diff --git a/certbot-apache/MANIFEST.in b/certbot-apache/MANIFEST.in
index 2316983bb..9e4913a03 100644
--- a/certbot-apache/MANIFEST.in
+++ b/certbot-apache/MANIFEST.in
@@ -1,7 +1,7 @@
 include LICENSE.txt
 include README.rst
 recursive-include tests *
-include certbot_apache/_internal/options-ssl-apache.conf
 recursive-include certbot_apache/_internal/augeas_lens *.aug
+recursive-include certbot_apache/_internal/tls_configs *.conf
 global-exclude __pycache__
 global-exclude *.py[cod]
diff --git a/certbot-apache/certbot_apache/_internal/apache_util.py b/certbot-apache/certbot_apache/_internal/apache_util.py
index 085ccddc8..ebc8a26c9 100644
--- a/certbot-apache/certbot_apache/_internal/apache_util.py
+++ b/certbot-apache/certbot_apache/_internal/apache_util.py
@@ -5,6 +5,8 @@ import logging
 import re
 import subprocess
 
+import pkg_resources
+
 from certbot import errors
 from certbot import util
 
@@ -241,3 +243,14 @@ def _get_runtime_cfg(command):
             "loaded because Apache is misconfigured.")
 
     return stdout
+
+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("_internal", "tls_configs", "{0}-options-ssl-apache.conf".format(prefix)))
diff --git a/certbot-apache/certbot_apache/_internal/configurator.py b/certbot-apache/certbot_apache/_internal/configurator.py
index 8daa28173..fc386404d 100644
--- a/certbot-apache/certbot_apache/_internal/configurator.py
+++ b/certbot-apache/certbot_apache/_internal/configurator.py
@@ -1,6 +1,7 @@
 """Apache Configurator."""
 # pylint: disable=too-many-lines
 from collections import defaultdict
+from distutils.version import LooseVersion
 import copy
 import fnmatch
 import logging
@@ -8,7 +9,6 @@ import re
 import socket
 import time
 
-import pkg_resources
 import six
 import zope.component
 import zope.interface
@@ -110,14 +110,29 @@ class ApacheConfigurator(common.Installer):
         handle_modules=False,
         handle_sites=False,
         challenge_location="/etc/apache2",
-        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
-            "certbot_apache", os.path.join("_internal", "options-ssl-apache.conf"))
     )
 
     def option(self, key):
         """Get a value from options"""
         return self.options.get(key)
 
+    def pick_apache_config(self, warn_on_no_mod_ssl=True):
+        """
+        Pick the appropriate TLS Apache configuration file for current version of Apache and OS.
+
+        :param bool warn_on_no_mod_ssl: True if we should warn if mod_ssl is not found.
+
+        :return: the path to the TLS Apache configuration file to use
+        :rtype: str
+        """
+        # Disabling TLS session tickets is supported by Apache 2.4.11+ and OpenSSL 1.0.2l+.
+        # So for old versions of Apache we pick a configuration without this option.
+        openssl_version = self.openssl_version(warn_on_no_mod_ssl)
+        if self.version < (2, 4, 11) or not openssl_version or\
+            LooseVersion(openssl_version) < LooseVersion('1.0.2l'):
+            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
@@ -184,6 +199,7 @@ class ApacheConfigurator(common.Installer):
         """
         version = kwargs.pop("version", None)
         use_parsernode = kwargs.pop("use_parsernode", False)
+        openssl_version = kwargs.pop("openssl_version", None)
         super(ApacheConfigurator, self).__init__(*args, **kwargs)
 
         # Add name_server association dict
@@ -209,6 +225,7 @@ class ApacheConfigurator(common.Installer):
         self.parser = None
         self.parser_root = None
         self.version = version
+        self._openssl_version = openssl_version
         self.vhosts = None
         self.options = copy.deepcopy(self.OS_DEFAULTS)
         self._enhance_func = {"redirect": self._enable_redirect,
@@ -225,6 +242,52 @@ class ApacheConfigurator(common.Installer):
         """Full absolute path to digest of updated SSL configuration file."""
         return os.path.join(self.config.config_dir, constants.UPDATED_MOD_SSL_CONF_DIGEST)
 
+    def _open_module_file(self, ssl_module_location):
+        """Extract the open lines of openssl_version for testing purposes"""
+        try:
+            with open(ssl_module_location, mode="rb") as f:
+                contents = f.read()
+        except IOError as error:
+            logger.debug(str(error), exc_info=True)
+            return None
+        return contents
+
+    def openssl_version(self, warn_on_no_mod_ssl=True):
+        """Lazily retrieve openssl version
+
+        :param bool warn_on_no_mod_ssl: `True` if we should warn if mod_ssl is not found. Set to
+            `False` when we know we'll try to enable mod_ssl later. This is currently debian/ubuntu,
+            when called from `prepare`.
+
+        :return: the OpenSSL version as a string, or None.
+        :rtype: str or None
+        """
+        if self._openssl_version:
+            return self._openssl_version
+        # Step 1. Check for LoadModule directive
+        try:
+            ssl_module_location = self.parser.modules['ssl_module']
+        except KeyError:
+            if warn_on_no_mod_ssl:
+                logger.warning("Could not find ssl_module; not disabling session tickets.")
+            return None
+        if not ssl_module_location:
+            logger.warning("Could not find ssl_module; not disabling session tickets.")
+            return None
+        ssl_module_location = self.parser.standard_path_from_server_root(ssl_module_location)
+        # Step 2. Grep in the .so for openssl version
+        contents = self._open_module_file(ssl_module_location)
+        if not contents:
+            logger.warning("Unable to read ssl_module file; not disabling session tickets.")
+            return None
+        # looks like: OpenSSL 1.0.2s  28 May 2019
+        matches = re.findall(br"OpenSSL ([0-9]\.[^ ]+) ", contents)
+        if not matches:
+            logger.warning("Could not find OpenSSL version; not disabling session tickets.")
+            return None
+        self._openssl_version = matches[0].decode('UTF-8')
+        return self._openssl_version
+
     def prepare(self):
         """Prepare the authenticator/installer.
 
