diff --git a/CHANGELOG.md b/CHANGELOG.md
index 57a895e07..ce7eac2e9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,9 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
   warnings described at https://github.com/certbot/josepy/issues/13.
 * Apache plugin now respects CERTBOT_DOCS environment variable when adding
   command line defaults.
+* The running of manual plugin hooks is now always included in Certbot's log
+  output.
+* Tests execution for certbot, certbot-apache and certbot-nginx packages now relies on pytest.
 
 ### Fixed
 
@@ -26,6 +29,7 @@ package with changes other than its version number was:
 * acme
 * certbot
 * certbot-apache
+* certbot-nginx
 
 More details about these changes can be found on our GitHub repo.
 
diff --git a/acme/examples/http01_example.py b/acme/examples/http01_example.py
new file mode 100644
index 000000000..79508f1b4
--- /dev/null
+++ b/acme/examples/http01_example.py
@@ -0,0 +1,240 @@
+"""Example ACME-V2 API for HTTP-01 challenge.
+
+Brief:
+
+This a complete usage example of the python-acme API.
+
+Limitations of this example:
+    - Works for only one Domain name
+    - Performs only HTTP-01 challenge
+    - Uses ACME-v2
+
+Workflow:
+    (Account creation)
+    - Create account key
+    - Register account and accept TOS
+    (Certificate actions)
+    - Select HTTP-01 within offered challenges by the CA server
+    - Set up http challenge resource
+    - Set up standalone web server
+    - Create domain private key and CSR
+    - Issue certificate
+    - Renew certificate
+    - Revoke certificate
+    (Account update actions)
+    - Change contact information
+    - Deactivate Account
+"""
+from contextlib import contextmanager
+from cryptography.hazmat.backends import default_backend
+from cryptography.hazmat.primitives.asymmetric import rsa
+import OpenSSL
+
+from acme import challenges
+from acme import client
+from acme import crypto_util
+from acme import errors
+from acme import messages
+from acme import standalone
+import josepy as jose
+
+# Constants:
+
+# This is the staging point for ACME-V2 within Let's Encrypt.
+DIRECTORY_URL = 'https://acme-staging-v02.api.letsencrypt.org/directory'
+
+USER_AGENT = 'python-acme-example'
+
+# Account key size
+ACC_KEY_BITS = 2048
+
+# Certificate private key size
+CERT_PKEY_BITS = 2048
+
+# Domain name for the certificate.
+DOMAIN = 'client.example.com'
+
+# If you are running Boulder locally, it is possible to configure any port
+# number to execute the challenge, but real CA servers will always use port
+# 80, as described in the ACME specification.
+PORT = 80
+
+
+# Useful methods and classes:
+
+
+def new_csr_comp(domain_name, pkey_pem=None):
+    """Create certificate signing request."""
+    if pkey_pem is None:
+        # Create private key.
+        pkey = OpenSSL.crypto.PKey()
+        pkey.generate_key(OpenSSL.crypto.TYPE_RSA, CERT_PKEY_BITS)
+        pkey_pem = OpenSSL.crypto.dump_privatekey(OpenSSL.crypto.FILETYPE_PEM,
+                                                  pkey)
+    csr_pem = crypto_util.make_csr(pkey_pem, [domain_name])
+    return pkey_pem, csr_pem
+
+
+def select_http01_chall(orderr):
+    """Extract authorization resource from within order resource."""
+    # Authorization Resource: authz.
+    # This object holds the offered challenges by the server and their status.
+    authz_list = orderr.authorizations
+
+    for authz in authz_list:
+        # Choosing challenge.
+        # authz.body.challenges is a set of ChallengeBody objects.
+        for i in authz.body.challenges:
+            # Find the supported challenge.
+            if isinstance(i.chall, challenges.HTTP01):
+                return i
+
+    raise Exception('HTTP-01 challenge was not offered by the CA server.')
+
+
+@contextmanager
+def challenge_server(http_01_resources):
+    """Manage standalone server set up and shutdown."""
+
+    # Setting up a fake server that binds at PORT and any address.
+    address = ('', PORT)
+    try:
+        servers = standalone.HTTP01DualNetworkedServers(address,
+                                                        http_01_resources)
+        # Start client standalone web server.
+        servers.serve_forever()
+        yield servers
+    finally:
+        # Shutdown client web server and unbind from PORT
+        servers.shutdown_and_server_close()
+
+
+def perform_http01(client_acme, challb, orderr):
+    """Set up standalone webserver and perform HTTP-01 challenge."""
+
+    response, validation = challb.response_and_validation(client_acme.net.key)
+
+    resource = standalone.HTTP01RequestHandler.HTTP01Resource(
+        chall=challb.chall, response=response, validation=validation)
+
+    with challenge_server({resource}):
+        # Let the CA server know that we are ready for the challenge.
+        client_acme.answer_challenge(challb, response)
+
+        # Wait for challenge status and then issue a certificate.
+        # It is possible to set a deadline time.
+        finalized_orderr = client_acme.poll_and_finalize(orderr)
+
+    return finalized_orderr.fullchain_pem
+
+
+# Main examples:
+
+
+def example_http():
+    """This example executes the whole process of fulfilling a HTTP-01
+    challenge for one specific domain.
+
+    The workflow consists of:
+    (Account creation)
+    - Create account key
+    - Register account and accept TOS
+    (Certificate actions)
+    - Select HTTP-01 within offered challenges by the CA server
+    - Set up http challenge resource
+    - Set up standalone web server
+    - Create domain private key and CSR
+    - Issue certificate
+    - Renew certificate
+    - Revoke certificate
+    (Account update actions)
+    - Change contact information
+    - Deactivate Account
+
+    """
+    # Create account key
+
+    acc_key = jose.JWKRSA(
+        key=rsa.generate_private_key(public_exponent=65537,
+                                     key_size=ACC_KEY_BITS,
+                                     backend=default_backend()))
+
+    # Register account and accept TOS
+
+    net = client.ClientNetwork(acc_key, user_agent=USER_AGENT)
+    directory = messages.Directory.from_json(net.get(DIRECTORY_URL).json())
+    client_acme = client.ClientV2(directory, net=net)
+
+    # Terms of Service URL is in client_acme.directory.meta.terms_of_service
+    # Registration Resource: regr
+    # Creates account with contact information.
+    email = ('fake@example.com')
+    regr = client_acme.new_account(
+        messages.NewRegistration.from_data(
+            email=email, terms_of_service_agreed=True))
+
+    # Create domain private key and CSR
+    pkey_pem, csr_pem = new_csr_comp(DOMAIN)
+
+    # Issue certificate
+
+    orderr = client_acme.new_order(csr_pem)
+
+    # Select HTTP-01 within offered challenges by the CA server
+    challb = select_http01_chall(orderr)
+
+    # The certificate is ready to be used in the variable "fullchain_pem".
+    fullchain_pem = perform_http01(client_acme, challb, orderr)
+
+    # Renew certificate
+
+    _, csr_pem = new_csr_comp(DOMAIN, pkey_pem)
+
+    orderr = client_acme.new_order(csr_pem)
+
+    challb = select_http01_chall(orderr)
+
+    # Performing challenge
+    fullchain_pem = perform_http01(client_acme, challb, orderr)
+
+    # Revoke certificate
+
+    fullchain_com = jose.ComparableX509(
+        OpenSSL.crypto.load_certificate(
+            OpenSSL.crypto.FILETYPE_PEM, fullchain_pem))
+
+    try:
+        client_acme.revoke(fullchain_com, 0)  # revocation reason = 0
+    except errors.ConflictError:
+        # Certificate already revoked.
+        pass
+
+    # Query registration status.
+    client_acme.net.account = regr
+    try:
+        regr = client_acme.query_registration(regr)
+    except errors.Error as err:
+        if err.typ == messages.OLD_ERROR_PREFIX + 'unauthorized' \
+                or err.typ == messages.ERROR_PREFIX + 'unauthorized':
+            # Status is deactivated.
+            pass
+        raise
+
+    # Change contact information
+
+    email = 'newfake@example.com'
+    regr = client_acme.update_registration(
+        regr.update(
+            body=regr.body.update(
+                contact=('mailto:' + email,)
+            )
+        )
+    )
+
+    # Deactivate account/registration
+
+    regr = client_acme.deactivate_registration(regr)
+
+
+if __name__ == "__main__":
+    example_http()
diff --git a/acme/setup.py b/acme/setup.py
index 79d6d3389..6cb5c3f92 100644
--- a/acme/setup.py
+++ b/acme/setup.py
@@ -36,6 +36,7 @@ docs_extras = [
     'sphinx_rtd_theme',
 ]
 
