current
         event loop.
         """
         return attach_win32_input(self, input_ready_callback)
 
-    def detach(self) -> ContextManager[None]:
+    def detach(self) -> AbstractContextManager[None]:
         """
         Return a context manager that makes sure that this input is not active
         in the current event loop.
@@ -111,12 +114,12 @@ def flush_keys(self) -> list[KeyPress]:
     def closed(self) -> bool:
         return False
 
-    def raw_mode(self) -> ContextManager[None]:
+    def raw_mode(self) -> AbstractContextManager[None]:
         return raw_mode(
             use_win10_virtual_terminal_input=self._use_virtual_terminal_input
         )
 
-    def cooked_mode(self) -> ContextManager[None]:
+    def cooked_mode(self) -> AbstractContextManager[None]:
         return cooked_mode()
 
     def fileno(self) -> int:
diff --git a/src/prompt_toolkit/input/win32_pipe.py b/src/prompt_toolkit/input/win32_pipe.py
index 0bafa49eab..309903f3f5 100644
--- a/src/prompt_toolkit/input/win32_pipe.py
+++ b/src/prompt_toolkit/input/win32_pipe.py
@@ -4,10 +4,10 @@
 
 assert sys.platform == "win32"
 
-from contextlib import contextmanager
+from collections.abc import Callable, Iterator
+from contextlib import AbstractContextManager, contextmanager
 from ctypes import windll
 from ctypes.wintypes import HANDLE
-from typing import Callable, ContextManager, Iterator
 
 from prompt_toolkit.eventloop.win32 import create_win32_event
 
@@ -81,14 +81,16 @@ def handle(self) -> HANDLE:
         "The handle used for registering this pipe in the event loop."
         return self._event
 
-    def attach(self, input_ready_callback: Callable[[], None]) -> ContextManager[None]:
+    def attach(
+        self, input_ready_callback: Callable[[], None]
+    ) -> AbstractContextManager[None]:
         """
         Return a context manager that makes this input active in the current
         event loop.
         """
         return attach_win32_input(self, input_ready_callback)
 
-    def detach(self) -> ContextManager[None]:
+    def detach(self) -> AbstractContextManager[None]:
         """
         Return a context manager that makes sure that this input is not active
         in the current event loop.
@@ -138,10 +140,10 @@ def send_text(self, text: str) -> None:
         # Set event.
         windll.kernel32.SetEvent(self._event)
 
-    def raw_mode(self) -> ContextManager[None]:
+    def raw_mode(self) -> AbstractContextManager[None]:
         return DummyContext()
 
-    def cooked_mode(self) -> ContextManager[None]:
+    def cooked_mode(self) -> AbstractContextManager[None]:
         return DummyContext()
 
     def close(self) -> None:
diff --git a/src/prompt_toolkit/key_binding/bindings/named_commands.py b/src/prompt_toolkit/key_binding/bindings/named_commands.py
index 8ea8dd03de..2c2403e267 100644
--- a/src/prompt_toolkit/key_binding/bindings/named_commands.py
+++ b/src/prompt_toolkit/key_binding/bindings/named_commands.py
@@ -6,7 +6,8 @@
 
 from __future__ import annotations
 
-from typing import Callable, TypeVar, Union, cast
+from collections.abc import Callable
+from typing import TypeVar, cast
 
 from prompt_toolkit.document import Document
 from prompt_toolkit.enums import EditingMode
@@ -26,7 +27,7 @@
 
 # Typing.
 _Handler = Callable[[KeyPressEvent], None]
-_HandlerOrBinding = Union[_Handler, Binding]
+_HandlerOrBinding = _Handler | Binding
 _T = TypeVar("_T", bound=_HandlerOrBinding)
 E = KeyPressEvent
 
diff --git a/src/prompt_toolkit/key_binding/bindings/vi.py b/src/prompt_toolkit/key_binding/bindings/vi.py
index d68a31f29a..e3fca1b981 100644
--- a/src/prompt_toolkit/key_binding/bindings/vi.py
+++ b/src/prompt_toolkit/key_binding/bindings/vi.py
@@ -3,9 +3,10 @@
 
 import codecs
 import string
+from collections.abc import Callable, Iterable
 from enum import Enum
 from itertools import accumulate
-from typing import Callable, Iterable, Tuple, TypeVar
+from typing import TypeVar
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.buffer import Buffer, indent, reshape_text, unindent
@@ -422,7 +423,7 @@ def load_vi_bindings() -> KeyBindingsBase:
     # (Note: Always take the navigation bindings in read-only mode, even when
     #  ViState says different.)
 
