diff --git a/.azure-pipelines/templates/steps/tox-steps.yml b/.azure-pipelines/templates/steps/tox-steps.yml
index a993677b1..e7f3ac70c 100644
--- a/.azure-pipelines/templates/steps/tox-steps.yml
+++ b/.azure-pipelines/templates/steps/tox-steps.yml
@@ -1,3 +1,5 @@
+# This does not include the dependencies needed to build cryptography. See
+# https://cryptography.io/en/latest/installation/
 steps:
   # We run brew update because we've seen attempts to install an older version
   # of a package fail. See
@@ -12,14 +14,8 @@ steps:
       set -e
       sudo apt-get update
       sudo apt-get install -y --no-install-recommends \
-        python3-dev \
-        gcc \
         libaugeas0 \
-        libssl-dev \
-        libffi-dev \
-        ca-certificates \
-        nginx-light \
-        openssl
+        nginx-light
       sudo systemctl stop nginx
       sudo sysctl net.ipv4.ip_unprivileged_port_start=0
     condition: startswith(variables['IMAGE_NAME'], 'ubuntu')
diff --git a/Dockerfile-dev b/Dockerfile-dev
index 895dbdc0b..7c7530305 100644
--- a/Dockerfile-dev
+++ b/Dockerfile-dev
@@ -7,10 +7,11 @@ EXPOSE 80 443
 WORKDIR /opt/certbot/src
 
 COPY . .
+# This does not include the dependencies needed to build cryptography. See
+# https://cryptography.io/en/latest/installation/#building-cryptography-on-linux
 RUN apt-get update && \
-    DEBIAN_FRONTEND=noninteractive apt-get install apache2 git python3-dev \
-        python3-venv gcc libaugeas0 libssl-dev libffi-dev ca-certificates \
-        openssl nginx-light -y --no-install-recommends && \
+    DEBIAN_FRONTEND=noninteractive apt-get install apache2 git python3-venv \
+        libaugeas0 nginx-light -y --no-install-recommends && \
     apt-get clean && \
     rm -rf /var/lib/apt/lists/* \
            /tmp/* \
diff --git a/certbot-ci/certbot_integration_tests/utils/pebble_ocsp_server.py b/certbot-ci/certbot_integration_tests/utils/pebble_ocsp_server.py
index 1749b03da..72520bd8b 100755
--- a/certbot-ci/certbot_integration_tests/utils/pebble_ocsp_server.py
+++ b/certbot-ci/certbot_integration_tests/utils/pebble_ocsp_server.py
@@ -37,7 +37,9 @@ class _ProxyHandler(BaseHTTPServer.BaseHTTPRequestHandler):
                                verify=False, timeout=10)
         issuer_cert = x509.load_pem_x509_certificate(request.content, default_backend())
 
-        content_len = int(self.headers.get('Content-Length'))
+        raw_content_len = self.headers.get('Content-Length')
+        assert isinstance(raw_content_len, str)
+        content_len = int(raw_content_len)
 
         ocsp_request = ocsp.load_der_ocsp_request(self.rfile.read(content_len))
         response = requests.get('{0}/cert-status-by-serial/{1}'.format(
diff --git a/certbot-compatibility-test/Dockerfile b/certbot-compatibility-test/Dockerfile
index 646f2c99e..0dfeddcff 100644
--- a/certbot-compatibility-test/Dockerfile
+++ b/certbot-compatibility-test/Dockerfile
@@ -1,9 +1,10 @@
 FROM debian:buster
 MAINTAINER Brad Warren <bmw@eff.org>
 
+# This does not include the dependencies needed to build cryptography. See
+# https://cryptography.io/en/latest/installation/#building-cryptography-on-linux
 RUN apt-get update && \
-    apt install python3-dev python3-venv gcc libaugeas0 libssl-dev \
-                 libffi-dev ca-certificates openssl -y
+    apt install python3-venv libaugeas0 -y
 
 WORKDIR /opt/certbot/src
 
diff --git a/certbot/certbot/compat/filesystem.py b/certbot/certbot/compat/filesystem.py
index b975f95b5..13fc44098 100644
--- a/certbot/certbot/compat/filesystem.py
+++ b/certbot/certbot/compat/filesystem.py
@@ -274,9 +274,9 @@ def open(file_path: str, flags: int, mode: int = 0o777) -> int:  # pylint: disab
         return os.open(file_path, flags ^ os.O_CREAT ^ os.O_EXCL)
 