+
 class PyTest(TestCommand):
     user_options = []
 
@@ -50,6 +51,7 @@ class PyTest(TestCommand):
         errno = pytest.main(shlex.split(self.pytest_args))
         sys.exit(errno)
 
+
 setup(
     name='acme',
     version=version,
@@ -82,7 +84,7 @@ setup(
         'dev': dev_extras,
         'docs': docs_extras,
     },
-    tests_require=["pytest"],
     test_suite='acme',
+    tests_require=["pytest"],
     cmdclass={"test": PyTest},
 )
diff --git a/certbot-apache/setup.py b/certbot-apache/setup.py
index 52528a536..5d15611dd 100644
--- a/certbot-apache/setup.py
+++ b/certbot-apache/setup.py
@@ -1,5 +1,7 @@
 from setuptools import setup
 from setuptools import find_packages
+from setuptools.command.test import test as TestCommand
+import sys
 
 
 version = '0.32.0.dev0'
@@ -21,6 +23,22 @@ docs_extras = [
     'sphinx_rtd_theme',
 ]
 
+
+class PyTest(TestCommand):
+    user_options = []
+
+    def initialize_options(self):
+        TestCommand.initialize_options(self)
+        self.pytest_args = ''
+
+    def run_tests(self):
+        import shlex
+        # import here, cause outside the eggs aren't loaded
+        import pytest
+        errno = pytest.main(shlex.split(self.pytest_args))
+        sys.exit(errno)
+
+
 setup(
     name='certbot-apache',
     version=version,
@@ -64,4 +82,6 @@ setup(
         ],
     },
     test_suite='certbot_apache',
+    tests_require=["pytest"],
+    cmdclass={"test": PyTest},
 )
diff --git a/certbot-nginx/certbot_nginx/configurator.py b/certbot-nginx/certbot_nginx/configurator.py
index dd0bf9e8b..ffe1ddac7 100644
--- a/certbot-nginx/certbot_nginx/configurator.py
+++ b/certbot-nginx/certbot_nginx/configurator.py
@@ -13,6 +13,7 @@ import zope.interface
 from acme import challenges
 from acme import crypto_util as acme_crypto_util
 
+from certbot import compat
 from certbot import constants as core_constants
 from certbot import crypto_util
 from certbot import errors
@@ -164,9 +165,7 @@ class NginxConfigurator(common.Installer):
             util.lock_dir_until_exit(self.conf('server-root'))
         except (OSError, errors.LockError):
             logger.debug('Encountered error:', exc_info=True)
-            raise errors.PluginError(
-                'Unable to lock %s', self.conf('server-root'))
-
+            raise errors.PluginError('Unable to lock {0}'.format(self.conf('server-root')))
 
     # Entry point in main.py for installing cert
     def deploy_cert(self, domain, cert_path, key_path,
@@ -899,7 +898,7 @@ class NginxConfigurator(common.Installer):
         have permissions of root.
 