-    TransformFunction = Tuple[Tuple[str, ...], Filter, Callable[[str], str]]
+    TransformFunction = tuple[tuple[str, ...], Filter, Callable[[str], str]]
 
     vi_transform_functions: list[TransformFunction] = [
         # Rot 13 transformation
diff --git a/src/prompt_toolkit/key_binding/key_bindings.py b/src/prompt_toolkit/key_binding/key_bindings.py
index cf37c6d90d..5fd56394ba 100644
--- a/src/prompt_toolkit/key_binding/key_bindings.py
+++ b/src/prompt_toolkit/key_binding/key_bindings.py
@@ -38,15 +38,11 @@ def my_key_binding(event):
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
+from collections.abc import Callable, Coroutine, Hashable, Sequence
 from inspect import isawaitable
 from typing import (
     TYPE_CHECKING,
     Any,
-    Callable,
-    Coroutine,
-    Hashable,
-    Sequence,
-    Tuple,
     TypeVar,
     Union,
     cast,
@@ -147,7 +143,7 @@ def __repr__(self) -> str:
 
 
 # Sequence of keys presses.
-KeysTuple = Tuple[Union[Keys, str], ...]
+KeysTuple = tuple[Keys | str, ...]
 
 
 class KeyBindingsBase(metaclass=ABCMeta):
@@ -200,7 +196,7 @@ def bindings(self) -> list[Binding]:
     # `add` and `remove` don't have to be part of this interface.
 
 
-T = TypeVar("T", bound=Union[KeyHandlerCallable, Binding])
+T = TypeVar("T", bound=KeyHandlerCallable | Binding)
 
 
 class KeyBindings(KeyBindingsBase):
@@ -348,7 +344,7 @@ def remove(self, *args: Keys | str | KeyHandlerCallable) -> None:
 
         else:
             assert len(args) > 0
-            args = cast(Tuple[Union[Keys, str]], args)
+            args = cast(tuple[Keys | str], args)
 
             # Remove this sequence of key bindings.
             keys = tuple(_parse_key(k) for k in args)
diff --git a/src/prompt_toolkit/key_binding/key_processor.py b/src/prompt_toolkit/key_binding/key_processor.py
index e2070a14f0..c0e60575cc 100644
--- a/src/prompt_toolkit/key_binding/key_processor.py
+++ b/src/prompt_toolkit/key_binding/key_processor.py
@@ -11,7 +11,8 @@
 import weakref
 from asyncio import Task, sleep
 from collections import deque
-from typing import TYPE_CHECKING, Any, Generator
+from collections.abc import Generator
+from typing import TYPE_CHECKING, Any
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.enums import EditingMode
diff --git a/src/prompt_toolkit/key_binding/vi_state.py b/src/prompt_toolkit/key_binding/vi_state.py
index 0543911e32..cb1a1b140e 100644
--- a/src/prompt_toolkit/key_binding/vi_state.py
+++ b/src/prompt_toolkit/key_binding/vi_state.py
@@ -1,7 +1,8 @@
 from __future__ import annotations
 
+from collections.abc import Callable
 from enum import Enum
-from typing import TYPE_CHECKING, Callable
+from typing import TYPE_CHECKING
 
 from prompt_toolkit.clipboard import ClipboardData
 
diff --git a/src/prompt_toolkit/layout/containers.py b/src/prompt_toolkit/layout/containers.py
index f6fe381f5a..fbc54d8c06 100644
--- a/src/prompt_toolkit/layout/containers.py
+++ b/src/prompt_toolkit/layout/containers.py
@@ -6,9 +6,10 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
+from collections.abc import Callable, Sequence
 from enum import Enum
 from functools import partial
-from typing import TYPE_CHECKING, Callable, Sequence, Union, cast
+from typing import TYPE_CHECKING, Union, cast
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.cache import SimpleCache
@@ -52,7 +53,7 @@
 from .utils import explode_text_fragments
 
 if TYPE_CHECKING:
-    from typing_extensions import Protocol, TypeGuard
+    from typing import Protocol, TypeGuard
 
     from prompt_toolkit.key_binding.key_bindings import NotImplementedOrNone
 
diff --git a/src/prompt_toolkit/layout/controls.py b/src/prompt_toolkit/layout/controls.py
index 5083c8286d..7178945646 100644
--- a/src/prompt_toolkit/layout/controls.py
+++ b/src/prompt_toolkit/layout/controls.py
@@ -6,7 +6,8 @@
 