@@ -271,8 +334,12 @@ class ApacheConfigurator(common.Installer):
         # Get all of the available vhosts
         self.vhosts = self.get_virtual_hosts()
 
+        # We may try to enable mod_ssl later. If so, we shouldn't warn if we can't find it now.
+        # This is currently only true for debian/ubuntu.
+        warn_on_no_mod_ssl = not self.option("handle_modules")
         self.install_ssl_options_conf(self.mod_ssl_conf,
-                                      self.updated_mod_ssl_conf_digest)
+                                      self.updated_mod_ssl_conf_digest,
+                                      warn_on_no_mod_ssl)
 
         # Prevent two Apache plugins from modifying a config at once
         try:
@@ -1241,6 +1308,14 @@ class ApacheConfigurator(common.Installer):
                 self.enable_mod("socache_shmcb", temp=temp)
             if "ssl_module" not in self.parser.modules:
                 self.enable_mod("ssl", temp=temp)
+                # Make sure we're not throwing away any unwritten changes to the config
+                self.parser.ensure_augeas_state()
+                self.parser.aug.load()
+                self.parser.reset_modules() # Reset to load the new ssl_module path
+                # Call again because now we can gate on openssl version
+                self.install_ssl_options_conf(self.mod_ssl_conf,
+                                              self.updated_mod_ssl_conf_digest,
+                                              warn_on_no_mod_ssl=True)
 
     def make_vhost_ssl(self, nonssl_vhost):
         """Makes an ssl_vhost version of a nonssl_vhost.
@@ -2454,14 +2529,19 @@ class ApacheConfigurator(common.Installer):
             self.restart()
             self.parser.reset_modules()
 
-    def install_ssl_options_conf(self, options_ssl, options_ssl_digest):
-        """Copy Certbot's SSL options file into the system's config dir if required."""
+    def install_ssl_options_conf(self, options_ssl, options_ssl_digest, warn_on_no_mod_ssl=True):
+        """Copy Certbot's SSL options file into the system's config dir if required.
+
+        :param bool warn_on_no_mod_ssl: True if we should warn if mod_ssl is not found.
+        """
 
         # 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.
-        return common.install_version_controlled_file(options_ssl, options_ssl_digest,
-            self.option("MOD_SSL_CONF_SRC"), constants.ALL_SSL_OPTIONS_HASHES)
+        apache_config_path = self.pick_apache_config(warn_on_no_mod_ssl)
+
+        return common.install_version_controlled_file(
+            options_ssl, options_ssl_digest, apache_config_path, constants.ALL_SSL_OPTIONS_HASHES)
 
     def enable_autohsts(self, _unused_lineage, domains):
         """
diff --git a/certbot-apache/certbot_apache/_internal/constants.py b/certbot-apache/certbot_apache/_internal/constants.py
index a37bebac5..68d29406e 100644
--- a/certbot-apache/certbot_apache/_internal/constants.py
+++ b/certbot-apache/certbot_apache/_internal/constants.py
@@ -26,6 +26,7 @@ ALL_SSL_OPTIONS_HASHES = [
     '06675349e457eae856120cdebb564efe546f0b87399f2264baeb41e442c724c7',
     '5cc003edd93fb9cd03d40c7686495f8f058f485f75b5e764b789245a386e6daf',
     '007cd497a56a3bb8b6a2c1aeb4997789e7e38992f74e44cc5d13a625a738ac73',
+    '34783b9e2210f5c4a23bced2dfd7ec289834716673354ed7c7abf69fe30192a3',
 ]
 """SHA256 hashes of the contents of previous versions of all versions of MOD_SSL_CONF_SRC"""
 
diff --git a/certbot-apache/certbot_apache/_internal/override_arch.py b/certbot-apache/certbot_apache/_internal/override_arch.py
index 2765bd238..54202c087 100644
--- a/certbot-apache/certbot_apache/_internal/override_arch.py
+++ b/certbot-apache/certbot_apache/_internal/override_arch.py
@@ -1,9 +1,7 @@
 """ Distribution specific override class for Arch Linux """
-import pkg_resources
 import zope.interface
 
 from certbot import interfaces
-from certbot.compat import os
 from certbot_apache._internal import configurator
 
 
@@ -26,6 +24,4 @@ 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", os.path.join("_internal", "options-ssl-apache.conf"))
     )
diff --git a/certbot-apache/certbot_apache/_internal/override_centos.py b/certbot-apache/certbot_apache/_internal/override_centos.py
index 2ab160c2f..0de882519 100644
--- a/certbot-apache/certbot_apache/_internal/override_centos.py
+++ b/certbot-apache/certbot_apache/_internal/override_centos.py
@@ -1,14 +1,12 @@
 """ Distribution specific override class for CentOS family (RHEL, Fedora) """
 import logging
 
-import pkg_resources
 import zope.interface
 
 from acme.magic_typing import List
 from certbot import errors
 from certbot import interfaces
 from certbot import util
-from certbot.compat import os
 from certbot.errors import MisconfigurationError
 from certbot_apache._internal import apache_util
 from certbot_apache._internal import configurator
@@ -37,8 +35,6 @@ 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", os.path.join("_internal", "options-ssl-apache.conf"))
     )
 
     def config_test(self):
diff --git a/certbot-apache/certbot_apache/_internal/override_darwin.py b/certbot-apache/certbot_apache/_internal/override_darwin.py
index 00faff623..f19823866 100644
--- a/certbot-apache/certbot_apache/_internal/override_darwin.py
+++ b/certbot-apache/certbot_apache/_internal/override_darwin.py
@@ -1,9 +1,7 @@
 """ Distribution specific override class for macOS """
-import pkg_resources
 import zope.interface
 
 from certbot import interfaces
-from certbot.compat import os
 from certbot_apache._internal import configurator
 
 
@@ -26,6 +24,4 @@ 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", os.path.join("_internal", "options-ssl-apache.conf"))
     )
diff --git a/certbot-apache/certbot_apache/_internal/override_debian.py b/certbot-apache/certbot_apache/_internal/override_debian.py
index 77ced6a3f..c977fb43e 100644
--- a/certbot-apache/certbot_apache/_internal/override_debian.py
+++ b/certbot-apache/certbot_apache/_internal/override_debian.py
@@ -1,7 +1,6 @@
 """ Distribution specific override class for Debian family (Ubuntu/Debian) """
 import logging
 