         """
-        uid = os.geteuid()
+        uid = compat.os_geteuid()
         util.make_or_verify_dir(
             self.config.work_dir, core_constants.CONFIG_DIRS_MODE, uid)
         util.make_or_verify_dir(
diff --git a/certbot-nginx/certbot_nginx/parser.py b/certbot-nginx/certbot_nginx/parser.py
index 622eb8d55..c5f780d94 100644
--- a/certbot-nginx/certbot_nginx/parser.py
+++ b/certbot-nginx/certbot_nginx/parser.py
@@ -81,9 +81,9 @@ class NginxParser(object):
 
         """
         if not os.path.isabs(path):
-            return os.path.join(self.root, path)
+            return os.path.normpath(os.path.join(self.root, path))
         else:
-            return path
+            return os.path.normpath(path)
 
     def _build_addr_to_ssl(self):
         """Builds a map from address to whether it listens on ssl in any server block
diff --git a/certbot-nginx/certbot_nginx/tests/configurator_test.py b/certbot-nginx/certbot_nginx/tests/configurator_test.py
index 957588e2a..706e2637a 100644
--- a/certbot-nginx/certbot_nginx/tests/configurator_test.py
+++ b/certbot-nginx/certbot_nginx/tests/configurator_test.py
@@ -1,7 +1,6 @@
 # pylint: disable=too-many-public-methods
 """Test for certbot_nginx.configurator."""
 import os
-import shutil
 import unittest
 
 import mock
@@ -33,12 +32,6 @@ class NginxConfiguratorTest(util.NginxTest):
         self.config = util.get_nginx_configurator(
             self.config_path, self.config_dir, self.work_dir, self.logs_dir)
 
-    def tearDown(self):
-        shutil.rmtree(self.temp_dir)
-        shutil.rmtree(self.config_dir)
-        shutil.rmtree(self.work_dir)
-        shutil.rmtree(self.logs_dir)
-
     @mock.patch("certbot_nginx.configurator.util.exe_exists")
     def test_prepare_no_install(self, mock_exe_exists):
         mock_exe_exists.return_value = False
@@ -69,8 +62,11 @@ class NginxConfiguratorTest(util.NginxTest):
 
     def test_prepare_locked(self):
         server_root = self.config.conf("server-root")
+
+        from certbot import util as certbot_util
+        certbot_util._LOCKS[server_root].release()  # pylint: disable=protected-access
+
         self.config.config_test = mock.Mock()
-        os.remove(os.path.join(server_root, ".certbot.lock"))
         certbot_test_util.lock_and_call(self._test_prepare_locked, server_root)
 
     @mock.patch("certbot_nginx.configurator.util.exe_exists")
@@ -88,11 +84,11 @@ class NginxConfiguratorTest(util.NginxTest):
     def test_get_all_names(self, mock_gethostbyaddr):
         mock_gethostbyaddr.return_value = ('155.225.50.69.nephoscale.net', [], [])
         names = self.config.get_all_names()
-        self.assertEqual(names, set(
-            ["155.225.50.69.nephoscale.net", "www.example.org", "another.alias",
+        self.assertEqual(names, {
+            "155.225.50.69.nephoscale.net", "www.example.org", "another.alias",
              "migration.com", "summer.com", "geese.com", "sslon.com",
              "globalssl.com", "globalsslsetssl.com", "ipv6.com", "ipv6ssl.com",
-             "headers.com"]))
+             "headers.com"})
 
     def test_supported_enhancements(self):
         self.assertEqual(['redirect', 'ensure-http-header', 'staple-ocsp'],
@@ -171,6 +167,7 @@ class NginxConfiguratorTest(util.NginxTest):
                    'abc.www.foo.com': "etc_nginx/foo.conf",
                    'www.bar.co.uk': "etc_nginx/nginx.conf",
                    'ipv6.com': "etc_nginx/sites-enabled/ipv6.com"}
+        conf_path = {key: os.path.normpath(value) for key, value in conf_path.items()}
 
         vhost = self.config.choose_vhosts(name)[0]
         path = os.path.relpath(vhost.filep, self.temp_dir)
diff --git a/certbot-nginx/certbot_nginx/tests/http_01_test.py b/certbot-nginx/certbot_nginx/tests/http_01_test.py
index ed3c257ee..41c4b95fc 100644
--- a/certbot-nginx/certbot_nginx/tests/http_01_test.py
+++ b/certbot-nginx/certbot_nginx/tests/http_01_test.py
@@ -1,6 +1,5 @@
 """Tests for certbot_nginx.http_01"""
 import unittest
-import shutil
 
 import mock
 import six
@@ -54,11 +53,6 @@ class HttpPerformTest(util.NginxTest):
         from certbot_nginx import http_01
         self.http01 = http_01.NginxHttp01(config)
 