     # Windows: general case, we call os.open, let exceptions be thrown, then chmod if all is fine.
-    handle = os.open(file_path, flags)
+    fd = os.open(file_path, flags)
     chmod(file_path, mode)
-    return handle
+    return fd
 
 
 def makedirs(file_path: str, mode: int = 0o777) -> None:
diff --git a/certbot/docs/contributing.rst b/certbot/docs/contributing.rst
index d16884da2..532f6df6c 100644
--- a/certbot/docs/contributing.rst
+++ b/certbot/docs/contributing.rst
@@ -41,13 +41,11 @@ Install and configure the OS system dependencies required to run Certbot.
 
    # For APT-based distributions (e.g. Debian, Ubuntu ...)
    sudo apt update
-   sudo apt install python3-dev python3-venv gcc libaugeas0 libssl-dev \
-                    libffi-dev ca-certificates openssl
+   sudo apt install python3-venv libaugeas0
    # For RPM-based distributions (e.g. Fedora, CentOS ...)
    # NB1: old distributions will use yum instead of dnf
-   # NB2: RHEL-based distributions use python3X-devel instead of python3-devel (e.g. python36-devel)
-   sudo dnf install python3-devel gcc augeas-libs openssl-devel libffi-devel \
-                    redhat-rpm-config ca-certificates openssl
+   # NB2: RHEL-based distributions use python3X instead of python3 (e.g. python38)
+   sudo dnf install python3 augeas-libs
    # For macOS installations with Homebrew already installed and configured
    # NB: If you also run `brew install python` you don't need the ~/lib
    #     directory created below, however, Certbot's Apache plugin won't work
@@ -57,6 +55,12 @@ Install and configure the OS system dependencies required to run Certbot.
    mkdir ~/lib
    ln -s $(brew --prefix)/lib/libaugeas* ~/lib
 
+.. note:: If you have trouble creating the virtual environment below, you may
+   need to install additional dependencies. See the `cryptography project's
+   site`_ for more information.
+
+.. _`cryptography project's site`: https://cryptography.io/en/latest/installation.html#building-cryptography-on-linux
+
 Set up the Python virtual environment that will host your Certbot local instance.
 
 .. code-block:: shell
diff --git a/certbot/setup.py b/certbot/setup.py
index 0ab157d94..2e60c30a7 100644
--- a/certbot/setup.py
+++ b/certbot/setup.py
@@ -95,9 +95,11 @@ test_extras = [
     'pytest-xdist',
     'setuptools',
     'tox',
+    'types-httplib2',
     'types-pyOpenSSL',
     'types-pyRFC3339',
     'types-pytz',
+    'types-pywin32',
     'types-requests',
     'types-setuptools',
     'types-six',
diff --git a/letstest/scripts/bootstrap_os_packages.sh b/letstest/scripts/bootstrap_os_packages.sh
index fbdca71e5..84cd2df30 100755
--- a/letstest/scripts/bootstrap_os_packages.sh
+++ b/letstest/scripts/bootstrap_os_packages.sh
@@ -1,6 +1,9 @@
 #!/bin/sh
 #
 # Install OS dependencies for test farm tests.
+#
+# This does not include the dependencies needed to build cryptography. See
+# https://cryptography.io/en/latest/installation/#building-cryptography-on-linux
 
 set -ex  # Work even if somebody does "sh thisscript.sh".
 
diff --git a/snap/snapcraft.yaml b/snap/snapcraft.yaml
index 88a884c6d..5fdde3124 100644
--- a/snap/snapcraft.yaml
+++ b/snap/snapcraft.yaml
@@ -79,6 +79,7 @@ parts:
       - libffi-dev
       - python3-dev
       - cargo
+      - pkg-config
     build-environment:
       # We set this environment variable while building to try and increase the
       # stability of fetching the rust crates needed to build the cryptography
diff --git a/tools/docker/Dockerfile b/tools/docker/Dockerfile
index be995f3a1..029640ab8 100644
--- a/tools/docker/Dockerfile
+++ b/tools/docker/Dockerfile
@@ -34,6 +34,7 @@ RUN apk add --no-cache --virtual .build-deps \
         python3-dev \
         cargo \
         git \
+        pkgconfig \
     && python tools/pip_install.py --no-cache-dir \
             --editable src/acme \
             --editable src/certbot \
diff --git a/tools/pinning/current/pyproject.toml b/tools/pinning/current/pyproject.toml
index 20cc75a73..dd5b68c0b 100644
--- a/tools/pinning/current/pyproject.toml
+++ b/tools/pinning/current/pyproject.toml
@@ -66,6 +66,11 @@ cryptography = "!= 37.0.3"
 # https://github.com/python-poetry/poetry-plugin-export/issues/168 is resolved.
 poetry = "<1.3.0"
 