 import time
 from abc import ABCMeta, abstractmethod
-from typing import TYPE_CHECKING, Callable, Hashable, Iterable, NamedTuple
+from collections.abc import Callable, Hashable, Iterable
+from typing import TYPE_CHECKING, NamedTuple
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.buffer import Buffer
diff --git a/src/prompt_toolkit/layout/dimension.py b/src/prompt_toolkit/layout/dimension.py
index eec6c6924c..28fdc9b959 100644
--- a/src/prompt_toolkit/layout/dimension.py
+++ b/src/prompt_toolkit/layout/dimension.py
@@ -5,7 +5,8 @@
 
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Any, Callable, Union
+from collections.abc import Callable
+from typing import TYPE_CHECKING
 
 __all__ = [
     "Dimension",
@@ -18,7 +19,7 @@
 ]
 
 if TYPE_CHECKING:
-    from typing_extensions import TypeGuard
+    from typing import TypeGuard
 
 
 class Dimension:
@@ -169,14 +170,8 @@ def max_layout_dimensions(dimensions: list[Dimension]) -> Dimension:
         return Dimension()
 
 
-# Anything that can be converted to a dimension.
-AnyDimension = Union[
-    None,  # None is a valid dimension that will fit anything.
-    int,
-    Dimension,
-    # Callable[[], 'AnyDimension']  # Recursive definition not supported by mypy.
-    Callable[[], Any],
-]
+# Anything that can be converted to a dimension
+AnyDimension = None | int | Dimension | Callable[[], "AnyDimension"]
 
 
 def to_dimension(value: AnyDimension) -> Dimension:
diff --git a/src/prompt_toolkit/layout/layout.py b/src/prompt_toolkit/layout/layout.py
index f9b7110925..1af6afce8e 100644
--- a/src/prompt_toolkit/layout/layout.py
+++ b/src/prompt_toolkit/layout/layout.py
@@ -4,7 +4,7 @@
 
 from __future__ import annotations
 
-from typing import Generator, Iterable, Union
+from collections.abc import Generator, Iterable
 
 from prompt_toolkit.buffer import Buffer
 
@@ -23,7 +23,7 @@
     "walk",
 ]
 
-FocusableElement = Union[str, Buffer, UIControl, AnyContainer]
+FocusableElement = str | Buffer | UIControl | AnyContainer
 
 
 class Layout:
diff --git a/src/prompt_toolkit/layout/margins.py b/src/prompt_toolkit/layout/margins.py
index 737a74d29b..68e3e11904 100644
--- a/src/prompt_toolkit/layout/margins.py
+++ b/src/prompt_toolkit/layout/margins.py
@@ -5,7 +5,8 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import TYPE_CHECKING, Callable
+from collections.abc import Callable
+from typing import TYPE_CHECKING
 
 from prompt_toolkit.filters import FilterOrBool, to_filter
 from prompt_toolkit.formatted_text import (
diff --git a/src/prompt_toolkit/layout/menus.py b/src/prompt_toolkit/layout/menus.py
index 612e8ab6a3..168792e507 100644
--- a/src/prompt_toolkit/layout/menus.py
+++ b/src/prompt_toolkit/layout/menus.py
@@ -1,8 +1,9 @@
 from __future__ import annotations
 
 import math
+from collections.abc import Callable, Iterable, Sequence
 from itertools import zip_longest
-from typing import TYPE_CHECKING, Callable, Iterable, Sequence, TypeVar, cast
+from typing import TYPE_CHECKING, TypeVar, cast
 from weakref import WeakKeyDictionary
 
 from prompt_toolkit.application.current import get_app
diff --git a/src/prompt_toolkit/layout/mouse_handlers.py b/src/prompt_toolkit/layout/mouse_handlers.py
index 52deac1456..31cf54a656 100644
--- a/src/prompt_toolkit/layout/mouse_handlers.py
+++ b/src/prompt_toolkit/layout/mouse_handlers.py
@@ -1,7 +1,8 @@
 from __future__ import annotations
 
 from collections import defaultdict
-from typing import TYPE_CHECKING, Callable
+from collections.abc import Callable
+from typing import TYPE_CHECKING
 
 from prompt_toolkit.mouse_events import MouseEvent
 
diff --git a/src/prompt_toolkit/layout/processors.py b/src/prompt_toolkit/layout/processors.py
index 666e79c66d..139f07c3e9 100644
--- a/src/prompt_toolkit/layout/processors.py
+++ b/src/prompt_toolkit/layout/processors.py
@@ -10,7 +10,8 @@
 
