Merge branch 'master-uptsream' into apache-integration-tests

# Conflicts: # .travis.yml # tox.ini
List support for Python 3.8 (#7392 )
2019-09-25 19:59:54 +02:00 · 2019-09-24 11:38:38 -07:00 · 2019-09-23 17:20:11 -07:00 · 2019-09-23 12:29:18 -07:00 · 2019-09-20 17:21:07 +02:00 · 2019-09-17 15:24:53 -07:00
132 changed files with 2648 additions and 941 deletions
--- a/.codecov.yml
+++ b/.codecov.yml
@@ -6,13 +6,13 @@ coverage:
        flags: linux
        # Fixed target instead of auto set by #7173, can
        # be removed when flags in Codecov are added back.
-        target: 97.5
+        target: 97.4
        threshold: 0.1
        base: auto
      windows:
        flags: windows
        # Fixed target instead of auto set by #7173, can
        # be removed when flags in Codecov are added back.
-        target: 97.6
+        target: 97.7
        threshold: 0.1
        base: auto
--- a/.coveragerc
+++ b/.coveragerc
@@ -1,2 +1,5 @@
+[run]
+omit = */setup.py
+
 [report]
 omit = */setup.py
--- a/.travis.yml
+++ b/.travis.yml
@@ -1,13 +1,26 @@
 language: python
+dist: xenial

 cache:
    directories:
        - $HOME/.cache/pip

 before_script:
+  # Install required apt packages
+  - |
+    if [[ "$TRAVIS_OS_NAME" != "osx" ]]; then
+      ./certbot-auto --non-interactive --os-packages-only
+      sudo -E apt-get -yq --no-install-suggests --no-install-recommends install nginx-light
+      sudo -E /etc/init.d/nginx stop
+      sudo -E apt-get -yq --no-install-suggests --no-install-recommends install apache2
+      sudo -E /etc/init.d/apache2 stop
+      sudo -E chmod 777 -R /var/lib/apache2/module
+    fi
  - 'if [[ "$TRAVIS_OS_NAME" == "osx" ]]; then ulimit -n 1024 ; fi'
  # On Travis, the fastest parallelization for integration tests has proved to be 4.
  - 'if [[ "$TOXENV" == *"integration"* ]]; then export PYTEST_ADDOPTS="--numprocesses 4"; fi'
+  # Use Travis retry feature for farm tests since they are flaky
+  - 'if [[ "$TOXENV" == "travis-test-farm"* ]]; then export TRAVIS_RETRY=travis_retry; fi'
  - export TOX_TESTENV_PASSENV=TRAVIS

 # Only build pushes to the master branch, PRs, and branches beginning with
@@ -37,34 +50,209 @@ matrix:
    # Main test suite
    - python: "2.7"
      env: ACME_SERVER=pebble TOXENV=integration
-      sudo: required
-      services: docker
      <<: *not-on-master
-# container-based infrastructure
-sudo: false

-addons:
-  apt:
-    packages:  # Keep in sync with letsencrypt-auto-source/pieces/bootstrappers/deb_common.sh and Boulder.
-    - python-dev
-    - gcc
-    - libaugeas0
-    - libssl-dev
-    - libffi-dev
-    - ca-certificates
-    # For certbot-nginx integration testing
-    - nginx-light
-    - openssl
+    # This job is always executed, including on master
+    - python: "2.7"
+      env: TOXENV=py27-cover FYI="py27 tests + code coverage"
+
+    - python: "2.7"
+      env: TOXENV=lint
+      <<: *not-on-master
+    - python: "3.4"
+      env: TOXENV=mypy
+      <<: *not-on-master
+    - python: "3.5"
+      env: TOXENV=mypy
+      <<: *not-on-master
+    - python: "2.7"
+      # Ubuntu Trusty or older must be used because the oldest version of
+      # cryptography we support cannot be compiled against the version of
+      # OpenSSL in Xenial or newer.
+      dist: trusty
+      env: TOXENV='py27-{acme,apache,certbot,dns,nginx}-oldest'
+      <<: *not-on-master
+    - python: "3.4"
+      env: TOXENV=py34
+      <<: *not-on-master
+    - python: "3.7"
+      env: TOXENV=py37
+      <<: *not-on-master
+    - python: "3.8-dev"
+      env: TOXENV=py38
+      <<: *not-on-master
+    - env: TOXENV=apache_compat
+      <<: *not-on-master
+    - env: TOXENV=le_auto_xenial
+      <<: *not-on-master
+    - python: "2.7"
+      env: TOXENV=apacheconftest-with-pebble
+      <<: *not-on-master
+    - python: "2.7"
+      env: TOXENV=nginxroundtrip
+      <<: *not-on-master
+
+    # Extended test suite on cron jobs and pushes to tested branches other than master
+    - env: TOXENV=nginx_compat
+      <<: *extended-test-suite
+    - python: "2.7"
+      env:
+        - TOXENV=travis-test-farm-apache2
+        - secure: "f+j/Lj9s1lcuKo5sEFrlRd1kIAMnIJI4z0MTI7QF8jl9Fkmbx7KECGzw31TNgzrOSzxSapHbcueFYvNCLKST+kE/8ogMZBbwqXfEDuKpyF6BY3uYoJn+wPVE5pIb8Hhe08xPte8TTDSMIyHI3EyTfcAKrIreauoArePvh/cRvSw="
+      <<: *extended-test-suite
+    - python: "2.7"
+      env:
+        - TOXENV=travis-test-farm-leauto-upgrades
+        - secure: "f+j/Lj9s1lcuKo5sEFrlRd1kIAMnIJI4z0MTI7QF8jl9Fkmbx7KECGzw31TNgzrOSzxSapHbcueFYvNCLKST+kE/8ogMZBbwqXfEDuKpyF6BY3uYoJn+wPVE5pIb8Hhe08xPte8TTDSMIyHI3EyTfcAKrIreauoArePvh/cRvSw="
+      git:
+        depth: false  # This is needed to have the history to checkout old versions of certbot-auto.
+      <<: *extended-test-suite
+    - python: "2.7"
+      env:
+        - TOXENV=travis-test-farm-certonly-standalone
+        - secure: "f+j/Lj9s1lcuKo5sEFrlRd1kIAMnIJI4z0MTI7QF8jl9Fkmbx7KECGzw31TNgzrOSzxSapHbcueFYvNCLKST+kE/8ogMZBbwqXfEDuKpyF6BY3uYoJn+wPVE5pIb8Hhe08xPte8TTDSMIyHI3EyTfcAKrIreauoArePvh/cRvSw="
+      <<: *extended-test-suite
+    - python: "2.7"
+      env:
+        - TOXENV=travis-test-farm-sdists
+        - secure: "f+j/Lj9s1lcuKo5sEFrlRd1kIAMnIJI4z0MTI7QF8jl9Fkmbx7KECGzw31TNgzrOSzxSapHbcueFYvNCLKST+kE/8ogMZBbwqXfEDuKpyF6BY3uYoJn+wPVE5pIb8Hhe08xPte8TTDSMIyHI3EyTfcAKrIreauoArePvh/cRvSw="
+      <<: *extended-test-suite
+    - python: "3.7"
+      env: TOXENV=py37 CERTBOT_NO_PIN=1
+      <<: *extended-test-suite
+    - python: "2.7"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "2.7"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "2.7"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration-certbot-oldest
+      # Ubuntu Trusty or older must be used because the oldest version of
+      # cryptography we support cannot be compiled against the version of
+      # OpenSSL in Xenial or newer.
+      dist: trusty
+      <<: *extended-test-suite
+    - python: "2.7"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration-certbot-oldest
+      # Ubuntu Trusty or older must be used because the oldest version of
+      # cryptography we support cannot be compiled against the version of
+      # OpenSSL in Xenial or newer.
+      dist: trusty
+      <<: *extended-test-suite
+    - python: "2.7"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration-nginx-oldest
+      # Ubuntu Trusty or older must be used because the oldest version of
+      # cryptography we support cannot be compiled against the version of
+      # OpenSSL in Xenial or newer.
+      dist: trusty
+      <<: *extended-test-suite
+    - python: "2.7"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration-nginx-oldest
+      # Ubuntu Trusty or older must be used because the oldest version of
+      # cryptography we support cannot be compiled against the version of
+      # OpenSSL in Xenial or newer.
+      dist: trusty
+      <<: *extended-test-suite
+    - python: "3.4"
+      env: TOXENV=py34
+      <<: *extended-test-suite
+    - python: "3.5"
+      env: TOXENV=py35
+      <<: *extended-test-suite
+    - python: "3.6"
+      env: TOXENV=py36
+      <<: *extended-test-suite
+    - python: "3.7"
+      env: TOXENV=py37
+      <<: *extended-test-suite
+    - python: "3.8-dev"
+      env: TOXENV=py38
+      <<: *extended-test-suite
+    - python: "3.4"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.4"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.5"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.5"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.6"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.6"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.7"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.7"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.8-dev"
+      env: ACME_SERVER=boulder-v1 TOXENV=integration
+      <<: *extended-test-suite
+    - python: "3.8-dev"
+      env: ACME_SERVER=boulder-v2 TOXENV=integration
+      <<: *extended-test-suite
+    - env: TOXENV=le_auto_jessie
+      <<: *extended-test-suite
+    - env: TOXENV=le_auto_centos6
+      <<: *extended-test-suite
+    - env: TOXENV=docker_dev
+      <<: *extended-test-suite
+    - language: generic
+      env: TOXENV=py27
+      os: osx
+      # Using this osx_image is a workaround for
+      # https://travis-ci.community/t/xcode-8-3-homebrew-outdated-error/3798.
+      osx_image: xcode10.2
+      addons:
+        homebrew:
+          packages:
+            - augeas
+            - python2
+      <<: *extended-test-suite
+    - language: generic
+      env: TOXENV=py3
+      os: osx
+      # Using this osx_image is a workaround for
+      # https://travis-ci.community/t/xcode-8-3-homebrew-outdated-error/3798.
+      osx_image: xcode10.2
+      addons:
+        homebrew:
+          packages:
+            - augeas
+            - python3
+      <<: *extended-test-suite

 # tools/pip_install.py is used to pin packages to a known working version
 # except in tests where the environment variable CERTBOT_NO_PIN is set.
 # virtualenv is listed here explicitly to make sure it is upgraded when
 # CERTBOT_NO_PIN is set to work around failures we've seen when using an older
 # version of virtualenv.
-install: "tools/pip_install.py -U codecov tox virtualenv"
-script: tox
+install: 'tools/pip_install.py -U codecov tox virtualenv'
+# Most of the time TRAVIS_RETRY is an empty string, and has no effect on the
+# script command. It is set only to `travis_retry` during farm tests, in
+# order to trigger the Travis retry feature, and compensate the inherent
+# flakiness of these specific tests.
+script: '$TRAVIS_RETRY tox'

 after_success: '[ "$TOXENV" == "py27-cover" ] && codecov -F linux'

 notifications:
  email: false
+  irc:
+    channels:
+      # This is set to a secure variable to prevent forks from sending
+      # notifications. This value was created by installing
+      # https://github.com/travis-ci/travis.rb and running
+      # `travis encrypt "chat.freenode.net#certbot-devel"`.
+      - secure: "EWW66E2+KVPZyIPR8ViENZwfcup4Gx3/dlimmAZE0WuLwxDCshBBOd3O8Rf6pBokEoZlXM5eDT6XdyJj8n0DLslgjO62pExdunXpbcMwdY7l1ELxX2/UbnDTE6UnPYa09qVBHNG7156Z6yE0x2lH4M9Ykvp0G0cubjPQHylAwo0="
+    on_cancel: never
+    on_success: never
+    on_failure: always
--- a/AUTHORS.md
+++ b/AUTHORS.md
@@ -162,6 +162,7 @@ Authors
 * [Michael Schumacher](https://github.com/schumaml)
 * [Michael Strache](https://github.com/Jarodiv)
 * [Michael Sverdlin](https://github.com/sveder)
+* [Michael Watters](https://github.com/blackknight36)
 * [Michal Moravec](https://github.com/https://github.com/Majkl578)
 * [Michal Papis](https://github.com/mpapis)
 * [Minn Soe](https://github.com/MinnSoe)
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,7 +2,59 @@

 Certbot adheres to [Semantic Versioning](https://semver.org/).

-## 0.37.0 - master
+## 0.39.0 - master
+
+### Added
+
+* Support for Python 3.8 was added to Certbot and all of its components.
+
+### Changed
+
+* Don't send OCSP requests for expired certificates
+
+### Fixed
+
+*
+
+More details about these changes can be found on our GitHub repo.
+
+## 0.38.0 - 2019-09-03
+
+### Added
+
+* Disable session tickets for Nginx users when appropriate.
+
+### Changed
+
+* If Certbot fails to rollback your server configuration, the error message
+  links to the Let's Encrypt forum. Change the link to the Help category now
+  that the Server category has been closed.
+* Replace platform.linux_distribution with distro.linux_distribution as a step
+  towards Python 3.8 support in Certbot.
+
+### Fixed
+
+* Fixed OS detection in the Apache plugin on Scientific Linux.
+
+More details about these changes can be found on our GitHub repo.
+
+## 0.37.2 - 2019-08-21
+
+* Stop disabling TLS session tickets in Nginx as it caused TLS failures on
+  some systems.
+
+More details about these changes can be found on our GitHub repo.
+
+## 0.37.1 - 2019-08-08
+
+### Fixed
+
+* Stop disabling TLS session tickets in Apache as it caused TLS failures on
+  some systems.
+
+More details about these changes can be found on our GitHub repo.
+
+## 0.37.0 - 2019-08-07

 ### Added

@@ -11,11 +63,12 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).

 ### Changed

-*
+* Follow updated Mozilla recommendations for Nginx ssl_protocols, ssl_ciphers,
+  and ssl_prefer_server_ciphers

 ### Fixed

-*
+* Fix certbot-auto failures on RHEL 8.

 More details about these changes can be found on our GitHub repo.

--- a/acme/setup.py
+++ b/acme/setup.py
@@ -3,7 +3,7 @@ from setuptools import find_packages
 from setuptools.command.test import test as TestCommand
 import sys

-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Please update tox.ini when modifying dependency version requirements
 install_requires = [
@@ -73,6 +73,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
    ],
--- a/appveyor.yml
+++ b/appveyor.yml
@@ -4,6 +4,7 @@ environment:
  matrix:
    - TOXENV: py35
    - TOXENV: py37-cover
+    - TOXENV: integration-certbot

 branches:
  only:
@@ -24,14 +25,16 @@ init:

 install:
  # Use Python 3.7 by default
-  - "SET PATH=C:\\Python37;C:\\Python37\\Scripts;%PATH%"
+  - SET PATH=C:\\Python37;C:\\Python37\\Scripts;%PATH%
+  # Using 4 processes is proven to be the most efficient integration tests config for AppVeyor
+  - IF %TOXENV%==integration-certbot SET PYTEST_ADDOPTS=--numprocesses=4
  # Check env
-  - "python --version"
+  - python --version
  # Upgrade pip to avoid warnings
-  - "python -m pip install --upgrade pip"
+  - python -m pip install --upgrade pip
  # Ready to install tox and coverage
  # tools/pip_install.py is used to pin packages to a known working version.
-  - "python tools\\pip_install.py tox codecov"
+  - python tools\\pip_install.py tox codecov

 build: off

--- a/certbot-apache/MANIFEST.in
+++ b/certbot-apache/MANIFEST.in
@@ -5,4 +5,3 @@ recursive-include certbot_apache/tests/testdata *
 include certbot_apache/centos-options-ssl-apache.conf
 include certbot_apache/options-ssl-apache.conf
 recursive-include certbot_apache/augeas_lens *.aug
-recursive-include certbot_apache/tls_configs *.conf
--- a/certbot-apache/certbot_apache/apache_util.py
+++ b/certbot-apache/certbot_apache/apache_util.py
@@ -1,8 +1,6 @@
 """ Utility functions for certbot-apache plugin """
 import binascii

-import pkg_resources
-
 from certbot import util
 from certbot.compat import os

@@ -107,15 +105,3 @@ def parse_define_file(filepath, varname):
 def unique_id():
    """ Returns an unique id to be used as a VirtualHost identifier"""
    return binascii.hexlify(os.urandom(16)).decode("utf-8")
-
-
-def find_ssl_apache_conf(prefix):
-    """
-    Find a TLS Apache config file in the dedicated storage.
-    :param str prefix: prefix of the TLS Apache config file to find
-    :return: the path the TLS Apache config file
-    :rtype: str
-    """
-    return pkg_resources.resource_filename(
-        "certbot_apache",
-        os.path.join("tls_configs", "{0}-options-ssl-apache.conf".format(prefix)))
--- a/certbot-apache/certbot_apache/tls_configs/centos-current-options-ssl-apache.conf
+++ b/certbot-apache/certbot_apache/tls_configs/centos-current-options-ssl-apache.conf
@@ -10,10 +10,16 @@ SSLEngine on
 SSLProtocol             all -SSLv2 -SSLv3
 SSLCipherSuite          ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS
 SSLHonorCipherOrder     on
-SSLSessionTickets       off

 SSLOptions +StrictRequire

 # Add vhost name to log entries:
 LogFormat "%h %l %u %t \"%r\" %>s %b \"%{Referer}i\" \"%{User-agent}i\"" vhost_combined
 LogFormat "%v %h %l %u %t \"%r\" %>s %b" vhost_common
+
+#CustomLog /var/log/apache2/access.log vhost_combined
+#LogLevel warn
+#ErrorLog /var/log/apache2/error.log
+
+# Always ensure Cookies have "Secure" set (JAH 2012/1)
+#Header edit Set-Cookie (?i)^(.*)(;\s*secure)??((\s*;)?(.*)) "$1; Secure$3$4"
--- a/certbot-apache/certbot_apache/configurator.py
+++ b/certbot-apache/certbot_apache/configurator.py
@@ -9,6 +9,7 @@ import time

 from collections import defaultdict

+import pkg_resources
 import six

 import zope.component
@@ -109,24 +110,14 @@ class ApacheConfigurator(common.Installer):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/apache2",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "options-ssl-apache.conf")
    )

    def option(self, key):
        """Get a value from options"""
        return self.options.get(key)

-    def pick_apache_config(self):
-        """
-        Pick the appropriate TLS Apache configuration file for current version of Apache and OS.
-        :return: the path to the TLS Apache configuration file to use
-        :rtype: str
-        """
-        # Disabling TLS session tickets is supported by Apache 2.4.11+.
-        # So for old versions of Apache we pick a configuration without this option.
-        if self.version < (2, 4, 11):
-            return apache_util.find_ssl_apache_conf("old")
-        return apache_util.find_ssl_apache_conf("current")
-
    def _prepare_options(self):
        """
        Set the values possibly changed by command line parameters to
@@ -2348,9 +2339,8 @@ class ApacheConfigurator(common.Installer):
        # XXX if we ever try to enforce a local privilege boundary (eg, running
        # certbot for unprivileged users via setuid), this function will need
        # to be modified.
-        apache_config_path = self.pick_apache_config()
-        return common.install_version_controlled_file(
-            options_ssl, options_ssl_digest, apache_config_path, constants.ALL_SSL_OPTIONS_HASHES)
+        return common.install_version_controlled_file(options_ssl, options_ssl_digest,
+            self.option("MOD_SSL_CONF_SRC"), constants.ALL_SSL_OPTIONS_HASHES)

    def enable_autohsts(self, _unused_lineage, domains):
        """
--- a/certbot-apache/certbot_apache/entrypoint.py
+++ b/certbot-apache/certbot_apache/entrypoint.py
@@ -31,6 +31,8 @@ OVERRIDE_CLASSES = {
    "gentoo base system": override_gentoo.GentooConfigurator,
    "opensuse": override_suse.OpenSUSEConfigurator,
    "suse": override_suse.OpenSUSEConfigurator,
+    "scientific": override_centos.CentOSConfigurator,
+    "scientific linux": override_centos.CentOSConfigurator,
 }


--- a/certbot-apache/certbot_apache/tls_configs/current-options-ssl-apache.conf
+++ b/certbot-apache/certbot_apache/tls_configs/current-options-ssl-apache.conf
@@ -11,10 +11,16 @@ SSLProtocol             all -SSLv2 -SSLv3
 SSLCipherSuite          ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS
 SSLHonorCipherOrder     on
 SSLCompression          off
-SSLSessionTickets       off

 SSLOptions +StrictRequire

 # Add vhost name to log entries:
 LogFormat "%h %l %u %t \"%r\" %>s %b \"%{Referer}i\" \"%{User-agent}i\"" vhost_combined
 LogFormat "%v %h %l %u %t \"%r\" %>s %b" vhost_common
+
+#CustomLog /var/log/apache2/access.log vhost_combined
+#LogLevel warn
+#ErrorLog /var/log/apache2/error.log
+
+# Always ensure Cookies have "Secure" set (JAH 2012/1)
+#Header edit Set-Cookie (?i)^(.*)(;\s*secure)??((\s*;)?(.*)) "$1; Secure$3$4"
--- a/certbot-apache/certbot_apache/override_arch.py
+++ b/certbot-apache/certbot_apache/override_arch.py
@@ -1,4 +1,6 @@
 """ Distribution specific override class for Arch Linux """
+import pkg_resources
+
 import zope.interface

 from certbot import interfaces
@@ -24,4 +26,6 @@ class ArchConfigurator(configurator.ApacheConfigurator):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/httpd/conf",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "options-ssl-apache.conf")
    )
--- a/certbot-apache/certbot_apache/override_centos.py
+++ b/certbot-apache/certbot_apache/override_centos.py
@@ -1,6 +1,7 @@
 """ Distribution specific override class for CentOS family (RHEL, Fedora) """
 import logging