-import pkg_resources
 import zope.interface
 
 from certbot import errors
@@ -34,8 +33,6 @@ class DebianConfigurator(configurator.ApacheConfigurator):
         handle_modules=True,
         handle_sites=True,
         challenge_location="/etc/apache2",
-        MOD_SSL_CONF_SRC=pkg_resources.resource_filename(
-            "certbot_apache", os.path.join("_internal", "options-ssl-apache.conf"))
     )
 
     def enable_site(self, vhost):
diff --git a/certbot-apache/certbot_apache/_internal/override_fedora.py b/certbot-apache/certbot_apache/_internal/override_fedora.py
index 8197b0dcd..2436c76cc 100644
--- a/certbot-apache/certbot_apache/_internal/override_fedora.py
+++ b/certbot-apache/certbot_apache/_internal/override_fedora.py
@@ -1,11 +1,9 @@
 """ Distribution specific override class for Fedora 29+ """
-import pkg_resources
 import zope.interface
 
 from certbot import errors
 from certbot import interfaces
 from certbot import util
-from certbot.compat import os
 from certbot_apache._internal import apache_util
 from certbot_apache._internal import configurator
 from certbot_apache._internal import parser
@@ -31,9 +29,6 @@ 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", os.path.join("_internal", "options-ssl-apache.conf"))
     )
 
     def config_test(self):
diff --git a/certbot-apache/certbot_apache/_internal/override_gentoo.py b/certbot-apache/certbot_apache/_internal/override_gentoo.py
index c215771e6..6b7416c0d 100644
--- a/certbot-apache/certbot_apache/_internal/override_gentoo.py
+++ b/certbot-apache/certbot_apache/_internal/override_gentoo.py
@@ -1,9 +1,7 @@
 """ Distribution specific override class for Gentoo Linux """
-import pkg_resources
 import zope.interface
 
 from certbot import interfaces
-from certbot.compat import os
 from certbot_apache._internal import apache_util
 from certbot_apache._internal import configurator
 from certbot_apache._internal import parser
@@ -29,8 +27,6 @@ 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", os.path.join("_internal", "options-ssl-apache.conf"))
     )
 
     def _prepare_options(self):
diff --git a/certbot-apache/certbot_apache/_internal/override_suse.py b/certbot-apache/certbot_apache/_internal/override_suse.py
index 0c9219e6d..895e0cb05 100644
--- a/certbot-apache/certbot_apache/_internal/override_suse.py
+++ b/certbot-apache/certbot_apache/_internal/override_suse.py
@@ -1,9 +1,7 @@
 """ Distribution specific override class for OpenSUSE """
-import pkg_resources
 import zope.interface
 
 from certbot import interfaces
-from certbot.compat import os
 from certbot_apache._internal import configurator
 
 
@@ -26,6 +24,4 @@ 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", os.path.join("_internal", "options-ssl-apache.conf"))
     )
diff --git a/certbot-apache/certbot_apache/_internal/parser.py b/certbot-apache/certbot_apache/_internal/parser.py
index 992672913..82d7df6aa 100644
--- a/certbot-apache/certbot_apache/_internal/parser.py
+++ b/certbot-apache/certbot_apache/_internal/parser.py
@@ -9,7 +9,6 @@ import six
 
 from acme.magic_typing import Dict
 from acme.magic_typing import List
-from acme.magic_typing import Set
 from certbot import errors
 from certbot.compat import os
 from certbot_apache._internal import apache_util
@@ -52,7 +51,7 @@ class ApacheParser(object):
                 "version 1.2.0 or higher, please make sure you have you have "
                 "those installed.")
 
-        self.modules = set()  # type: Set[str]
+        self.modules = {}  # type: Dict[str, str]
         self.parser_paths = {}  # type: Dict[str, List[str]]
         self.variables = {}  # type: Dict[str, str]
 
@@ -249,14 +248,14 @@ class ApacheParser(object):
     def add_mod(self, mod_name):
         """Shortcut for updating parser modules."""
         if mod_name + "_module" not in self.modules:
-            self.modules.add(mod_name + "_module")
+            self.modules[mod_name + "_module"] = None
         if "mod_" + mod_name + ".c" not in self.modules:
-            self.modules.add("mod_" + mod_name + ".c")
+            self.modules["mod_" + mod_name + ".c"] = None
 
     def reset_modules(self):
         """Reset the loaded modules list. This is called from cleanup to clear
         temporarily loaded modules."""
-        self.modules = set()
+        self.modules = {}
         self.update_modules()
         self.parse_modules()
 
@@ -267,7 +266,7 @@ class ApacheParser(object):
             the iteration issue.  Else... parse and enable mods at same time.
 
         """
-        mods = set()  # type: Set[str]
+        mods = {}  # type: Dict[str, str]
         matches = self.find_dir("LoadModule")
         iterator = iter(matches)
         # Make sure prev_size != cur_size for do: while: iteration
@@ -281,8 +280,8 @@ class ApacheParser(object):
                 mod_name = self.get_arg(match_name)
                 mod_filename = self.get_arg(match_filename)
                 if mod_name and mod_filename:
-                    mods.add(mod_name)
-                    mods.add(os.path.basename(mod_filename)[:-2] + "c")
+                    mods[mod_name] = mod_filename
+                    mods[os.path.basename(mod_filename)[:-2] + "c"] = mod_filename
                 else:
                     logger.debug("Could not read LoadModule directive from Augeas path: %s",
                                  match_name[6:])
@@ -621,7 +620,7 @@ class ApacheParser(object):
 
     def exclude_dirs(self, matches):
         """Exclude directives that are not loaded into the configuration."""
-        filters = [("ifmodule", self.modules), ("ifdefine", self.variables)]
+        filters = [("ifmodule", self.modules.keys()), ("ifdefine", self.variables)]
 
         valid_matches = []
 
@@ -662,6 +661,25 @@ class ApacheParser(object):
 
         return True
 
+    def standard_path_from_server_root(self, arg):
+        """Ensure paths are consistent and absolute
+
+        :param str arg: Argument of directive
+
+        :returns: Standardized argument path
+        :rtype: str
+        """
+        # Remove beginning and ending quotes
+        arg = arg.strip("'\"")
+
+        # Standardize the include argument based on server root
+        if not arg.startswith("/"):
+            # Normpath will condense ../
+            arg = os.path.normpath(os.path.join(self.root, arg))
+        else:
+            arg = os.path.normpath(arg)
+        return arg
+
     def _get_include_path(self, arg):
         """Converts an Apache Include directive into Augeas path.
 
@@ -682,16 +700,7 @@ class ApacheParser(object):
         # if matchObj.group() != arg:
         #     logger.error("Error: Invalid regexp characters in %s", arg)
         #     return []
-
-        # Remove beginning and ending quotes
-        arg = arg.strip("'\"")
-
-        # Standardize the include argument based on server root
-        if not arg.startswith("/"):
-            # Normpath will condense ../
-            arg = os.path.normpath(os.path.join(self.root, arg))
-        else:
-            arg = os.path.normpath(arg)
+        arg = self.standard_path_from_server_root(arg)
 