 import re
 from abc import ABCMeta, abstractmethod
-from typing import TYPE_CHECKING, Callable, Hashable, cast
+from collections.abc import Callable, Hashable
+from typing import TYPE_CHECKING, cast
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.cache import SimpleCache
diff --git a/src/prompt_toolkit/layout/screen.py b/src/prompt_toolkit/layout/screen.py
index 475f540d11..be3e7b7e92 100644
--- a/src/prompt_toolkit/layout/screen.py
+++ b/src/prompt_toolkit/layout/screen.py
@@ -1,7 +1,8 @@
 from __future__ import annotations
 
 from collections import defaultdict
-from typing import TYPE_CHECKING, Callable
+from collections.abc import Callable
+from typing import TYPE_CHECKING
 
 from prompt_toolkit.cache import FastDictCache
 from prompt_toolkit.data_structures import Point
diff --git a/src/prompt_toolkit/layout/utils.py b/src/prompt_toolkit/layout/utils.py
index 373fe52a5a..cba84bcb5d 100644
--- a/src/prompt_toolkit/layout/utils.py
+++ b/src/prompt_toolkit/layout/utils.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
-from typing import TYPE_CHECKING, Iterable, List, TypeVar, cast, overload
+from collections.abc import Iterable
+from typing import TYPE_CHECKING, TypeVar, cast, overload
 
 from prompt_toolkit.formatted_text.base import OneStyleAndTextTuple
 
@@ -14,7 +15,7 @@
 _T = TypeVar("_T", bound=OneStyleAndTextTuple)
 
 
-class _ExplodedList(List[_T]):
+class _ExplodedList(list[_T]):
     """
     Wrapper around a list, that marks it as 'exploded'.
 
@@ -52,7 +53,7 @@ def __setitem__(
             int_index = index.__index__()
             index = slice(int_index, int_index + 1)
         if isinstance(value, tuple):  # In case of `OneStyleAndTextTuple`.
-            value = cast("List[_T]", [value])
+            value = cast("list[_T]", [value])
 
         super().__setitem__(index, explode_text_fragments(value))
 
diff --git a/src/prompt_toolkit/lexers/base.py b/src/prompt_toolkit/lexers/base.py
index c61e2b9d32..e8536908bf 100644
--- a/src/prompt_toolkit/lexers/base.py
+++ b/src/prompt_toolkit/lexers/base.py
@@ -5,7 +5,7 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import Callable, Hashable
+from collections.abc import Callable, Hashable
 
 from prompt_toolkit.document import Document
 from prompt_toolkit.formatted_text.base import StyleAndTextTuples
diff --git a/src/prompt_toolkit/lexers/pygments.py b/src/prompt_toolkit/lexers/pygments.py
index ff972d4a8d..696d90e82e 100644
--- a/src/prompt_toolkit/lexers/pygments.py
+++ b/src/prompt_toolkit/lexers/pygments.py
@@ -9,7 +9,8 @@
 
 import re
 from abc import ABCMeta, abstractmethod
-from typing import TYPE_CHECKING, Callable, Dict, Generator, Iterable, Tuple
+from collections.abc import Callable, Generator, Iterable
+from typing import TYPE_CHECKING
 
 from prompt_toolkit.document import Document
 from prompt_toolkit.filters import FilterOrBool, to_filter
@@ -123,7 +124,7 @@ def from_pygments_lexer_cls(cls, lexer_cls: type[PygmentsLexerCls]) -> RegexSync
         return cls(p)
 
 
-class _TokenCache(Dict[Tuple[str, ...], str]):
+class _TokenCache(dict[tuple[str, ...], str]):
     """
     Cache that converts Pygments tokens into `prompt_toolkit` style objects.
 
@@ -219,7 +220,7 @@ def lex_document(self, document: Document) -> Callable[[int], StyleAndTextTuples
         Create a lexer function that takes a line number and returns the list
         of (style_str, text) tuples as the Pygments lexer returns for that line.
         """
-        LineGenerator = Generator[Tuple[int, StyleAndTextTuples], None, None]
+        LineGenerator = Generator[tuple[int, StyleAndTextTuples], None, None]
 