+import pkg_resources
 import zope.interface

 from certbot import errors
@@ -38,6 +39,8 @@ class CentOSConfigurator(configurator.ApacheConfigurator):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/httpd/conf.d",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "centos-options-ssl-apache.conf")
    )

    def config_test(self):
@@ -72,18 +75,6 @@ class CentOSConfigurator(configurator.ApacheConfigurator):
        # Finish with actual config check to see if systemctl restart helped
        super(CentOSConfigurator, self).config_test()

-    def pick_apache_config(self):
-        """
-        Pick the appropriate TLS Apache configuration file for current version of Apache and OS.
-        :return: the path to the TLS Apache configuration file to use
-        :rtype: str
-        """
-        # Disabling TLS session tickets is supported by Apache 2.4.11+.
-        # So for old versions of Apache we pick a configuration without this option.
-        if self.version < (2, 4, 11):
-            return apache_util.find_ssl_apache_conf("centos-old")
-        return apache_util.find_ssl_apache_conf("centos-current")
-
    def _prepare_options(self):
        """
        Override the options dictionary initialization in order to support
--- a/certbot-apache/certbot_apache/override_darwin.py
+++ b/certbot-apache/certbot_apache/override_darwin.py
@@ -1,4 +1,6 @@
 """ Distribution specific override class for macOS """
+import pkg_resources
+
 import zope.interface

 from certbot import interfaces
@@ -24,4 +26,6 @@ class DarwinConfigurator(configurator.ApacheConfigurator):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/apache2/other",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "options-ssl-apache.conf")
    )
--- a/certbot-apache/certbot_apache/override_debian.py
+++ b/certbot-apache/certbot_apache/override_debian.py
@@ -1,6 +1,7 @@
 """ Distribution specific override class for Debian family (Ubuntu/Debian) """
 import logging

+import pkg_resources
 import zope.interface

 from certbot import errors
@@ -34,6 +35,8 @@ class DebianConfigurator(configurator.ApacheConfigurator):
        handle_modules=True,
        handle_sites=True,
        challenge_location="/etc/apache2",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "options-ssl-apache.conf")
    )

    def enable_site(self, vhost):
--- a/certbot-apache/certbot_apache/override_fedora.py
+++ b/certbot-apache/certbot_apache/override_fedora.py
@@ -1,4 +1,5 @@
 """ Distribution specific override class for Fedora 29+ """
+import pkg_resources
 import zope.interface

 from certbot import errors
@@ -30,6 +31,9 @@ class FedoraConfigurator(configurator.ApacheConfigurator):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/httpd/conf.d",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            # TODO: eventually newest version of Fedora will need their own config
+            "certbot_apache", "centos-options-ssl-apache.conf")
    )

    def config_test(self):
--- a/certbot-apache/certbot_apache/override_gentoo.py
+++ b/certbot-apache/certbot_apache/override_gentoo.py
@@ -1,4 +1,6 @@
 """ Distribution specific override class for Gentoo Linux """
+import pkg_resources
+
 import zope.interface

 from certbot import interfaces
@@ -27,6 +29,8 @@ class GentooConfigurator(configurator.ApacheConfigurator):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/apache2/vhosts.d",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "options-ssl-apache.conf")
    )

    def _prepare_options(self):
--- a/certbot-apache/certbot_apache/override_suse.py
+++ b/certbot-apache/certbot_apache/override_suse.py
@@ -1,4 +1,6 @@
 """ Distribution specific override class for OpenSUSE """
+import pkg_resources
+
 import zope.interface

 from certbot import interfaces
@@ -24,4 +26,6 @@ class OpenSUSEConfigurator(configurator.ApacheConfigurator):
        handle_modules=False,
        handle_sites=False,
        challenge_location="/etc/apache2/vhosts.d",
+        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
+            "certbot_apache", "options-ssl-apache.conf")
    )
--- a/certbot-apache/certbot_apache/tests/centos_test.py
+++ b/certbot-apache/certbot_apache/tests/centos_test.py
@@ -190,13 +190,6 @@ class MultipleVhostsTestCentOS(util.ApacheTest):
                                       errors.SubprocessError]
        self.assertRaises(errors.MisconfigurationError, self.config.restart)

-    def test_pick_correct_tls_config(self):
-        self.config.version = (2, 4, 10)
-        self.assertTrue('centos-old' in self.config.pick_apache_config())
-
-        self.config.version = (2, 4, 11)
-        self.assertTrue('centos-current' in self.config.pick_apache_config())
-

 if __name__ == "__main__":
    unittest.main()  # pragma: no cover
--- a/certbot-apache/certbot_apache/tests/configurator_test.py
+++ b/certbot-apache/certbot_apache/tests/configurator_test.py
@@ -1706,7 +1706,7 @@ class InstallSslOptionsConfTest(util.ApacheTest):
                                             self.config.updated_mod_ssl_conf_digest)

    def _current_ssl_options_hash(self):
-        return crypto_util.sha256sum(self.config.pick_apache_config())
+        return crypto_util.sha256sum(self.config.option("MOD_SSL_CONF_SRC"))

    def _assert_current_file(self):
        self.assertTrue(os.path.isfile(self.config.mod_ssl_conf))
@@ -1742,7 +1742,7 @@ class InstallSslOptionsConfTest(util.ApacheTest):
            self.assertFalse(mock_logger.warning.called)
        self.assertTrue(os.path.isfile(self.config.mod_ssl_conf))
        self.assertEqual(crypto_util.sha256sum(
-            self.config.pick_apache_config()),
+            self.config.option("MOD_SSL_CONF_SRC")),
            self._current_ssl_options_hash())
        self.assertNotEqual(crypto_util.sha256sum(self.config.mod_ssl_conf),
            self._current_ssl_options_hash())
@@ -1758,31 +1758,18 @@ class InstallSslOptionsConfTest(util.ApacheTest):
                "%s has been manually modified; updated file "
                "saved to %s. We recommend updating %s for security purposes.")
        self.assertEqual(crypto_util.sha256sum(
-            self.config.pick_apache_config()),
+            self.config.option("MOD_SSL_CONF_SRC")),
            self._current_ssl_options_hash())
        # only print warning once
        with mock.patch("certbot.plugins.common.logger") as mock_logger:
            self._call()
            self.assertFalse(mock_logger.warning.called)

-    def test_ssl_config_files_hash_in_all_hashes(self):
-        """
-        It is really critical that all TLS Apache config files have their SHA256 hash registered in
-        constants.ALL_SSL_OPTIONS_HASHES. Otherwise Certbot will mistakenly assume that the config
-        file has been manually edited by the user, and will refuse to update it.
-        This test ensures that all necessary hashes are present.
-        """
+    def test_current_file_hash_in_all_hashes(self):
        from certbot_apache.constants import ALL_SSL_OPTIONS_HASHES
-        import pkg_resources
-        tls_configs_dir = pkg_resources.resource_filename("certbot_apache", "tls_configs")
-        all_files = [os.path.join(tls_configs_dir, name) for name in os.listdir(tls_configs_dir)
-                     if name.endswith('options-ssl-apache.conf')]
-        self.assertTrue(all_files)
-        for one_file in all_files:
-            file_hash = crypto_util.sha256sum(one_file)
-            self.assertTrue(file_hash in ALL_SSL_OPTIONS_HASHES,
-                            "Constants.ALL_SSL_OPTIONS_HASHES must be appended with the sha256 "
-                            "hash of {0} when it is updated.".format(one_file))
+        self.assertTrue(self._current_ssl_options_hash() in ALL_SSL_OPTIONS_HASHES,
+            "Constants.ALL_SSL_OPTIONS_HASHES must be appended"
+            " with the sha256 hash of self.config.mod_ssl_conf when it is updated.")


 if __name__ == "__main__":
--- a/certbot-apache/certbot_apache/tests/http_01_test.py
+++ b/certbot-apache/certbot_apache/tests/http_01_test.py
@@ -7,6 +7,7 @@ from acme.magic_typing import List  # pylint: disable=unused-import, no-name-in-

 from certbot import achallenges
 from certbot import errors
+from certbot.compat import filesystem
 from certbot.compat import os
 from certbot.tests import acme_util

@@ -180,7 +181,7 @@ class ApacheHttp01Test(util.ApacheTest):
        self.assertEqual(self.http.perform(), expected_response)

        self.assertTrue(os.path.isdir(self.http.challenge_dir))
-        self._has_min_permissions(self.http.challenge_dir, 0o755)
+        self.assertTrue(filesystem.has_min_permissions(self.http.challenge_dir, 0o755))
        self._test_challenge_conf()

        for achall in achalls:
@@ -218,15 +219,10 @@ class ApacheHttp01Test(util.ApacheTest):
        name = os.path.join(self.http.challenge_dir, achall.chall.encode("token"))
        validation = achall.validation(self.account_key)

-        self._has_min_permissions(name, 0o644)
+        self.assertTrue(filesystem.has_min_permissions(name, 0o644))
        with open(name, 'rb') as f:
            self.assertEqual(f.read(), validation.encode())

-    def _has_min_permissions(self, path, min_mode):
-        """Tests the given file has at least the permissions in mode."""
-        st_mode = os.stat(path).st_mode
-        self.assertEqual(st_mode, st_mode | min_mode)
-

 if __name__ == "__main__":
    unittest.main()  # pragma: no cover
--- a/certbot-apache/certbot_apache/tls_configs/centos-old-options-ssl-apache.conf
+++ b/certbot-apache/certbot_apache/tls_configs/centos-old-options-ssl-apache.conf
@@ -1,18 +0,0 @@
-# This file contains important security parameters. If you modify this file
-# manually, Certbot will be unable to automatically provide future security
-# updates. Instead, Certbot will print and log an error message with a path to
-# the up-to-date file that you will need to refer to when manually updating
-# this file.
-
-SSLEngine on
-
-# Intermediate configuration, tweak to your needs
-SSLProtocol             all -SSLv2 -SSLv3
-SSLCipherSuite          ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS
-SSLHonorCipherOrder     on
-
-SSLOptions +StrictRequire
-
-# Add vhost name to log entries:
-LogFormat "%h %l %u %t \"%r\" %>s %b \"%{Referer}i\" \"%{User-agent}i\"" vhost_combined
-LogFormat "%v %h %l %u %t \"%r\" %>s %b" vhost_common
--- a/certbot-apache/certbot_apache/tls_configs/old-options-ssl-apache.conf
+++ b/certbot-apache/certbot_apache/tls_configs/old-options-ssl-apache.conf
@@ -1,19 +0,0 @@
-# This file contains important security parameters. If you modify this file
-# manually, Certbot will be unable to automatically provide future security
-# updates. Instead, Certbot will print and log an error message with a path to
-# the up-to-date file that you will need to refer to when manually updating
-# this file.
-
-SSLEngine on
-
-# Intermediate configuration, tweak to your needs
-SSLProtocol             all -SSLv2 -SSLv3
-SSLCipherSuite          ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS
-SSLHonorCipherOrder     on
-SSLCompression          off
-
-SSLOptions +StrictRequire
-
-# Add vhost name to log entries:
-LogFormat "%h %l %u %t \"%r\" %>s %b \"%{Referer}i\" \"%{User-agent}i\"" vhost_combined
-LogFormat "%v %h %l %u %t \"%r\" %>s %b" vhost_common
--- a/certbot-apache/setup.py
+++ b/certbot-apache/setup.py
@@ -4,13 +4,13 @@ from setuptools.command.test import test as TestCommand
 import sys


