diff --git a/Lib/ensurepip/__init__.py b/Lib/ensurepip/__init__.py
index 651f876e24b..94f1b6604cb 100644
--- a/Lib/ensurepip/__init__.py
+++ b/Lib/ensurepip/__init__.py
@@ -10,8 +10,8 @@ from importlib import resources
 
 __all__ = ["version", "bootstrap"]
 _PACKAGE_NAMES = ('setuptools', 'pip')
-_SETUPTOOLS_VERSION = "57.4.0"
-_PIP_VERSION = "21.2.3"
+_SETUPTOOLS_VERSION = "58.1.0"
+_PIP_VERSION = "21.2.4"
 _PROJECTS = [
     ("setuptools", _SETUPTOOLS_VERSION, "py3"),
     ("pip", _PIP_VERSION, "py3"),
@@ -41,7 +41,7 @@ def _find_packages(path):
     # comparison since this case should not happen.
     filenames = sorted(filenames)
     for filename in filenames:
-        # filename is like 'pip-20.2.3-py2.py3-none-any.whl'
+        # filename is like 'pip-21.2.4-py3-none-any.whl'
         if not filename.endswith(".whl"):
             continue
         for name in _PACKAGE_NAMES:
@@ -51,7 +51,7 @@ def _find_packages(path):
         else:
             continue
 
-        # Extract '20.2.2' from 'pip-20.2.2-py2.py3-none-any.whl'
+        # Extract '21.2.4' from 'pip-21.2.4-py3-none-any.whl'
         version = filename.removeprefix(prefix).partition('-')[0]
         wheel_path = os.path.join(path, filename)
         packages[name] = _Package(version, None, wheel_path)
diff --git a/Lib/ensurepip/_bundled/pip-21.2.3-py3-none-any.whl b/Lib/ensurepip/_bundled/pip-21.2.3-py3-none-any.whl
deleted file mode 100644
index d417df63d9e..00000000000
Binary files a/Lib/ensurepip/_bundled/pip-21.2.3-py3-none-any.whl and /dev/null differ
diff --git a/Lib/ensurepip/_bundled/pip-21.2.4-py3-none-any.whl b/Lib/ensurepip/_bundled/pip-21.2.4-py3-none-any.whl
new file mode 100644
index 00000000000..46d3012c59b
Binary files /dev/null and b/Lib/ensurepip/_bundled/pip-21.2.4-py3-none-any.whl differ
diff --git a/Lib/ensurepip/_bundled/setuptools-57.4.0-py3-none-any.whl b/Lib/ensurepip/_bundled/setuptools-58.1.0-py3-none-any.whl
similarity index 80%
rename from Lib/ensurepip/_bundled/setuptools-57.4.0-py3-none-any.whl
rename to Lib/ensurepip/_bundled/setuptools-58.1.0-py3-none-any.whl
index af8f8ba2100..18c8c22958f 100644
Binary files a/Lib/ensurepip/_bundled/setuptools-57.4.0-py3-none-any.whl and b/Lib/ensurepip/_bundled/setuptools-58.1.0-py3-none-any.whl differ
diff --git a/Misc/NEWS.d/next/Library/2021-10-01-23-07-02.bpo-45343.ixmctD.rst b/Misc/NEWS.d/next/Library/2021-10-01-23-07-02.bpo-45343.ixmctD.rst
new file mode 100644
index 00000000000..8dac4e6a252
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2021-10-01-23-07-02.bpo-45343.ixmctD.rst
@@ -0,0 +1 @@
+Update bundled pip to 21.2.4 and setuptools to 58.1.0