         # Attempts to add a transform to the file if one does not already exist
         if os.path.isdir(arg):
diff --git a/certbot-apache/certbot_apache/_internal/tls_configs/current-options-ssl-apache.conf b/certbot-apache/certbot_apache/_internal/tls_configs/current-options-ssl-apache.conf
new file mode 100644
index 000000000..32a2c3335
--- /dev/null
+++ b/certbot-apache/certbot_apache/_internal/tls_configs/current-options-ssl-apache.conf
@@ -0,0 +1,19 @@
+# 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 -TLSv1 -TLSv1.1
+SSLCipherSuite          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
+SSLHonorCipherOrder     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
diff --git a/certbot-apache/certbot_apache/_internal/options-ssl-apache.conf b/certbot-apache/certbot_apache/_internal/tls_configs/old-options-ssl-apache.conf
similarity index 100%
rename from certbot-apache/certbot_apache/_internal/options-ssl-apache.conf
rename to certbot-apache/certbot_apache/_internal/tls_configs/old-options-ssl-apache.conf
diff --git a/certbot-apache/tests/autohsts_test.py b/certbot-apache/tests/autohsts_test.py
index c9901ecdb..8e4f15d6b 100644
--- a/certbot-apache/tests/autohsts_test.py
+++ b/certbot-apache/tests/autohsts_test.py
@@ -20,10 +20,10 @@ class AutoHSTSTest(util.ApacheTest):
 
         self.config = util.get_apache_configurator(
             self.config_path, self.vhost_path, self.config_dir, self.work_dir)
-        self.config.parser.modules.add("headers_module")
-        self.config.parser.modules.add("mod_headers.c")
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["headers_module"] = None
+        self.config.parser.modules["mod_headers.c"] = None
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
 
         self.vh_truth = util.get_vh_truth(
             self.temp_dir, "debian_apache_2_4/multiple_vhosts")
@@ -42,8 +42,8 @@ class AutoHSTSTest(util.ApacheTest):
     @mock.patch("certbot_apache._internal.configurator.ApacheConfigurator.restart")
     @mock.patch("certbot_apache._internal.configurator.ApacheConfigurator.enable_mod")
     def test_autohsts_enable_headers_mod(self, mock_enable, _restart):
-        self.config.parser.modules.discard("headers_module")
-        self.config.parser.modules.discard("mod_header.c")
+        self.config.parser.modules.pop("headers_module", None)
+        self.config.parser.modules.pop("mod_header.c", None)
         self.config.enable_autohsts(mock.MagicMock(), ["ocspvhost.com"])
         self.assertTrue(mock_enable.called)
 
diff --git a/certbot-apache/tests/centos_test.py b/certbot-apache/tests/centos_test.py
index 55fee3faa..5e334c51e 100644
--- a/certbot-apache/tests/centos_test.py
+++ b/certbot-apache/tests/centos_test.py
@@ -126,7 +126,7 @@ class MultipleVhostsTestCentOS(util.ApacheTest):
                 return mod_val
             return ""
         mock_get.side_effect = mock_get_cfg
-        self.config.parser.modules = set()
+        self.config.parser.modules = {}
         self.config.parser.variables = {}
 
         with mock.patch("certbot.util.get_os_info") as mock_osi:
diff --git a/certbot-apache/tests/configurator_test.py b/certbot-apache/tests/configurator_test.py
index cbb052155..54f4c9251 100644
--- a/certbot-apache/tests/configurator_test.py
+++ b/certbot-apache/tests/configurator_test.py
@@ -341,9 +341,9 @@ class MultipleVhostsTest(util.ApacheTest):
     def test_deploy_cert_enable_new_vhost(self):
         # Create
         ssl_vhost = self.config.make_vhost_ssl(self.vh_truth[0])
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
 
         self.assertFalse(ssl_vhost.enabled)
         self.config.deploy_cert(
@@ -377,9 +377,9 @@ class MultipleVhostsTest(util.ApacheTest):
                     # pragma: no cover
 
     def test_deploy_cert(self):
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
         # Patch _add_dummy_ssl_directives to make sure we write them correctly
         # pylint: disable=protected-access
         orig_add_dummy = self.config._add_dummy_ssl_directives
@@ -459,9 +459,9 @@ class MultipleVhostsTest(util.ApacheTest):
         method is called with an invalid vhost parameter. Currently this tests
         that a PluginError is appropriately raised when important directives
         are missing in an SSL module."""
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
 
         def side_effect(*args):
             """Mocks case where an SSLCertificateFile directive can be found
@@ -544,7 +544,8 @@ class MultipleVhostsTest(util.ApacheTest):
                 call_found = True
         self.assertTrue(call_found)
 
-    def test_prepare_server_https(self):
+    @mock.patch("certbot_apache._internal.parser.ApacheParser.reset_modules")
+    def test_prepare_server_https(self, mock_reset):
         mock_enable = mock.Mock()
         self.config.enable_mod = mock_enable
 
@@ -570,7 +571,8 @@ class MultipleVhostsTest(util.ApacheTest):
 
         self.assertEqual(mock_add_dir.call_count, 2)
 
-    def test_prepare_server_https_named_listen(self):
+    @mock.patch("certbot_apache._internal.parser.ApacheParser.reset_modules")
+    def test_prepare_server_https_named_listen(self, mock_reset):
         mock_find = mock.Mock()
         mock_find.return_value = ["test1", "test2", "test3"]
         mock_get = mock.Mock()
@@ -608,7 +610,8 @@ class MultipleVhostsTest(util.ApacheTest):
         # self.config.prepare_server_https("8080", temp=True)
         # self.assertEqual(self.listens, 0)
 
-    def test_prepare_server_https_needed_listen(self):
+    @mock.patch("certbot_apache._internal.parser.ApacheParser.reset_modules")
+    def test_prepare_server_https_needed_listen(self, mock_reset):
         mock_find = mock.Mock()
         mock_find.return_value = ["test1", "test2"]
         mock_get = mock.Mock()
@@ -624,8 +627,8 @@ class MultipleVhostsTest(util.ApacheTest):
         self.config.prepare_server_https("443")
         self.assertEqual(mock_add_dir.call_count, 1)
 
-    def test_prepare_server_https_mixed_listen(self):
-
+    @mock.patch("certbot_apache._internal.parser.ApacheParser.reset_modules")
+    def test_prepare_server_https_mixed_listen(self, mock_reset):
         mock_find = mock.Mock()
         mock_find.return_value = ["test1", "test2"]
         mock_get = mock.Mock()
@@ -904,7 +907,7 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot_apache._internal.display_ops.select_vhost")
     @mock.patch("certbot.util.exe_exists")
     def test_enhance_unknown_vhost(self, mock_exe, mock_sel_vhost, mock_get):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         mock_exe.return_value = True
         ssl_vh1 = obj.VirtualHost(
             "fp1", "ap1", set([obj.Addr(("*", "443"))]),
@@ -942,8 +945,8 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.exe_exists")
     def test_ocsp_stapling(self, mock_exe):
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 4, 7))
         mock_exe.return_value = True
 