         # Cache of already lexed lines.
         cache: dict[int, StyleAndTextTuples] = {}
diff --git a/src/prompt_toolkit/output/flush_stdout.py b/src/prompt_toolkit/output/flush_stdout.py
index daf58efee6..556e968251 100644
--- a/src/prompt_toolkit/output/flush_stdout.py
+++ b/src/prompt_toolkit/output/flush_stdout.py
@@ -3,8 +3,9 @@
 import errno
 import os
 import sys
+from collections.abc import Iterator
 from contextlib import contextmanager
-from typing import IO, Iterator, TextIO
+from typing import IO, TextIO
 
 __all__ = ["flush_stdout"]
 
diff --git a/src/prompt_toolkit/output/vt100.py b/src/prompt_toolkit/output/vt100.py
index 57826b9409..b2fe073a13 100644
--- a/src/prompt_toolkit/output/vt100.py
+++ b/src/prompt_toolkit/output/vt100.py
@@ -12,7 +12,8 @@
 import io
 import os
 import sys
-from typing import Callable, Dict, Hashable, Iterable, Sequence, TextIO, Tuple
+from collections.abc import Callable, Hashable, Iterable, Sequence
+from typing import TextIO
 
 from prompt_toolkit.cursor_shapes import CursorShape
 from prompt_toolkit.data_structures import Size
@@ -139,7 +140,7 @@ def _get_closest_ansi_color(r: int, g: int, b: int, exclude: Sequence[str] = ())
     return match
 
 
-_ColorCodeAndName = Tuple[int, str]
+_ColorCodeAndName = tuple[int, str]
 
 
 class _16ColorCache:
@@ -183,7 +184,7 @@ def _get(
         return code, match
 
 
-class _256ColorCache(Dict[Tuple[int, int, int], int]):
+class _256ColorCache(dict[tuple[int, int, int], int]):
     """
     Cache which maps (r, g, b) tuples to 256 colors.
     """
@@ -254,7 +255,7 @@ def __missing__(self, value: tuple[int, int, int]) -> int:
 _256_colors = _256ColorCache()
 
 
-class _EscapeCodeCache(Dict[Attrs, str]):
+class _EscapeCodeCache(dict[Attrs, str]):
     """
     Cache for VT100 escape codes. It maps
     (fgcolor, bgcolor, bold, underline, strike, italic, blink, reverse, hidden, dim) tuples to VT100
diff --git a/src/prompt_toolkit/output/win32.py b/src/prompt_toolkit/output/win32.py
index 1c0cc4eec8..1bf0cbbbc2 100644
--- a/src/prompt_toolkit/output/win32.py
+++ b/src/prompt_toolkit/output/win32.py
@@ -5,9 +5,10 @@
 assert sys.platform == "win32"
 
 import os
+from collections.abc import Callable
 from ctypes import ArgumentError, byref, c_char, c_long, c_uint, c_ulong, pointer
 from ctypes.wintypes import DWORD, HANDLE
-from typing import Callable, TextIO, TypeVar
+from typing import TextIO, TypeVar
 
 from prompt_toolkit.cursor_shapes import CursorShape
 from prompt_toolkit.data_structures import Size
diff --git a/src/prompt_toolkit/patch_stdout.py b/src/prompt_toolkit/patch_stdout.py
index 47da779398..1695c1639a 100644
--- a/src/prompt_toolkit/patch_stdout.py
+++ b/src/prompt_toolkit/patch_stdout.py
@@ -25,8 +25,9 @@
 import sys
 import threading
 import time
+from collections.abc import Generator
 from contextlib import contextmanager
-from typing import Generator, TextIO, cast
+from typing import TextIO, cast
 
 from .application import get_app_session, run_in_terminal
 from .output import Output
diff --git a/src/prompt_toolkit/renderer.py b/src/prompt_toolkit/renderer.py
index 8d5e03c19e..fcfde223e1 100644
--- a/src/prompt_toolkit/renderer.py
+++ b/src/prompt_toolkit/renderer.py
@@ -7,8 +7,9 @@
 
 from asyncio import FIRST_COMPLETED, Future, ensure_future, sleep, wait
 from collections import deque
+from collections.abc import Callable, Hashable
 from enum import Enum
-from typing import TYPE_CHECKING, Any, Callable, Dict, Hashable
+from typing import TYPE_CHECKING, Any
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.cursor_shapes import CursorShape
@@ -267,7 +268,7 @@ class HeightIsUnknownError(Exception):
     "Information unavailable. Did not yet receive the CPR response."
 