+# setuptools 67.5.0 deprecated pkg_resources which we still use. Let's pin it
+# back until this is fixed. Doing this work is being tracked by
+# https://github.com/certbot/certbot/issues/9606.
+setuptools = "<67.5.0"
+
 [tool.poetry.dev-dependencies]
 
 [build-system]
diff --git a/tools/requirements.txt b/tools/requirements.txt
index 45db89e65..27e95b6e7 100644
--- a/tools/requirements.txt
+++ b/tools/requirements.txt
@@ -11,55 +11,55 @@ appnope==0.1.3 ; python_version >= "3.7" and python_version < "4.0" and sys_plat
 astroid==2.13.5 ; python_full_version >= "3.7.2" and python_version < "4.0"
 attrs==22.2.0 ; python_version >= "3.7" and python_version < "4.0"
 azure-devops==6.0.0b4 ; python_version >= "3.7" and python_version < "4.0"
-babel==2.11.0 ; python_version >= "3.7" and python_version < "4.0"
+babel==2.12.1 ; python_version >= "3.7" and python_version < "4.0"
 backcall==0.2.0 ; python_version >= "3.7" and python_version < "4.0"
 backports-cached-property==1.0.2 ; python_version >= "3.7" and python_version < "3.8"
 bcrypt==4.0.1 ; python_version >= "3.7" and python_version < "4.0"
-beautifulsoup4==4.11.2 ; python_version >= "3.7" and python_version < "4.0"
+beautifulsoup4==4.12.0 ; python_version >= "3.7" and python_version < "4.0"
 bleach==6.0.0 ; python_version >= "3.7" and python_version < "4.0"
-boto3==1.26.65 ; python_version >= "3.7" and python_version < "4.0"
-botocore==1.29.65 ; python_version >= "3.7" and python_version < "4.0"
+boto3==1.26.105 ; python_version >= "3.7" and python_version < "4.0"
+botocore==1.29.105 ; python_version >= "3.7" and python_version < "4.0"
 cachecontrol==0.12.11 ; python_version >= "3.7" and python_version < "4.0"
 cachetools==5.3.0 ; python_version >= "3.7" and python_version < "4.0"
 cachy==0.3.0 ; python_version >= "3.7" and python_version < "4.0"
 certifi==2022.12.7 ; python_version >= "3.7" and python_version < "4"
 cffi==1.15.1 ; python_version >= "3.7" and python_version < "4.0"
-charset-normalizer==3.0.1 ; python_version >= "3.7" and python_version < "4"
+charset-normalizer==3.1.0 ; python_version >= "3.7" and python_version < "4"
 cleo==1.0.0a5 ; python_version >= "3.7" and python_version < "4.0"
 cloudflare==2.11.1 ; python_version >= "3.7" and python_version < "4.0"
 colorama==0.4.6 ; python_version < "4.0" and sys_platform == "win32" and python_version >= "3.7" or python_version >= "3.7" and python_version < "4.0" and platform_system == "Windows"
 configargparse==1.5.3 ; python_version >= "3.7" and python_version < "4.0"
 configobj==5.0.8 ; python_version >= "3.7" and python_version < "4.0"
-coverage==7.1.0 ; python_version >= "3.7" and python_version < "4.0"
+coverage==7.2.2 ; python_version >= "3.7" and python_version < "4.0"
 crashtest==0.3.1 ; python_version >= "3.7" and python_version < "4.0"
-cryptography==39.0.1 ; python_version >= "3.7" and python_version < "4.0"
-cython==0.29.33 ; python_version >= "3.7" and python_version < "4.0"
+cryptography==40.0.1 ; python_version >= "3.7" and python_version < "4.0"
+cython==0.29.34 ; python_version >= "3.7" and python_version < "4.0"
 decorator==5.1.1 ; python_version >= "3.7" and python_version < "4.0"
 dill==0.3.6 ; python_full_version >= "3.7.2" and python_version < "4.0"
 distlib==0.3.6 ; python_version >= "3.7" and python_version < "4.0"
 distro==1.8.0 ; python_version >= "3.7" and python_version < "4.0"