@@ -969,8 +972,8 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.exe_exists")
     def test_ocsp_stapling_twice(self, mock_exe):
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 4, 7))
         mock_exe.return_value = True
 
@@ -997,8 +1000,8 @@ class MultipleVhostsTest(util.ApacheTest):
     def test_ocsp_unsupported_apache_version(self, mock_exe):
         mock_exe.return_value = True
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 2, 0))
         self.config.choose_vhost("certbot.demo")
 
@@ -1021,8 +1024,8 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.exe_exists")
     def test_http_header_hsts(self, mock_exe, _):
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("headers_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["headers_module"] = None
         mock_exe.return_value = True
 
         # This will create an ssl vhost for certbot.demo
@@ -1042,9 +1045,9 @@ class MultipleVhostsTest(util.ApacheTest):
         self.assertEqual(len(hsts_header), 4)
 
     def test_http_header_hsts_twice(self):
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["mod_ssl.c"] = None
         # skip the enable mod
-        self.config.parser.modules.add("headers_module")
+        self.config.parser.modules["headers_module"] = None
 
         # This will create an ssl vhost for encryption-example.demo
         self.config.choose_vhost("encryption-example.demo")
@@ -1060,8 +1063,8 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.exe_exists")
     def test_http_header_uir(self, mock_exe, _):
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("headers_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["headers_module"] = None
 
         mock_exe.return_value = True
 
@@ -1084,9 +1087,9 @@ class MultipleVhostsTest(util.ApacheTest):
         self.assertEqual(len(uir_header), 4)
 
     def test_http_header_uir_twice(self):
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["mod_ssl.c"] = None
         # skip the enable mod
-        self.config.parser.modules.add("headers_module")
+        self.config.parser.modules["headers_module"] = None
 
         # This will create an ssl vhost for encryption-example.demo
         self.config.choose_vhost("encryption-example.demo")
@@ -1101,7 +1104,7 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.run_script")
     @mock.patch("certbot.util.exe_exists")
     def test_redirect_well_formed_http(self, mock_exe, _):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.parser.update_runtime_variables = mock.Mock()
         mock_exe.return_value = True
         self.config.get_version = mock.Mock(return_value=(2, 2))
@@ -1127,7 +1130,7 @@ class MultipleVhostsTest(util.ApacheTest):
 
     def test_rewrite_rule_exists(self):
         # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 3, 9))
         self.config.parser.add_dir(
             self.vh_truth[3].path, "RewriteRule", ["Unknown"])
@@ -1136,7 +1139,7 @@ class MultipleVhostsTest(util.ApacheTest):
 
     def test_rewrite_engine_exists(self):
         # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 3, 9))
         self.config.parser.add_dir(
             self.vh_truth[3].path, "RewriteEngine", "on")
@@ -1146,7 +1149,7 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.run_script")
     @mock.patch("certbot.util.exe_exists")
     def test_redirect_with_existing_rewrite(self, mock_exe, _):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.parser.update_runtime_variables = mock.Mock()
         mock_exe.return_value = True
         self.config.get_version = mock.Mock(return_value=(2, 2, 0))
@@ -1180,7 +1183,7 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot.util.run_script")
     @mock.patch("certbot.util.exe_exists")
     def test_redirect_with_old_https_redirection(self, mock_exe, _):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.parser.update_runtime_variables = mock.Mock()
         mock_exe.return_value = True
         self.config.get_version = mock.Mock(return_value=(2, 2, 0))
@@ -1209,7 +1212,7 @@ class MultipleVhostsTest(util.ApacheTest):
 
 
     def test_redirect_with_conflict(self):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         ssl_vh = obj.VirtualHost(
             "fp", "ap", set([obj.Addr(("*", "443")),
                              obj.Addr(("zombo.com",))]),
@@ -1222,7 +1225,7 @@ class MultipleVhostsTest(util.ApacheTest):
 
     def test_redirect_two_domains_one_vhost(self):
         # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 3, 9))
 
         # Creates ssl vhost for the domain
@@ -1237,7 +1240,7 @@ class MultipleVhostsTest(util.ApacheTest):
 
     def test_redirect_from_previous_run(self):
         # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 3, 9))
         self.config.choose_vhost("red.blue.purple.com")
         self.config.enhance("red.blue.purple.com", "redirect")
@@ -1250,7 +1253,7 @@ class MultipleVhostsTest(util.ApacheTest):
             self.config.enhance, "green.blue.purple.com", "redirect")
 
     def test_create_own_redirect(self):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 3, 9))
         # For full testing... give names...
         self.vh_truth[1].name = "default.com"
@@ -1261,7 +1264,7 @@ class MultipleVhostsTest(util.ApacheTest):
         self.assertEqual(len(self.config.vhosts), 13)
 
     def test_create_own_redirect_for_old_apache_version(self):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
         self.config.get_version = mock.Mock(return_value=(2, 2))
         # For full testing... give names...
         self.vh_truth[1].name = "default.com"
@@ -1326,9 +1329,9 @@ class MultipleVhostsTest(util.ApacheTest):
     def test_deploy_cert_not_parsed_path(self):
         # Make sure that we add include to root config for vhosts when
         # handle-sites is false
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("socache_shmcb_module")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["socache_shmcb_module"] = None
         tmp_path = filesystem.realpath(tempfile.mkdtemp("vhostroot"))
         filesystem.chmod(tmp_path, 0o755)
         mock_p = "certbot_apache._internal.configurator.ApacheConfigurator._get_ssl_vhost_path"
@@ -1441,8 +1444,8 @@ class MultipleVhostsTest(util.ApacheTest):
     @mock.patch("certbot_apache._internal.configurator.ApacheConfigurator._choose_vhosts_wildcard")
     def test_enhance_wildcard_after_install(self, mock_choose):
         # pylint: disable=protected-access
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("headers_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["headers_module"] = None
         self.vh_truth[3].ssl = True
         self.config._wildcard_vhosts["*.certbot.demo"] = [self.vh_truth[3]]
         self.config.enhance("*.certbot.demo", "ensure-http-header",
@@ -1453,8 +1456,8 @@ class MultipleVhostsTest(util.ApacheTest):
     def test_enhance_wildcard_no_install(self, mock_choose):
         self.vh_truth[3].ssl = True
         mock_choose.return_value = [self.vh_truth[3]]
-        self.config.parser.modules.add("mod_ssl.c")
-        self.config.parser.modules.add("headers_module")
+        self.config.parser.modules["mod_ssl.c"] = None
+        self.config.parser.modules["headers_module"] = None
         self.config.enhance("*.certbot.demo", "ensure-http-header",
                             "Upgrade-Insecure-Requests")
         self.assertTrue(mock_choose.called)
@@ -1638,7 +1641,7 @@ class MultiVhostsTest(util.ApacheTest):
 
