diff --git a/Lib/ensurepip/__init__.py b/Lib/ensurepip/__init__.py
index ecfaee5640ea98..f3152a55d4430c 100644
--- a/Lib/ensurepip/__init__.py
+++ b/Lib/ensurepip/__init__.py
@@ -9,13 +9,13 @@
 __all__ = ["version", "bootstrap"]
 
 
-_SETUPTOOLS_VERSION = "41.2.0"
+_SETUPTOOLS_VERSION = "47.1.0"
 
-_PIP_VERSION = "19.2.3"
+_PIP_VERSION = "20.1.1"
 
 _PROJECTS = [
-    ("setuptools", _SETUPTOOLS_VERSION),
-    ("pip", _PIP_VERSION),
+    ("setuptools", _SETUPTOOLS_VERSION, "py3"),
+    ("pip", _PIP_VERSION, "py2.py3"),
 ]
 
 
@@ -104,8 +104,8 @@ def _bootstrap(*, root=None, upgrade=False, user=False,
         # Put our bundled wheels into a temporary directory and construct the
         # additional paths that need added to sys.path
         additional_paths = []
-        for project, version in _PROJECTS:
-            wheel_name = "{}-{}-py2.py3-none-any.whl".format(project, version)
+        for project, version, py_tag in _PROJECTS:
+            wheel_name = "{}-{}-{}-none-any.whl".format(project, version, py_tag)
             whl = pkgutil.get_data(
                 "ensurepip",
                 "_bundled/{}".format(wheel_name),
diff --git a/Lib/ensurepip/_bundled/pip-19.2.3-py2.py3-none-any.whl b/Lib/ensurepip/_bundled/pip-19.2.3-py2.py3-none-any.whl
deleted file mode 100644
index 8118df8ac1940f..00000000000000
Binary files a/Lib/ensurepip/_bundled/pip-19.2.3-py2.py3-none-any.whl and /dev/null differ
diff --git a/Lib/ensurepip/_bundled/pip-20.1.1-py2.py3-none-any.whl b/Lib/ensurepip/_bundled/pip-20.1.1-py2.py3-none-any.whl
new file mode 100644
index 00000000000000..ea1d0f7c8604a4
Binary files /dev/null and b/Lib/ensurepip/_bundled/pip-20.1.1-py2.py3-none-any.whl differ
diff --git a/Lib/ensurepip/_bundled/setuptools-41.2.0-py2.py3-none-any.whl b/Lib/ensurepip/_bundled/setuptools-47.1.0-py3-none-any.whl
similarity index 65%
rename from Lib/ensurepip/_bundled/setuptools-41.2.0-py2.py3-none-any.whl
rename to Lib/ensurepip/_bundled/setuptools-47.1.0-py3-none-any.whl
index 82df6f63f4ee97..f87867ff98254a 100644
Binary files a/Lib/ensurepip/_bundled/setuptools-41.2.0-py2.py3-none-any.whl and b/Lib/ensurepip/_bundled/setuptools-47.1.0-py3-none-any.whl differ
diff --git a/Lib/test/test_venv.py b/Lib/test/test_venv.py
index bc4e95f2b1ecb1..7e05138a80dc8a 100644
--- a/Lib/test/test_venv.py
+++ b/Lib/test/test_venv.py
@@ -480,7 +480,7 @@ def do_test_with_pip(self, system_site_packages):
         #    executing pip with sudo, you may want sudo's -H flag."
         # where $HOME is replaced by the HOME environment variable.
         err = re.sub("^(WARNING: )?The directory .* or its parent directory "
-                     "is not owned by the current user .*$", "",
+                     "is not owned or is not writable by the current user.*$", "",
                      err, flags=re.MULTILINE)
         self.assertEqual(err.rstrip(), "")
         # Being fairly specific regarding the expected behaviour for the
diff --git a/Misc/NEWS.d/next/Library/2020-05-28-16-51-00.bpo-38488.hFQNgA.rst b/Misc/NEWS.d/next/Library/2020-05-28-16-51-00.bpo-38488.hFQNgA.rst
new file mode 100644
index 00000000000000..c44da9fecb605b
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2020-05-28-16-51-00.bpo-38488.hFQNgA.rst
@@ -0,0 +1 @@
+Update ensurepip to install pip 20.1.1 and setuptools 47.1.0.