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.29.0',
-    'certbot>=0.37.0.dev0',
+    'certbot>=0.39.0.dev0',
    'mock',
    'python-augeas',
    'setuptools',
@@ -62,6 +62,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/228
+++ b/228
@@ -31,7 +31,7 @@ if [ -z "$VENV_PATH" ]; then
 fi
 VENV_BIN="$VENV_PATH/bin"
 BOOTSTRAP_VERSION_PATH="$VENV_PATH/certbot-auto-bootstrap-version.txt"
-LE_AUTO_VERSION="0.36.0"
+LE_AUTO_VERSION="0.38.0"
 BASENAME=$(basename $0)
 USAGE="Usage: $BASENAME [OPTIONS]
 A self-updating wrapper script for the Certbot ACME client. When run, updates
@@ -755,13 +755,31 @@ elif [ -f /etc/redhat-release ]; then
  prev_le_python="$LE_PYTHON"
  unset LE_PYTHON
  DeterminePythonVersion "NOCRASH"
-  # Starting to Fedora 29, python2 is on a deprecation path. Let's move to python3 then.
+
  RPM_DIST_NAME=`(. /etc/os-release 2> /dev/null && echo $ID) || echo "unknown"`
-  RPM_DIST_VERSION=0
-  if [ "$RPM_DIST_NAME" = "fedora" ]; then
-    RPM_DIST_VERSION=`(. /etc/os-release 2> /dev/null && echo $VERSION_ID) || echo "0"`
+
+  # Set RPM_DIST_VERSION to VERSION_ID from /etc/os-release after splitting on
+  # '.' characters (e.g. "8.0" becomes "8"). If the command exits with an
+  # error, RPM_DIST_VERSION is set to "unknown".
+  RPM_DIST_VERSION=$( (. /etc/os-release 2> /dev/null && echo "$VERSION_ID") | cut -d '.' -f1 || echo "unknown")
+
+  # If RPM_DIST_VERSION is an empty string or it contains any nonnumeric
+  # characters, the value is unexpected so we set RPM_DIST_VERSION to 0.
+  if [ -z "$RPM_DIST_VERSION" ] || [ -n "$(echo "$RPM_DIST_VERSION" | tr -d '[0-9]')" ]; then
+     RPM_DIST_VERSION=0
  fi
+
+  # Starting to Fedora 29, python2 is on a deprecation path. Let's move to python3 then.
+  # RHEL 8 also uses python3 by default.
  if [ "$RPM_DIST_NAME" = "fedora" -a "$RPM_DIST_VERSION" -ge 29 -o "$PYVER" -eq 26 ]; then
+    RPM_USE_PYTHON_3=1
+  elif [ "$RPM_DIST_NAME" = "rhel" -a "$RPM_DIST_VERSION" -ge 8 ]; then
+    RPM_USE_PYTHON_3=1
+  else
+    RPM_USE_PYTHON_3=0
+  fi
+
+  if [ "$RPM_USE_PYTHON_3" = 1 ]; then
    Bootstrap() {
      BootstrapMessage "RedHat-based OSes that will use Python3"
      BootstrapRpmPython3
@@ -775,6 +793,7 @@ elif [ -f /etc/redhat-release ]; then
    }
    BOOTSTRAP_VERSION="BootstrapRpmCommon $BOOTSTRAP_RPM_COMMON_VERSION"
  fi
+
  LE_PYTHON="$prev_le_python"
 elif [ -f /etc/os-release ] && `grep -q openSUSE /etc/os-release` ; then
  Bootstrap() {
@@ -1115,73 +1134,76 @@ if [ "$1" = "--le-auto-phase2" ]; then
 # To generate this, do (with docker and package hashin installed):
 # ```
 # letsencrypt-auto-source/rebuild_dependencies.py \
-#   letsencrypt-auto-sources/pieces/dependency-requirements.txt
+#   letsencrypt-auto-source/pieces/dependency-requirements.txt
+# ```
+# If you want to update a single dependency, run commands similar to these:
+# ```
+# pip install hashin
+# hashin -r dependency-requirements.txt cryptography==1.5.2
 # ```
 ConfigArgParse==0.14.0 \
    --hash=sha256:2e2efe2be3f90577aca9415e32cb629aa2ecd92078adbe27b53a03e53ff12e91
 asn1crypto==0.24.0 \
    --hash=sha256:2f1adbb7546ed199e3c90ef23ec95c5cf3585bac7d11fb7eb562a3fe89c64e87 \
    --hash=sha256:9d5c20441baf0cb60a4ac34cc447c6c189024b6b4c6cd7877034f4965c464e49
-certifi==2019.3.9 \
-    --hash=sha256:59b7658e26ca9c7339e00f8f4636cdfe59d34fa37b9b04f6f9e9926b3cece1a5 \
-    --hash=sha256:b26104d6835d1f5e49452a26eb2ff87fe7090b89dfcaee5ea2212697e1e1d7ae
-cffi==1.12.2 \
-    --hash=sha256:00b97afa72c233495560a0793cdc86c2571721b4271c0667addc83c417f3d90f \
-    --hash=sha256:0ba1b0c90f2124459f6966a10c03794082a2f3985cd699d7d63c4a8dae113e11 \
-    --hash=sha256:0bffb69da295a4fc3349f2ec7cbe16b8ba057b0a593a92cbe8396e535244ee9d \
-    --hash=sha256:21469a2b1082088d11ccd79dd84157ba42d940064abbfa59cf5f024c19cf4891 \
-    --hash=sha256:2e4812f7fa984bf1ab253a40f1f4391b604f7fc424a3e21f7de542a7f8f7aedf \
-    --hash=sha256:2eac2cdd07b9049dd4e68449b90d3ef1adc7c759463af5beb53a84f1db62e36c \
-    --hash=sha256:2f9089979d7456c74d21303c7851f158833d48fb265876923edcb2d0194104ed \
-    --hash=sha256:3dd13feff00bddb0bd2d650cdb7338f815c1789a91a6f68fdc00e5c5ed40329b \
-    --hash=sha256:4065c32b52f4b142f417af6f33a5024edc1336aa845b9d5a8d86071f6fcaac5a \
-    --hash=sha256:51a4ba1256e9003a3acf508e3b4f4661bebd015b8180cc31849da222426ef585 \
-    --hash=sha256:59888faac06403767c0cf8cfb3f4a777b2939b1fbd9f729299b5384f097f05ea \
-    --hash=sha256:59c87886640574d8b14910840327f5cd15954e26ed0bbd4e7cef95fa5aef218f \
-    --hash=sha256:610fc7d6db6c56a244c2701575f6851461753c60f73f2de89c79bbf1cc807f33 \
-    --hash=sha256:70aeadeecb281ea901bf4230c6222af0248c41044d6f57401a614ea59d96d145 \
-    --hash=sha256:71e1296d5e66c59cd2c0f2d72dc476d42afe02aeddc833d8e05630a0551dad7a \
-    --hash=sha256:8fc7a49b440ea752cfdf1d51a586fd08d395ff7a5d555dc69e84b1939f7ddee3 \
-    --hash=sha256:9b5c2afd2d6e3771d516045a6cfa11a8da9a60e3d128746a7fe9ab36dfe7221f \
-    --hash=sha256:9c759051ebcb244d9d55ee791259ddd158188d15adee3c152502d3b69005e6bd \
-    --hash=sha256:b4d1011fec5ec12aa7cc10c05a2f2f12dfa0adfe958e56ae38dc140614035804 \
-    --hash=sha256:b4f1d6332339ecc61275bebd1f7b674098a66fea11a00c84d1c58851e618dc0d \
-    --hash=sha256:c030cda3dc8e62b814831faa4eb93dd9a46498af8cd1d5c178c2de856972fd92 \
-    --hash=sha256:c2e1f2012e56d61390c0e668c20c4fb0ae667c44d6f6a2eeea5d7148dcd3df9f \
-    --hash=sha256:c37c77d6562074452120fc6c02ad86ec928f5710fbc435a181d69334b4de1d84 \
-    --hash=sha256:c8149780c60f8fd02752d0429246088c6c04e234b895c4a42e1ea9b4de8d27fb \
-    --hash=sha256:cbeeef1dc3c4299bd746b774f019de9e4672f7cc666c777cd5b409f0b746dac7 \
-    --hash=sha256:e113878a446c6228669144ae8a56e268c91b7f1fafae927adc4879d9849e0ea7 \
-    --hash=sha256:e21162bf941b85c0cda08224dade5def9360f53b09f9f259adb85fc7dd0e7b35 \
-    --hash=sha256:fb6934ef4744becbda3143d30c6604718871495a5e36c408431bf33d9c146889
+certifi==2019.6.16 \
+    --hash=sha256:046832c04d4e752f37383b628bc601a7ea7211496b4638f6514d0e5b9acc4939 \
+    --hash=sha256:945e3ba63a0b9f577b1395204e13c3a231f9bc0223888be653286534e5873695
+cffi==1.12.3 \
+    --hash=sha256:041c81822e9f84b1d9c401182e174996f0bae9991f33725d059b771744290774 \
+    --hash=sha256:046ef9a22f5d3eed06334d01b1e836977eeef500d9b78e9ef693f9380ad0b83d \
+    --hash=sha256:066bc4c7895c91812eff46f4b1c285220947d4aa46fa0a2651ff85f2afae9c90 \
+    --hash=sha256:066c7ff148ae33040c01058662d6752fd73fbc8e64787229ea8498c7d7f4041b \
+    --hash=sha256:2444d0c61f03dcd26dbf7600cf64354376ee579acad77aef459e34efcb438c63 \
+    --hash=sha256:300832850b8f7967e278870c5d51e3819b9aad8f0a2c8dbe39ab11f119237f45 \
+    --hash=sha256:34c77afe85b6b9e967bd8154e3855e847b70ca42043db6ad17f26899a3df1b25 \
+    --hash=sha256:46de5fa00f7ac09f020729148ff632819649b3e05a007d286242c4882f7b1dc3 \
+    --hash=sha256:4aa8ee7ba27c472d429b980c51e714a24f47ca296d53f4d7868075b175866f4b \
+    --hash=sha256:4d0004eb4351e35ed950c14c11e734182591465a33e960a4ab5e8d4f04d72647 \
+    --hash=sha256:4e3d3f31a1e202b0f5a35ba3bc4eb41e2fc2b11c1eff38b362de710bcffb5016 \
+    --hash=sha256:50bec6d35e6b1aaeb17f7c4e2b9374ebf95a8975d57863546fa83e8d31bdb8c4 \
+    --hash=sha256:55cad9a6df1e2a1d62063f79d0881a414a906a6962bc160ac968cc03ed3efcfb \
+    --hash=sha256:5662ad4e4e84f1eaa8efce5da695c5d2e229c563f9d5ce5b0113f71321bcf753 \
+    --hash=sha256:59b4dc008f98fc6ee2bb4fd7fc786a8d70000d058c2bbe2698275bc53a8d3fa7 \
+    --hash=sha256:73e1ffefe05e4ccd7bcea61af76f36077b914f92b76f95ccf00b0c1b9186f3f9 \
+    --hash=sha256:a1f0fd46eba2d71ce1589f7e50a9e2ffaeb739fb2c11e8192aa2b45d5f6cc41f \
+    --hash=sha256:a2e85dc204556657661051ff4bab75a84e968669765c8a2cd425918699c3d0e8 \
+    --hash=sha256:a5457d47dfff24882a21492e5815f891c0ca35fefae8aa742c6c263dac16ef1f \
+    --hash=sha256:a8dccd61d52a8dae4a825cdbb7735da530179fea472903eb871a5513b5abbfdc \
+    --hash=sha256:ae61af521ed676cf16ae94f30fe202781a38d7178b6b4ab622e4eec8cefaff42 \
+    --hash=sha256:b012a5edb48288f77a63dba0840c92d0504aa215612da4541b7b42d849bc83a3 \
+    --hash=sha256:d2c5cfa536227f57f97c92ac30c8109688ace8fa4ac086d19d0af47d134e2909 \
+    --hash=sha256:d42b5796e20aacc9d15e66befb7a345454eef794fdb0737d1af593447c6c8f45 \
+    --hash=sha256:dee54f5d30d775f525894d67b1495625dd9322945e7fee00731952e0368ff42d \
+    --hash=sha256:e070535507bd6aa07124258171be2ee8dfc19119c28ca94c9dfb7efd23564512 \
+    --hash=sha256:e1ff2748c84d97b065cc95429814cdba39bcbd77c9c85c89344b317dc0d9cbff \
+    --hash=sha256:ed851c75d1e0e043cbf5ca9a8e1b13c4c90f3fbd863dacb01c0808e2b5204201
 chardet==3.0.4 \
    --hash=sha256:84ab92ed1c4d4f16916e05906b6b75a6c0fb5db821cc65e70cbd64a3e2a5eaae \
    --hash=sha256:fc323ffcaeaed0e0a02bf4d117757b98aed530d9ed4531e3e15460124c106691
 configobj==5.0.6 \
    --hash=sha256:a2f5650770e1c87fb335af19a9b7eb73fc05ccf22144eb68db7d00cd2bcb0902
-cryptography==2.6.1 \
-    --hash=sha256:066f815f1fe46020877c5983a7e747ae140f517f1b09030ec098503575265ce1 \
-    --hash=sha256:210210d9df0afba9e000636e97810117dc55b7157c903a55716bb73e3ae07705 \
-    --hash=sha256:26c821cbeb683facb966045e2064303029d572a87ee69ca5a1bf54bf55f93ca6 \
-    --hash=sha256:2afb83308dc5c5255149ff7d3fb9964f7c9ee3d59b603ec18ccf5b0a8852e2b1 \
-    --hash=sha256:2db34e5c45988f36f7a08a7ab2b69638994a8923853dec2d4af121f689c66dc8 \
-    --hash=sha256:409c4653e0f719fa78febcb71ac417076ae5e20160aec7270c91d009837b9151 \
-    --hash=sha256:45a4f4cf4f4e6a55c8128f8b76b4c057027b27d4c67e3fe157fa02f27e37830d \
-    --hash=sha256:48eab46ef38faf1031e58dfcc9c3e71756a1108f4c9c966150b605d4a1a7f659 \
-    --hash=sha256:6b9e0ae298ab20d371fc26e2129fd683cfc0cfde4d157c6341722de645146537 \
-    --hash=sha256:6c4778afe50f413707f604828c1ad1ff81fadf6c110cb669579dea7e2e98a75e \
-    --hash=sha256:8c33fb99025d353c9520141f8bc989c2134a1f76bac6369cea060812f5b5c2bb \
-    --hash=sha256:9873a1760a274b620a135054b756f9f218fa61ca030e42df31b409f0fb738b6c \
-    --hash=sha256:9b069768c627f3f5623b1cbd3248c5e7e92aec62f4c98827059eed7053138cc9 \
-    --hash=sha256:9e4ce27a507e4886efbd3c32d120db5089b906979a4debf1d5939ec01b9dd6c5 \
-    --hash=sha256:acb424eaca214cb08735f1a744eceb97d014de6530c1ea23beb86d9c6f13c2ad \
-    --hash=sha256:c8181c7d77388fe26ab8418bb088b1a1ef5fde058c6926790c8a0a3d94075a4a \
-    --hash=sha256:d4afbb0840f489b60f5a580a41a1b9c3622e08ecb5eec8614d4fb4cd914c4460 \
-    --hash=sha256:d9ed28030797c00f4bc43c86bf819266c76a5ea61d006cd4078a93ebf7da6bfd \
-    --hash=sha256:e603aa7bb52e4e8ed4119a58a03b60323918467ef209e6ff9db3ac382e5cf2c6
-# Package enum34 needs to be explicitly limited to Python2.x, in order to avoid
-# certbot-auto failures on Python 3.6+ which enum34 doesn't support. See #5456.
-enum34==1.1.6 ; python_version < '3.4' \
+cryptography==2.7 \
+    --hash=sha256:24b61e5fcb506424d3ec4e18bca995833839bf13c59fc43e530e488f28d46b8c \
+    --hash=sha256:25dd1581a183e9e7a806fe0543f485103232f940fcfc301db65e630512cce643 \
+    --hash=sha256:3452bba7c21c69f2df772762be0066c7ed5dc65df494a1d53a58b683a83e1216 \
+    --hash=sha256:41a0be220dd1ed9e998f5891948306eb8c812b512dc398e5a01846d855050799 \
+    --hash=sha256:5751d8a11b956fbfa314f6553d186b94aa70fdb03d8a4d4f1c82dcacf0cbe28a \
+    --hash=sha256:5f61c7d749048fa6e3322258b4263463bfccefecb0dd731b6561cb617a1d9bb9 \
+    --hash=sha256:72e24c521fa2106f19623a3851e9f89ddfdeb9ac63871c7643790f872a305dfc \
+    --hash=sha256:7b97ae6ef5cba2e3bb14256625423413d5ce8d1abb91d4f29b6d1a081da765f8 \
+    --hash=sha256:961e886d8a3590fd2c723cf07be14e2a91cf53c25f02435c04d39e90780e3b53 \
+    --hash=sha256:96d8473848e984184b6728e2c9d391482008646276c3ff084a1bd89e15ff53a1 \
+    --hash=sha256:ae536da50c7ad1e002c3eee101871d93abdc90d9c5f651818450a0d3af718609 \
+    --hash=sha256:b0db0cecf396033abb4a93c95d1602f268b3a68bb0a9cc06a7cff587bb9a7292 \
+    --hash=sha256:cfee9164954c186b191b91d4193989ca994703b2fff406f71cf454a2d3c7327e \
+    --hash=sha256:e6347742ac8f35ded4a46ff835c60e68c22a536a8ae5c4422966d06946b6d4c6 \
+    --hash=sha256:f27d93f0139a3c056172ebb5d4f9056e770fdf0206c2f422ff2ebbad142e09ed \
+    --hash=sha256:f57b76e46a58b63d1c6375017f4564a28f19a5ca912691fd2e4261b3414b618d
+distro==1.4.0 \
+    --hash=sha256:362dde65d846d23baee4b5c058c8586f219b5a54be1cf5fc6ff55c4578392f57 \
+    --hash=sha256:eedf82a470ebe7d010f1872c17237c79ab04097948800029994fa458e52fb4b4
+enum34==1.1.6 \
    --hash=sha256:2d81cbbe0e73112bdfe6ef8576f2238f2ba27dd0d55752a776c41d38b7da2850 \
    --hash=sha256:644837f692e5f550741432dd3f223bbb9852018674981b1664e5dc339387588a \
    --hash=sha256:6bd0f6ad48ec2aa117d3d141940d484deccda84d4fcd884f5c3d93c23ecd8c79 \
@@ -1197,18 +1219,18 @@ idna==2.8 \
 ipaddress==1.0.22 \
    --hash=sha256:64b28eec5e78e7510698f6d4da08800a5c575caa4a286c93d651c5d3ff7b6794 \
    --hash=sha256:b146c751ea45cad6188dd6cf2d9b757f6f4f8d6ffb96a023e6f2e26eea02a72c
-josepy==1.1.0 \
-    --hash=sha256:1309a25aac3caeff5239729c58ff9b583f7d022ffdb1553406ddfc8e5b52b76e \
-    --hash=sha256:fb5c62c77d26e04df29cb5ecd01b9ce69b6fcc9e521eb1ca193b7faa2afa7086
+josepy==1.2.0 \
+    --hash=sha256:8ea15573203f28653c00f4ac0142520777b1c59d9eddd8da3f256c6ba3cac916 \
+    --hash=sha256:9cec9a839fe9520f0420e4f38e7219525daccce4813296627436fe444cd002d3
 mock==1.3.0 \
    --hash=sha256:1e247dbecc6ce057299eb7ee019ad68314bb93152e81d9a6110d35f4d5eca0f6 \
    --hash=sha256:3f573a18be94de886d1191f27c168427ef693e8dcfcecf95b170577b2eb69cbb
 parsedatetime==2.4 \
    --hash=sha256:3d817c58fb9570d1eec1dd46fa9448cd644eeed4fb612684b02dfda3a79cb84b \
    --hash=sha256:9ee3529454bf35c40a77115f5a596771e59e1aee8c53306f346c461b8e913094
-pbr==5.1.3 \
-    --hash=sha256:8257baf496c8522437e8a6cfe0f15e00aedc6c0e0e7c9d55eeeeab31e0853843 \
-    --hash=sha256:8c361cc353d988e4f5b998555c88098b9d5964c2e11acf7b0d21925a66bb5824
+pbr==5.4.2 \
+    --hash=sha256:56e52299170b9492513c64be44736d27a512fa7e606f21942160b68ce510b4bc \
+    --hash=sha256:9b321c204a88d8ab5082699469f52cc94c5da45c51f114113d01b3d993c24cdf
 pyOpenSSL==19.0.0 \
    --hash=sha256:aeca66338f6de19d1aa46ed634c3b9ae519a64b458f8468aec688e7e3c20f200 \
    --hash=sha256:c727930ad54b10fc157015014b666f2d8b41f70c0d03e83ab67624fd3dd5d1e6
@@ -1217,14 +1239,14 @@ pyRFC3339==1.1 \
    --hash=sha256:81b8cbe1519cdb79bed04910dd6fa4e181faf8c88dff1e1b987b5f7ab23a5b1a
 pycparser==2.19 \
    --hash=sha256:a988718abfad80b6b157acce7bf130a30876d27603738ac39f140993246b25b3
-pyparsing==2.3.1 \
-    --hash=sha256:66c9268862641abcac4a96ba74506e594c884e3f57690a696d21ad8210ed667a \
-    --hash=sha256:f6c5ef0d7480ad048c054c37632c67fca55299990fff127850181659eea33fc3
+pyparsing==2.4.2 \
+    --hash=sha256:6f98a7b9397e206d78cc01df10131398f1c8b8510a2f4d97d9abd82e1aacdd80 \
+    --hash=sha256:d9338df12903bbf5d65a0e4e87c2161968b10d2e489652bb47001d82a9b028b4
 python-augeas==0.5.0 \
    --hash=sha256:67d59d66cdba8d624e0389b87b2a83a176f21f16a87553b50f5703b23f29bac2
-pytz==2018.9 \
-    --hash=sha256:32b0891edff07e28efe91284ed9c31e123d84bea3fd98e1f72be2508f43ef8d9 \
-    --hash=sha256:d5f05e487007e29e03409f9398d074e158d920d36eb82eaf66fb1136b0c5374c
+pytz==2019.2 \
+    --hash=sha256:26c0b32e437e54a18161324a2fca3c4b9846b74a8dccddd843113109e1116b32 \
+    --hash=sha256:c894d57500a4cd2d5c71114aaab77dbab5eabd9022308ce5ac9bb93a60a6f0c7
 requests==2.21.0 \
    --hash=sha256:502a824f31acdacb3a35b6690b5fbf0bc41d63a24a45c4004352b0242707598e \
    --hash=sha256:7bf2a778576d825600030a110f3c0e3e8edc51dfaafe1c146e39a2027784957b
@@ -1234,15 +1256,15 @@ requests-toolbelt==0.9.1 \
 six==1.12.0 \
    --hash=sha256:3350809f0555b11f552448330d0b52d5f24c91a322ea4a15ef22629740f3761c \
    --hash=sha256:d16a0141ec1a18405cd4ce8b4613101da75da0e9a7aec5bdd4fa804d0e0eba73
-urllib3==1.24.2 \
-    --hash=sha256:4c291ca23bbb55c76518905869ef34bdd5f0e46af7afe6861e8375643ffee1a0 \
-    --hash=sha256:9a247273df709c4fedb38c711e44292304f73f39ab01beda9f6b9fc375669ac3
+urllib3==1.24.3 \
+    --hash=sha256:2393a695cd12afedd0dcb26fe5d50d0cf248e5a66f75dbd89a3d4eb333a61af4 \
+    --hash=sha256:a637e5fae88995b256e3409dc4d52c2e2e0ba32c42a6365fee8bbd2238de3cfb
 zope.component==4.5 \
    --hash=sha256:6edfd626c3b593b72895a8cfcf79bff41f4619194ce996a85bce31ac02b94e55 \
    --hash=sha256:984a06ba3def0b02b1117fa4c45b56e772e8c29c0340820fbf367e440a93a3a4
-zope.deferredimport==4.3 \
-    --hash=sha256:2ddef5a7ecfff132a2dd796253366ecf9748a446e30f1a0b3a636aec9d9c05c5 \
-    --hash=sha256:4aae9cbacb2146cca58e62be0a914f0cec034d3b2d41135ea212ca8a96f4b5ec
+zope.deferredimport==4.3.1 \
+    --hash=sha256:57b2345e7b5eef47efcd4f634ff16c93e4265de3dcf325afc7315ade48d909e1 \
+    --hash=sha256:9a0c211df44aa95f1c4e6d2626f90b400f56989180d3ef96032d708da3d23e0a
 zope.deprecation==4.4.0 \
    --hash=sha256:0d453338f04bacf91bbfba545d8bcdf529aa829e67b705eac8c1a7fdce66e2df \
    --hash=sha256:f1480b74995958b24ce37b0ef04d3663d2683e5d6debc96726eff18acf4ea113
@@ -1290,18 +1312,18 @@ zope.interface==4.6.0 \
    --hash=sha256:d788a3999014ddf416f2dc454efa4a5dbeda657c6aba031cf363741273804c6b \
    --hash=sha256:eed88ae03e1ef3a75a0e96a55a99d7937ed03e53d0cffc2451c208db445a2966 \
    --hash=sha256:f99451f3a579e73b5dd58b1b08d1179791d49084371d9a47baad3b22417f0317
-zope.proxy==4.3.1 \
-    --hash=sha256:0cbcfcafaa3b5fde7ba7a7b9a2b5f09af25c9b90087ad65f9e61359fed0ca63b \
-    --hash=sha256:3de631dd5054a3a20b9ebff0e375f39c0565f1fb9131200d589a6a8f379214cd \
-    --hash=sha256:5429134d04d42262f4dac25f6dea907f6334e9a751ffc62cb1d40226fb52bdeb \
-    --hash=sha256:563c2454b2d0f23bca54d2e0e4d781149b7b06cb5df67e253ca3620f37202dd2 \
-    --hash=sha256:5bcf773345016b1461bb07f70c635b9386e5eaaa08e37d3939dcdf12d3fdbec5 \
-    --hash=sha256:8d84b7aef38c693874e2f2084514522bf73fd720fde0ce2a9352a51315ffa475 \
-    --hash=sha256:90de9473c05819b36816b6cb957097f809691836ed3142648bf62da84b4502fe \
-    --hash=sha256:dd592a69fe872445542a6e1acbefb8e28cbe6b4007b8f5146da917e49b155cc3 \
-    --hash=sha256:e7399ab865399fce322f9cefc6f2f3e4099d087ba581888a9fea1bbe1db42a08 \
-    --hash=sha256:e7d1c280d86d72735a420610df592aac72332194e531a8beff43a592c3a1b8eb \
-    --hash=sha256:e90243fee902adb0c39eceb3c69995c0f2004bc3fdb482fbf629efc656d124ed
+zope.proxy==4.3.2 \
+    --hash=sha256:320a7619992e42142549ebf61e14ce27683b4d14b0cbc45f7c037ba64edb560c \
+    --hash=sha256:824d4dbabbb7deb84f25fdb96ea1eeca436a1802c3c8d323b3eb4ac9d527d41c \
+    --hash=sha256:8a32eb9c94908f3544da2dae3f4a9e6961d78819b88ac6b6f4a51cee2d65f4a0 \
+    --hash=sha256:96265fd3bc3ea646f98482e16307a69de21402eeaaaaf4b841c1161ac2f71bb0 \
+    --hash=sha256:ab6d6975d9c51c13cac828ff03168de21fb562b0664c59bcdc4a4b10f39a5b17 \
+    --hash=sha256:af10cb772391772463f65a58348e2de5ecc06693c16d2078be276dc068bcbb54 \
+    --hash=sha256:b8fd3a3de3f7b6452775e92af22af5977b17b69ac86a38a3ddfe870e40a0d05f \
+    --hash=sha256:bb7088f1bed3b8214284a5e425dc23da56f2f28e8815b7580bfed9e245b6c0b6 \
+    --hash=sha256:bc29b3665eac34f14c4aef5224bef045efcfb1a7d12d78c8685858de5fbf21c0 \
+    --hash=sha256:c39fa6a159affeae5fe31b49d9f5b12bd674fe77271a9a324408b271440c50a7 \
+    --hash=sha256:e946a036ac5b9f897e986ac9dc950a34cffc857d88eae6727b8434fbc4752366

 # Contains the requirements for the letsencrypt package.
 #
@@ -1314,18 +1336,18 @@ letsencrypt==0.7.0 \
    --hash=sha256:105a5fb107e45bcd0722eb89696986dcf5f08a86a321d6aef25a0c7c63375ade \
    --hash=sha256:c36e532c486a7e92155ee09da54b436a3c420813ec1c590b98f635d924720de9

-certbot==0.36.0 \
-    --hash=sha256:486cee6c4861762fe4a94b4f44f7d227034d026d1a8d7ba2911ef4e86a737613 \
-    --hash=sha256:bf6745b823644cdca8461150455aeb67d417f87f80b9ec774c716e9587ef20a2
-acme==0.36.0 \
-    --hash=sha256:5570c8e87383fbc733224fd0f7d164313b67dd9c21deafe9ddc8e769441f0c86 \
-    --hash=sha256:0461ee3c882d865e98e624561843dc135fa1a1412b15603d7ebfbb392de6a668
-certbot-apache==0.36.0 \
-    --hash=sha256:2537f7fb67a38b6d1ed5ee79f6a799090ca609695ac3799bb840b2fb677ac98d \
-    --hash=sha256:458d20a3e9e8a88563d3deb0bbe38752bd2b80100f0e5854e4069390c1b4e5cd
-certbot-nginx==0.36.0 \
-    --hash=sha256:4303b54adf2030671c54bb3964c1f43aec0f677045e0cdb6d4fb931268d08310 \
-    --hash=sha256:4c34e6114dd8204b6667f101579dd9ab2b38fef0dd5a15702585edcb2aefb322
+certbot==0.38.0 \
+    --hash=sha256:618abf3ae17c2fc3cb99baa4bf000dd5e2d7875b7811f5ef1edf6ebd7a33945f \
+    --hash=sha256:c27712101794e3adf54f3a3067c63be5caa507a930a79865bc654b6864121c6b
+acme==0.38.0 \
+    --hash=sha256:6231571b4a94d6d621b28bef6f6d4846b3c2ebca840f9718d3212036c3bd2af8 \
+    --hash=sha256:1c1e9c0826a8f72d670b0ca28b7e6392ce4781eb33222f35133705b6551885d8
+certbot-apache==0.38.0 \
+    --hash=sha256:0b5a2c2bcc430470b5131941ebdfde0a13e28dec38918c1a4ebea5dd35ad38bc \
+    --hash=sha256:2d335543e0ae9292303238736907ce6b321ac49eb49fe4e0b775abdc0ba57c62
+certbot-nginx==0.38.0 \
+    --hash=sha256:af82944e171d2e93c81438b185f8051e742c6f47f7382cb1a647b1c7ca2b53f2 \
+    --hash=sha256:cecd1fa3de6e19980fdb9c3b3269b15b7da71b5748ee7ae5caddcc18dbb208ac

 UNLIKELY_EOF
    # -------------------------------------------------------------------------
--- a/certbot-ci/certbot_integration_tests/.coveragerc
+++ b/certbot-ci/certbot_integration_tests/.coveragerc
@@ -2,6 +2,7 @@
 # Avoid false warnings because certbot packages are not installed in the thread that executes
 # the coverage: indeed, certbot is launched as a CLI from a subprocess.
 disable_warnings = module-not-imported,no-data-collected
+omit = **/*_test.py,**/tests/*,**/dns_common*,**/certbot_nginx/parser_obj.py