 
-class _StyleStringToAttrsCache(Dict[str, Attrs]):
+class _StyleStringToAttrsCache(dict[str, Attrs]):
     """
     A cache structure that maps style strings to :class:`.Attr`.
     (This is an important speed up.)
@@ -289,7 +290,7 @@ def __missing__(self, style_str: str) -> Attrs:
         return attrs
 
 
-class _StyleStringHasStyleCache(Dict[str, bool]):
+class _StyleStringHasStyleCache(dict[str, bool]):
     """
     Cache for remember which style strings don't render the default output
     style (default fg/bg, no underline and no reverse and no blink). That way
diff --git a/src/prompt_toolkit/shortcuts/choice_input.py b/src/prompt_toolkit/shortcuts/choice_input.py
index 95ffd0b5b4..8e34343cc0 100644
--- a/src/prompt_toolkit/shortcuts/choice_input.py
+++ b/src/prompt_toolkit/shortcuts/choice_input.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
-from typing import Generic, Sequence, TypeVar
+from collections.abc import Sequence
+from typing import Generic, TypeVar
 
 from prompt_toolkit.application import Application
 from prompt_toolkit.filters import (
diff --git a/src/prompt_toolkit/shortcuts/dialogs.py b/src/prompt_toolkit/shortcuts/dialogs.py
index d12bbb03aa..9236b5e31c 100644
--- a/src/prompt_toolkit/shortcuts/dialogs.py
+++ b/src/prompt_toolkit/shortcuts/dialogs.py
@@ -1,7 +1,8 @@
 from __future__ import annotations
 
 import functools
-from typing import Any, Callable, Sequence, TypeVar
+from collections.abc import Callable, Sequence
+from typing import Any, TypeVar
 
 from prompt_toolkit.application import Application
 from prompt_toolkit.application.current import get_app
diff --git a/src/prompt_toolkit/shortcuts/progress_bar/base.py b/src/prompt_toolkit/shortcuts/progress_bar/base.py
index a7c2a527d8..a8b796627a 100644
--- a/src/prompt_toolkit/shortcuts/progress_bar/base.py
+++ b/src/prompt_toolkit/shortcuts/progress_bar/base.py
@@ -17,13 +17,9 @@
 import signal
 import threading
 import traceback
+from collections.abc import Callable, Iterable, Iterator, Sequence, Sized
 from typing import (
-    Callable,
     Generic,
-    Iterable,
-    Iterator,
-    Sequence,
-    Sized,
     TextIO,
     TypeVar,
     cast,
diff --git a/src/prompt_toolkit/shortcuts/prompt.py b/src/prompt_toolkit/shortcuts/prompt.py
index 68cfeb9aa0..f14ecd80c8 100644
--- a/src/prompt_toolkit/shortcuts/prompt.py
+++ b/src/prompt_toolkit/shortcuts/prompt.py
@@ -28,10 +28,11 @@
 from __future__ import annotations
 
 from asyncio import get_running_loop
+from collections.abc import Callable, Iterator
 from contextlib import contextmanager
 from enum import Enum
 from functools import partial
-from typing import TYPE_CHECKING, Callable, Generic, Iterator, TypeVar, Union, cast
+from typing import TYPE_CHECKING, Generic, TypeVar, Union, cast
 
 from prompt_toolkit.application import Application
 from prompt_toolkit.application.current import get_app
@@ -520,17 +521,21 @@ def accept(buff: Buffer) -> bool:
             # enable_history_search is enabled. (First convert to Filter,
             # to avoid doing bitwise operations on bool objects.)
             complete_while_typing=Condition(
-                lambda: is_true(self.complete_while_typing)
-                and not is_true(self.enable_history_search)
-                and not self.complete_style == CompleteStyle.READLINE_LIKE
+                lambda: (
+                    is_true(self.complete_while_typing)
+                    and not is_true(self.enable_history_search)
+                    and not self.complete_style == CompleteStyle.READLINE_LIKE
+                )
             ),
             validate_while_typing=dyncond("validate_while_typing"),
             enable_history_search=dyncond("enable_history_search"),
             validator=DynamicValidator(lambda: self.validator),
             completer=DynamicCompleter(
-                lambda: ThreadedCompleter(self.completer)
-                if self.complete_in_thread and self.completer
-                else self.completer
+                lambda: (
+                    ThreadedCompleter(self.completer)
+                    if self.complete_in_thread and self.completer
+                    else self.completer
+                )
             ),
             history=self.history,
             auto_suggest=DynamicAutoSuggest(lambda: self.auto_suggest),
@@ -654,15 +659,19 @@ def multi_column_complete_style() -> bool:
                     ConditionalContainer(
                         default_buffer_window,
                         Condition(
-                            lambda: get_app().layout.current_control
-                            != search_buffer_control
+                            lambda: (
+                                get_app().layout.current_control
+                                != search_buffer_control
+                            )
                         ),
                     ),
                     ConditionalContainer(
                         Window(search_buffer_control),
                         Condition(
-                            lambda: get_app().layout.current_control
-                            == search_buffer_control
+                            lambda: (
+                                get_app().layout.current_control
+                                == search_buffer_control
+                            )
                         ),
                     ),
                 ]
diff --git a/src/prompt_toolkit/styles/base.py b/src/prompt_toolkit/styles/base.py
index 1e044679f0..9144a77c88 100644
--- a/src/prompt_toolkit/styles/base.py
+++ b/src/prompt_toolkit/styles/base.py
@@ -5,7 +5,8 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import Callable, Hashable, NamedTuple
+from collections.abc import Callable, Hashable
+from typing import NamedTuple
 