 dns-lexicon==3.11.7 ; python_version >= "3.7" and python_version < "4.0"
 dnspython==2.3.0 ; python_version >= "3.7" and python_version < "4.0"
-docutils==0.17.1 ; python_version >= "3.7" and python_version < "4.0"
+docutils==0.18.1 ; python_version >= "3.7" and python_version < "4.0"
 dulwich==0.20.50 ; python_version >= "3.7" and python_version < "4.0"
-exceptiongroup==1.1.0 ; python_version >= "3.7" and python_version < "3.11"
+exceptiongroup==1.1.1 ; python_version >= "3.7" and python_version < "3.11"
 execnet==1.9.0 ; python_version >= "3.7" and python_version < "4.0"
 fabric==3.0.0 ; python_version >= "3.7" and python_version < "4.0"
-filelock==3.9.0 ; python_version >= "3.7" and python_version < "4.0"
+filelock==3.10.7 ; python_version >= "3.7" and python_version < "4.0"
 google-api-core==2.11.0 ; python_version >= "3.7" and python_version < "4.0"
-google-api-python-client==2.77.0 ; python_version >= "3.7" and python_version < "4.0"
+google-api-python-client==2.83.0 ; python_version >= "3.7" and python_version < "4.0"
 google-auth-httplib2==0.1.0 ; python_version >= "3.7" and python_version < "4.0"
-google-auth==2.16.0 ; python_version >= "3.7" and python_version < "4.0"
-googleapis-common-protos==1.58.0 ; python_version >= "3.7" and python_version < "4.0"
+google-auth==2.17.1 ; python_version >= "3.7" and python_version < "4.0"
+googleapis-common-protos==1.59.0 ; python_version >= "3.7" and python_version < "4.0"
 html5lib==1.1 ; python_version >= "3.7" and python_version < "4.0"
-httplib2==0.21.0 ; python_version >= "3.7" and python_version < "4.0"
+httplib2==0.22.0 ; python_version >= "3.7" and python_version < "4.0"
 idna==3.4 ; python_version >= "3.7" and python_version < "4"
 imagesize==1.4.1 ; python_version >= "3.7" and python_version < "4.0"
 importlib-metadata==4.13.0 ; python_version >= "3.7" and python_version < "4.0"
-importlib-resources==5.10.2 ; python_version >= "3.7" and python_version < "3.9"
+importlib-resources==5.12.0 ; python_version >= "3.7" and python_version < "3.9"
 iniconfig==2.0.0 ; python_version >= "3.7" and python_version < "4.0"
 invoke==2.0.0 ; python_version >= "3.7" and python_version < "4.0"
-ipdb==0.13.11 ; python_version >= "3.7" and python_version < "4.0"
+ipdb==0.13.13 ; python_version >= "3.7" and python_version < "4.0"
 ipython==7.34.0 ; python_version >= "3.7" and python_version < "4.0"
 isodate==0.6.1 ; python_version >= "3.7" and python_version < "4.0"
 isort==5.11.5 ; python_full_version >= "3.7.2" and python_version < "4.0"
@@ -75,25 +75,25 @@ jsonschema==4.17.3 ; python_version >= "3.7" and python_version < "4.0"
 keyring==23.13.1 ; python_version >= "3.7" and python_version < "4.0"
 lazy-object-proxy==1.9.0 ; python_full_version >= "3.7.2" and python_version < "4.0"
 lockfile==0.12.2 ; python_version >= "3.7" and python_version < "4.0"
-markdown-it-py==2.1.0 ; python_version >= "3.7" and python_version < "4.0"
+markdown-it-py==2.2.0 ; python_version >= "3.7" and python_version < "4.0"
 markupsafe==2.1.2 ; python_version >= "3.7" and python_version < "4.0"
 matplotlib-inline==0.1.6 ; python_version >= "3.7" and python_version < "4.0"
 mccabe==0.7.0 ; python_full_version >= "3.7.2" and python_version < "4.0"
 mdurl==0.1.2 ; python_version >= "3.7" and python_version < "4.0"
-more-itertools==9.0.0 ; python_version >= "3.7" and python_version < "4.0"