 [report]
 # Exclude unit tests in coverage during integration tests.
--- a/certbot-ci/certbot_integration_tests/apache_tests/init.py
+++ b/certbot-ci/certbot_integration_tests/apache_tests/init.py
--- a/certbot-ci/certbot_integration_tests/apache_tests/apache_config.py
+++ b/certbot-ci/certbot_integration_tests/apache_tests/apache_config.py
@@ -0,0 +1,171 @@
+import shutil
+import subprocess
+import os
+
+import pkg_resources
+import getpass
+
+
+def construct_apache_config_dir(apache_root, http_port, https_port, key_path=None,
+                                cert_path=None, wtf_prefix='le'):
+    config_path = os.path.join(apache_root, 'config')
+    shutil.copytree('/etc/apache2', config_path, symlinks=True)
+
+    webroot_path = os.path.join(apache_root, 'www')
+    os.mkdir(webroot_path)
+    with open(os.path.join(webroot_path, 'index.html'), 'w') as file_h:
+        file_h.write('Hello World!')
+
+    main_config_path = os.path.join(config_path, 'apache2.conf')
+    with open(main_config_path, 'w') as file_h:
+        file_h.write('''\
+ServerRoot "{config}"
+DefaultRuntimeDir ${{APACHE_RUN_DIR}}
+PidFile ${{APACHE_PID_FILE}}
+Timeout 300
+KeepAlive On
+MaxKeepAliveRequests 100
+KeepAliveTimeout 5
+User ${{APACHE_RUN_USER}}
+Group ${{APACHE_RUN_GROUP}}
+HostnameLookups Off
+ErrorLog ${{APACHE_LOG_DIR}}/error.log
+LogLevel warn
+
+IncludeOptional mods-enabled/*.load
+IncludeOptional mods-enabled/*.conf
+
+Include ports.conf
+
+<Directory />
+    Options FollowSymLinks
+    AllowOverride None
+    Require all denied
+</Directory>
+
+<Directory /usr/share>
+    AllowOverride None
+    Require all granted
+</Directory>
+
+<Directory {webroot}/>
+    Options Indexes FollowSymLinks
+    AllowOverride None
+    Require all granted
+</Directory>
+
+AccessFileName .htaccess
+
+<FilesMatch "^\.ht">
+    Require all denied
+</FilesMatch>
+
+LogFormat "%v:%p %h %l %u %t \\"%r\\" %>s %O \\"%{{Referer}}i\\" \\"%{{User-Agent}}i\\"" vhost_combined
+LogFormat "%h %l %u %t \\"%r\\" %>s %O \\"%{{Referer}}i\\" \\"%{{User-Agent}}i\\"" combined
+LogFormat "%h %l %u %t \\"%r\\" %>s %O" common
+LogFormat "%{{Referer}}i -> %U" referer
+LogFormat "%{{User-agent}}i" agent
+
+IncludeOptional conf-enabled/*.conf
+IncludeOptional sites-enabled/*.conf
+'''.format(config=config_path, webroot=webroot_path))
+
+    with open(os.path.join(config_path, 'ports.conf'), 'w') as file_h:
+        file_h.write('''\
+Listen {http}
+<IfModule ssl_module>
+    Listen {https}
+</IfModule>
+<IfModule mod_gnutls.c>
+    Listen {https}
+</IfModule>
+'''.format(http=http_port, https=https_port))
+
+    new_environ = os.environ.copy()
+    new_environ['APACHE_CONFDIR'] = config_path
+
+    run_path = os.path.join(apache_root, 'run')
+    lock_path = os.path.join(apache_root, 'lock')
+    logs_path = os.path.join(apache_root, 'logs')
+    os.mkdir(run_path)
+    os.mkdir(lock_path)
+    os.mkdir(logs_path)
+
+    user = getpass.getuser()
+    user = user if user != 'root' else 'www-data'
+    group = user
+
+    pid_file = os.path.join(run_path, 'apache.pid')
+
+    with open(os.path.join(config_path, 'envvars'), 'w') as file_h:
+        file_h.write('''\
+unset HOME
+export APACHE_RUN_USER={user}
+export APACHE_RUN_GROUP={group}
+export APACHE_PID_FILE={pid_file}
+export APACHE_RUN_DIR={run_path}
+export APACHE_LOCK_DIR={lock_path}
+export APACHE_LOG_DIR={logs_path}
+export LANG=C
+'''.format(user=user, group=group, pid_file=pid_file,
+           run_path=run_path, lock_path=lock_path, logs_path=logs_path))
+
+    new_environ['APACHE_RUN_USER'] = user
+    new_environ['APACHE_RUN_GROUP'] = group
+    new_environ['APACHE_PID_FILE'] = pid_file
+    new_environ['APACHE_RUN_DIR'] = run_path
+    new_environ['APACHE_LOCK_DIR'] = lock_path
+    new_environ['APACHE_LOG_DIR'] = logs_path
+
+    le_host = 'apache.{0}.wtf'.format(wtf_prefix)
+
+    with open(os.path.join(config_path, 'sites-available', '000-default.conf'), 'w') as file_h:
+        file_h.write('''\
+<VirtualHost *:{http}>
+    ServerAdmin webmaster@localhost
+    ServerName {le_host}
+    DocumentRoot {webroot}
+    
+    ErrorLog ${{APACHE_LOG_DIR}}/error.log
+    CustomLog ${{APACHE_LOG_DIR}}/access.log combined
+</VirtualHost>
+'''.format(http=http_port, le_host=le_host, webroot=webroot_path))
+
+    key_path = key_path if key_path \
+        else pkg_resources.resource_filename('certbot_integration_tests', 'assets/key.pem')
+    cert_path = cert_path if cert_path \
+        else pkg_resources.resource_filename('certbot_integration_tests', 'assets/cert.pem')
+
+    with open(os.path.join(config_path, 'sites-available', 'default-ssl.conf'), 'w') as file_h:
+        file_h.write('''\
+<IfModule mod_ssl.c>
+    <VirtualHost _default_:{https}>
+        ServerAdmin webmaster@localhost
+        ServerName {le_host}
+        DocumentRoot {webroot}
+        
+        ErrorLog ${{APACHE_LOG_DIR}}/error.log
+        CustomLog ${{APACHE_LOG_DIR}}/access.log combined
+        
+        SSLEngine on
+        SSLCertificateFile {cert_path}
+        SSLCertificateKeyFile {key_path}
+        
+        <FilesMatch "\.(cgi|shtml|phtml|php)$">
+            SSLOptions +StdEnvVars
+        </FilesMatch>
+        
+        <Directory /usr/lib/cgi-bin>
+            SSLOptions +StdEnvVars
+        </Directory>
+    </VirtualHost>
+</IfModule>
+'''.format(https=https_port, le_host=le_host, webroot=webroot_path,
+           cert_path=cert_path, key_path=key_path))
+
+    return new_environ, config_path, pid_file
+
+
+def test():
+    env = construct_apache_config_dir('/tmp/test1', 5001, 5002)
+    subprocess.call(['apache2ctl', '-DFOREGROUND'], env=env)
--- a/certbot-ci/certbot_integration_tests/apache_tests/context.py
+++ b/certbot-ci/certbot_integration_tests/apache_tests/context.py
@@ -0,0 +1,51 @@
+import errno
+import os
+import signal
+import subprocess
+
+from certbot_integration_tests.certbot_tests import context as certbot_context
+from certbot_integration_tests.apache_tests import apache_config
+from certbot_integration_tests.utils import certbot_call
+
+
+class IntegrationTestsContext(certbot_context.IntegrationTestsContext):
+    def __init__(self, request):
+        super(IntegrationTestsContext, self).__init__(request)
+
+        subprocess.check_output(['chmod', '+x', self.workspace])
+
+        self.apache_root = os.path.join(self.workspace, 'apache')
+        os.mkdir(self.apache_root)
+
+        self.env, self.config_dir, self.pid_file = apache_config.construct_apache_config_dir(
+            self.apache_root, self.http_01_port, self.tls_alpn_01_port,
+            wtf_prefix=self.worker_id)
+
+    def cleanup(self):
+        self._stop_apache()
+        super(IntegrationTestsContext, self).cleanup()
+
+    def certbot_test_apache(self, args):
+        command = ['--authenticator', 'apache', '--installer', 'apache',
+                   '--apache-server-root', self.config_dir,
+                   '--apache-challenge-location', self.apache_root]
+        command.extend(args)
+
+        return certbot_call.certbot_test(
+            command, self.directory_url, self.http_01_port, self.tls_alpn_01_port,
+            self.config_dir, self.workspace, env=self.env, force_renew=True)
+
+    def _stop_apache(self):
+        try:
+            with open(self.pid_file) as file_h:
+                pid = int(file_h.read().strip())
+        except BaseException:
+            pid = None
+
+        if pid:
+            try:
+                os.kill(pid, signal.SIGTERM)
+            except OSError as err:
+                # Ignore "No such process" error, Apache may already be stopped.
+                if err.errno != errno.ESRCH:
+                    raise
--- a/certbot-ci/certbot_integration_tests/apache_tests/test_main.py
+++ b/certbot-ci/certbot_integration_tests/apache_tests/test_main.py
@@ -0,0 +1,18 @@
+import pytest
+
+from certbot_integration_tests.apache_tests import context as apache_context
+
+
+@pytest.fixture()
+def context(request):
+    # Fixture request is a built-in pytest fixture describing current test request.
+    integration_test_context = apache_context.IntegrationTestsContext(request)
+    try:
+        yield integration_test_context
+    finally:
+        integration_test_context.cleanup()
+
+
+def test_it(context):
+    command = ['-d', 'apache.{0}.wtf'.format(context.worker_id)]
+    context.certbot_test_apache(command)
--- a/certbot-ci/certbot_integration_tests/assets/hook.py
+++ b/certbot-ci/certbot_integration_tests/assets/hook.py
@@ -0,0 +1,11 @@
+#!/usr/bin/env python
+import sys
+import os
+
+hook_script_type = os.path.basename(os.path.dirname(sys.argv[1]))
+if hook_script_type == 'deploy' and ('RENEWED_DOMAINS' not in os.environ or 'RENEWED_LINEAGE' not in os.environ):
+    sys.stderr.write('Environment variables not properly set!\n')
+    sys.exit(1)
+
+with open(sys.argv[2], 'a') as file_h:
+    file_h.write(hook_script_type + '\n')
--- a/certbot-ci/certbot_integration_tests/certbot_tests/assertions.py
+++ b/certbot-ci/certbot_integration_tests/certbot_tests/assertions.py
@@ -1,6 +1,17 @@
 """This module contains advanced assertions for the certbot integration tests."""
 import os
-import grp
+try:
+    import grp
+    POSIX_MODE = True
+except ImportError:
+    import win32api
+    import win32security
+    import ntsecuritycon
+    POSIX_MODE = False
+
+EVERYBODY_SID = 'S-1-1-0'
+SYSTEM_SID = 'S-1-5-18'
+ADMINS_SID = 'S-1-5-32-544'


 def assert_hook_execution(probe_path, probe_content):
@@ -10,9 +21,10 @@ def assert_hook_execution(probe_path, probe_content):
    :param probe_content: content expected when the hook is executed
    """
    with open(probe_path, 'r') as file:
-        lines = file.readlines()
+        data = file.read()

-    assert '{0}{1}'.format(probe_content, os.linesep) in lines
+    lines = [line.strip() for line in data.splitlines()]
+    assert probe_content in lines


 def assert_saved_renew_hook(config_dir, lineage):
@@ -38,16 +50,51 @@ def assert_cert_count_for_lineage(config_dir, lineage, count):
    assert len(certs) == count


-def assert_equals_permissions(file1, file2, mask):
+def assert_equals_group_permissions(file1, file2):
    """
-    Assert that permissions on two files are identical in respect to a given umask.
+    Assert that two files have the same permissions for group owner.
    :param file1: first file path to compare
    :param file2: second file path to compare
-    :param mask: 3-octal representation of a POSIX umask under which the two files mode
-                 should match (eg. 0o074 will test RWX on group and R on world)
    """
-    mode_file1 = os.stat(file1).st_mode & mask
-    mode_file2 = os.stat(file2).st_mode & mask
+    # On Windows there is no group, so this assertion does nothing on this platform
+    if POSIX_MODE:
+        mode_file1 = os.stat(file1).st_mode & 0o070
+        mode_file2 = os.stat(file2).st_mode & 0o070
+
+        assert mode_file1 == mode_file2
+
+
+def assert_equals_world_read_permissions(file1, file2):
+    """
+    Assert that two files have the same read permissions for everyone.
+    :param file1: first file path to compare
+    :param file2: second file path to compare
+    """
+    if POSIX_MODE:
+        mode_file1 = os.stat(file1).st_mode & 0o004
+        mode_file2 = os.stat(file2).st_mode & 0o004
+    else:
+        everybody = win32security.ConvertStringSidToSid(EVERYBODY_SID)
+
+        security1 = win32security.GetFileSecurity(file1, win32security.DACL_SECURITY_INFORMATION)
+        dacl1 = security1.GetSecurityDescriptorDacl()
+
+        mode_file1 = dacl1.GetEffectiveRightsFromAcl({
+            'TrusteeForm': win32security.TRUSTEE_IS_SID,
+            'TrusteeType': win32security.TRUSTEE_IS_USER,
+            'Identifier': everybody,
+        })
+        mode_file1 = mode_file1 & ntsecuritycon.FILE_GENERIC_READ
+
+        security2 = win32security.GetFileSecurity(file2, win32security.DACL_SECURITY_INFORMATION)
+        dacl2 = security2.GetSecurityDescriptorDacl()
+
+        mode_file2 = dacl2.GetEffectiveRightsFromAcl({
+            'TrusteeForm': win32security.TRUSTEE_IS_SID,
+            'TrusteeType': win32security.TRUSTEE_IS_USER,
+            'Identifier': everybody,
+        })
+        mode_file2 = mode_file2 & ntsecuritycon.FILE_GENERIC_READ

    assert mode_file1 == mode_file2

@@ -57,20 +104,57 @@ def assert_equals_group_owner(file1, file2):
    Assert that two files have the same group owner.
    :param file1: first file path to compare
    :param file2: second file path to compare
-    :return:
    """
-    group_owner_file1 = grp.getgrgid(os.stat(file1).st_gid)[0]
-    group_owner_file2 = grp.getgrgid(os.stat(file2).st_gid)[0]
+    # On Windows there is no group, so this assertion does nothing on this platform
+    if POSIX_MODE:
+        group_owner_file1 = grp.getgrgid(os.stat(file1).st_gid)[0]
+        group_owner_file2 = grp.getgrgid(os.stat(file2).st_gid)[0]

-    assert group_owner_file1 == group_owner_file2
+        assert group_owner_file1 == group_owner_file2


-def assert_world_permissions(file, mode):
+def assert_world_no_permissions(file):
    """
-    Assert that a file has the expected world permission.
-    :param file: file path to check
-    :param mode: world permissions mode expected
+    Assert that the given file is not world-readable.
+    :param file: path of the file to check
    """
-    mode_file_all = os.stat(file).st_mode & 0o007
+    if POSIX_MODE:
+        mode_file_all = os.stat(file).st_mode & 0o007
+        assert mode_file_all == 0
+    else:
+        security = win32security.GetFileSecurity(file, win32security.DACL_SECURITY_INFORMATION)
+        dacl = security.GetSecurityDescriptorDacl()
+        mode = dacl.GetEffectiveRightsFromAcl({
+            'TrusteeForm': win32security.TRUSTEE_IS_SID,
+            'TrusteeType': win32security.TRUSTEE_IS_USER,
+            'Identifier': win32security.ConvertStringSidToSid(EVERYBODY_SID),
+        })

-    assert mode_file_all == mode
+        assert not mode
+
+
+def assert_world_read_permissions(file):
+    """
+    Assert that the given file is world-readable, but not world-writable or world-executable.
+    :param file: path of the file to check
+    """
+    if POSIX_MODE:
+        mode_file_all = os.stat(file).st_mode & 0o007
+        assert mode_file_all == 4
+    else:
+        security = win32security.GetFileSecurity(file, win32security.DACL_SECURITY_INFORMATION)
+        dacl = security.GetSecurityDescriptorDacl()
+        mode = dacl.GetEffectiveRightsFromAcl({
+            'TrusteeForm': win32security.TRUSTEE_IS_SID,
+            'TrusteeType': win32security.TRUSTEE_IS_USER,
+            'Identifier': win32security.ConvertStringSidToSid(EVERYBODY_SID),
+        })
+
+        assert not mode & ntsecuritycon.FILE_GENERIC_WRITE
+        assert not mode & ntsecuritycon.FILE_GENERIC_EXECUTE
+        assert mode & ntsecuritycon.FILE_GENERIC_READ == ntsecuritycon.FILE_GENERIC_READ
+
+
+def _get_current_user():
+    account_name = win32api.GetUserNameEx(win32api.NameSamCompatible)
+    return win32security.LookupAccountName(None, account_name)[0]
--- a/certbot-ci/certbot_integration_tests/certbot_tests/context.py
+++ b/certbot-ci/certbot_integration_tests/certbot_tests/context.py
@@ -1,10 +1,11 @@
 """Module to handle the context of integration tests."""
+import logging
 import os
 import shutil
 import sys
 import tempfile

-from certbot_integration_tests.utils import misc, certbot_call
+from certbot_integration_tests.utils import certbot_call


 class IntegrationTestsContext(object):
@@ -19,7 +20,7 @@ class IntegrationTestsContext(object):
            self.worker_id = 'primary'
            acme_xdist = request.config.acme_xdist

-        self.acme_server =acme_xdist['acme_server']
+        self.acme_server = acme_xdist['acme_server']
        self.directory_url = acme_xdist['directory_url']
        self.tls_alpn_01_port = acme_xdist['https_port'][self.worker_id]
        self.http_01_port = acme_xdist['http_port'][self.worker_id]
@@ -30,7 +31,10 @@ class IntegrationTestsContext(object):

        self.workspace = tempfile.mkdtemp()
        self.config_dir = os.path.join(self.workspace, 'conf')
-        self.hook_probe = tempfile.mkstemp(dir=self.workspace)[1]
+
+        probe = tempfile.mkstemp(dir=self.workspace)
+        os.close(probe[0])
+        self.hook_probe = probe[1]

        self.manual_dns_auth_hook = (
            '{0} -c "import os; import requests; import json; '
--- a/certbot-ci/certbot_integration_tests/certbot_tests/test_main.py
+++ b/certbot-ci/certbot_integration_tests/certbot_tests/test_main.py
@@ -11,8 +11,11 @@ from os.path import join, exists
 import pytest
 from certbot_integration_tests.certbot_tests import context as certbot_context
 from certbot_integration_tests.certbot_tests.assertions import (
-    assert_hook_execution, assert_saved_renew_hook, assert_cert_count_for_lineage,
-    assert_world_permissions, assert_equals_group_owner, assert_equals_permissions,
+    assert_hook_execution, assert_saved_renew_hook,
+    assert_cert_count_for_lineage,
+    assert_world_no_permissions, assert_world_read_permissions,
+    assert_equals_group_owner, assert_equals_group_permissions, assert_equals_world_read_permissions,
+    EVERYBODY_SID
 )
 from certbot_integration_tests.utils import misc

@@ -84,9 +87,9 @@ def test_http_01(context):
        context.certbot([
            '--domains', certname, '--preferred-challenges', 'http-01', 'run',
            '--cert-name', certname,
-            '--pre-hook', 'echo wtf.pre >> "{0}"'.format(context.hook_probe),
-            '--post-hook', 'echo wtf.post >> "{0}"'.format(context.hook_probe),
-            '--deploy-hook', 'echo deploy >> "{0}"'.format(context.hook_probe)
+            '--pre-hook', misc.echo('wtf_pre', context.hook_probe),
+            '--post-hook', misc.echo('wtf_post', context.hook_probe),
+            '--deploy-hook', misc.echo('deploy', context.hook_probe),
        ])

    assert_hook_execution(context.hook_probe, 'deploy')
@@ -104,9 +107,9 @@ def test_manual_http_auth(context):
            '--cert-name', certname,
            '--manual-auth-hook', scripts[0],
            '--manual-cleanup-hook', scripts[1],
-            '--pre-hook', 'echo wtf.pre >> "{0}"'.format(context.hook_probe),
-            '--post-hook', 'echo wtf.post >> "{0}"'.format(context.hook_probe),
-            '--renew-hook', 'echo renew >> "{0}"'.format(context.hook_probe)
+            '--pre-hook', misc.echo('wtf_pre', context.hook_probe),
+            '--post-hook', misc.echo('wtf_post', context.hook_probe),
+            '--renew-hook', misc.echo('renew', context.hook_probe),
        ])

    with pytest.raises(AssertionError):
@@ -122,9 +125,9 @@ def test_manual_dns_auth(context):
        'run', '--cert-name', certname,
        '--manual-auth-hook', context.manual_dns_auth_hook,
        '--manual-cleanup-hook', context.manual_dns_cleanup_hook,
-        '--pre-hook', 'echo wtf.pre >> "{0}"'.format(context.hook_probe),
-        '--post-hook', 'echo wtf.post >> "{0}"'.format(context.hook_probe),
-        '--renew-hook', 'echo renew >> "{0}"'.format(context.hook_probe)
+        '--pre-hook', misc.echo('wtf_pre', context.hook_probe),
+        '--post-hook', misc.echo('wtf_post', context.hook_probe),
+        '--renew-hook', misc.echo('renew', context.hook_probe),
    ])

    with pytest.raises(AssertionError):
@@ -173,21 +176,19 @@ def test_renew_files_permissions(context):
    certname = context.get_domain('renew')
    context.certbot(['-d', certname])

