diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index c8db776e..23adde8b 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -13,7 +13,7 @@ concurrency:
 env:
   FORCE_COLOR: "1"
   TOX_TESTENV_PASSENV: "FORCE_COLOR"
-  MIN_PYTHON_VERSION: "3.6"
+  MIN_PYTHON_VERSION: "3.7"
   DEFAULT_PYTHON_VERSION: "3.9"
 
 jobs:
@@ -33,7 +33,6 @@ jobs:
     strategy:
       matrix:
         python-version:
-          - "3.6"
           - "3.7"
           - "3.8"
           - "3.9"
diff --git a/.readthedocs.yaml b/.readthedocs.yaml
index 83c0eeca..981657e0 100644
--- a/.readthedocs.yaml
+++ b/.readthedocs.yaml
@@ -15,7 +15,7 @@ formats:
 
 python:
   # Mininum supported Python version
-  version: "3.6"
+  version: "3.7"
   # Install twine first, because RTD uses `--upgrade-strategy eager`,
   # which installs the latest version of docutils via readme_renderer.
   # However, Sphinx 4.2.0 requires docutils>=0.14,<0.18.
diff --git a/changelog/869.feature.rst b/changelog/869.feature.rst
new file mode 100644
index 00000000..2c165214
--- /dev/null
+++ b/changelog/869.feature.rst
@@ -0,0 +1 @@
+Drop support for Python 3.6.
diff --git a/docs/conf.py b/docs/conf.py
index 1f00d233..f5d6e25b 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -286,7 +286,7 @@
 
 # TODO: Try to add these to intersphinx_mapping
 nitpick_ignore_regex = [
-    (r"py:.*", r"(pkginfo|IO).*"),
+    (r"py:.*", r"pkginfo.*"),
 ]
 
 # -- Options for apidoc output ------------------------------------------------
diff --git a/setup.cfg b/setup.cfg
index 578a846d..19cfe643 100644
--- a/setup.cfg
+++ b/setup.cfg
@@ -23,7 +23,6 @@ classifiers =
     Programming Language :: Python
     Programming Language :: Python :: 3
     Programming Language :: Python :: 3 :: Only
-    Programming Language :: Python :: 3.6
     Programming Language :: Python :: 3.7
     Programming Language :: Python :: 3.8
     Programming Language :: Python :: 3.9
@@ -34,7 +33,7 @@ classifiers =
 packages =
     twine
     twine.commands
-python_requires = >=3.6
+python_requires = >=3.7
 install_requires=
     pkginfo >= 1.8.1
     readme-renderer >= 21.0
diff --git a/tox.ini b/tox.ini
index 12ec03ec..65cba7d2 100644
--- a/tox.ini
+++ b/tox.ini
@@ -1,6 +1,6 @@
 [tox]
 minversion = 3.3
-envlist = lint,types,py{36,37,38,39,310},integration,docs
+envlist = lint,types,py{37,38,39,310},integration,docs
 isolated_build = True
 
 [testenv]
diff --git a/twine/settings.py b/twine/settings.py
index 7ea5d4b1..d93e59b5 100644
--- a/twine/settings.py
+++ b/twine/settings.py
@@ -11,11 +11,13 @@
 # distributed under the License is distributed on an "AS IS" BASIS,
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
+from __future__ import annotations
+
 # limitations under the License.
 import argparse
 import contextlib
 import logging
-from typing import Any, ContextManager, Optional, cast
+from typing import Any, Optional, cast
 
 from twine import auth
 from twine import exceptions
@@ -136,7 +138,7 @@ def password(self) -> Optional[str]:
             # Workaround for https://github.com/python/mypy/issues/5858
             return cast(Optional[str], self.auth.password)
 
-    def _allow_noninteractive(self) -> ContextManager[None]:
+    def _allow_noninteractive(self) -> contextlib.AbstractContextManager[None]:
         """Bypass NonInteractive error when client cert is present."""
         suppressed = (exceptions.NonInteractive,) if self.client_cert else ()
         return contextlib.suppress(*suppressed)