-msgpack==1.0.4 ; python_version >= "3.7" and python_version < "4.0"
+more-itertools==9.1.0 ; python_version >= "3.7" and python_version < "4.0"
+msgpack==1.0.5 ; python_version >= "3.7" and python_version < "4.0"
 msrest==0.6.21 ; python_version >= "3.7" and python_version < "4.0"
 mypy-extensions==1.0.0 ; python_version >= "3.7" and python_version < "4.0"
-mypy==1.0.0 ; python_version >= "3.7" and python_version < "4.0"
+mypy==1.1.1 ; python_version >= "3.7" and python_version < "4.0"
 oauth2client==4.1.3 ; python_version >= "3.7" and python_version < "4.0"
 oauthlib==3.2.2 ; python_version >= "3.7" and python_version < "4.0"
 packaging==23.0 ; python_version >= "3.7" and python_version < "4.0"
-paramiko==3.0.0 ; python_version >= "3.7" and python_version < "4.0"
+paramiko==3.1.0 ; python_version >= "3.7" and python_version < "4.0"
 parsedatetime==2.6 ; python_version >= "3.7" and python_version < "4.0"
 parso==0.8.3 ; python_version >= "3.7" and python_version < "4.0"
 pexpect==4.8.0 ; python_version >= "3.7" and python_version < "4.0"
 pickleshare==0.7.5 ; python_version >= "3.7" and python_version < "4.0"
-pip==23.0 ; python_version >= "3.7" and python_version < "4.0"
+pip==23.0.1 ; python_version >= "3.7" and python_version < "4.0"
 pkginfo==1.9.6 ; python_version >= "3.7" and python_version < "4.0"
 pkgutil-resolve-name==1.3.10 ; python_version >= "3.7" and python_version < "3.9"
 platformdirs==2.6.2 ; python_version < "4.0" and python_version >= "3.7"
@@ -102,8 +102,8 @@ ply==3.11 ; python_version >= "3.7" and python_version < "4.0"
 poetry-core==1.3.2 ; python_version >= "3.7" and python_version < "4.0"
 poetry-plugin-export==1.2.0 ; python_version >= "3.7" and python_version < "4.0"
 poetry==1.2.2 ; python_version >= "3.7" and python_version < "4.0"
-prompt-toolkit==3.0.36 ; python_version >= "3.7" and python_version < "4.0"
-protobuf==4.21.12 ; python_version >= "3.7" and python_version < "4.0"
+prompt-toolkit==3.0.38 ; python_version >= "3.7" and python_version < "4.0"
+protobuf==4.22.1 ; python_version >= "3.7" and python_version < "4.0"
 ptyprocess==0.7.0 ; python_version >= "3.7" and python_version < "4.0"
 py==1.11.0 ; python_version >= "3.7" and python_version < "4.0"
 pyasn1-modules==0.2.8 ; python_version >= "3.7" and python_version < "4.0"
@@ -114,19 +114,19 @@ pylev==1.4.0 ; python_version >= "3.7" and python_version < "4.0"
 pylint==2.15.5 ; python_full_version >= "3.7.2" and python_version < "4.0"
 pynacl==1.5.0 ; python_version >= "3.7" and python_version < "4.0"
 pynsist==2.7 ; python_version >= "3.7" and python_version < "4.0"
-pyopenssl==23.0.0 ; python_version >= "3.7" and python_version < "4.0"
+pyopenssl==23.1.1 ; python_version >= "3.7" and python_version < "4.0"
 pyparsing==3.0.9 ; python_version >= "3.7" and python_version < "4.0"
 pyrfc3339==1.1 ; python_version >= "3.7" and python_version < "4.0"
 pyrsistent==0.19.3 ; python_version >= "3.7" and python_version < "4.0"
 pytest-cov==4.0.0 ; python_version >= "3.7" and python_version < "4.0"
-pytest-xdist==3.2.0 ; python_version >= "3.7" and python_version < "4.0"
-pytest==7.2.1 ; python_version >= "3.7" and python_version < "4.0"
+pytest-xdist==3.2.1 ; python_version >= "3.7" and python_version < "4.0"
+pytest==7.2.2 ; python_version >= "3.7" and python_version < "4.0"
 python-augeas==1.1.0 ; python_version >= "3.7" and python_version < "4.0"