     @certbot_util.patch_get_utility()
     def test_make_vhost_ssl_with_existing_rewrite_rule(self, mock_get_utility):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
 
         ssl_vhost = self.config.make_vhost_ssl(self.vh_truth[4])
 
@@ -1658,7 +1661,7 @@ class MultiVhostsTest(util.ApacheTest):
 
     @certbot_util.patch_get_utility()
     def test_make_vhost_ssl_with_existing_rewrite_conds(self, mock_get_utility):
-        self.config.parser.modules.add("rewrite_module")
+        self.config.parser.modules["rewrite_module"] = None
 
         ssl_vhost = self.config.make_vhost_ssl(self.vh_truth[3])
 
@@ -1700,7 +1703,7 @@ class InstallSslOptionsConfTest(util.ApacheTest):
                                              self.config.updated_mod_ssl_conf_digest)
 
     def _current_ssl_options_hash(self):
-        return crypto_util.sha256sum(self.config.option("MOD_SSL_CONF_SRC"))
+        return crypto_util.sha256sum(self.config.pick_apache_config())
 
     def _assert_current_file(self):
         self.assertTrue(os.path.isfile(self.config.mod_ssl_conf))
@@ -1736,7 +1739,7 @@ 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.option("MOD_SSL_CONF_SRC")),
+            self.config.pick_apache_config()),
             self._current_ssl_options_hash())
         self.assertNotEqual(crypto_util.sha256sum(self.config.mod_ssl_conf),
             self._current_ssl_options_hash())
@@ -1752,19 +1755,99 @@ 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.option("MOD_SSL_CONF_SRC")),
+            self.config.pick_apache_config()),
             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_current_file_hash_in_all_hashes(self):
+    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.
+        """
         from certbot_apache._internal.constants import ALL_SSL_OPTIONS_HASHES
-        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.")
+        import pkg_resources
 
+        tls_configs_dir = pkg_resources.resource_filename(
+            "certbot_apache", os.path.join("_internal", "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))
+
+    def test_openssl_version(self):
+        self.config._openssl_version = None
+        some_string_contents = b"""
+            SSLOpenSSLConfCmd
+            OpenSSL configuration command
+            SSLv3 not supported by this version of OpenSSL
+            '%s': invalid OpenSSL configuration command
+            OpenSSL 1.0.2g  1 Mar 2016
+            OpenSSL
+            AH02407: "SSLOpenSSLConfCmd %s %s" failed for %s
+            AH02556: "SSLOpenSSLConfCmd %s %s" applied to %s
+            OpenSSL 1.0.2g  1 Mar 2016
+            """
+        self.config.parser.modules['ssl_module'] = '/fake/path'
+        with mock.patch("certbot_apache._internal.configurator."
+            "ApacheConfigurator._open_module_file") as mock_omf:
+            mock_omf.return_value = some_string_contents
+            self.assertEqual(self.config.openssl_version(), "1.0.2g")
+
+    def test_current_version(self):
+        self.config.version = (2, 4, 10)
+        self.config._openssl_version = '1.0.2m'
+        self.assertTrue('old' in self.config.pick_apache_config())
+
+        self.config.version = (2, 4, 11)
+        self.config._openssl_version = '1.0.2m'
+        self.assertTrue('current' in self.config.pick_apache_config())
+
+        self.config._openssl_version = '1.0.2a'
+        self.assertTrue('old' in self.config.pick_apache_config())
+
+    def test_openssl_version_warns(self):
+        self.config._openssl_version = '1.0.2a'
+        self.assertEqual(self.config.openssl_version(), '1.0.2a')
+
+        self.config._openssl_version = None
+        with mock.patch("certbot_apache._internal.configurator.logger.warning") as mock_log:
+            self.assertEqual(self.config.openssl_version(), None)
+            self.assertTrue("Could not find ssl_module" in mock_log.call_args[0][0])
+
+        self.config._openssl_version = None
+        self.config.parser.modules['ssl_module'] = None
+        with mock.patch("certbot_apache._internal.configurator.logger.warning") as mock_log:
+            self.assertEqual(self.config.openssl_version(), None)
+            self.assertTrue("Could not find ssl_module" in mock_log.call_args[0][0])
+
+        self.config.parser.modules['ssl_module'] = "/fake/path"
+        with mock.patch("certbot_apache._internal.configurator.logger.warning") as mock_log:
+            # Check that correct logger.warning was printed
+            self.assertEqual(self.config.openssl_version(), None)
+            self.assertTrue("Unable to read" in mock_log.call_args[0][0])
+
+        contents_missing_openssl = b"these contents won't match the regex"
+        with mock.patch("certbot_apache._internal.configurator."
+            "ApacheConfigurator._open_module_file") as mock_omf:
+            mock_omf.return_value = contents_missing_openssl
+            with mock.patch("certbot_apache._internal.configurator.logger.warning") as mock_log:
+                # Check that correct logger.warning was printed
+                self.assertEqual(self.config.openssl_version(), None)
+                self.assertTrue("Could not find OpenSSL" in mock_log.call_args[0][0])
+
+    def test_open_module_file(self):
+        mock_open = mock.mock_open(read_data="testing 12 3")
+        with mock.patch("six.moves.builtins.open", mock_open):
+            self.assertEqual(self.config._open_module_file("/nonsense/"), "testing 12 3")
 
 if __name__ == "__main__":
     unittest.main()  # pragma: no cover
diff --git a/certbot-apache/tests/debian_test.py b/certbot-apache/tests/debian_test.py
index 400e503fb..7a65bb7b1 100644
--- a/certbot-apache/tests/debian_test.py
+++ b/certbot-apache/tests/debian_test.py
@@ -61,8 +61,8 @@ class MultipleVhostsTestDebian(util.ApacheTest):
     def test_deploy_cert_enable_new_vhost(self):
         # Create
         ssl_vhost = self.config.make_vhost_ssl(self.vh_truth[0])
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
         self.assertFalse(ssl_vhost.enabled)
         self.config.deploy_cert(
             "encryption-example.demo", "example/cert.pem", "example/key.pem",
@@ -92,8 +92,8 @@ class MultipleVhostsTestDebian(util.ApacheTest):
             self.config_path, self.vhost_path, self.config_dir,
             self.work_dir, version=(2, 4, 16))
         self.config = self.mock_deploy_cert(self.config)
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
 
         # Get the default 443 vhost
         self.config.assoc["random.demo"] = self.vh_truth[1]
@@ -128,8 +128,8 @@ class MultipleVhostsTestDebian(util.ApacheTest):
             self.config_path, self.vhost_path, self.config_dir,
             self.work_dir, version=(2, 4, 16))
         self.config = self.mock_deploy_cert(self.config)
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
 
