diff --git a/Lib/ensurepip/__init__.py b/Lib/ensurepip/__init__.py
index 45c0981abbddbf..f28ab11ed40082 100644
--- a/Lib/ensurepip/__init__.py
+++ b/Lib/ensurepip/__init__.py
@@ -11,8 +11,8 @@
 
 __all__ = ["version", "bootstrap"]
 _PACKAGE_NAMES = ('setuptools', 'pip')
-_SETUPTOOLS_VERSION = "56.0.0"
-_PIP_VERSION = "21.1.3"
+_SETUPTOOLS_VERSION = "57.4.0"
+_PIP_VERSION = "21.2.3"
 _PROJECTS = [
     ("setuptools", _SETUPTOOLS_VERSION, "py3"),
     ("pip", _PIP_VERSION, "py3"),
diff --git a/Lib/ensurepip/_bundled/pip-21.1.3-py3-none-any.whl b/Lib/ensurepip/_bundled/pip-21.1.3-py3-none-any.whl
deleted file mode 100644
index d96a40a9291fb2..00000000000000
Binary files a/Lib/ensurepip/_bundled/pip-21.1.3-py3-none-any.whl and /dev/null differ
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
new file mode 100644
index 00000000000000..d417df63d9ec19
Binary files /dev/null and b/Lib/ensurepip/_bundled/pip-21.2.3-py3-none-any.whl differ
diff --git a/Lib/ensurepip/_bundled/setuptools-56.0.0-py3-none-any.whl b/Lib/ensurepip/_bundled/setuptools-57.4.0-py3-none-any.whl
similarity index 65%
rename from Lib/ensurepip/_bundled/setuptools-56.0.0-py3-none-any.whl
rename to Lib/ensurepip/_bundled/setuptools-57.4.0-py3-none-any.whl
index 264ef10e826679..af8f8ba21003b1 100644
Binary files a/Lib/ensurepip/_bundled/setuptools-56.0.0-py3-none-any.whl and b/Lib/ensurepip/_bundled/setuptools-57.4.0-py3-none-any.whl differ
diff --git a/Misc/NEWS.d/next/Library/2021-08-06-19-15-52.bpo-44581.oFDBTB.rst b/Misc/NEWS.d/next/Library/2021-08-06-19-15-52.bpo-44581.oFDBTB.rst
new file mode 100644
index 00000000000000..99f08065b9d2f0
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2021-08-06-19-15-52.bpo-44581.oFDBTB.rst
@@ -0,0 +1 @@
+Upgrade bundled pip to 21.2.3 and setuptools to 57.4.0