-    def tearDown(self):
-        shutil.rmtree(self.temp_dir)
-        shutil.rmtree(self.config_dir)
-        shutil.rmtree(self.work_dir)
-
     def test_perform0(self):
         responses = self.http01.perform()
         self.assertEqual([], responses)
diff --git a/certbot-nginx/certbot_nginx/tests/parser_test.py b/certbot-nginx/certbot_nginx/tests/parser_test.py
index f6f28e42b..3a68f7f24 100644
--- a/certbot-nginx/certbot_nginx/tests/parser_test.py
+++ b/certbot-nginx/certbot_nginx/tests/parser_test.py
@@ -67,9 +67,15 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
 
     def test_abs_path(self):
         nparser = parser.NginxParser(self.config_path)
-        self.assertEqual('/etc/nginx/*', nparser.abs_path('/etc/nginx/*'))
-        self.assertEqual(os.path.join(self.config_path, 'foo/bar/'),
-                         nparser.abs_path('foo/bar/'))
+        if os.name != 'nt':
+            self.assertEqual('/etc/nginx/*', nparser.abs_path('/etc/nginx/*'))
+            self.assertEqual(os.path.join(self.config_path, 'foo/bar'),
+                             nparser.abs_path('foo/bar'))
+        else:
+            self.assertEqual('C:\\etc\\nginx\\*', nparser.abs_path('C:\\etc\\nginx\\*'))
+            self.assertEqual(os.path.join(self.config_path, 'foo\\bar'),
+                             nparser.abs_path('foo\\bar'))
+
 
     def test_filedump(self):
         nparser = parser.NginxParser(self.config_path)
diff --git a/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py b/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py
index 72b65911c..62ca085ef 100644
--- a/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py
+++ b/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py
@@ -1,6 +1,5 @@
 """Tests for certbot_nginx.tls_sni_01"""
 import unittest
-import shutil
 
 import mock
 import six
@@ -55,11 +54,6 @@ class TlsSniPerformTest(util.NginxTest):
         from certbot_nginx import tls_sni_01
         self.sni = tls_sni_01.NginxTlsSni01(config)
 
-    def tearDown(self):
-        shutil.rmtree(self.temp_dir)
-        shutil.rmtree(self.config_dir)
-        shutil.rmtree(self.work_dir)
-
     @mock.patch("certbot_nginx.configurator"
                 ".NginxConfigurator.choose_vhosts")
     def test_perform(self, mock_choose):
diff --git a/certbot-nginx/certbot_nginx/tests/util.py b/certbot-nginx/certbot_nginx/tests/util.py
index ad1af2b96..ef669dac0 100644
--- a/certbot-nginx/certbot_nginx/tests/util.py
+++ b/certbot-nginx/certbot_nginx/tests/util.py
@@ -4,6 +4,8 @@ import os
 import pkg_resources
 import tempfile
 import unittest
+import shutil
+import warnings
 
 import josepy as jose
 import mock
@@ -33,6 +35,22 @@ class NginxTest(unittest.TestCase):  # pylint: disable=too-few-public-methods
         self.rsa512jwk = jose.JWKRSA.load(test_util.load_vector(
             "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)
+
+        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)
+
 
 def get_data_filename(filename):
     """Gets the filename of a test data file."""
diff --git a/certbot-nginx/local-oldest-requirements.txt b/certbot-nginx/local-oldest-requirements.txt
index bcd02d197..db6b261f0 100644
--- a/certbot-nginx/local-oldest-requirements.txt
+++ b/certbot-nginx/local-oldest-requirements.txt
@@ -1,2 +1,2 @@
-acme[dev]==0.26.0
-certbot[dev]==0.22.0
+acme[dev]==0.29.0
+-e .[dev]
diff --git a/certbot-nginx/setup.py b/certbot-nginx/setup.py
index f78473ada..8984704a6 100644
--- a/certbot-nginx/setup.py
+++ b/certbot-nginx/setup.py
@@ -1,5 +1,7 @@
 from setuptools import setup
 from setuptools import find_packages
+from setuptools.command.test import test as TestCommand
+import sys
 
 
 version = '0.32.0.dev0'
@@ -21,6 +23,22 @@ docs_extras = [
     'sphinx_rtd_theme',
 ]
 
+
+class PyTest(TestCommand):
+    user_options = []
+
+    def initialize_options(self):
+        TestCommand.initialize_options(self)
+        self.pytest_args = ''
+
+    def run_tests(self):
+        import shlex
+        # import here, cause outside the eggs aren't loaded
+        import pytest
+        errno = pytest.main(shlex.split(self.pytest_args))
+        sys.exit(errno)
+
+
 setup(
     name='certbot-nginx',
     version=version,
@@ -64,4 +82,6 @@ setup(
         ],
     },
     test_suite='certbot_nginx',
+    tests_require=["pytest"],
+    cmdclass={"test": PyTest},
 )
diff --git a/certbot/cli.py b/certbot/cli.py
index 31f55711f..398124510 100644
--- a/certbot/cli.py
+++ b/certbot/cli.py
@@ -108,7 +108,7 @@ manage your account with Let's Encrypt:
 
 # This is the short help for certbot --help, where we disable argparse
 # altogether
-HELP_USAGE = """
+HELP_AND_VERSION_USAGE = """
 More detailed help:
 
   -h, --help [TOPIC]    print this message, or detailed help on a topic;
@@ -117,6 +117,8 @@ More detailed help:
    all, automation, commands, paths, security, testing, or any of the
    subcommands or plugins (certonly, renew, install, register, nginx,
    apache, standalone, webroot, etc.)
+
+  --version             print the version number
 """
 