+    privkey1 = join(context.config_dir, 'archive', certname, 'privkey1.pem')
+    privkey2 = join(context.config_dir, 'archive', certname, 'privkey2.pem')
+
    assert_cert_count_for_lineage(context.config_dir, certname, 1)
-    assert_world_permissions(
-        join(context.config_dir, 'archive', certname, 'privkey1.pem'), 0)
+    assert_world_no_permissions(privkey1)

    context.certbot(['renew'])

    assert_cert_count_for_lineage(context.config_dir, certname, 2)
-    assert_world_permissions(
-        join(context.config_dir, 'archive', certname, 'privkey2.pem'), 0)
-    assert_equals_group_owner(
-        join(context.config_dir, 'archive', certname, 'privkey1.pem'),
-        join(context.config_dir, 'archive', certname, 'privkey2.pem'))
-    assert_equals_permissions(
-        join(context.config_dir, 'archive', certname, 'privkey1.pem'),
-        join(context.config_dir, 'archive', certname, 'privkey2.pem'), 0o074)
+    assert_world_no_permissions(privkey2)
+    assert_equals_group_owner(privkey1, privkey2)
+    assert_equals_world_read_permissions(privkey1, privkey2)
+    assert_equals_group_permissions(privkey1, privkey2)


 def test_renew_with_hook_scripts(context):
@@ -211,15 +212,35 @@ def test_renew_files_propagate_permissions(context):

    assert_cert_count_for_lineage(context.config_dir, certname, 1)

-    os.chmod(join(context.config_dir, 'archive', certname, 'privkey1.pem'), 0o444)
+    privkey1 = join(context.config_dir, 'archive', certname, 'privkey1.pem')
+    privkey2 = join(context.config_dir, 'archive', certname, 'privkey2.pem')
+
+    if os.name != 'nt':
+        os.chmod(privkey1, 0o444)
+    else:
+        import win32security
+        import ntsecuritycon
+        # Get the current DACL of the private key
+        security = win32security.GetFileSecurity(privkey1, win32security.DACL_SECURITY_INFORMATION)
+        dacl = security.GetSecurityDescriptorDacl()
+        # Create a read permission for Everybody group
+        everybody = win32security.ConvertStringSidToSid(EVERYBODY_SID)
+        dacl.AddAccessAllowedAce(win32security.ACL_REVISION, ntsecuritycon.FILE_GENERIC_READ, everybody)
+        # Apply the updated DACL to the private key
+        security.SetSecurityDescriptorDacl(1, dacl, 0)
+        win32security.SetFileSecurity(privkey1, win32security.DACL_SECURITY_INFORMATION, security)
+
    context.certbot(['renew'])

    assert_cert_count_for_lineage(context.config_dir, certname, 2)
-    assert_world_permissions(
-        join(context.config_dir, 'archive', certname, 'privkey2.pem'), 4)
-    assert_equals_permissions(
-        join(context.config_dir, 'archive', certname, 'privkey1.pem'),
-        join(context.config_dir, 'archive', certname, 'privkey2.pem'), 0o074)
+    if os.name != 'nt':
+        # On Linux, read world permissions + all group permissions will be copied from the previous private key
+        assert_world_read_permissions(privkey2)
+        assert_equals_world_read_permissions(privkey1, privkey2)
+        assert_equals_group_permissions(privkey1, privkey2)
+    else:
+        # On Windows, world will never have any permissions, and group permission is irrelevant for this platform
+        assert_world_no_permissions(privkey2)


 def test_graceful_renew_it_is_not_time(context):
@@ -229,7 +250,7 @@ def test_graceful_renew_it_is_not_time(context):

    assert_cert_count_for_lineage(context.config_dir, certname, 1)

-    context.certbot(['renew', '--deploy-hook', 'echo deploy >> "{0}"'.format(context.hook_probe)],
+    context.certbot(['renew', '--deploy-hook', misc.echo('deploy', context.hook_probe)],
                    force_renew=False)

    assert_cert_count_for_lineage(context.config_dir, certname, 1)
@@ -250,7 +271,7 @@ def test_graceful_renew_it_is_time(context):
    with open(join(context.config_dir, 'renewal', '{0}.conf'.format(certname)), 'w') as file:
        file.writelines(lines)

-    context.certbot(['renew', '--deploy-hook', 'echo deploy >> "{0}"'.format(context.hook_probe)],
+    context.certbot(['renew', '--deploy-hook', misc.echo('deploy', context.hook_probe)],
                    force_renew=False)

    assert_cert_count_for_lineage(context.config_dir, certname, 2)
@@ -317,9 +338,9 @@ def test_renew_hook_override(context):
    context.certbot([
        'certonly', '-d', certname,
        '--preferred-challenges', 'http-01',
-        '--pre-hook', 'echo pre >> "{0}"'.format(context.hook_probe),
-        '--post-hook', 'echo post >> "{0}"'.format(context.hook_probe),
-        '--deploy-hook', 'echo deploy >> "{0}"'.format(context.hook_probe)
+        '--pre-hook', misc.echo('pre', context.hook_probe),
+        '--post-hook', misc.echo('post', context.hook_probe),
+        '--deploy-hook', misc.echo('deploy', context.hook_probe),
    ])

    assert_hook_execution(context.hook_probe, 'pre')
@@ -330,14 +351,14 @@ def test_renew_hook_override(context):
    open(context.hook_probe, 'w').close()
    context.certbot([
        'renew', '--cert-name', certname,
-        '--pre-hook', 'echo pre-override >> "{0}"'.format(context.hook_probe),
-        '--post-hook', 'echo post-override >> "{0}"'.format(context.hook_probe),
-        '--deploy-hook', 'echo deploy-override >> "{0}"'.format(context.hook_probe)
+        '--pre-hook', misc.echo('pre_override', context.hook_probe),
+        '--post-hook', misc.echo('post_override', context.hook_probe),
+        '--deploy-hook', misc.echo('deploy_override', context.hook_probe),
    ])

-    assert_hook_execution(context.hook_probe, 'pre-override')
-    assert_hook_execution(context.hook_probe, 'post-override')
-    assert_hook_execution(context.hook_probe, 'deploy-override')
+    assert_hook_execution(context.hook_probe, 'pre_override')
+    assert_hook_execution(context.hook_probe, 'post_override')
+    assert_hook_execution(context.hook_probe, 'deploy_override')
    with pytest.raises(AssertionError):
        assert_hook_execution(context.hook_probe, 'pre')
    with pytest.raises(AssertionError):
@@ -349,11 +370,11 @@ def test_renew_hook_override(context):
    open(context.hook_probe, 'w').close()
    context.certbot(['renew', '--cert-name', certname])

-    assert_hook_execution(context.hook_probe, 'pre-override')
-    assert_hook_execution(context.hook_probe, 'post-override')
-    assert_hook_execution(context.hook_probe, 'deploy-override')
+    assert_hook_execution(context.hook_probe, 'pre_override')
+    assert_hook_execution(context.hook_probe, 'post_override')
+    assert_hook_execution(context.hook_probe, 'deploy_override')
+

-    
 def test_invalid_domain_with_dns_challenge(context):
    """Test certificate issuance failure with DNS-01 challenge."""
    # Manual dns auth hooks from misc are designed to fail if the domain contains 'fail-*'.
@@ -512,7 +533,7 @@ def test_revoke_multiple_lineages(context):
        data = file.read()

    data = re.sub('archive_dir = .*\n',
-                  'archive_dir = {0}\n'.format(join(context.config_dir, 'archive', cert1)),
+                  'archive_dir = {0}\n'.format(join(context.config_dir, 'archive', cert1).replace('\\', '\\\\')),
                  data)

    with open(join(context.config_dir, 'renewal', '{0}.conf'.format(cert2)), 'w') as file:
@@ -555,11 +576,9 @@ def test_ocsp_status_stale(context):

 def test_ocsp_status_live(context):
    """Test retrieval of OCSP statuses for live config"""
-    if context.acme_server == 'pebble':
-        pytest.skip('Pebble does not support OCSP status requests.')
+    cert = context.get_domain('ocsp-check')

    # OSCP 1: Check live certificate OCSP status (VALID)
-    cert = context.get_domain('ocsp-check')
    context.certbot(['--domains', cert])
    output = context.certbot(['certificates'])

--- a/certbot-ci/certbot_integration_tests/utils/acme_server.py
+++ b/certbot-ci/certbot_integration_tests/utils/acme_server.py
@@ -134,6 +134,13 @@ class ACMEServer(object):
            [challtestsrv_path, '-management', ':{0}'.format(CHALLTESTSRV_PORT), '-defaultIPv6', '""',
             '-defaultIPv4', '127.0.0.1', '-http01', '""', '-tlsalpn01', '""', '-https01', '""'])

+        # pebble_ocsp_server is imported here and not at the top of module in order to avoid a useless
+        # ImportError, in the case where cryptography dependency is too old to support ocsp, but
+        # Boulder is used instead of Pebble, so pebble_ocsp_server is not used. This is the typical
+        # situation of integration-certbot-oldest tox testenv.
+        from certbot_integration_tests.utils import pebble_ocsp_server
+        self._launch_process([sys.executable, pebble_ocsp_server.__file__])
+
        # Wait for the ACME CA server to be up.
        print('=> Waiting for pebble instance to respond...')
        misc.check_until_timeout(self.acme_xdist['directory_url'])
--- a/certbot-ci/certbot_integration_tests/utils/certbot_call.py
+++ b/certbot-ci/certbot_integration_tests/utils/certbot_call.py
@@ -6,12 +6,12 @@ import subprocess
 import sys
 import os

-from certbot_integration_tests.utils import misc
+import certbot_integration_tests
 from certbot_integration_tests.utils.constants import *


 def certbot_test(certbot_args, directory_url, http_01_port, tls_alpn_01_port,
-                 config_dir, workspace, force_renew=True):
+                 config_dir, workspace, env=None, force_renew=True):
    """
    Invoke the certbot executable available in PATH in a test context for the given args.
    The test context consists in running certbot in debug mode, with various flags suitable
@@ -23,28 +23,70 @@ def certbot_test(certbot_args, directory_url, http_01_port, tls_alpn_01_port,
    :param int tls_alpn_01_port: port for the TLS-ALPN-01 challenges
    :param str config_dir: certbot configuration directory to use
    :param str workspace: certbot current directory to use
+    :param obj env: the environment variables to use (default: None, then current env will be used)
    :param bool force_renew: set False to not force renew existing certificates (default: True)
    :return: stdout as string
    :rtype: str
    """
+    new_environ = env if env else os.environ.copy()
    command, env = _prepare_args_env(certbot_args, directory_url, http_01_port, tls_alpn_01_port,
-                                     config_dir, workspace, force_renew)
+                                     config_dir, workspace, force_renew, new_environ)

    return subprocess.check_output(command, universal_newlines=True, cwd=workspace, env=env)


-def _prepare_args_env(certbot_args, directory_url, http_01_port, tls_alpn_01_port,
-                      config_dir, workspace, force_renew):
-    new_environ = os.environ.copy()
+def _prepare_environ(workspace, new_environ):
+    new_environ = new_environ.copy()
    new_environ['TMPDIR'] = workspace

+    # So, pytest is nice, and a little too nice for our usage.
+    # In order to help user to call seamlessly any piece of python code without requiring to
+    # install it as a full-fledged setuptools distribution for instance, it may inject the path
+    # to the test files into the PYTHONPATH. This allows the python interpreter to import
+    # as modules any python file available at this path.
+    # See https://docs.pytest.org/en/3.2.5/pythonpath.html for the explanation and description.
+    # However this behavior is not good in integration tests, in particular the nginx oldest ones.
+    # Indeed during these kind of tests certbot is installed as a transitive dependency to
+    # certbot-nginx. Here is the trick: this certbot version is not necessarily the same as
+    # the certbot codebase lying in current working directory. For instance in oldest tests
+    # certbot==0.36.0 may be installed while the codebase corresponds to certbot==0.37.0.dev0.
+    # Then during a pytest run, PYTHONPATH contains the path to the Certbot codebase, so invoking
+    # certbot will import the modules from the codebase (0.37.0.dev0), not from the
+    # required/installed version (0.36.0).
+    # This will lead to funny and totally incomprehensible errors. To avoid that, we ensure that
+    # if PYTHONPATH is set, it does not contain the path to the root of the codebase.
+    if new_environ.get('PYTHONPATH'):
+        # certbot_integration_tests.__file__ is:
+        # '/path/to/certbot/certbot-ci/certbot_integration_tests/__init__.pyc'
+        # ... and we want '/path/to/certbot'
+        certbot_root = os.path.dirname(os.path.dirname(os.path.dirname(certbot_integration_tests.__file__)))
+        python_paths = [path for path in new_environ['PYTHONPATH'].split(':') if path != certbot_root]
+        new_environ['PYTHONPATH'] = ':'.join(python_paths)
+
+    return new_environ
+
+
+def _compute_additional_args(workspace, environ, force_renew):
    additional_args = []
-    if misc.get_certbot_version() >= LooseVersion('0.30.0'):
+    output = subprocess.check_output(['certbot', '--version'],
+                                     universal_newlines=True, stderr=subprocess.STDOUT,
+                                     cwd=workspace, env=environ)
+    version_str = output.split(' ')[1].strip()  # Typical response is: output = 'certbot 0.31.0.dev0'
+    if LooseVersion(version_str) >= LooseVersion('0.30.0'):
        additional_args.append('--no-random-sleep-on-renew')

    if force_renew:
        additional_args.append('--renew-by-default')

+    return additional_args
+
+
+def _prepare_args_env(certbot_args, directory_url, http_01_port, tls_alpn_01_port,
+                      config_dir, workspace, force_renew, new_environ):
+
+    new_environ = _prepare_environ(workspace, new_environ)
+    additional_args = _compute_additional_args(workspace, new_environ, force_renew)
+
    command = [
        'certbot',
        '--server', directory_url,
--- a/certbot-ci/certbot_integration_tests/utils/constants.py
+++ b/certbot-ci/certbot_integration_tests/utils/constants.py
@@ -5,3 +5,5 @@ CHALLTESTSRV_PORT = 8055
 BOULDER_V1_DIRECTORY_URL = 'http://localhost:4000/directory'
 BOULDER_V2_DIRECTORY_URL = 'http://localhost:4001/directory'
 PEBBLE_DIRECTORY_URL = 'https://localhost:14000/dir'
+PEBBLE_MANAGEMENT_URL = 'https://localhost:15000'
+MOCK_OCSP_SERVER_PORT = 4002
--- a/certbot-ci/certbot_integration_tests/utils/misc.py
+++ b/certbot-ci/certbot_integration_tests/utils/misc.py
@@ -3,9 +3,11 @@ Misc module contains stateless functions that could be used during pytest execut
 or outside during setup/teardown of the integration tests environment.
 """
 import contextlib
+import logging
 import errno
 import multiprocessing
 import os
+import re
 import shutil
 import stat
 import subprocess
@@ -23,7 +25,6 @@ from cryptography.hazmat.primitives.asymmetric import ec
 from cryptography.hazmat.primitives.serialization import Encoding, PrivateFormat, NoEncryption
 from six.moves import socketserver, SimpleHTTPServer

-
 RSA_KEY_TYPE = 'rsa'
 ECDSA_KEY_TYPE = 'ecdsa'

@@ -63,6 +64,10 @@ class GracefulTCPServer(socketserver.TCPServer):
    allow_reuse_address = True


+def _run_server(port):
+    GracefulTCPServer(('', port), SimpleHTTPServer.SimpleHTTPRequestHandler).serve_forever()
+
+
@contextlib.contextmanager
 def create_http_server(port):
    """
@@ -75,10 +80,7 @@ def create_http_server(port):
    current_cwd = os.getcwd()
    webroot = tempfile.mkdtemp()

-    def run():
-        GracefulTCPServer(('', port), SimpleHTTPServer.SimpleHTTPRequestHandler).serve_forever()
-
-    process = multiprocessing.Process(target=run)
+    process = multiprocessing.Process(target=_run_server, args=(port,))

    try:
        # SimpleHTTPServer is designed to serve files from the current working directory at the
@@ -120,15 +122,9 @@ def generate_test_file_hooks(config_dir, hook_probe):
    :param str config_dir: current certbot config directory
    :param hook_probe: path to the hook probe to test hook scripts execution
    """
-    if sys.platform == 'win32':
-        extension = 'bat'
-    else:
-        extension = 'sh'
+    hook_path = pkg_resources.resource_filename('certbot_integration_tests', 'assets/hook.py')

-    renewal_hooks_dirs = list_renewal_hooks_dirs(config_dir)
-    renewal_deploy_hook_path = os.path.join(renewal_hooks_dirs[1], 'hook.sh')
-
-    for hook_dir in renewal_hooks_dirs:
+    for hook_dir in list_renewal_hooks_dirs(config_dir):
        # We want an equivalent of bash `chmod -p $HOOK_DIR, that does not fail if one folder of
        # the hierarchy already exists. It is not the case of os.makedirs. Python 3 has an
        # optional parameter `exists_ok` to not fail on existing dir, but Python 2.7 does not.
@@ -138,26 +134,25 @@ def generate_test_file_hooks(config_dir, hook_probe):
        except OSError as error:
            if error.errno != errno.EEXIST:
                raise
-        hook_path = os.path.join(hook_dir, 'hook.{0}'.format(extension))
-        if extension == 'sh':
-            data = '''\
-#!/bin/bash -xe
-if [ "$0" = "{0}" ]; then
-    if [ -z "$RENEWED_DOMAINS" -o -z "$RENEWED_LINEAGE" ]; then
-        echo "Environment variables not properly set!" >&2
-        exit 1
-    fi
-fi
-echo $(basename $(dirname "$0")) >> "{1}"\
-'''.format(renewal_deploy_hook_path, hook_probe)
-        else:
-            # TODO: Write the equivalent bat file for Windows
-            data = '''\

-'''
-        with open(hook_path, 'w') as file:
-            file.write(data)
-        os.chmod(hook_path, os.stat(hook_path).st_mode | stat.S_IEXEC)
+        if os.name != 'nt':
+            entrypoint_script_path = os.path.join(hook_dir, 'entrypoint.sh')
+            entrypoint_script = '''\
+#!/usr/bin/env bash
+set -e
+"{0}" "{1}" "{2}" "{3}"
+'''.format(sys.executable, hook_path, entrypoint_script_path, hook_probe)
+        else:
+            entrypoint_script_path = os.path.join(hook_dir, 'entrypoint.bat')
+            entrypoint_script = '''\
+@echo off
+"{0}" "{1}" "{2}" "{3}"
+            '''.format(sys.executable, hook_path, entrypoint_script_path, hook_probe)
+
+        with open(entrypoint_script_path, 'w') as file_h:
+            file_h.write(entrypoint_script)
+
+        os.chmod(entrypoint_script_path, os.stat(entrypoint_script_path).st_mode | stat.S_IEXEC)


@contextlib.contextmanager
@@ -194,7 +189,7 @@ for _ in range(0, 10):
    except requests.exceptions.ConnectionError:
        pass
 raise ValueError('Error, url did not respond after 10 attempts: {{0}}'.format(url))
-'''.format(http_server_root, http_port))
+'''.format(http_server_root.replace('\\', '\\\\'), http_port))
        os.chmod(auth_script_path, 0o755)

        cleanup_script_path = os.path.join(tempdir, 'cleanup.py')
@@ -205,7 +200,7 @@ import os
 import shutil
 well_known = os.path.join('{0}', '.well-known')
 shutil.rmtree(well_known)
-'''.format(http_server_root))
+'''.format(http_server_root.replace('\\', '\\\\')))
        os.chmod(cleanup_script_path, 0o755)

        yield ('{0} {1}'.format(sys.executable, auth_script_path),
@@ -214,18 +209,6 @@ shutil.rmtree(well_known)
        shutil.rmtree(tempdir)


-def get_certbot_version():
-    """
-    Find the version of the certbot available in PATH.
-    :return str: the certbot version
-    """
-    output = subprocess.check_output(['certbot', '--version'],
-                                     universal_newlines=True, stderr=subprocess.STDOUT)
-    # Typical response is: output = 'certbot 0.31.0.dev0'
-    version_str = output.split(' ')[1].strip()
-    return LooseVersion(version_str)
-
-
 def generate_csr(domains, key_path, csr_path, key_type=RSA_KEY_TYPE):
    """
    Generate a private key, and a CSR for the given domains using this key.
@@ -288,4 +271,32 @@ def load_sample_data_path(workspace):
    original = pkg_resources.resource_filename('certbot_integration_tests', 'assets/sample-config')
    copied = os.path.join(workspace, 'sample-config')
    shutil.copytree(original, copied, symlinks=True)
+
+    if os.name == 'nt':
+        # Fix the symlinks on Windows since GIT is not creating them upon checkout
+        for lineage in ['a.encryption-example.com', 'b.encryption-example.com']:
+            current_live = os.path.join(copied, 'live', lineage)
+            for name in os.listdir(current_live):
+                if name != 'README':
+                    current_file = os.path.join(current_live, name)
+                    with open(current_file) as file_h:
+                        src = file_h.read()
+                    os.unlink(current_file)
+                    os.symlink(os.path.join(current_live, src), current_file)
+
    return copied
+
+
+def echo(keyword, path=None):
+    """
+    Generate a platform independent executable command
+    that echoes the given keyword into the given file.
+    :param keyword: the keyword to echo (must be a single keyword)
+    :param path: path to the file were keyword is echoed
+    :return: the executable command
+    """
+    if not re.match(r'^\w+$', keyword):
+        raise ValueError('Error, keyword `{0}` is not a single keyword.'
+                         .format(keyword))
+    return '{0} -c "from __future__ import print_function; print(\'{1}\')"{2}'.format(
+        os.path.basename(sys.executable), keyword, ' >> "{0}"'.format(path) if path else '')
--- a/certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py
+++ b/certbot-ci/certbot_integration_tests/utils/pebble_artifacts.py
@@ -1,19 +1,18 @@
 import json
-import platform
 import os
 import stat

 import pkg_resources
 import requests

-PEBBLE_VERSION = 'v2.1.0'
+from certbot_integration_tests.utils.constants import MOCK_OCSP_SERVER_PORT
+
+PEBBLE_VERSION = 'v2.2.1'
 ASSETS_PATH = pkg_resources.resource_filename('certbot_integration_tests', 'assets')


 def fetch(workspace):
-    suffix = '{0}-{1}{2}'.format(platform.system().lower(),
-                                 platform.machine().lower().replace('x86_64', 'amd64'),
-                                 '.exe' if platform.system() == 'Windows' else '')
+    suffix = 'linux-amd64' if os.name != 'nt' else 'windows-amd64.exe'

    pebble_path = _fetch_asset('pebble', suffix)
    challtestsrv_path = _fetch_asset('pebble-challtestsrv', suffix)
@@ -42,10 +41,12 @@ def _build_pebble_config(workspace):
        file_h.write(json.dumps({
            'pebble': {
                'listenAddress': '0.0.0.0:14000',
+                'managementListenAddress': '0.0.0.0:15000',
                'certificate': os.path.join(ASSETS_PATH, 'cert.pem'),
                'privateKey': os.path.join(ASSETS_PATH, 'key.pem'),
                'httpPort': 5002,
                'tlsPort': 5001,
+                'ocspResponderURL': 'http://127.0.0.1:{0}'.format(MOCK_OCSP_SERVER_PORT),
            },
        }))

