diff --git a/.github/workflows/run-tests.yml b/.github/workflows/run-tests.yml
index e7273028cf..cf5f0b4b91 100644
--- a/.github/workflows/run-tests.yml
+++ b/.github/workflows/run-tests.yml
@@ -9,7 +9,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        python-version: [2.7, 3.5, 3.6, 3.7, 3.8, 3.9]
+        python-version: [2.7, 3.6, 3.7, 3.8, 3.9]
         os: [ubuntu-18.04, macOS-latest, windows-latest]
         include:
           # pypy3 on Mac OS currently fails trying to compile
diff --git a/HISTORY.md b/HISTORY.md
index 6a6040c974..fad775a81f 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -24,6 +24,13 @@ dev
 
   Python2 still depends upon the `chardet` module.
 
+**Deprecations**
+
+- The `requests[security]` extra has been converted to a no-op install.
+  PyOpenSSL is no longer the recommended secure option for Requests.
+
+- Requests has officially dropped support for Python 3.5.
+
 2.25.1 (2020-12-16)
 -------------------
 
diff --git a/README.md b/README.md
index 4dd588811a..1372f1fefc 100644
--- a/README.md
+++ b/README.md
@@ -33,7 +33,7 @@ Requests is available on PyPI:
 $ python -m pip install requests
 ```
 
-Requests officially supports Python 2.7 & 3.5+.
+Requests officially supports Python 2.7 & 3.6+.
 
 ## Supported Features & Best–Practices
 
diff --git a/docs/community/faq.rst b/docs/community/faq.rst
index 19732aedac..177eaec4eb 100644
--- a/docs/community/faq.rst
+++ b/docs/community/faq.rst
@@ -55,7 +55,7 @@ Chris Adams gave an excellent summary on
 Python 3 Support?
 -----------------
 
-Yes! Requests officially supports Python 2.7 & 3.5+ and PyPy.
+Yes! Requests officially supports Python 2.7 & 3.6+ and PyPy.
 
 Python 2 Support?
 -----------------
diff --git a/docs/index.rst b/docs/index.rst
index 4f8a9e4d86..49bda6dc2b 100644
--- a/docs/index.rst
+++ b/docs/index.rst
@@ -68,7 +68,7 @@ Requests is ready for today's web.
 - Chunked Requests
 - ``.netrc`` Support
 
-Requests officially supports Python 2.7 & 3.5+, and runs great on PyPy.
+Requests officially supports Python 2.7 & 3.6+, and runs great on PyPy.
 
 
 The User Guide
diff --git a/setup.py b/setup.py
index 1e5ffaa2f0..c2e1d2bcd0 100755
--- a/setup.py
+++ b/setup.py
@@ -91,7 +91,6 @@ def run_tests(self):
         'Programming Language :: Python :: 2',
         'Programming Language :: Python :: 2.7',
         'Programming Language :: Python :: 3',
-        'Programming Language :: Python :: 3.5',
         'Programming Language :: Python :: 3.6',
         'Programming Language :: Python :: 3.7',
         'Programming Language :: Python :: 3.8',
@@ -102,7 +101,7 @@ def run_tests(self):
     cmdclass={'test': PyTest},
     tests_require=test_requirements,
     extras_require={
-        'security': ['pyOpenSSL >= 0.14', 'cryptography>=1.3.4'],
+        'security': [],
         'socks': ['PySocks>=1.5.6, !=1.5.7'],
         'socks:sys_platform == "win32" and python_version == "2.7"': ['win_inet_pton'],
         'use_chardet_on_py3': ['chardet>=3.0.2,<5']
diff --git a/tox.ini b/tox.ini
index c8a63ee476..5e3d53774e 100644
--- a/tox.ini
+++ b/tox.ini
@@ -1,5 +1,5 @@
 [tox]
-envlist = py{27,35,36,37,38}-{default,use_chardet_on_py3}
+envlist = py{27,36,37,38,39}-{default,use_chardet_on_py3}
 
 [testenv]
 deps = -rrequirements-dev.txt