         # Get the default 443 vhost
         self.config.assoc["random.demo"] = self.vh_truth[1]
@@ -143,8 +143,8 @@ class MultipleVhostsTestDebian(util.ApacheTest):
             self.config_path, self.vhost_path, self.config_dir,
             self.work_dir, version=(2, 4, 7))
         self.config = self.mock_deploy_cert(self.config)
-        self.config.parser.modules.add("ssl_module")
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["ssl_module"] = None
+        self.config.parser.modules["mod_ssl.c"] = None
 
         # Get the default 443 vhost
         self.config.assoc["random.demo"] = self.vh_truth[1]
@@ -157,7 +157,7 @@ class MultipleVhostsTestDebian(util.ApacheTest):
     @mock.patch("certbot.util.exe_exists")
     def test_ocsp_stapling_enable_mod(self, mock_exe, _):
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["mod_ssl.c"] = None
         self.config.get_version = mock.Mock(return_value=(2, 4, 7))
         mock_exe.return_value = True
         # This will create an ssl vhost for certbot.demo
@@ -169,7 +169,7 @@ class MultipleVhostsTestDebian(util.ApacheTest):
     @mock.patch("certbot.util.exe_exists")
     def test_ensure_http_header_enable_mod(self, mock_exe, _):
         self.config.parser.update_runtime_variables = mock.Mock()
-        self.config.parser.modules.add("mod_ssl.c")
+        self.config.parser.modules["mod_ssl.c"] = None
         mock_exe.return_value = True
 
         # This will create an ssl vhost for certbot.demo
diff --git a/certbot-apache/tests/fedora_test.py b/certbot-apache/tests/fedora_test.py
index cb1614278..7f1d6526f 100644
--- a/certbot-apache/tests/fedora_test.py
+++ b/certbot-apache/tests/fedora_test.py
@@ -120,7 +120,7 @@ class MultipleVhostsTestFedora(util.ApacheTest):
                 return mod_val
             return ""
         mock_get.side_effect = mock_get_cfg
-        self.config.parser.modules = set()
+        self.config.parser.modules = {}
         self.config.parser.variables = {}
 
         with mock.patch("certbot.util.get_os_info") as mock_osi:
diff --git a/certbot-apache/tests/gentoo_test.py b/certbot-apache/tests/gentoo_test.py
index fb5d192d0..3b35dde54 100644
--- a/certbot-apache/tests/gentoo_test.py
+++ b/certbot-apache/tests/gentoo_test.py
@@ -117,7 +117,7 @@ class MultipleVhostsTestGentoo(util.ApacheTest):
                 return mod_val
             return None  # pragma: no cover
         mock_get.side_effect = mock_get_cfg
-        self.config.parser.modules = set()
+        self.config.parser.modules = {}
 
         with mock.patch("certbot.util.get_os_info") as mock_osi:
             # Make sure we have the have the Gentoo httpd constants
diff --git a/certbot-apache/tests/http_01_test.py b/certbot-apache/tests/http_01_test.py
index 85b17ca28..7d9019702 100644
--- a/certbot-apache/tests/http_01_test.py
+++ b/certbot-apache/tests/http_01_test.py
@@ -40,8 +40,8 @@ class ApacheHttp01Test(util.ApacheTest):
 
         modules = ["ssl", "rewrite", "authz_core", "authz_host"]
         for mod in modules:
-            self.config.parser.modules.add("mod_{0}.c".format(mod))
-            self.config.parser.modules.add(mod + "_module")
+            self.config.parser.modules["mod_{0}.c".format(mod)] = None
+            self.config.parser.modules[mod + "_module"] = None
 
         from certbot_apache._internal.http_01 import ApacheHttp01
         self.http = ApacheHttp01(self.config)
@@ -52,24 +52,24 @@ class ApacheHttp01Test(util.ApacheTest):
     @mock.patch("certbot_apache._internal.configurator.ApacheConfigurator.enable_mod")
     def test_enable_modules_apache_2_2(self, mock_enmod):
         self.config.version = (2, 2)
-        self.config.parser.modules.remove("authz_host_module")
-        self.config.parser.modules.remove("mod_authz_host.c")
+        del self.config.parser.modules["authz_host_module"]
+        del self.config.parser.modules["mod_authz_host.c"]
 
         enmod_calls = self.common_enable_modules_test(mock_enmod)
         self.assertEqual(enmod_calls[0][0][0], "authz_host")
 
     @mock.patch("certbot_apache._internal.configurator.ApacheConfigurator.enable_mod")
     def test_enable_modules_apache_2_4(self, mock_enmod):
-        self.config.parser.modules.remove("authz_core_module")
-        self.config.parser.modules.remove("mod_authz_core.c")
+        del self.config.parser.modules["authz_core_module"]
+        del self.config.parser.modules["mod_authz_host.c"]
 
         enmod_calls = self.common_enable_modules_test(mock_enmod)
         self.assertEqual(enmod_calls[0][0][0], "authz_core")
 
     def common_enable_modules_test(self, mock_enmod):
         """Tests enabling mod_rewrite and other modules."""
-        self.config.parser.modules.remove("rewrite_module")
-        self.config.parser.modules.remove("mod_rewrite.c")
+        del self.config.parser.modules["rewrite_module"]
+        del self.config.parser.modules["mod_rewrite.c"]
 
         self.http.prepare_http01_modules()
 
diff --git a/certbot-apache/tests/parser_test.py b/certbot-apache/tests/parser_test.py
index f5a0a3d11..299eb4567 100644
--- a/certbot-apache/tests/parser_test.py
+++ b/certbot-apache/tests/parser_test.py
@@ -114,7 +114,7 @@ class BasicParserTest(util.ParserTest):
         """
         from certbot_apache._internal.parser import get_aug_path
         # This makes sure that find_dir will work
-        self.parser.modules.add("mod_ssl.c")
+        self.parser.modules["mod_ssl.c"] = "/fake/path"
 
         self.parser.add_dir_to_ifmodssl(
             get_aug_path(self.parser.loc["default"]),
@@ -128,7 +128,7 @@ class BasicParserTest(util.ParserTest):
     def test_add_dir_to_ifmodssl_multiple(self):
         from certbot_apache._internal.parser import get_aug_path
         # This makes sure that find_dir will work
-        self.parser.modules.add("mod_ssl.c")
+        self.parser.modules["mod_ssl.c"] = "/fake/path"
 
         self.parser.add_dir_to_ifmodssl(
             get_aug_path(self.parser.loc["default"]),
@@ -260,7 +260,7 @@ class BasicParserTest(util.ParserTest):
         expected_vars = {"TEST": "", "U_MICH": "", "TLS": "443",
                          "example_path": "Documents/path"}
 
