diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index ae532223..ff164f9b 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -21,6 +21,7 @@ jobs:
       matrix:
         os: [ubuntu-latest, macos-latest, windows-latest]
         python-version: [3.6, 3.7, 3.8, 3.9, "3.10.0-rc.2"]
+        pyopenssl: [0, 1]
     runs-on: ${{ matrix.os }}
     steps:
       - uses: actions/checkout@v2
@@ -33,8 +34,12 @@ jobs:
           python -m pip install --upgrade pip wheel
           python -m pip install --upgrade '.[dev]'
           python -m pytest --verbose ./httpie ./tests
+        env:
+          HTTPIE_TEST_WITH_PYOPENSSL: ${{ matrix.pyopenssl }}
       - name: Linux & Mac setup
         if: matrix.os != 'windows-latest'
         run: |
           make install
           make test
+        env:
+          HTTPIE_TEST_WITH_PYOPENSSL: ${{ matrix.pyopenssl }}
diff --git a/setup.py b/setup.py
index acde80a0..22c14212 100644
--- a/setup.py
+++ b/setup.py
@@ -19,6 +19,7 @@ dev_require = [
     'flake8-deprecated',
     'flake8-mutable',
     'flake8-tuple',
+    'pyopenssl',
     'pytest-cov',
     'twine',
     'wheel',
diff --git a/tests/conftest.py b/tests/conftest.py
index ff79ed17..a65df162 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -1,4 +1,6 @@
+import os
 import socket
+
 import pytest
 from pytest_httpbin import certs
 
@@ -41,3 +43,19 @@ def httpbin_with_chunked_support(_httpbin_with_chunked_support_available):
     if _httpbin_with_chunked_support_available:
         return HTTPBIN_WITH_CHUNKED_SUPPORT
     pytest.skip(f'{HTTPBIN_WITH_CHUNKED_SUPPORT_DOMAIN} not resolvable')
+
+
+@pytest.fixture(autouse=True, scope='session')
+def pyopenssl_inject():
+    """
+    Injects `pyOpenSSL` module to make sure `requests` will use it.
+    <https://github.com/psf/requests/pull/5443#issuecomment-645740394>
+    """
+    if os.getenv('HTTPIE_TEST_WITH_PYOPENSSL', '0') == '1':
+        try:
+            import urllib3.contrib.pyopenssl
+            urllib3.contrib.pyopenssl.inject_into_urllib3()
+        except ModuleNotFoundError:
+            pytest.fail('Missing "pyopenssl" module.')
+
+    yield
diff --git a/tests/test_ssl.py b/tests/test_ssl.py
index 7b3807d9..e7192448 100644
--- a/tests/test_ssl.py
+++ b/tests/test_ssl.py
@@ -1,11 +1,14 @@
+import os
+import ssl
+
 import pytest
 import pytest_httpbin.certs
 import requests.exceptions
-import ssl
 import urllib3
 
 from httpie.ssl import AVAILABLE_SSL_VERSION_ARG_MAPPING, DEFAULT_SSL_CIPHERS
 from httpie.status import ExitStatus
+
 from .utils import HTTP_OK, TESTS_ROOT, http
 
 
@@ -17,6 +20,7 @@ try:
     ssl_errors = (
         requests.exceptions.SSLError,
         OpenSSL.SSL.Error,
+        ValueError,  # TODO: Remove with OSS-65
     )
 except ImportError:
     ssl_errors = (
@@ -54,6 +58,8 @@ def test_ssl_version(httpbin_secure, ssl_version):
                 root = root.__context__
             if isinstance(root, ssl.SSLError) and root.reason == "TLSV1_ALERT_PROTOCOL_VERSION":
                 pytest.skip(f'Unsupported TLS version: {ssl_version}')
+        elif 'No such protocol' in str(e):  # TODO: Remove with OSS-65
+            pytest.skip(f'Unsupported TLS version: {ssl_version}')
         else:
             raise
 
@@ -149,3 +155,13 @@ def test_ciphers_none_can_be_selected(httpbin_secure):
     #   <https://marc.info/?l=openbsd-ports&m=159251948515635&w=2>
     #   http: error: Error: [('SSL routines', '(UNKNOWN)SSL_internal', 'no cipher match')]
     assert 'cipher' in r.stderr
+
+
+def test_pyopenssl_presence():
+    using_pyopenssl = os.getenv('HTTPIE_TEST_WITH_PYOPENSSL', '0')
+    if using_pyopenssl == '0':
+        assert not urllib3.util.ssl_.IS_PYOPENSSL
+        assert not urllib3.util.IS_PYOPENSSL
+    else:
+        assert urllib3.util.ssl_.IS_PYOPENSSL
+        assert urllib3.util.IS_PYOPENSSL