 
@@ -566,7 +568,7 @@ class HelpfulArgumentParser(object):
 
         usage = SHORT_USAGE
         if help_arg == True:
-            self.notify(usage + COMMAND_OVERVIEW % (apache_doc, nginx_doc) + HELP_USAGE)
+            self.notify(usage + COMMAND_OVERVIEW % (apache_doc, nginx_doc) + HELP_AND_VERSION_USAGE)
             sys.exit(0)
         elif help_arg in self.COMMANDS_TOPICS:
             self.notify(usage + self._list_subcommands())
diff --git a/certbot/compat.py b/certbot/compat.py
index 3b5d068a6..f533f5954 100644
--- a/certbot/compat.py
+++ b/certbot/compat.py
@@ -13,13 +13,6 @@ import stat
 
 from certbot import errors
 
-try:
-    # Linux specific
-    import fcntl # pylint: disable=import-error
-except ImportError:
-    # Windows specific
-    import msvcrt # pylint: disable=import-error
-
 UNPRIVILEGED_SUBCOMMANDS_ALLOWED = [
     'certificates', 'enhance', 'revoke', 'delete',
     'register', 'unregister', 'config_changes', 'plugins']
@@ -118,55 +111,6 @@ def readline_with_timeout(timeout, prompt):
         return sys.stdin.readline()
 
 
-def lock_file(fd):
-    """
-    Lock the file linked to the specified file descriptor.
-
-    :param int fd: The file descriptor of the file to lock.
-
-    """
-    if 'fcntl' in sys.modules:
-        # Linux specific
-        fcntl.lockf(fd, fcntl.LOCK_EX | fcntl.LOCK_NB)
-    else:
-        # Windows specific
-        msvcrt.locking(fd, msvcrt.LK_NBLCK, 1)
-
-
-def release_locked_file(fd, path):
-    """
-    Remove, close, and release a lock file specified by its file descriptor and its path.
-
-    :param int fd: The file descriptor of the lock file.
-    :param str path: The path of the lock file.
-
-    """
-    # Linux specific
-    #
-    # It is important the lock file is removed before it's released,
-    # otherwise:
-    #
-    # process A: open lock file
-    # process B: release lock file
-    # process A: lock file
-    # process A: check device and inode
-    # process B: delete file
-    # process C: open and lock a different file at the same path
-    try:
-        os.remove(path)
-    except OSError as err:
-        if err.errno == errno.EACCES:
-            # Windows specific
-            # We will not be able to remove a file before closing it.
-            # To avoid race conditions described for Linux, we will not delete the lockfile,
-            # just close it to be reused on the next Certbot call.
-            pass
-        else:
-            raise
-    finally:
-        os.close(fd)
-
-
 def compare_file_modes(mode1, mode2):
     """Return true if the two modes can be considered as equals for this platform"""
     if os.name != 'nt':
diff --git a/certbot/hooks.py b/certbot/hooks.py
index d5239a437..7d2e42fcd 100644
--- a/certbot/hooks.py
+++ b/certbot/hooks.py
@@ -93,8 +93,7 @@ def _run_pre_hook_if_necessary(command):
     if command in executed_pre_hooks:
         logger.info("Pre-hook command already run, skipping: %s", command)
     else:
-        logger.info("Running pre-hook command: %s", command)
-        _run_hook(command)
+        _run_hook("pre-hook", command)
         executed_pre_hooks.add(command)
 
 
@@ -126,8 +125,7 @@ def post_hook(config):
             _run_eventually(cmd)
     # certonly / run
     elif cmd:
-        logger.info("Running post-hook command: %s", cmd)
-        _run_hook(cmd)
+        _run_hook("post-hook", cmd)
 
 
 post_hooks = []  # type: List[str]
@@ -149,8 +147,7 @@ def _run_eventually(command):
 def run_saved_post_hooks():
     """Run any post hooks that were saved up in the course of the 'renew' verb"""
     for cmd in post_hooks:
-        logger.info("Running post-hook command: %s", cmd)
-        _run_hook(cmd)
+        _run_hook("post-hook", cmd)
 
 
 def deploy_hook(config, domains, lineage_path):
@@ -220,23 +217,30 @@ def _run_deploy_hook(command, domains, lineage_path, dry_run):
 
     os.environ["RENEWED_DOMAINS"] = " ".join(domains)
     os.environ["RENEWED_LINEAGE"] = lineage_path
-    logger.info("Running deploy-hook command: %s", command)
-    _run_hook(command)
+    _run_hook("deploy-hook", command)
 
 
-def _run_hook(shell_cmd):
+def _run_hook(cmd_name, shell_cmd):
     """Run a hook command.
 
-    :returns: stderr if there was any"""
+    :param str cmd_name: the user facing name of the hook being run
+    :param shell_cmd: shell command to execute
+    :type shell_cmd: `list` of `str` or `str`
 
-    err, _ = execute(shell_cmd)
+    :returns: stderr if there was any"""
+    err, _ = execute(cmd_name, shell_cmd)
     return err
 
 
-def execute(shell_cmd):
+def execute(cmd_name, shell_cmd):
     """Run a command.
 