-        self.parser.modules = set()
+        self.parser.modules = {}
         with mock.patch(
             "certbot_apache._internal.parser.ApacheParser.parse_file") as mock_parse:
             self.parser.update_runtime_variables()
@@ -282,7 +282,7 @@ class BasicParserTest(util.ParserTest):
                  os.path.dirname(self.parser.loc["root"]))
 
         mock_cfg.return_value = inc_val
-        self.parser.modules = set()
+        self.parser.modules = {}
 
         with mock.patch(
             "certbot_apache._internal.parser.ApacheParser.parse_file") as mock_parse:
diff --git a/certbot-apache/tests/util.py b/certbot-apache/tests/util.py
index ccd0b274d..4994103f3 100644
--- a/certbot-apache/tests/util.py
+++ b/certbot-apache/tests/util.py
@@ -85,7 +85,8 @@ def get_apache_configurator(
         config_dir, work_dir, version=(2, 4, 7),
         os_info="generic",
         conf_vhost_path=None,
-        use_parsernode=False):
+        use_parsernode=False,
+        openssl_version="1.1.1a"):
     """Create an Apache Configurator with the specified options.
 
     :param conf: Function that returns binary paths. self.conf in Configurator
@@ -118,7 +119,8 @@ def get_apache_configurator(
                     except KeyError:
                         config_class = configurator.ApacheConfigurator
                     config = config_class(config=mock_le_config, name="apache",
-                                          version=version, use_parsernode=use_parsernode)
+                                          version=version, use_parsernode=use_parsernode,
+                                          openssl_version=openssl_version)
                     if not conf_vhost_path:
                         config_class.OS_DEFAULTS["vhost_root"] = vhost_path
                     else:
diff --git a/certbot/CHANGELOG.md b/certbot/CHANGELOG.md
index c35af0d0f..2f551c8ab 100644
--- a/certbot/CHANGELOG.md
+++ b/certbot/CHANGELOG.md
@@ -6,6 +6,7 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 
 ### Added
 
+* Turn off session tickets for apache plugin by default when appropriate.
 * Added serial number of certificate to the output of `certbot certificates`
 * Expose two new environment variables in the authenticator and cleanup scripts used by
   the `manual` plugin: `CERTBOT_REMAINING_CHALLENGES` is equal to the number of challenges
@@ -31,9 +32,9 @@ More details about these changes can be found on our GitHub repo.
 
 ### Added
 
-* Added certbot.ocsp Certbot's API. The certbot.ocsp module can be used to 
+* Added certbot.ocsp Certbot's API. The certbot.ocsp module can be used to
   determine the OCSP status of certificates.
-* Don't verify the existing certificate in HTTP01Response.simple_verify, for 
+* Don't verify the existing certificate in HTTP01Response.simple_verify, for
   compatibility with the real-world ACME challenge checks.
 * Added support for `$hostname` in nginx `server_name` directive
 
@@ -42,7 +43,7 @@ More details about these changes can be found on our GitHub repo.
 * Certbot will now renew certificates early if they have been revoked according
   to OCSP.
 * Fix acme module warnings when response Content-Type includes params (e.g. charset).
-* Fixed issue where webroot plugin would incorrectly raise `Read-only file system` 
+* Fixed issue where webroot plugin would incorrectly raise `Read-only file system`
   error when creating challenge directories (issue #7165).
 
 ### Fixed
diff --git a/tests/letstest/scripts/test_apache2.sh b/tests/letstest/scripts/test_apache2.sh
index 9af39e8bb..9c3b95a31 100755
--- a/tests/letstest/scripts/test_apache2.sh
+++ b/tests/letstest/scripts/test_apache2.sh
@@ -58,6 +58,22 @@ if [ $? -ne 0 ] ; then
     FAIL=1
 fi
 
+# Check that ssl_module detection is working on various systems
+if [ "$OS_TYPE" = "ubuntu" ] ; then
+    MOD_SSL_LOCATION="/usr/lib/apache2/modules/mod_ssl.so"
+    APACHE_NAME=apache2ctl
+elif [ "$OS_TYPE" = "centos" ]; then
+    MOD_SSL_LOCATION="/etc/httpd/modules/mod_ssl.so"
+    APACHE_NAME=httpd
+fi
+OPENSSL_VERSION=$(strings "$MOD_SSL_LOCATION" | egrep -o -m1 '^OpenSSL ([0-9]\.[^ ]+) ' | tail -c +9)
+APACHE_VERSION=$(sudo $APACHE_NAME -v | egrep -o 'Apache/([0-9]\.[^ ]+)' | tail -c +8)
+"$PYTHON_NAME" tests/letstest/scripts/test_openssl_version.py "$OPENSSL_VERSION" "$APACHE_VERSION"
+if [ $? -ne 0 ] ; then
+    FAIL=1
+fi
+
+
 if [ "$OS_TYPE" = "ubuntu" ] ; then
     export SERVER="$BOULDER_URL"
     "$VENV_PATH/bin/tox" -e apacheconftest
diff --git a/tests/letstest/scripts/test_openssl_version.py b/tests/letstest/scripts/test_openssl_version.py
new file mode 100644
index 000000000..c55441c5d
--- /dev/null
+++ b/tests/letstest/scripts/test_openssl_version.py
@@ -0,0 +1,30 @@
+#!/usr/bin/env python
+# Test script for OpenSSL version checking
+from distutils.version import LooseVersion
+import sys
+
+
+def main(openssl_version, apache_version):
+    if not openssl_version.strip():
+        raise Exception("No OpenSSL version found.")
+    if not apache_version.strip():
+        raise Exception("No Apache version found.")
+    conf_file_location = "/etc/letsencrypt/options-ssl-apache.conf"
+    with open(conf_file_location) as f:
+        contents = f.read()
+    if LooseVersion(apache_version.strip()) < LooseVersion('2.4.11') or \
+        LooseVersion(openssl_version.strip()) < LooseVersion('1.0.2l'):
+        # should be old version
+        # assert SSLSessionTickets not in conf file
+        if "SSLSessionTickets" in contents:
+            raise Exception("Apache or OpenSSL version is too old, "
+                "but SSLSessionTickets is set.")
+    else:
+        # should be current version
+        # assert SSLSessionTickets in conf file
+        if "SSLSessionTickets" not in contents:
+            raise Exception("Apache and OpenSSL versions are sufficiently new, "
+                "but SSLSessionTickets is not set.")
+
+if __name__ == '__main__':
+    main(*sys.argv[1:])