--- a/certbot-ci/certbot_integration_tests/utils/pebble_ocsp_server.py
+++ b/certbot-ci/certbot_integration_tests/utils/pebble_ocsp_server.py
@@ -0,0 +1,71 @@
+#!/usr/bin/env python
+"""
+This runnable module interfaces itself with the Pebble management interface in order
+to serve a mock OCSP responder during integration tests against Pebble.
+"""
+import datetime
+import re
+
+import requests
+from dateutil import parser
+
+from cryptography.hazmat.backends import default_backend
+from cryptography.hazmat.primitives import serialization, hashes
+from cryptography import x509
+from cryptography.x509 import ocsp
+from six.moves import BaseHTTPServer
+
+from certbot_integration_tests.utils.misc import GracefulTCPServer
+from certbot_integration_tests.utils.constants import MOCK_OCSP_SERVER_PORT, PEBBLE_MANAGEMENT_URL
+
+
+class _ProxyHandler(BaseHTTPServer.BaseHTTPRequestHandler):
+    def do_POST(self):
+        request = requests.get(PEBBLE_MANAGEMENT_URL + '/intermediate-keys/0', verify=False)
+        issuer_key = serialization.load_pem_private_key(request.content, None, default_backend())
+
+        request = requests.get(PEBBLE_MANAGEMENT_URL + '/intermediates/0', verify=False)
+        issuer_cert = x509.load_pem_x509_certificate(request.content, default_backend())
+
+        try:
+            content_len = int(self.headers.getheader('content-length', 0))
+        except AttributeError:
+            content_len = int(self.headers.get('Content-Length'))
+
+        ocsp_request = ocsp.load_der_ocsp_request(self.rfile.read(content_len))
+        response = requests.get('{0}/cert-status-by-serial/{1}'.format(
+            PEBBLE_MANAGEMENT_URL, str(hex(ocsp_request.serial_number)).replace('0x', '')), verify=False)
+
+        if not response.ok:
+            ocsp_response = ocsp.OCSPResponseBuilder.build_unsuccessful(ocsp.OCSPResponseStatus.UNAUTHORIZED)
+        else:
+            data = response.json()
+
+            now = datetime.datetime.utcnow()
+            cert = x509.load_pem_x509_certificate(data['Certificate'].encode(), default_backend())
+            if data['Status'] != 'Revoked':
+                ocsp_status, revocation_time, revocation_reason = ocsp.OCSPCertStatus.GOOD, None, None
+            else:
+                ocsp_status, revocation_reason = ocsp.OCSPCertStatus.REVOKED, x509.ReasonFlags.unspecified
+                revoked_at = re.sub(r'( \+\d{4}).*$', r'\1', data['RevokedAt'])  # "... +0000 UTC" => "+0000"
+                revocation_time = parser.parse(revoked_at)
+
+            ocsp_response = ocsp.OCSPResponseBuilder().add_response(
+                cert=cert, issuer=issuer_cert, algorithm=hashes.SHA1(),
+                cert_status=ocsp_status,
+                this_update=now, next_update=now + datetime.timedelta(hours=1),
+                revocation_time=revocation_time, revocation_reason=revocation_reason
+            ).responder_id(
+                ocsp.OCSPResponderEncoding.NAME, issuer_cert
+            ).sign(issuer_key, hashes.SHA256())
+
+        self.send_response(200)
+        self.end_headers()
+        self.wfile.write(ocsp_response.public_bytes(serialization.Encoding.DER))
+
+
+if __name__ == '__main__':
+    try:
+        GracefulTCPServer(('', MOCK_OCSP_SERVER_PORT), _ProxyHandler).serve_forever()
+    except KeyboardInterrupt:
+        pass
--- a/certbot-ci/setup.py
+++ b/certbot-ci/setup.py
@@ -1,5 +1,7 @@
-from setuptools import setup
-from setuptools import find_packages
+import sys
+
+from distutils.version import StrictVersion
+from setuptools import setup, find_packages, __version__ as setuptools_version


 version = '0.32.0.dev0'
@@ -11,11 +13,23 @@ install_requires = [
    'pytest',
    'pytest-cov',
    'pytest-xdist',
+    'python-dateutil',
    'pyyaml',
    'requests',
    'six',
 ]

+# Add pywin32 on Windows platforms to handle low-level system calls.
+# This dependency needs to be added using environment markers to avoid its installation on Linux.
+# However environment markers are supported only with setuptools >= 36.2.
+# So this dependency is not added for old Linux distributions with old setuptools,
+# in order to allow these systems to build certbot from sources.
+if StrictVersion(setuptools_version) >= StrictVersion('36.2'):
+    install_requires.append("pywin32>=224 ; sys_platform == 'win32'")
+elif 'bdist_wheel' in sys.argv[1:]:
+    raise RuntimeError('Error, you are trying to build certbot wheels using an old version '
+                       'of setuptools. Version 36.2+ of setuptools is required.')
+
 setup(
    name='certbot-ci',
    version=version,
@@ -37,6 +51,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
    ],
--- a/certbot-compatibility-test/setup.py
+++ b/certbot-compatibility-test/setup.py
@@ -4,7 +4,7 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 install_requires = [
    'certbot',
@@ -47,6 +47,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
    ],
--- a/certbot-dns-cloudflare/local-oldest-requirements.txt
+++ b/certbot-dns-cloudflare/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.29.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-cloudflare/setup.py
+++ b/certbot-dns-cloudflare/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.29.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'cloudflare>=1.5.1',
    'mock',
    'setuptools',
@@ -43,6 +43,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-cloudxns/local-oldest-requirements.txt
+++ b/certbot-dns-cloudxns/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-cloudxns/setup.py
+++ b/certbot-dns-cloudxns/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.2.1',  # Support for >1 TXT record per name
    'mock',
    'setuptools',
@@ -43,6 +43,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-digitalocean/local-oldest-requirements.txt
+++ b/certbot-dns-digitalocean/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.29.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-digitalocean/setup.py
+++ b/certbot-dns-digitalocean/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.29.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'mock',
    'python-digitalocean>=1.11',
    'setuptools',
@@ -44,6 +44,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-dnsimple/local-oldest-requirements.txt
+++ b/certbot-dns-dnsimple/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-dnsimple/setup.py
+++ b/certbot-dns-dnsimple/setup.py
@@ -3,13 +3,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'mock',
    'setuptools',
    'zope.interface',
@@ -55,6 +55,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-dnsmadeeasy/local-oldest-requirements.txt
+++ b/certbot-dns-dnsmadeeasy/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-dnsmadeeasy/setup.py
+++ b/certbot-dns-dnsmadeeasy/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.2.1',  # Support for >1 TXT record per name
    'mock',
    'setuptools',
@@ -43,6 +43,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-gehirn/local-oldest-requirements.txt
+++ b/certbot-dns-gehirn/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-gehirn/setup.py
+++ b/certbot-dns-gehirn/setup.py
@@ -2,12 +2,12 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Please update tox.ini when modifying dependency version requirements
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.1.22',
    'mock',
    'setuptools',
@@ -41,6 +41,8 @@ setup(
        'Programming Language :: Python :: 3.4',
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
+        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-google/local-oldest-requirements.txt
+++ b/certbot-dns-google/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.29.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-google/setup.py
+++ b/certbot-dns-google/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.29.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    # 1.5 is the first version that supports oauth2client>=2.0
    'google-api-python-client>=1.5',
    'mock',
@@ -48,6 +48,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-linode/local-oldest-requirements.txt
+++ b/certbot-dns-linode/local-oldest-requirements.txt
@@ -1,4 +1,4 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
 dns-lexicon==2.2.3
--- a/certbot-dns-linode/setup.py
+++ b/certbot-dns-linode/setup.py
@@ -1,12 +1,12 @@
 from setuptools import setup
 from setuptools import find_packages

-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Please update tox.ini when modifying dependency version requirements
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.2.3',
    'mock',
    'setuptools',
@@ -41,6 +41,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-luadns/local-oldest-requirements.txt
+++ b/certbot-dns-luadns/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-luadns/setup.py
+++ b/certbot-dns-luadns/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.2.1',  # Support for >1 TXT record per name
    'mock',
    'setuptools',
@@ -43,6 +43,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-nsone/local-oldest-requirements.txt
+++ b/certbot-dns-nsone/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-nsone/setup.py
+++ b/certbot-dns-nsone/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.2.1',  # Support for >1 TXT record per name
    'mock',
    'setuptools',
@@ -43,6 +43,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-ovh/local-oldest-requirements.txt
+++ b/certbot-dns-ovh/local-oldest-requirements.txt
@@ -1,4 +1,4 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
 dns-lexicon==2.7.14
--- a/certbot-dns-ovh/setup.py
+++ b/certbot-dns-ovh/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.7.14',  # Correct proxy use on OVH provider
    'mock',
    'setuptools',
@@ -42,6 +42,8 @@ setup(
        'Programming Language :: Python :: 3.4',
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
+        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-rfc2136/local-oldest-requirements.txt
+++ b/certbot-dns-rfc2136/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.29.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-rfc2136/setup.py
+++ b/certbot-dns-rfc2136/setup.py
@@ -2,13 +2,13 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.29.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dnspython',
    'mock',
    'setuptools',
@@ -43,6 +43,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-route53/local-oldest-requirements.txt
+++ b/certbot-dns-route53/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.29.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-route53/setup.py
+++ b/certbot-dns-route53/setup.py
@@ -1,13 +1,13 @@
 from setuptools import setup
 from setuptools import find_packages

-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
 install_requires = [
    'acme>=0.29.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'boto3',
    'mock',
    'setuptools',
@@ -37,6 +37,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-dns-sakuracloud/local-oldest-requirements.txt
+++ b/certbot-dns-sakuracloud/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.31.0
-certbot[dev]==0.34.0
+-e .[dev]
--- a/certbot-dns-sakuracloud/setup.py
+++ b/certbot-dns-sakuracloud/setup.py
@@ -2,12 +2,12 @@ from setuptools import setup
 from setuptools import find_packages


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Please update tox.ini when modifying dependency version requirements
 install_requires = [
    'acme>=0.31.0',
-    'certbot>=0.34.0',
+    'certbot>=0.39.0.dev0',
    'dns-lexicon>=2.1.23',
    'mock',
    'setuptools',
@@ -41,6 +41,8 @@ setup(
        'Programming Language :: Python :: 3.4',
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
+        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot-nginx/MANIFEST.in
+++ b/certbot-nginx/MANIFEST.in
@@ -2,5 +2,4 @@ include LICENSE.txt
 include README.rst
 recursive-include docs *
 recursive-include certbot_nginx/tests/testdata *
-include certbot_nginx/options-ssl-nginx.conf
-include certbot_nginx/options-ssl-nginx-old.conf
+recursive-include certbot_nginx/tls_configs *.conf
--- a/certbot-nginx/certbot_nginx/configurator.py
+++ b/certbot-nginx/certbot_nginx/configurator.py
@@ -1,4 +1,6 @@
 """Nginx Configuration"""
+# https://github.com/PyCQA/pylint/issues/73
+from distutils.version import LooseVersion # pylint: disable=no-name-in-module,import-error
 import logging
 import re
 import socket
@@ -91,8 +93,12 @@ class NginxConfigurator(common.Installer):
        :param tup version: version of Nginx as a tuple (1, 4, 7)
            (used mostly for unittesting)

+        :param tup openssl_version: version of OpenSSL linked to Nginx as a tuple (1, 4, 7)
+            (used mostly for unittesting)
+
        """
        version = kwargs.pop("version", None)
+        openssl_version = kwargs.pop("openssl_version", None)
        super(NginxConfigurator, self).__init__(*args, **kwargs)

        # Verify that all directories and files exist with proper permissions
@@ -115,6 +121,7 @@ class NginxConfigurator(common.Installer):
        # These will be set in the prepare function
        self.parser = None
        self.version = version
+        self.openssl_version = openssl_version
        self._enhance_func = {"redirect": self._enable_redirect,
                              "ensure-http-header": self._set_http_header,
                              "staple-ocsp": self._enable_ocsp_stapling}
@@ -124,10 +131,35 @@ class NginxConfigurator(common.Installer):
    @property
    def mod_ssl_conf_src(self):
        """Full absolute path to SSL configuration file source."""
-        config_filename = "options-ssl-nginx.conf"
-        if self.version < (1, 5, 9):
-            config_filename = "options-ssl-nginx-old.conf"
-        return pkg_resources.resource_filename("certbot_nginx", config_filename)
+
+        # Why all this complexity? Well, we want to support Mozilla's intermediate
+        # recommendations. But TLS1.3 is only supported by newer versions of Nginx.
+        # And as for session tickets, our ideal is to turn them off across the board.
+        # But! Turning them off at all is only supported with new enough versions of
+        # Nginx. And older versions of OpenSSL have a bug that leads to browser errors
+        # given certain configurations. While we'd prefer to have forward secrecy, we'd
+        # rather fail open than error out. Unfortunately, Nginx can be compiled against
+        # many versions of OpenSSL. So we have to check both for the two different features,
+        # leading to four different combinations of options.
+        # For a complete history, check out https://github.com/certbot/certbot/issues/7322
+
+        use_tls13 = self.version >= (1, 13, 0)
+        session_tix_off = self.version >= (1, 5, 9) and self.openssl_version and\
+            LooseVersion(self.openssl_version) >= LooseVersion('1.0.2l')
+
+        if use_tls13:
+            if session_tix_off:
+                config_filename = "options-ssl-nginx.conf"
+            else:
+                config_filename = "options-ssl-nginx-tls13-session-tix-on.conf"
+        else:
+            if session_tix_off:
+                config_filename = "options-ssl-nginx-tls12-only.conf"
+            else:
+                config_filename = "options-ssl-nginx-old.conf"
+
+        return pkg_resources.resource_filename(
+            "certbot_nginx", os.path.join("tls_configs", config_filename))

    @property
    def mod_ssl_conf(self):
@@ -166,6 +198,9 @@ class NginxConfigurator(common.Installer):
        if self.version is None:
            self.version = self.get_version()

+        if self.openssl_version is None:
+            self.openssl_version = self._get_openssl_version()
+
        self.install_ssl_options_conf(self.mod_ssl_conf, self.updated_mod_ssl_conf_digest)

        self.install_ssl_dhparams()
@@ -906,17 +941,14 @@ class NginxConfigurator(common.Installer):
        util.make_or_verify_dir(self.config.backup_dir, core_constants.CONFIG_DIRS_MODE)
        util.make_or_verify_dir(self.config.config_dir, core_constants.CONFIG_DIRS_MODE)

-    def get_version(self):
-        """Return version of Nginx Server.
+    def _nginx_version(self):
+        """Return results of nginx -V

-        Version is returned as tuple. (ie. 2.4.7 = (2, 4, 7))
-
-        :returns: version
-        :rtype: tuple
+        :returns: version text
+        :rtype: str

        :raises .PluginError:
-            Unable to find Nginx version or version is unsupported
-
+            Unable to run Nginx version command
        """
        try:
            proc = subprocess.Popen(
@@ -929,6 +961,21 @@ class NginxConfigurator(common.Installer):
            logger.debug(str(error), exc_info=True)
            raise errors.PluginError(
                "Unable to run %s -V" % self.conf('ctl'))
+        return text
+
+    def get_version(self):
+        """Return version of Nginx Server.
+
+        Version is returned as tuple. (ie. 2.4.7 = (2, 4, 7))
+
+        :returns: version
+        :rtype: tuple
+
+        :raises .PluginError:
+            Unable to find Nginx version or version is unsupported
+
+        """
+        text = self._nginx_version()

        version_regex = re.compile(r"nginx version: ([^/]+)/([0-9\.]*)", re.IGNORECASE)
        version_matches = version_regex.findall(text)
@@ -961,6 +1008,28 @@ class NginxConfigurator(common.Installer):

        return nginx_version

+    def _get_openssl_version(self):
+        """Return version of OpenSSL linked to Nginx.
+
+        Version is returned as string. If no version can be found, empty string is returned.
+
+        :returns: openssl_version
+        :rtype: str
+
+        :raises .PluginError:
+            Unable to run Nginx version command
+        """
+        text = self._nginx_version()
+
+        matches = re.findall(r"running with OpenSSL ([^ ]+) ", text)
+        if not matches:
+            matches = re.findall(r"built with OpenSSL ([^ ]+) ", text)
+            if not matches:
+                logger.warning("NGINX configured with OpenSSL alternatives is not officially"
+                    "supported by Certbot.")
+                return ""
+        return matches[0]
+
    def more_info(self):
        """Human-readable string to help understand the module"""
        return (
--- a/certbot-nginx/certbot_nginx/constants.py
+++ b/certbot-nginx/certbot_nginx/constants.py
@@ -22,12 +22,6 @@ MOD_SSL_CONF_DEST = "options-ssl-nginx.conf"
 UPDATED_MOD_SSL_CONF_DIGEST = ".updated-options-ssl-nginx-conf-digest.txt"
 """Name of the hash of the updated or informed mod_ssl_conf as saved in `IConfig.config_dir`."""