 __all__ = [
     "Attrs",
diff --git a/src/prompt_toolkit/styles/style.py b/src/prompt_toolkit/styles/style.py
index 8aab8e1b21..388a87e8d3 100644
--- a/src/prompt_toolkit/styles/style.py
+++ b/src/prompt_toolkit/styles/style.py
@@ -6,8 +6,9 @@
 
 import itertools
 import re
+from collections.abc import Hashable
 from enum import Enum
-from typing import Hashable, TypeVar
+from typing import TypeVar
 
 from prompt_toolkit.cache import SimpleCache
 
diff --git a/src/prompt_toolkit/styles/style_transformation.py b/src/prompt_toolkit/styles/style_transformation.py
index e8d5b0a89f..7db723c393 100644
--- a/src/prompt_toolkit/styles/style_transformation.py
+++ b/src/prompt_toolkit/styles/style_transformation.py
@@ -13,8 +13,8 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
+from collections.abc import Callable, Hashable, Sequence
 from colorsys import hls_to_rgb, rgb_to_hls
-from typing import Callable, Hashable, Sequence
 
 from prompt_toolkit.cache import memoized
 from prompt_toolkit.filters import FilterOrBool, to_filter
diff --git a/src/prompt_toolkit/utils.py b/src/prompt_toolkit/utils.py
index 1a99a2868a..142142a0f4 100644
--- a/src/prompt_toolkit/utils.py
+++ b/src/prompt_toolkit/utils.py
@@ -5,14 +5,11 @@
 import sys
 import threading
 from collections import deque
+from collections.abc import Callable, Generator
+from contextlib import AbstractContextManager
 from typing import (
-    Callable,
-    ContextManager,
-    Dict,
-    Generator,
     Generic,
     TypeVar,
-    Union,
 )
 
 from wcwidth import wcwidth
@@ -112,7 +109,7 @@ def __isub__(self, handler: Callable[[_Sender], None]) -> Event[_Sender]:
         return self
 
 
-class DummyContext(ContextManager[None]):
+class DummyContext(AbstractContextManager[None]):
     """
     (contextlib.nested is not available on Py3)
     """
@@ -124,7 +121,7 @@ def __exit__(self, *a: object) -> None:
         pass
 
 
-class _CharSizesCache(Dict[str, int]):
+class _CharSizesCache(dict[str, int]):
     """
     Cache for wcwidth sizes.
     """
@@ -303,7 +300,7 @@ def to_int(value: Callable[[], int] | int) -> int:
         return int(value)
 
 
-AnyFloat = Union[Callable[[], float], float]
+AnyFloat = Callable[[], float] | float
 
 
 def to_float(value: AnyFloat) -> float:
diff --git a/src/prompt_toolkit/validation.py b/src/prompt_toolkit/validation.py
index 2b35d1fcc9..d33fa38796 100644
--- a/src/prompt_toolkit/validation.py
+++ b/src/prompt_toolkit/validation.py
@@ -6,7 +6,7 @@
 from __future__ import annotations
 
 from abc import ABCMeta, abstractmethod
-from typing import Callable
+from collections.abc import Callable
 
 from prompt_toolkit.eventloop import run_in_executor_with_context
 
diff --git a/src/prompt_toolkit/widgets/base.py b/src/prompt_toolkit/widgets/base.py
index b8c2d671bd..d2bcacf2e4 100644
--- a/src/prompt_toolkit/widgets/base.py
+++ b/src/prompt_toolkit/widgets/base.py
@@ -15,8 +15,9 @@
 