+    :param str cmd_name: the user facing name of the hook being run
+    :param shell_cmd: shell command to execute
+    :type shell_cmd: `list` of `str` or `str`
+
     :returns: `tuple` (`str` stderr, `str` stdout)"""
+    logger.info("Running %s command: %s", cmd_name, shell_cmd)
 
     # universal_newlines causes Popen.communicate()
     # to return str objects instead of bytes in Python 3
@@ -245,12 +249,12 @@ def execute(shell_cmd):
     out, err = cmd.communicate()
     base_cmd = os.path.basename(shell_cmd.split(None, 1)[0])
     if out:
-        logger.info('Output from %s:\n%s', base_cmd, out)
+        logger.info('Output from %s command %s:\n%s', cmd_name, base_cmd, out)
     if cmd.returncode != 0:
-        logger.error('Hook command "%s" returned error code %d',
-                     shell_cmd, cmd.returncode)
+        logger.error('%s command "%s" returned error code %d',
+                     cmd_name, shell_cmd, cmd.returncode)
     if err:
-        logger.error('Error output from %s:\n%s', base_cmd, err)
+        logger.error('Error output from %s command %s:\n%s', cmd_name, base_cmd, err)
     return (err, out)
 
 
diff --git a/certbot/lock.py b/certbot/lock.py
index 3ff46518d..760a12b8f 100644
--- a/certbot/lock.py
+++ b/certbot/lock.py
@@ -1,15 +1,23 @@
-"""Implements file locks for locking files and directories in UNIX."""
+"""Implements file locks compatible with Linux and Windows for locking files and directories."""
 import errno
 import logging
 import os
+try:
+    import fcntl  # pylint: disable=import-error
+except ImportError:
+    import msvcrt  # pylint: disable=import-error
+    POSIX_MODE = False
+else:
+    POSIX_MODE = True
 
-from certbot import compat
 from certbot import errors
+from acme.magic_typing import Optional, Callable  # pylint: disable=unused-import, no-name-in-module
 
 logger = logging.getLogger(__name__)
 
 
 def lock_dir(dir_path):
+    # type: (str) -> LockFile
     """Place a lock file on the directory at dir_path.
 
     The lock file is placed in the root of dir_path with the name
@@ -27,34 +35,99 @@ def lock_dir(dir_path):
 
 
 class LockFile(object):
-    """A UNIX lock file.
-
-    This lock file is released when the locked file is closed or the
-    process exits. It cannot be used to provide synchronization between
-    threads. It is based on the lock_file package by Martin Horcicka.
-
+    """
+    Platform independent file lock system.
+    LockFile accepts a parameter, the path to a file acting as a lock. Once the LockFile,
+    instance is created, the associated file is 'locked from the point of view of the OS,
+    meaning that if another instance of Certbot try at the same time to acquire the same lock,
+    it will raise an Exception. Calling release method will release the lock, and make it
+    available to every other instance.
+    Upon exit, Certbot will also release all the locks.
+    This allows us to protect a file or directory from being concurrently accessed
+    or modified by two Certbot instances.
+    LockFile is platform independent: it will proceed to the appropriate OS lock mechanism
+    depending on Linux or Windows.
     """
     def __init__(self, path):
-        """Initialize and acquire the lock file.
-
-        :param str path: path to the file to lock
-
-        :raises errors.LockError: if unable to acquire the lock
-
+        # type: (str) -> None
+        """
+        Create a LockFile instance on the given file path, and acquire lock.
+        :param str path: the path to the file that will hold a lock
         """
-        super(LockFile, self).__init__()
         self._path = path
-        self._fd = None
+        mechanism = _UnixLockMechanism if POSIX_MODE else _WindowsLockMechanism
+        self._lock_mechanism = mechanism(path)
 
         self.acquire()
 
+    def __repr__(self):
+        # type: () -> str
+        repr_str = '{0}({1}) <'.format(self.__class__.__name__, self._path)
+        if self.is_locked():
+            repr_str += 'acquired>'
+        else:
+            repr_str += 'released>'
+        return repr_str
+
     def acquire(self):
-        """Acquire the lock file.
-
-        :raises errors.LockError: if lock is already held
-        :raises OSError: if unable to open or stat the lock file
-
+        # type: () -> None
         """
+        Acquire the lock on the file, forbidding any other Certbot instance to acquire it.
+        :raises errors.LockError: if unable to acquire the lock
+        """
+        self._lock_mechanism.acquire()
+
+    def release(self):
+        # type: () -> None
+        """
+        Release the lock on the file, allowing any other Certbot instance to acquire it.
+        """
+        self._lock_mechanism.release()
+
+    def is_locked(self):
+        # type: () -> bool
+        """
+        Check if the file is currently locked.
+        :return: True if the file is locked, False otherwise
+        """
+        return self._lock_mechanism.is_locked()
+
+
+class _BaseLockMechanism(object):
+    def __init__(self, path):
+        # type: (str) -> None
+        """
+        Create a lock file mechanism for Unix.
+        :param str path: the path to the lock file
+        """
+        self._path = path
+        self._fd = None  # type: Optional[int]
+
+    def is_locked(self):
+        # type: () -> bool
+        """Check if lock file is currently locked.
+        :return: True if the lock file is locked
+        :rtype: bool
+        """
+        return self._fd is not None
+
+    def acquire(self):  # pylint: disable=missing-docstring
+        pass  # pragma: no cover
+
+    def release(self):  # pylint: disable=missing-docstring
+        pass  # pragma: no cover
+
+
+class _UnixLockMechanism(_BaseLockMechanism):
+    """
+    A UNIX lock file mechanism.
+    This lock file is released when the locked file is closed or the
+    process exits. It cannot be used to provide synchronization between
+    threads. It is based on the lock_file package by Martin Horcicka.
+    """
+    def acquire(self):
+        # type: () -> None
+        """Acquire the lock."""
         while self._fd is None:
             # Open the file
             fd = os.open(self._path, os.O_CREAT | os.O_WRONLY, 0o600)
@@ -68,33 +141,29 @@ class LockFile(object):
                     os.close(fd)
 