-SSL_OPTIONS_HASHES_NEW = [
-    '63e2bddebb174a05c9d8a7cf2adf72f7af04349ba59a1a925fe447f73b2f1abf',
-    '2901debc7ecbc10917edd9084c05464c9c5930b463677571eaf8c94bffd11ae2',
-]
-"""SHA256 hashes of the contents of versions of MOD_SSL_CONF_SRC for nginx >= 1.5.9"""
-
 ALL_SSL_OPTIONS_HASHES = [
    '0f81093a1465e3d4eaa8b0c14e77b2a2e93568b0fc1351c2b87893a95f0de87c',
    '9a7b32c49001fed4cff8ad24353329472a50e86ade1ef9b2b9e43566a619612e',
@@ -36,7 +30,14 @@ ALL_SSL_OPTIONS_HASHES = [
    '394732f2bbe3e5e637c3fb5c6e980a1f1b90b01e2e8d6b7cff41dde16e2a756d',
    '4b16fec2bcbcd8a2f3296d886f17f9953ffdcc0af54582452ca1e52f5f776f16',
    'c052ffff0ad683f43bffe105f7c606b339536163490930e2632a335c8d191cc4',
-] + SSL_OPTIONS_HASHES_NEW
+    '02329eb19930af73c54b3632b3165d84571383b8c8c73361df940cb3894dd426',
+    '63e2bddebb174a05c9d8a7cf2adf72f7af04349ba59a1a925fe447f73b2f1abf',
+    '2901debc7ecbc10917edd9084c05464c9c5930b463677571eaf8c94bffd11ae2',
+    '30baca73ed9a5b0e9a69ea40e30482241d8b1a7343aa79b49dc5d7db0bf53b6c',
+    '02329eb19930af73c54b3632b3165d84571383b8c8c73361df940cb3894dd426',
+    '108c4555058a087496a3893aea5d9e1cee0f20a3085d44a52dc1a66522299ac3',
+    'd5e021706ecdccc7090111b0ae9a29ef61523e927f020e410caf0a1fd7063981',
+]
 """SHA256 hashes of the contents of all versions of MOD_SSL_CONF_SRC"""

 def os_constant(key):
--- a/certbot-nginx/certbot_nginx/options-ssl-nginx-old.conf
+++ b/certbot-nginx/certbot_nginx/options-ssl-nginx-old.conf
@@ -1,13 +0,0 @@
-# This file contains important security parameters. If you modify this file
-# manually, Certbot will be unable to automatically provide future security
-# updates. Instead, Certbot will print and log an error message with a path to
-# the up-to-date file that you will need to refer to when manually updating
-# this file.
-
-ssl_session_cache shared:le_nginx_SSL:10m;
-ssl_session_timeout 1440m;
-
-ssl_protocols TLSv1 TLSv1.1 TLSv1.2;
-ssl_prefer_server_ciphers on;
-
-ssl_ciphers "ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS";
--- a/certbot-nginx/certbot_nginx/options-ssl-nginx.conf
+++ b/certbot-nginx/certbot_nginx/options-ssl-nginx.conf
@@ -1,14 +0,0 @@
-# This file contains important security parameters. If you modify this file
-# manually, Certbot will be unable to automatically provide future security
-# updates. Instead, Certbot will print and log an error message with a path to
-# the up-to-date file that you will need to refer to when manually updating
-# this file.
-
-ssl_session_cache shared:le_nginx_SSL:10m;
-ssl_session_timeout 1440m;
-ssl_session_tickets off;
-
-ssl_protocols TLSv1 TLSv1.1 TLSv1.2;
-ssl_prefer_server_ciphers on;
-
-ssl_ciphers "ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-AES128-SHA256:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA-AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA-AES256-SHA384:ECDHE-ECDSA-AES256-SHA:ECDHE-RSA-AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128-SHA:DHE-RSA-AES256-SHA256:DHE-RSA-AES256-SHA:ECDHE-ECDSA-DES-CBC3-SHA:ECDHE-RSA-DES-CBC3-SHA:EDH-RSA-DES-CBC3-SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128-SHA256:AES256-SHA256:AES128-SHA:AES256-SHA:DES-CBC3-SHA:!DSS";
--- a/certbot-nginx/certbot_nginx/tests/configurator_test.py
+++ b/certbot-nginx/certbot_nginx/tests/configurator_test.py
@@ -394,6 +394,68 @@ class NginxConfiguratorTest(util.NginxTest):
        mock_popen.side_effect = OSError("Can't find program")
        self.assertRaises(errors.PluginError, self.config.get_version)

+    @mock.patch("certbot_nginx.configurator.subprocess.Popen")
+    def test_get_openssl_version(self, mock_popen):
+        # pylint: disable=protected-access
+        mock_popen().communicate.return_value = (
+            "", """
+                nginx version: nginx/1.15.5
+                built by gcc 5.4.0 20160609 (Ubuntu 5.4.0-6ubuntu1~16.04.9)
+                built with OpenSSL 1.0.2g  1 Mar 2016
+                TLS SNI support enabled
+                configure arguments:
+            """)
+        self.assertEqual(self.config._get_openssl_version(), "1.0.2g")
+
+        mock_popen().communicate.return_value = (
+            "", """
+                nginx version: nginx/1.15.5
+                built by gcc 5.4.0 20160609 (Ubuntu 5.4.0-6ubuntu1~16.04.9)
+                built with OpenSSL 1.0.2-beta1  1 Mar 2016
+                TLS SNI support enabled
+                configure arguments:
+            """)
+        self.assertEqual(self.config._get_openssl_version(), "1.0.2-beta1")
+
+        mock_popen().communicate.return_value = (
+            "", """
+                nginx version: nginx/1.15.5
+                built by gcc 5.4.0 20160609 (Ubuntu 5.4.0-6ubuntu1~16.04.9)
+                built with OpenSSL 1.0.2  1 Mar 2016
+                TLS SNI support enabled
+                configure arguments:
+            """)
+        self.assertEqual(self.config._get_openssl_version(), "1.0.2")
+
+        mock_popen().communicate.return_value = (
+            "", """
+                nginx version: nginx/1.15.5
+                built by gcc 5.4.0 20160609 (Ubuntu 5.4.0-6ubuntu1~16.04.9)
+                built with OpenSSL 1.0.2g  1 Mar 2016 (running with OpenSSL 1.0.2a  1 Mar 2016)
+                TLS SNI support enabled
+                configure arguments:
+            """)
+        self.assertEqual(self.config._get_openssl_version(), "1.0.2a")
+
+        mock_popen().communicate.return_value = (
+            "", """
+                nginx version: nginx/1.15.5
+                built by gcc 5.4.0 20160609 (Ubuntu 5.4.0-6ubuntu1~16.04.9)
+                built with LibreSSL 2.2.2
+                TLS SNI support enabled
+                configure arguments:
+            """)
+        self.assertEqual(self.config._get_openssl_version(), "")
+
+        mock_popen().communicate.return_value = (
+            "", """
+                nginx version: nginx/1.15.5
+                built by gcc 5.4.0 20160609 (Ubuntu 5.4.0-6ubuntu1~16.04.9)
+                TLS SNI support enabled
+                configure arguments:
+            """)
+        self.assertEqual(self.config._get_openssl_version(), "")
+
    @mock.patch("certbot_nginx.configurator.subprocess.Popen")
    def test_nginx_restart(self, mock_popen):
        mocked = mock_popen()
@@ -920,13 +982,12 @@ class InstallSslOptionsConfTest(util.NginxTest):
        self._assert_current_file()

    def test_prev_file_updates_to_current_old_nginx(self):
-        from certbot_nginx.constants import ALL_SSL_OPTIONS_HASHES, SSL_OPTIONS_HASHES_NEW
+        from certbot_nginx.constants import ALL_SSL_OPTIONS_HASHES
        self.config.version = (1, 5, 8)
        with mock.patch('certbot.crypto_util.sha256sum',
                new=self._mock_hash_except_ssl_conf_src(ALL_SSL_OPTIONS_HASHES[0])):
            self._call()
        self._assert_current_file()
-        self.assertTrue(self._current_ssl_options_hash() not in SSL_OPTIONS_HASHES_NEW)

    def test_manually_modified_current_file_does_not_update(self):
        with open(self.config.mod_ssl_conf, "a") as mod_ssl_conf:
@@ -963,15 +1024,50 @@ class InstallSslOptionsConfTest(util.NginxTest):
            "Constants.ALL_SSL_OPTIONS_HASHES must be appended"
            " with the sha256 hash of self.config.mod_ssl_conf when it is updated.")

-    def test_old_nginx_version_uses_old_config(self):
+    def test_ssl_config_files_hash_in_all_hashes(self):
+        """
+        It is really critical that all TLS Nginx config files have their SHA256 hash registered in
+        constants.ALL_SSL_OPTIONS_HASHES. Otherwise Certbot will mistakenly assume that the config
+        file has been manually edited by the user, and will refuse to update it.
+        This test ensures that all necessary hashes are present.
+        """
+        from certbot_nginx.constants import ALL_SSL_OPTIONS_HASHES
+        import pkg_resources
+        all_files = [
+            pkg_resources.resource_filename("certbot_nginx", os.path.join("tls_configs", x))
+            for x in ("options-ssl-nginx.conf",
+                      "options-ssl-nginx-old.conf",
+                      "options-ssl-nginx-tls12-only.conf")
+        ]
+        self.assertTrue(all_files)
+        for one_file in all_files:
+            file_hash = crypto_util.sha256sum(one_file)
+            self.assertTrue(file_hash in ALL_SSL_OPTIONS_HASHES,
+                            "Constants.ALL_SSL_OPTIONS_HASHES must be appended with the sha256 "
+                            "hash of {0} when it is updated.".format(one_file))
+
+    def test_nginx_version_uses_correct_config(self):
        self.config.version = (1, 5, 8)
+        self.config.openssl_version = "1.0.2g" # shouldn't matter
        self.assertEqual(os.path.basename(self.config.mod_ssl_conf_src),
                         "options-ssl-nginx-old.conf")
        self._call()
        self._assert_current_file()
        self.config.version = (1, 5, 9)
+        self.config.openssl_version = "1.0.2l"
+        self.assertEqual(os.path.basename(self.config.mod_ssl_conf_src),
+                         "options-ssl-nginx-tls12-only.conf")
+        self._call()
+        self._assert_current_file()
+        self.config.version = (1, 13, 0)
        self.assertEqual(os.path.basename(self.config.mod_ssl_conf_src),
                         "options-ssl-nginx.conf")
+        self._call()
+        self._assert_current_file()
+        self.config.version = (1, 13, 0)
+        self.config.openssl_version = "1.0.2k"
+        self.assertEqual(os.path.basename(self.config.mod_ssl_conf_src),
+                         "options-ssl-nginx-tls13-session-tix-on.conf")


 class DetermineDefaultServerRootTest(certbot_test_util.ConfigTestCase):
--- a/certbot-nginx/certbot_nginx/tests/parser_test.py
+++ b/certbot-nginx/certbot_nginx/tests/parser_test.py
@@ -30,8 +30,16 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
        self.assertEqual(nparser.root, self.config_path)

    def test_root_absolute(self):
-        nparser = parser.NginxParser(os.path.relpath(self.config_path))
-        self.assertEqual(nparser.root, self.config_path)
+        curr_dir = os.getcwd()
+        try:
+            # On Windows current directory may be on a different drive than self.tempdir.
+            # However a relative path between two different drives is invalid. So we move to
+            # self.tempdir to ensure that we stay on the same drive.
+            os.chdir(self.temp_dir)
+            nparser = parser.NginxParser(os.path.relpath(self.config_path))
+            self.assertEqual(nparser.root, self.config_path)
+        finally:
+            os.chdir(curr_dir)

    def test_root_no_trailing_slash(self):
        nparser = parser.NginxParser(self.config_path + os.path.sep)
--- a/certbot-nginx/certbot_nginx/tests/util.py
+++ b/certbot-nginx/certbot_nginx/tests/util.py
@@ -3,7 +3,6 @@ import copy
 import shutil
 import tempfile
 import unittest
-import warnings

 import josepy as jose
 import mock
@@ -11,6 +10,7 @@ import pkg_resources
 import zope.component

 from certbot import configuration
+from certbot import util
 from certbot.compat import os
 from certbot.plugins import common
 from certbot.tests import util as test_util
@@ -34,20 +34,16 @@ class NginxTest(unittest.TestCase):  # pylint: disable=too-few-public-methods
            "rsa512_key.pem"))

    def tearDown(self):
-        # On Windows we have various files which are not correctly closed at the time of tearDown.
-        # For know, we log them until a proper file close handling is written.
-        # Useful for development only, so no warning when we are on a CI process.
-        def onerror_handler(_, path, excinfo):
-            """On error handler"""
-            if not os.environ.get('APPVEYOR'):  # pragma: no cover
-                message = ('Following error occurred when deleting path {0}'
-                           'during tearDown process: {1}'.format(path, str(excinfo)))
-                warnings.warn(message)
+        # Cleanup opened resources after a test. This is usually done through atexit handlers in
+        # Certbot, but during tests, atexit will not run registered functions before tearDown is
+        # called and instead will run them right before the entire test process exits.
+        # It is a problem on Windows, that does not accept to clean resources before closing them.
+        util._release_locks()  # pylint: disable=protected-access

-        shutil.rmtree(self.temp_dir, onerror=onerror_handler)
-        shutil.rmtree(self.config_dir, onerror=onerror_handler)
-        shutil.rmtree(self.work_dir, onerror=onerror_handler)
-        shutil.rmtree(self.logs_dir, onerror=onerror_handler)
+        shutil.rmtree(self.temp_dir)
+        shutil.rmtree(self.config_dir)
+        shutil.rmtree(self.work_dir)
+        shutil.rmtree(self.logs_dir)


 def get_data_filename(filename):
@@ -58,7 +54,7 @@ def get_data_filename(filename):


 def get_nginx_configurator(
-        config_path, config_dir, work_dir, logs_dir, version=(1, 6, 2)):
+        config_path, config_dir, work_dir, logs_dir, version=(1, 6, 2), openssl_version="1.0.2g"):
    """Create an Nginx Configurator with the specified options."""

    backups = os.path.join(work_dir, "backups")
@@ -83,7 +79,8 @@ def get_nginx_configurator(
                    https_port=5001,
                ),
                name="nginx",
-                version=version)
+                version=version,
+                openssl_version=openssl_version)
            config.prepare()

    # Provide general config utility.
--- a/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx-old.conf
+++ b/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx-old.conf
@@ -0,0 +1,13 @@
+# This file contains important security parameters. If you modify this file
+# manually, Certbot will be unable to automatically provide future security
+# updates. Instead, Certbot will print and log an error message with a path to
+# the up-to-date file that you will need to refer to when manually updating
+# this file.
+
+ssl_session_cache shared:le_nginx_SSL:10m;
+ssl_session_timeout 1440m;
+
+ssl_protocols TLSv1.2;
+ssl_prefer_server_ciphers off;
+
+ssl_ciphers "ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384";
--- a/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx-tls12-only.conf
+++ b/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx-tls12-only.conf
@@ -0,0 +1,14 @@
+# This file contains important security parameters. If you modify this file
+# manually, Certbot will be unable to automatically provide future security
+# updates. Instead, Certbot will print and log an error message with a path to
+# the up-to-date file that you will need to refer to when manually updating
+# this file.
+
+ssl_session_cache shared:le_nginx_SSL:10m;
+ssl_session_timeout 1440m;
+ssl_session_tickets off;
+
+ssl_protocols TLSv1.2;
+ssl_prefer_server_ciphers off;
+
+ssl_ciphers "ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384";
--- a/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx-tls13-session-tix-on.conf
+++ b/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx-tls13-session-tix-on.conf
@@ -0,0 +1,13 @@
+# This file contains important security parameters. If you modify this file
+# manually, Certbot will be unable to automatically provide future security
+# updates. Instead, Certbot will print and log an error message with a path to
+# the up-to-date file that you will need to refer to when manually updating
+# this file.
+
+ssl_session_cache shared:le_nginx_SSL:10m;
+ssl_session_timeout 1440m;
+
+ssl_protocols TLSv1.2 TLSv1.3;
+ssl_prefer_server_ciphers off;
+
+ssl_ciphers "ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384";
--- a/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx.conf
+++ b/certbot-nginx/certbot_nginx/tls_configs/options-ssl-nginx.conf
@@ -0,0 +1,14 @@
+# This file contains important security parameters. If you modify this file
+# manually, Certbot will be unable to automatically provide future security
+# updates. Instead, Certbot will print and log an error message with a path to
+# the up-to-date file that you will need to refer to when manually updating
+# this file.
+
+ssl_session_cache shared:le_nginx_SSL:10m;
+ssl_session_timeout 1440m;
+ssl_session_tickets off;
+
+ssl_protocols TLSv1.2 TLSv1.3;
+ssl_prefer_server_ciphers off;
+
+ssl_ciphers "ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-GCM-SHA384:ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:DHE-RSA-AES128-GCM-SHA256:DHE-RSA-AES256-GCM-SHA384";
--- a/certbot-nginx/setup.py
+++ b/certbot-nginx/setup.py
@@ -4,7 +4,7 @@ from setuptools.command.test import test as TestCommand
 import sys


-version = '0.37.0.dev0'
+version = '0.39.0.dev0'

 # Remember to update local-oldest-requirements.txt when changing the minimum
 # acme/certbot version.
@@ -62,6 +62,7 @@ setup(
        'Programming Language :: Python :: 3.5',
        'Programming Language :: Python :: 3.6',
        'Programming Language :: Python :: 3.7',
+        'Programming Language :: Python :: 3.8',
        'Topic :: Internet :: WWW/HTTP',
        'Topic :: Security',
        'Topic :: System :: Installation/Setup',
--- a/certbot/init.py
+++ b/certbot/init.py
@@ -1,4 +1,4 @@
 """Certbot client."""

 # version number like 1.2.3a0, must have at least 2 parts, like 1.2
-__version__ = '0.37.0.dev0'
+__version__ = '0.39.0.dev0'
--- a/certbot/cert_manager.py
+++ b/certbot/cert_manager.py
@@ -262,7 +262,7 @@ def human_readable_cert_info(config, cert, skip_filter_checks=False):
        reasons.append('TEST_CERT')
    if cert.target_expiry <= now:
        reasons.append('EXPIRED')
-    if checker.ocsp_revoked(cert.cert, cert.chain):
+    elif checker.ocsp_revoked(cert):
        reasons.append('REVOKED')

    if reasons:
--- a/certbot/client.py
+++ b/certbot/client.py
@@ -624,7 +624,7 @@ class Client(object):
            reporter.add_message(
                "An error occurred and we failed to restore your config and "
                "restart your server. Please post to "
-                "https://community.letsencrypt.org/c/server-config "
+                "https://community.letsencrypt.org/c/help "
                "with details about your configuration and this error you received.",
                reporter.HIGH_PRIORITY)
            raise
--- a/certbot/compat/filesystem.py
+++ b/certbot/compat/filesystem.py
@@ -20,7 +20,7 @@ except ImportError:
 else:
    POSIX_MODE = False

-from acme.magic_typing import List  # pylint: disable=unused-import, no-name-in-module
+from acme.magic_typing import List, Union, Tuple  # pylint: disable=unused-import, no-name-in-module


 def chmod(file_path, mode):
@@ -166,11 +166,11 @@ def open(file_path, flags, mode=0o777):  # pylint: disable=redefined-builtin
        # See https://docs.microsoft.com/en-us/windows/desktop/api/securitybaseapi/nf-securitybaseapi-setsecuritydescriptordacl  # pylint: disable=line-too-long
        security.SetSecurityDescriptorDacl(1, dacl, 0)

+        handle = None
        try:
            handle = win32file.CreateFile(file_path, win32file.GENERIC_READ,
                                          win32file.FILE_SHARE_READ & win32file.FILE_SHARE_WRITE,
                                          attributes, disposition, 0, None)
-            handle.Close()
        except pywintypes.error as err:
            # Handle native windows errors into python errors to be consistent with the API
            # of os.open in the situation of a file already existing or locked.
@@ -179,6 +179,9 @@ def open(file_path, flags, mode=0o777):  # pylint: disable=redefined-builtin
            if err.winerror == winerror.ERROR_SHARING_VIOLATION:
                raise OSError(errno.EACCES, err.strerror)
            raise err
+        finally:
+            if handle:
+                handle.Close()

        # At this point, the file that did not exist has been created with proper permissions,
        # so os.O_CREAT and os.O_EXCL are not needed anymore. We remove them from the flags to
@@ -261,6 +264,7 @@ def replace(src, dst):


 def realpath(file_path):
+    # type: (str) -> str
    """
    Find the real path for the given path. This method resolves symlinks, including
    recursive symlinks, and is protected against symlinks that creates an infinite loop.
@@ -297,10 +301,11 @@ def realpath(file_path):
 # requires to be run under a privileged shell, so the user will always benefit
 # from the highest (privileged one) set of permissions on a given file.
 def is_executable(path):
+    # type: (str) -> bool
    """
    Is path an executable file?
    :param str path: path to test
-    :returns: True if path is an executable file
+    :return: True if path is an executable file
    :rtype: bool
    """
    if POSIX_MODE:
@@ -309,6 +314,118 @@ def is_executable(path):
    return _win_is_executable(path)


+def has_world_permissions(path):
+    # type: (str) -> bool
+    """
+    Check if everybody/world has any right (read/write/execute) on a file given its path
+    :param str path: path to test
+    :return: True if everybody/world has any right to the file
+    :rtype: bool
+    """
+    if POSIX_MODE:
+        return bool(stat.S_IMODE(os.stat(path).st_mode) & stat.S_IRWXO)
+
+    security = win32security.GetFileSecurity(path, win32security.DACL_SECURITY_INFORMATION)
+    dacl = security.GetSecurityDescriptorDacl()
+
+    return bool(dacl.GetEffectiveRightsFromAcl({
+        'TrusteeForm': win32security.TRUSTEE_IS_SID,
+        'TrusteeType': win32security.TRUSTEE_IS_USER,
+        'Identifier': win32security.ConvertStringSidToSid('S-1-1-0'),
+    }))
+
+
+def compute_private_key_mode(old_key, base_mode):
+    # type: (str, int) -> int
+    """
+    Calculate the POSIX mode to apply to a private key given the previous private key
+    :param str old_key: path to the previous private key
+    :param int base_mode: the minimum modes to apply to a private key
+    :return: the POSIX mode to apply
+    :rtype: int
+    """
+    if POSIX_MODE:
+        # On Linux, we keep read/write/execute permissions
+        # for group and read permissions for everybody.
+        old_mode = (stat.S_IMODE(os.stat(old_key).st_mode) &
+                    (stat.S_IRGRP | stat.S_IWGRP | stat.S_IXGRP | stat.S_IROTH))
+        return base_mode | old_mode
+
+    # On Windows, the mode returned by os.stat is not reliable,
+    # so we do not keep any permission from the previous private key.
+    return base_mode
+
+
+def has_same_ownership(path1, path2):
+    # type: (str, str) -> bool
+    """
+    Return True if the ownership of two files given their respective path is the same.
+    On Windows, ownership is checked against owner only, since files do not have a group owner.
+    :param str path1: path to the first file
+    :param str path2: path to the second file
+    :return: True if both files have the same ownership, False otherwise
+    :rtype: bool
+
+    """
+    if POSIX_MODE:
+        stats1 = os.stat(path1)
+        stats2 = os.stat(path2)
+        return (stats1.st_uid, stats1.st_gid) == (stats2.st_uid, stats2.st_gid)
+
+    security1 = win32security.GetFileSecurity(path1, win32security.OWNER_SECURITY_INFORMATION)
+    user1 = security1.GetSecurityDescriptorOwner()
+
+    security2 = win32security.GetFileSecurity(path2, win32security.OWNER_SECURITY_INFORMATION)
+    user2 = security2.GetSecurityDescriptorOwner()
+
+    return user1 == user2
+
+
+def has_min_permissions(path, min_mode):
+    # type: (str, int) -> bool
+    """
+    Check if a file given its path has at least the permissions defined by the given minimal mode.
+    On Windows, group permissions are ignored since files do not have a group owner.
+    :param str path: path to the file to check
+    :param int min_mode: the minimal permissions expected
+    :return: True if the file matches the minimal permissions expectations, False otherwise
+    :rtype: bool
+    """
+    if POSIX_MODE:
+        st_mode = os.stat(path).st_mode
+        return st_mode == st_mode | min_mode
+
+    # Resolve symlinks, to get a consistent result with os.stat on Linux,
+    # that follows symlinks by default.
+    path = realpath(path)
+
+    # Get owner sid of the file
+    security = win32security.GetFileSecurity(
+        path, win32security.OWNER_SECURITY_INFORMATION | win32security.DACL_SECURITY_INFORMATION)
+    user = security.GetSecurityDescriptorOwner()
+    dacl = security.GetSecurityDescriptorDacl()
+    min_dacl = _generate_dacl(user, min_mode)
+
+    for index in range(min_dacl.GetAceCount()):
+        min_ace = min_dacl.GetAce(index)
+
+        # On a given ACE, index 0 is the ACE type, 1 is the permission mask, and 2 is the SID.
+        # See: http://timgolden.me.uk/pywin32-docs/PyACL__GetAce_meth.html
+        mask = min_ace[1]
+        user = min_ace[2]
+
+        effective_mask = dacl.GetEffectiveRightsFromAcl({
+            'TrusteeForm': win32security.TRUSTEE_IS_SID,
+            'TrusteeType': win32security.TRUSTEE_IS_USER,
+            'Identifier': user,
+        })
+
+        if effective_mask != effective_mask | mask:
+            return False
+
+    return True
+
+
 def _win_is_executable(path):
    if not os.path.isfile(path):
        return False
@@ -469,8 +586,8 @@ def _compare_dacls(dacl1, dacl2):
    This method compare the two given DACLs to check if they are identical.
    Identical means here that they contains the same set of ACEs in the same order.
    """
-    return ([dacl1.GetAce(index) for index in range(0, dacl1.GetAceCount())] ==
-            [dacl2.GetAce(index) for index in range(0, dacl2.GetAceCount())])
+    return ([dacl1.GetAce(index) for index in range(dacl1.GetAceCount())] ==
+            [dacl2.GetAce(index) for index in range(dacl2.GetAceCount())])


 def _get_current_user():
--- a/certbot/compat/misc.py
+++ b/certbot/compat/misc.py
@@ -5,7 +5,6 @@ particular category.
 from __future__ import absolute_import

 import select
-import stat
 import sys

 try:
@@ -18,18 +17,6 @@ from certbot import errors
 from certbot.compat import os