 python-dateutil==2.8.2 ; python_version >= "3.7" and python_version < "4.0"
 python-digitalocean==1.17.0 ; python_version >= "3.7" and python_version < "4.0"
-pytz==2022.7.1 ; python_version >= "3.7" and python_version < "4.0"
+pytz==2023.3 ; python_version >= "3.7" and python_version < "4.0"
 pywin32-ctypes==0.2.0 ; python_version >= "3.7" and python_version < "4.0" and sys_platform == "win32"
-pywin32==305 ; python_version >= "3.7" and python_version < "4.0" and sys_platform == "win32"
+pywin32==306 ; python_version >= "3.7" and python_version < "4.0" and sys_platform == "win32"
 pyyaml==6.0 ; python_version >= "3.7" and python_version < "4.0"
 readme-renderer==37.3 ; python_version >= "3.7" and python_version < "4.0"
 requests-download==0.1.2 ; python_version >= "3.7" and python_version < "4.0"
@@ -135,49 +135,51 @@ requests-oauthlib==1.3.1 ; python_version >= "3.7" and python_version < "4.0"
 requests-toolbelt==0.9.1 ; python_version >= "3.7" and python_version < "4.0"
 requests==2.28.2 ; python_version >= "3.7" and python_version < "4"
 rfc3986==2.0.0 ; python_version >= "3.7" and python_version < "4.0"
-rich==13.3.1 ; python_version >= "3.7" and python_version < "4.0"
+rich==13.3.3 ; python_version >= "3.7" and python_version < "4.0"
 rsa==4.9 ; python_version >= "3.7" and python_version < "4"
 s3transfer==0.6.0 ; python_version >= "3.7" and python_version < "4.0"
 secretstorage==3.3.3 ; python_version >= "3.7" and python_version < "4.0" and sys_platform == "linux"
 semantic-version==2.10.0 ; python_version >= "3.7" and python_version < "4.0"
 setuptools-rust==1.5.2 ; python_version >= "3.7" and python_version < "4.0"
-setuptools==67.2.0 ; python_version >= "3.7" and python_version < "4.0"
+setuptools==67.4.0 ; python_version >= "3.7" and python_version < "4.0"
 shellingham==1.5.0.post1 ; python_version >= "3.7" and python_version < "4.0"
 six==1.16.0 ; python_version >= "3.7" and python_version < "4.0"
 snowballstemmer==2.2.0 ; python_version >= "3.7" and python_version < "4.0"
-soupsieve==2.3.2.post1 ; python_version >= "3.7" and python_version < "4.0"
-sphinx-rtd-theme==1.1.1 ; python_version >= "3.7" and python_version < "4.0"
+soupsieve==2.4 ; python_version >= "3.7" and python_version < "4.0"
+sphinx-rtd-theme==1.2.0 ; python_version >= "3.7" and python_version < "4.0"
 sphinx==5.3.0 ; python_version >= "3.7" and python_version < "4.0"
 sphinxcontrib-applehelp==1.0.2 ; python_version >= "3.7" and python_version < "4.0"
 sphinxcontrib-devhelp==1.0.2 ; python_version >= "3.7" and python_version < "4.0"
 sphinxcontrib-htmlhelp==2.0.0 ; python_version >= "3.7" and python_version < "4.0"
+sphinxcontrib-jquery==4.1 ; python_version >= "3.7" and python_version < "4.0"
 sphinxcontrib-jsmath==1.0.1 ; python_version >= "3.7" and python_version < "4.0"
 sphinxcontrib-qthelp==1.0.3 ; python_version >= "3.7" and python_version < "4.0"
 sphinxcontrib-serializinghtml==1.1.5 ; python_version >= "3.7" and python_version < "4.0"
 tldextract==3.4.0 ; python_version >= "3.7" and python_version < "4.0"
 tomli==2.0.1 ; python_version >= "3.7" and python_full_version <= "3.11.0a6"
-tomlkit==0.11.6 ; python_version < "4.0" and python_version >= "3.7"
+tomlkit==0.11.7 ; python_version < "4.0" and python_version >= "3.7"
 tox==3.28.0 ; python_version >= "3.7" and python_version < "4.0"