     def _try_lock(self, fd):
-        """Try to acquire the lock file without blocking.
-
+        # type: (int) -> None
+        """
+        Try to acquire the lock file without blocking.
         :param int fd: file descriptor of the opened file to lock
-
         """
         try:
-            compat.lock_file(fd)
+            fcntl.lockf(fd, fcntl.LOCK_EX | fcntl.LOCK_NB)
         except IOError as err:
             if err.errno in (errno.EACCES, errno.EAGAIN):
-                logger.debug(
-                    "A lock on %s is held by another process.", self._path)
-                raise errors.LockError(
-                    "Another instance of Certbot is already running.")
+                logger.debug('A lock on %s is held by another process.', self._path)
+                raise errors.LockError('Another instance of Certbot is already running.')
             raise
 
     def _lock_success(self, fd):
-        """Did we successfully grab the lock?
-
+        # type: (int) -> bool
+        """
+        Did we successfully grab the lock?
         Because this class deletes the locked file when the lock is
         released, it is possible another process removed and recreated
         the file between us opening the file and acquiring the lock.
-
         :param int fd: file descriptor of the opened file to lock
-
         :returns: True if the lock was successfully acquired
         :rtype: bool
-
         """
         try:
             stat1 = os.stat(self._path)
@@ -108,17 +177,75 @@ class LockFile(object):
         # the same device and inode, they're the same file.
         return stat1.st_dev == stat2.st_dev and stat1.st_ino == stat2.st_ino
 
-    def __repr__(self):
-        repr_str = '{0}({1}) <'.format(self.__class__.__name__, self._path)
-        if self._fd is None:
-            repr_str += 'released>'
-        else:
-            repr_str += 'acquired>'
-        return repr_str
+    def release(self):
+        # type: () -> None
+        """Remove, close, and release the lock file."""
+        # It is important the lock file is removed before it's released,
+        # otherwise:
+        #
+        # process A: open lock file
+        # process B: release lock file
+        # process A: lock file
+        # process A: check device and inode
+        # process B: delete file
+        # process C: open and lock a different file at the same path
+        try:
+            os.remove(self._path)
+        finally:
+            # Following check is done to make mypy happy: it ensure that self._fd, marked
+            # as Optional[int] is effectively int to make it compatible with os.close signature.
+            if self._fd is None:  # pragma: no cover
+                raise TypeError('Error, self._fd is None.')
+            try:
+                os.close(self._fd)
+            finally:
+                self._fd = None
+
+
+class _WindowsLockMechanism(_BaseLockMechanism):
+    """
+    A Windows lock file mechanism.
+    By default on Windows, acquiring a file handler gives exclusive access to the process
+    and results in an effective lock. However, it is possible to explicitly acquire the
+    file handler in shared access in terms of read and write, and this is done by os.open
+    and io.open in Python. So an explicit lock needs to be done through the call of
+    msvcrt.locking, that will lock the first byte of the file. In theory, it is also
+    possible to access a file in shared delete access, allowing other processes to delete an
+    opened file. But this needs also to be done explicitly by all processes using the Windows
+    low level APIs, and Python does not do it. As of Python 3.7 and below, Python developers
+    state that deleting a file opened by a process from another process is not possible with
+    os.open and io.open.
+    Consequently, mscvrt.locking is sufficient to obtain an effective lock, and the race
+    condition encountered on Linux is not possible on Windows, leading to a simpler workflow.
+    """
+    def acquire(self):
+        """Acquire the lock"""
+        open_mode = os.O_RDWR | os.O_CREAT | os.O_TRUNC
+
+        fd = os.open(self._path, open_mode, 0o600)
+        try:
+            msvcrt.locking(fd, msvcrt.LK_NBLCK, 1)
+        except (IOError, OSError) as err:
+            os.close(fd)
+            # Anything except EACCES is unexpected. Raise directly the error in that case.
+            if err.errno != errno.EACCES:
+                raise
+            logger.debug('A lock on %s is held by another process.', self._path)
+            raise errors.LockError('Another instance of Certbot is already running.')
+
+        self._fd = fd
 
     def release(self):
-        """Remove, close, and release the lock file."""
+        """Release the lock."""
         try:
-            compat.release_locked_file(self._fd, self._path)
+            msvcrt.locking(self._fd, msvcrt.LK_UNLCK, 1)
+            os.close(self._fd)
+
+            try:
+                os.remove(self._path)
+            except OSError as e:
+                # If the lock file cannot be removed, it is not a big deal.
+                # Likely another instance is acquiring the lock we just released.
+                logger.debug(str(e))
         finally:
             self._fd = None
diff --git a/certbot/plugins/manual.py b/certbot/plugins/manual.py
index 8723a1c62..123a5bfea 100644
--- a/certbot/plugins/manual.py
+++ b/certbot/plugins/manual.py
@@ -202,7 +202,7 @@ permitted by DNS standards.)
             os.environ.pop('CERTBOT_KEY_PATH', None)
             os.environ.pop('CERTBOT_SNI_DOMAIN', None)
         os.environ.update(env)
-        _, out = hooks.execute(self.conf('auth-hook'))
+        _, out = self._execute_hook('auth-hook')
         env['CERTBOT_AUTH_OUTPUT'] = out.strip()
         self.env[achall] = env
 