-# MASK_FOR_PRIVATE_KEY_PERMISSIONS defines what are the permissions flags to keep
-# when transferring the permissions from an old private key to a new one.
-if POSIX_MODE:
-    # On Linux, we keep read/write/execute permissions
-    # for group and read permissions for everybody.
-    MASK_FOR_PRIVATE_KEY_PERMISSIONS = stat.S_IRGRP | stat.S_IWGRP | stat.S_IXGRP | stat.S_IROTH
-else:
-    # On Windows, the mode returned by os.stat is not reliable,
-    # so we do not keep any permission from the previous private key.
-    MASK_FOR_PRIVATE_KEY_PERMISSIONS = 0
-
-
 # For Linux: define OS specific standard binary directories
 STANDARD_BINARY_DIRS = ["/usr/sbin", "/usr/local/bin", "/usr/local/sbin"] if POSIX_MODE else []

--- a/certbot/compat/os.py
+++ b/certbot/compat/os.py
@@ -116,3 +116,21 @@ def access(*unused_args, **unused_kwargs):
    raise RuntimeError('Usage of os.access() is forbidden. '
                       'Use certbot.compat.filesystem.check_mode() or '
                       'certbot.compat.filesystem.is_executable() instead.')
+
+
+# On Windows os.stat call result is inconsistent, with a lot of flags that are not set or
+# meaningless. We need to use specialized functions from the certbot.compat.filesystem module.
+def stat(*unused_args, **unused_kwargs):
+    """Method os.stat() is forbidden"""
+    raise RuntimeError('Usage of os.stat() is forbidden. '
+                       'Use certbot.compat.filesystem functions instead '
+                       '(eg. has_min_permissions, has_same_ownership).')
+
+
+# Method os.fstat has the same problem than os.stat, since it is the same function,
+# but accepting a file descriptor instead of a path.
+def fstat(*unused_args, **unused_kwargs):
+    """Method os.stat() is forbidden"""
+    raise RuntimeError('Usage of os.fstat() is forbidden. '
+                       'Use certbot.compat.filesystem functions instead '
+                       '(eg. has_min_permissions, has_same_ownership).')
--- a/certbot/lock.py
+++ b/certbot/lock.py
@@ -167,14 +167,18 @@ class _UnixLockMechanism(_BaseLockMechanism):
        :returns: True if the lock was successfully acquired
        :rtype: bool
        """
+        # Normally os module should not be imported in certbot codebase except in certbot.compat
+        # for the sake of compatibility over Windows and Linux.
+        # We make an exception here, since _lock_success is private and called only on Linux.
+        from os import stat, fstat  # pylint: disable=os-module-forbidden
        try:
-            stat1 = os.stat(self._path)
+            stat1 = stat(self._path)
        except OSError as err:
            if err.errno == errno.ENOENT:
                return False
            raise

-        stat2 = os.fstat(fd)
+        stat2 = fstat(fd)
        # If our locked file descriptor and the file on disk refer to
        # the same device and inode, they're the same file.
        return stat1.st_dev == stat2.st_dev and stat1.st_ino == stat2.st_ino
--- a/certbot/ocsp.py
+++ b/certbot/ocsp.py
@@ -16,11 +16,13 @@ from cryptography.hazmat.backends import default_backend
 from cryptography.hazmat.primitives import serialization
 from cryptography.hazmat.primitives import hashes  # type: ignore
 from cryptography.exceptions import UnsupportedAlgorithm, InvalidSignature
+import pytz
 import requests

 from acme.magic_typing import Optional, Tuple  # pylint: disable=unused-import, no-name-in-module
 from certbot import crypto_util
 from certbot import errors
+from certbot.storage import RenewableCert # pylint: disable=unused-import
 from certbot import util

 logger = logging.getLogger(__name__)
@@ -48,21 +50,29 @@ class RevocationChecker(object):
            else:
                self.host_args = lambda host: ["Host", host]

-    def ocsp_revoked(self, cert_path, chain_path):
-        # type: (str, str) -> bool
+    def ocsp_revoked(self, cert):
+        # type: (RenewableCert) -> bool
        """Get revoked status for a particular cert version.

        .. todo:: Make this a non-blocking call

-        :param str cert_path: Path to certificate
-        :param str chain_path: Path to intermediate cert
-        :returns: True if revoked; False if valid or the check failed
+        :param `.storage.RenewableCert` cert: Certificate object
+        :returns: True if revoked; False if valid or the check failed or cert is expired.
        :rtype: bool

        """
+        cert_path, chain_path = cert.cert, cert.chain
+
        if self.broken:
            return False

+        # Let's Encrypt doesn't update OCSP for expired certificates,
+        # so don't check OCSP if the cert is expired.
+        # https://github.com/certbot/certbot/issues/7152
+        now = pytz.UTC.fromutc(datetime.utcnow())
+        if cert.target_expiry <= now:
+            return False
+
        url, host = _determine_ocsp_server(cert_path)
        if not host or not url:
            return False
--- a/certbot/plugins/dns_common.py
+++ b/certbot/plugins/dns_common.py
@@ -2,7 +2,6 @@

 import abc
 import logging
-import stat
 from time import sleep

 import configobj
@@ -12,6 +11,7 @@ from acme import challenges

 from certbot import errors
 from certbot import interfaces
+from certbot.compat import filesystem
 from certbot.compat import os
 from certbot.display import ops
 from certbot.display import util as display_util
@@ -312,8 +312,7 @@ def validate_file_permissions(filename):

    validate_file(filename)

-    permissions = stat.S_IMODE(os.stat(filename).st_mode)
-    if permissions & stat.S_IRWXO:
+    if filesystem.has_world_permissions(filename):
        logger.warning('Unsafe permissions on credentials configuration file: %s', filename)


--- a/certbot/plugins/dns_common_test.py
+++ b/certbot/plugins/dns_common_test.py
@@ -7,14 +7,15 @@ import unittest
 import mock

 from certbot import errors
+from certbot import util
 from certbot.compat import os
 from certbot.display import util as display_util
 from certbot.plugins import dns_common
 from certbot.plugins import dns_test_common
-from certbot.tests import util
+from certbot.tests import util as test_util


-class DNSAuthenticatorTest(util.TempDirTestCase, dns_test_common.BaseAuthenticatorTest):
+class DNSAuthenticatorTest(test_util.TempDirTestCase, dns_test_common.BaseAuthenticatorTest):
    # pylint: disable=protected-access

    class _FakeDNSAuthenticator(dns_common.DNSAuthenticator):
@@ -50,7 +51,7 @@ class DNSAuthenticatorTest(util.TempDirTestCase, dns_test_common.BaseAuthenticat

        self.auth._cleanup.assert_called_once_with(dns_test_common.DOMAIN, mock.ANY, mock.ANY)

-    @util.patch_get_utility()
+    @test_util.patch_get_utility()
    def test_prompt(self, mock_get_utility):
        mock_display = mock_get_utility()
        mock_display.input.side_effect = ((display_util.OK, "",),
@@ -59,14 +60,14 @@ class DNSAuthenticatorTest(util.TempDirTestCase, dns_test_common.BaseAuthenticat
        self.auth._configure("other_key", "")
        self.assertEqual(self.auth.config.fake_other_key, "value")

-    @util.patch_get_utility()
+    @test_util.patch_get_utility()
    def test_prompt_canceled(self, mock_get_utility):
        mock_display = mock_get_utility()
        mock_display.input.side_effect = ((display_util.CANCEL, "c",),)

        self.assertRaises(errors.PluginError, self.auth._configure, "other_key", "")

-    @util.patch_get_utility()
+    @test_util.patch_get_utility()
    def test_prompt_file(self, mock_get_utility):
        path = os.path.join(self.tempdir, 'file.ini')
        open(path, "wb").close()
@@ -80,7 +81,7 @@ class DNSAuthenticatorTest(util.TempDirTestCase, dns_test_common.BaseAuthenticat
        self.auth._configure_file("file_path", "")
        self.assertEqual(self.auth.config.fake_file_path, path)

-    @util.patch_get_utility()
+    @test_util.patch_get_utility()
    def test_prompt_file_canceled(self, mock_get_utility):
        mock_display = mock_get_utility()
        mock_display.directory_select.side_effect = ((display_util.CANCEL, "c",),)
@@ -96,7 +97,7 @@ class DNSAuthenticatorTest(util.TempDirTestCase, dns_test_common.BaseAuthenticat

        self.assertEqual(credentials.conf("test"), "value")

-    @util.patch_get_utility()
+    @test_util.patch_get_utility()
    def test_prompt_credentials(self, mock_get_utility):
        bad_path = os.path.join(self.tempdir, 'bad-file.ini')
        dns_test_common.write({"fake_other": "other_value"}, bad_path)
@@ -116,7 +117,7 @@ class DNSAuthenticatorTest(util.TempDirTestCase, dns_test_common.BaseAuthenticat
        self.assertEqual(credentials.conf("test"), "value")


-class CredentialsConfigurationTest(util.TempDirTestCase):
+class CredentialsConfigurationTest(test_util.TempDirTestCase):
    class _MockLoggingHandler(logging.Handler):
        messages = None

@@ -150,14 +151,14 @@ class CredentialsConfigurationTest(util.TempDirTestCase):
        dns_common.logger.addHandler(log)

        path = os.path.join(self.tempdir, 'too-permissive-file.ini')
-        open(path, "wb").close()
+        util.safe_open(path, "wb", 0o744).close()

        dns_common.CredentialsConfiguration(path)

        self.assertEqual(1, len([_ for _ in log.messages['warning'] if _.startswith("Unsafe")]))


-class CredentialsConfigurationRequireTest(util.TempDirTestCase):
+class CredentialsConfigurationRequireTest(test_util.TempDirTestCase):

    def setUp(self):
        super(CredentialsConfigurationRequireTest, self).setUp()
--- a/certbot/plugins/webroot_test.py
+++ b/certbot/plugins/webroot_test.py
@@ -34,7 +34,13 @@ class AuthenticatorTest(unittest.TestCase):

    def setUp(self):
        from certbot.plugins.webroot import Authenticator
-        self.path = tempfile.mkdtemp()
+        # On Linux directories created by tempfile.mkdtemp inherit their permissions from their
+        # parent directory. So the actual permissions are inconsistent over various tests env.
+        # To circumvent this, a dedicated sub-workspace is created under the workspace, using
+        # filesystem.mkdir to get consistent permissions.
+        self.workspace = tempfile.mkdtemp()
+        self.path = os.path.join(self.workspace, 'webroot')
+        filesystem.mkdir(self.path)
        self.partial_root_challenge_path = os.path.join(
            self.path, ".well-known")
        self.root_challenge_path = os.path.join(
@@ -170,17 +176,12 @@ class AuthenticatorTest(unittest.TestCase):
        self.assertTrue(filesystem.check_mode(self.validation_path, 0o644))

        # Check permissions of the directories
-
        for dirpath, dirnames, _ in os.walk(self.path):
            for directory in dirnames:
                full_path = os.path.join(dirpath, directory)
                self.assertTrue(filesystem.check_mode(full_path, 0o755))

-        parent_gid = os.stat(self.path).st_gid
-        parent_uid = os.stat(self.path).st_uid
-
-        self.assertEqual(os.stat(self.validation_path).st_gid, parent_gid)
-        self.assertEqual(os.stat(self.validation_path).st_uid, parent_uid)
+        self.assertTrue(filesystem.has_same_ownership(self.validation_path, self.path))

    def test_perform_cleanup(self):
        self.auth.prepare()
--- a/certbot/storage.py
+++ b/certbot/storage.py
@@ -18,7 +18,6 @@ from certbot import crypto_util
 from certbot import error_handler
 from certbot import errors
 from certbot import util
-from certbot.compat import misc
 from certbot.compat import os
 from certbot.compat import filesystem
 from certbot.plugins import common as plugins_common
@@ -1107,9 +1106,7 @@ class RenewableCert(object):
                f.write(new_privkey)
            # Preserve gid and (mode & MASK_FOR_PRIVATE_KEY_PERMISSIONS)
            # from previous privkey in this lineage.
-            old_mode = (stat.S_IMODE(os.stat(old_privkey).st_mode) &
-                        misc.MASK_FOR_PRIVATE_KEY_PERMISSIONS)
-            mode = BASE_PRIVKEY_MODE | old_mode
+            mode = filesystem.compute_private_key_mode(old_privkey, BASE_PRIVKEY_MODE)
            filesystem.copy_ownership_and_apply_mode(
                old_privkey, target["privkey"], mode, copy_user=False, copy_group=True)

--- a/certbot/tests/cli_test.py
+++ b/certbot/tests/cli_test.py
@@ -23,21 +23,27 @@ PLUGINS = disco.PluginsRegistry.find_all()


 class TestReadFile(TempDirTestCase):
-    '''Test cli.read_file'''
-
-
+    """Test cli.read_file"""
    def test_read_file(self):
-        rel_test_path = os.path.relpath(os.path.join(self.tempdir, 'foo'))
-        self.assertRaises(
-            argparse.ArgumentTypeError, cli.read_file, rel_test_path)
+        curr_dir = os.getcwd()
+        try:
+            # On Windows current directory may be on a different drive than self.tempdir.
+            # However a relative path between two different drives is invalid. So we move to
+            # self.tempdir to ensure that we stay on the same drive.
+            os.chdir(self.tempdir)
+            rel_test_path = os.path.relpath(os.path.join(self.tempdir, 'foo'))
+            self.assertRaises(
+                argparse.ArgumentTypeError, cli.read_file, rel_test_path)

-        test_contents = b'bar\n'
-        with open(rel_test_path, 'wb') as f:
-            f.write(test_contents)
+            test_contents = b'bar\n'
+            with open(rel_test_path, 'wb') as f:
+                f.write(test_contents)

-        path, contents = cli.read_file(rel_test_path)
-        self.assertEqual(path, os.path.abspath(path))
-        self.assertEqual(contents, test_contents)
+            path, contents = cli.read_file(rel_test_path)
+            self.assertEqual(path, os.path.abspath(path))
+            self.assertEqual(contents, test_contents)
+        finally:
+            os.chdir(curr_dir)


 class FlagDefaultTest(unittest.TestCase):
--- a/certbot/tests/compat/filesystem_test.py
+++ b/certbot/tests/compat/filesystem_test.py
@@ -150,6 +150,24 @@ class WindowsChmodTests(TempDirTestCase):
        self.assertEqual(security_dacl.GetSecurityDescriptorDacl().GetAceCount(), 2)


+class ComputePrivateKeyModeTest(TempDirTestCase):
+    def setUp(self):
+        super(ComputePrivateKeyModeTest, self).setUp()
+        self.probe_path = _create_probe(self.tempdir)
+
+    def test_compute_private_key_mode(self):
+        filesystem.chmod(self.probe_path, 0o777)
+        new_mode = filesystem.compute_private_key_mode(self.probe_path, 0o600)
+
+        if POSIX_MODE:
+            # On Linux RWX permissions for group and R permission for world
+            # are persisted from the existing moe
+            self.assertEqual(new_mode, 0o674)
+        else:
+            # On Windows no permission is persisted
+            self.assertEqual(new_mode, 0o600)
+
+
@unittest.skipIf(POSIX_MODE, reason='Tests specific to Windows security')
 class WindowsOpenTest(TempDirTestCase):
    def test_new_file_correct_permissions(self):
@@ -210,15 +228,15 @@ class WindowsOpenTest(TempDirTestCase):
    def _test_one_creation(self, num, file_exist, flags):
        one_file = os.path.join(self.tempdir, str(num))
        if file_exist and not os.path.exists(one_file):
-            open(one_file, 'w').close()
+            with open(one_file, 'w'):
+                pass

        handler = None
        try:
            handler = filesystem.open(one_file, flags)
-        except BaseException as err:
+        finally:
            if handler:
                os.close(handler)
-            raise err


@unittest.skipIf(POSIX_MODE, reason='Test specific to Windows security')
@@ -262,14 +280,14 @@ class WindowsMkdirTests(test_util.TempDirTestCase):
        self.assertEqual(original_mkdir, std_os.mkdir)


-class CopyOwnershipTest(test_util.TempDirTestCase):
-    """Tests about replacement of chown: copy_ownership_and_apply_mode"""
+class OwnershipTest(test_util.TempDirTestCase):
+    """Tests about copy_ownership_and_apply_mode and has_same_ownership"""
    def setUp(self):
-        super(CopyOwnershipTest, self).setUp()
+        super(OwnershipTest, self).setUp()
        self.probe_path = _create_probe(self.tempdir)

    @unittest.skipIf(POSIX_MODE, reason='Test specific to Windows security')
-    def test_windows(self):
+    def test_copy_ownership_windows(self):
        system = win32security.ConvertStringSidToSid(SYSTEM_SID)
        security = win32security.SECURITY_ATTRIBUTES().SECURITY_DESCRIPTOR
        security.SetSecurityDescriptorOwner(system, False)
@@ -295,7 +313,7 @@ class CopyOwnershipTest(test_util.TempDirTestCase):
                          if dacl.GetAce(index)[2] == everybody])

    @unittest.skipUnless(POSIX_MODE, reason='Test specific to Linux security')
-    def test_linux(self):
+    def test_copy_ownership_linux(self):
        with mock.patch('os.chown') as mock_chown:
            with mock.patch('os.chmod') as mock_chmod:
                with mock.patch('os.stat') as mock_stat:
@@ -307,8 +325,18 @@ class CopyOwnershipTest(test_util.TempDirTestCase):
        mock_chown.assert_called_once_with(self.probe_path, 50, 51)
        mock_chmod.assert_called_once_with(self.probe_path, 0o700)

+    def test_has_same_ownership(self):
+        path1 = os.path.join(self.tempdir, 'test1')
+        path2 = os.path.join(self.tempdir, 'test2')
+
+        util.safe_open(path1, 'w').close()
+        util.safe_open(path2, 'w').close()
+
+        self.assertTrue(filesystem.has_same_ownership(path1, path2))
+

 class CheckPermissionsTest(test_util.TempDirTestCase):
+    """Tests relative to functions that check modes."""
    def setUp(self):
        super(CheckPermissionsTest, self).setUp()
        self.probe_path = _create_probe(self.tempdir)
@@ -353,6 +381,23 @@ class CheckPermissionsTest(test_util.TempDirTestCase):
            mock_owner.return_value = False
            self.assertFalse(filesystem.check_permissions(self.probe_path, 0o744))

+    def test_check_min_permissions(self):
+        filesystem.chmod(self.probe_path, 0o744)
+        self.assertTrue(filesystem.has_min_permissions(self.probe_path, 0o744))
+
+        filesystem.chmod(self.probe_path, 0o700)
+        self.assertFalse(filesystem.has_min_permissions(self.probe_path, 0o744))
+
+        filesystem.chmod(self.probe_path, 0o741)
+        self.assertFalse(filesystem.has_min_permissions(self.probe_path, 0o744))
+
+    def test_is_world_reachable(self):
+        filesystem.chmod(self.probe_path, 0o744)
+        self.assertTrue(filesystem.has_world_permissions(self.probe_path))
+
+        filesystem.chmod(self.probe_path, 0o700)
+        self.assertFalse(filesystem.has_world_permissions(self.probe_path))
+

 class OsReplaceTest(test_util.TempDirTestCase):
    """Test to ensure consistent behavior of rename method"""
--- a/certbot/tests/compat/os_test.py
+++ b/certbot/tests/compat/os_test.py
@@ -8,8 +8,8 @@ class OsTest(unittest.TestCase):
    """Unit tests for os module."""
    def test_forbidden_methods(self):
        # Checks for os module
-        for method in ['chmod', 'chown', 'open', 'mkdir',
-                       'makedirs', 'rename', 'replace', 'access']:
+        for method in ['chmod', 'chown', 'open', 'mkdir', 'makedirs', 'rename',
+                       'replace', 'access', 'stat', 'fstat']:
            self.assertRaises(RuntimeError, getattr(os, method))
        # Checks for os.path module
        for method in ['realpath']:
--- a/Show More
+++ b/Show More