diff --git a/README.rst b/README.rst
index 6e6716173..1f6b9affb 100644
--- a/README.rst
+++ b/README.rst
@@ -22,6 +22,17 @@ For more information on setting up your Python development environment, please r
 
 .. _`Python Development Environment Setup Guide`: https://cloud.google.com/python/setup
 
+Extras
+------
+
+google-auth has few extras that you can install. For example::
+
+    $ pip install google-auth[pyopenssl]
+
+Note that the extras pyopenssl and enterprise_cert should not be used together because they use conflicting versions of `cryptography`_.
+
+.. _`cryptography`: https://cryptography.io/en/latest/
+
 Supported Python Versions
 ^^^^^^^^^^^^^^^^^^^^^^^^^
 Python >= 3.6
diff --git a/setup.py b/setup.py
index 1fce9743e..79d31b87c 100644
--- a/setup.py
+++ b/setup.py
@@ -36,7 +36,7 @@
         "aiohttp >= 3.6.2, < 4.0.0dev; python_version>='3.6'",
         "requests >= 2.20.0, < 3.0.0dev",
     ],
-    "pyopenssl": "pyopenssl>=20.0.0",
+    "pyopenssl": ["pyopenssl>=20.0.0", "cryptography>=38.0.3"],
     "reauth": "pyu2f>=0.1.5",
     # Enterprise cert only works for OpenSSL 1.1.1. Newer versions of these
     # dependencies are built with OpenSSL 3.0 so we need to fix the version.
diff --git a/system_tests/secrets.tar.enc b/system_tests/secrets.tar.enc
index abfaddd92..d428e414d 100644
Binary files a/system_tests/secrets.tar.enc and b/system_tests/secrets.tar.enc differ