 traitlets==5.9.0 ; python_version >= "3.7" and python_version < "4.0"
 twine==4.0.2 ; python_version >= "3.7" and python_version < "4.0"
 typed-ast==1.5.4 ; python_version < "3.8" and python_version >= "3.7"
-types-docutils==0.19.1.3 ; python_version >= "3.7" and python_version < "4.0"
-types-pyopenssl==23.0.0.2 ; python_version >= "3.7" and python_version < "4.0"
-types-pyrfc3339==1.1.1.1 ; python_version >= "3.7" and python_version < "4.0"
-types-python-dateutil==2.8.19.6 ; python_version >= "3.7" and python_version < "4.0"
-types-pytz==2022.7.1.0 ; python_version >= "3.7" and python_version < "4.0"
-types-requests==2.28.11.12 ; python_version >= "3.7" and python_version < "4.0"
-types-setuptools==67.1.0.2 ; python_version >= "3.7" and python_version < "4.0"
-types-six==1.16.21.4 ; python_version >= "3.7" and python_version < "4.0"
-types-urllib3==1.26.25.5 ; python_version >= "3.7" and python_version < "4.0"
-typing-extensions==4.4.0 ; python_version >= "3.7" and python_version < "4.0"
+types-httplib2==0.22.0.1 ; python_version >= "3.7" and python_version < "4.0"
+types-pyopenssl==23.1.0.1 ; python_version >= "3.7" and python_version < "4.0"
+types-pyrfc3339==1.1.1.4 ; python_version >= "3.7" and python_version < "4.0"
+types-python-dateutil==2.8.19.12 ; python_version >= "3.7" and python_version < "4.0"
+types-pytz==2023.3.0.0 ; python_version >= "3.7" and python_version < "4.0"
+types-pywin32==306.0.0.1 ; python_version >= "3.7" and python_version < "4.0"
+types-requests==2.28.11.17 ; python_version >= "3.7" and python_version < "4.0"
+types-setuptools==67.6.0.7 ; python_version >= "3.7" and python_version < "4.0"
+types-six==1.16.21.8 ; python_version >= "3.7" and python_version < "4.0"
+types-urllib3==1.26.25.10 ; python_version >= "3.7" and python_version < "4.0"
+typing-extensions==4.5.0 ; python_version >= "3.7" and python_version < "4.0"
 uritemplate==4.1.1 ; python_version >= "3.7" and python_version < "4.0"
-urllib3==1.26.14 ; python_version >= "3.7" and python_version < "4.0"
-virtualenv==20.18.0 ; python_version >= "3.7" and python_version < "4.0"
+urllib3==1.26.15 ; python_version >= "3.7" and python_version < "4.0"
+virtualenv==20.21.0 ; python_version >= "3.7" and python_version < "4.0"
 wcwidth==0.2.6 ; python_version >= "3.7" and python_version < "4.0"
 webencodings==0.5.1 ; python_version >= "3.7" and python_version < "4.0"
-wheel==0.38.4 ; python_version >= "3.7" and python_version < "4.0"
-wrapt==1.14.1 ; python_full_version >= "3.7.2" and python_version < "4.0"
+wheel==0.40.0 ; python_version >= "3.7" and python_version < "4.0"
+wrapt==1.15.0 ; python_full_version >= "3.7.2" and python_version < "4.0"
 xattr==0.9.9 ; python_version >= "3.7" and python_version < "4.0" and sys_platform == "darwin"
 yarg==0.1.9 ; python_version >= "3.7" and python_version < "4.0"
-zipp==3.12.1 ; python_version >= "3.7" and python_version < "4.0"
+zipp==3.15.0 ; python_version >= "3.7" and python_version < "4.0"
diff --git a/tools/snap/generate_dnsplugins_snapcraft.sh b/tools/snap/generate_dnsplugins_snapcraft.sh
index 43f1b2077..1de5e584d 100755
--- a/tools/snap/generate_dnsplugins_snapcraft.sh
+++ b/tools/snap/generate_dnsplugins_snapcraft.sh
@@ -47,6 +47,7 @@ parts:
       - libffi-dev
       - python3-dev
       - cargo
+      - pkg-config
   certbot-metadata:
     plugin: dump
     source: .