 from __future__ import annotations
 
+from collections.abc import Callable, Sequence
 from functools import partial
-from typing import Callable, Generic, Sequence, TypeVar
+from typing import Generic, TypeVar
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.auto_suggest import AutoSuggest, DynamicAutoSuggest
diff --git a/src/prompt_toolkit/widgets/dialogs.py b/src/prompt_toolkit/widgets/dialogs.py
index 5f5f17026d..7f3cfe7695 100644
--- a/src/prompt_toolkit/widgets/dialogs.py
+++ b/src/prompt_toolkit/widgets/dialogs.py
@@ -4,7 +4,7 @@
 
 from __future__ import annotations
 
-from typing import Sequence
+from collections.abc import Sequence
 
 from prompt_toolkit.filters import has_completions, has_focus
 from prompt_toolkit.formatted_text import AnyFormattedText
diff --git a/src/prompt_toolkit/widgets/menus.py b/src/prompt_toolkit/widgets/menus.py
index c574c06799..9cb5de2bd2 100644
--- a/src/prompt_toolkit/widgets/menus.py
+++ b/src/prompt_toolkit/widgets/menus.py
@@ -1,6 +1,6 @@
 from __future__ import annotations
 
-from typing import Callable, Iterable, Sequence
+from collections.abc import Callable, Iterable, Sequence
 
 from prompt_toolkit.application.current import get_app
 from prompt_toolkit.filters import Condition
diff --git a/tests/test_key_binding.py b/tests/test_key_binding.py
index 1c60880af9..479559c61d 100644
--- a/tests/test_key_binding.py
+++ b/tests/test_key_binding.py
@@ -39,6 +39,10 @@ def set_dummy_app():
             input=pipe_input,
         )
 
+        def create_background_task(coroutine, **kw):
+            coroutine.close()
+            return None
+
         # Don't start background tasks for these tests. The `KeyProcessor`
         # wants to create a background task for flushing keys. We can ignore it
         # here for these tests.
@@ -46,7 +50,7 @@ def set_dummy_app():
         # the `Application` should pass its task group to the constructor of
         # `KeyProcessor`. That way, it doesn't have to do a lookup using
         # `get_app()`.
-        app.create_background_task = lambda *_, **kw: None
+        app.create_background_task = create_background_task
 
         with set_app(app):
             yield
diff --git a/tests/test_memory_leaks.py b/tests/test_memory_leaks.py
index 31ea7c8ce8..08afac5e28 100644
--- a/tests/test_memory_leaks.py
+++ b/tests/test_memory_leaks.py
@@ -2,8 +2,6 @@
 
 import gc
 
-import pytest
-
 from prompt_toolkit.shortcuts.prompt import PromptSession
 
 
@@ -16,8 +14,7 @@ def _count_prompt_session_instances() -> int:
     return len([obj for obj in objects if isinstance(obj, PromptSession)])
 
 
-# Fails in GitHub CI, probably due to GC differences.
-@pytest.mark.xfail(reason="Memory leak testing fails in GitHub CI.")
+# This test used to fail in GitHub CI, probably due to GC differences.
 def test_prompt_session_memory_leak() -> None:
     before_count = _count_prompt_session_instances()
 
diff --git a/tools/debug_input_cross_platform.py b/tools/debug_input_cross_platform.py
index d87cfcc03d..70a8f3f33d 100755
--- a/tools/debug_input_cross_platform.py
+++ b/tools/debug_input_cross_platform.py
@@ -16,7 +16,7 @@ async def main() -> None:
     done = asyncio.Event()
     input = create_input()
 
-    def keys_ready():
+    def keys_ready() -> None:
         for key_press in input.read_keys():
             print(key_press)
 
diff --git a/tools/debug_vt100_input.py b/tools/debug_vt100_input.py
index b74c06fb84..20722dcff5 100755
--- a/tools/debug_vt100_input.py
+++ b/tools/debug_vt100_input.py
@@ -10,17 +10,18 @@
 
 from prompt_toolkit.input.vt100 import raw_mode
 from prompt_toolkit.input.vt100_parser import Vt100Parser
+from prompt_toolkit.key_binding import KeyPress
 from prompt_toolkit.keys import Keys
 
 
-def callback(key_press):
+def callback(key_press: KeyPress) -> None:
     print(key_press)
 
     if key_press.key == Keys.ControlC:
         sys.exit(0)
 
 
-def main():
+def main() -> None:
     stream = Vt100Parser(callback)
 
     with raw_mode(sys.stdin.fileno()):