@@ -243,5 +243,8 @@ permitted by DNS standards.)
                 if 'CERTBOT_TOKEN' not in env:
                     os.environ.pop('CERTBOT_TOKEN', None)
                 os.environ.update(env)
-                hooks.execute(self.conf('cleanup-hook'))
+                self._execute_hook('cleanup-hook')
         self.reverter.recovery_routine()
+
+    def _execute_hook(self, hook_name):
+        return hooks.execute(self.option_name(hook_name), self.conf(hook_name))
diff --git a/certbot/tests/hook_test.py b/certbot/tests/hook_test.py
index f5bb0c8b5..90f639958 100644
--- a/certbot/tests/hook_test.py
+++ b/certbot/tests/hook_test.py
@@ -121,7 +121,7 @@ class PreHookTest(HookTest):
 
     def _test_nonrenew_common(self):
         mock_execute = self._call_with_mock_execute(self.config)
-        mock_execute.assert_called_once_with(self.config.pre_hook)
+        mock_execute.assert_called_once_with("pre-hook", self.config.pre_hook)
         self._test_no_executions_common()
 
     def test_no_hooks(self):
@@ -137,21 +137,21 @@ class PreHookTest(HookTest):
     def test_renew_disabled_dir_hooks(self):
         self.config.directory_hooks = False
         mock_execute = self._call_with_mock_execute(self.config)
-        mock_execute.assert_called_once_with(self.config.pre_hook)
+        mock_execute.assert_called_once_with("pre-hook", self.config.pre_hook)
         self._test_no_executions_common()
 
     def test_renew_no_overlap(self):
         self.config.verb = "renew"
         mock_execute = self._call_with_mock_execute(self.config)
-        mock_execute.assert_any_call(self.dir_hook)
-        mock_execute.assert_called_with(self.config.pre_hook)
+        mock_execute.assert_any_call("pre-hook", self.dir_hook)
+        mock_execute.assert_called_with("pre-hook", self.config.pre_hook)
         self._test_no_executions_common()
 
     def test_renew_with_overlap(self):
         self.config.pre_hook = self.dir_hook
         self.config.verb = "renew"
         mock_execute = self._call_with_mock_execute(self.config)
-        mock_execute.assert_called_once_with(self.dir_hook)
+        mock_execute.assert_called_once_with("pre-hook", self.dir_hook)
         self._test_no_executions_common()
 
     def _test_no_executions_common(self):
@@ -193,7 +193,7 @@ class PostHookTest(HookTest):
         for verb in ("certonly", "run",):
             self.config.verb = verb
             mock_execute = self._call_with_mock_execute(self.config)
-            mock_execute.assert_called_once_with(self.config.post_hook)
+            mock_execute.assert_called_once_with("post-hook", self.config.post_hook)
             self.assertFalse(self._get_eventually())
 
     def test_cert_only_and_run_without_hook(self):
@@ -277,12 +277,12 @@ class RunSavedPostHooksTest(HookTest):
 
         calls = mock_execute.call_args_list
         for actual_call, expected_arg in zip(calls, self.eventually):
-            self.assertEqual(actual_call[0][0], expected_arg)
+            self.assertEqual(actual_call[0][1], expected_arg)
 
     def test_single(self):
         self.eventually = ["foo"]
         mock_execute = self._call_with_mock_execute_and_eventually()
-        mock_execute.assert_called_once_with(self.eventually[0])
+        mock_execute.assert_called_once_with("post-hook", self.eventually[0])
 
 
 class RenewalHookTest(HookTest):
@@ -360,7 +360,7 @@ class DeployHookTest(RenewalHookTest):
         self.config.deploy_hook = "foo"
         mock_execute = self._call_with_mock_execute(
             self.config, domains, lineage)
-        mock_execute.assert_called_once_with(self.config.deploy_hook)
+        mock_execute.assert_called_once_with("deploy-hook", self.config.deploy_hook)
 
 
 class RenewHookTest(RenewalHookTest):
@@ -384,7 +384,7 @@ class RenewHookTest(RenewalHookTest):
         self.config.directory_hooks = False
         mock_execute = self._call_with_mock_execute(
             self.config, ["example.org"], "/foo/bar")
-        mock_execute.assert_called_once_with(self.config.renew_hook)
+        mock_execute.assert_called_once_with("deploy-hook", self.config.renew_hook)
 
     @mock.patch("certbot.hooks.logger")
     def test_dry_run(self, mock_logger):
@@ -408,13 +408,13 @@ class RenewHookTest(RenewalHookTest):
         self.config.renew_hook = self.dir_hook
         mock_execute = self._call_with_mock_execute(
             self.config, ["example.net", "example.org"], "/foo/bar")
-        mock_execute.assert_called_once_with(self.dir_hook)
+        mock_execute.assert_called_once_with("deploy-hook", self.dir_hook)
 
     def test_no_overlap(self):
         mock_execute = self._call_with_mock_execute(
             self.config, ["example.org"], "/foo/bar")
-        mock_execute.assert_any_call(self.dir_hook)
-        mock_execute.assert_called_with(self.config.renew_hook)
+        mock_execute.assert_any_call("deploy-hook", self.dir_hook)
+        mock_execute.assert_called_with("deploy-hook", self.config.renew_hook)
 
 
 class ExecuteTest(unittest.TestCase):
@@ -433,18 +433,22 @@ class ExecuteTest(unittest.TestCase):
 
     def _test_common(self, returncode, stdout, stderr):
         given_command = "foo"
+        given_name = "foo-hook"
         with mock.patch("certbot.hooks.Popen") as mock_popen:
             mock_popen.return_value.communicate.return_value = (stdout, stderr)
             mock_popen.return_value.returncode = returncode
             with mock.patch("certbot.hooks.logger") as mock_logger:
-                self.assertEqual(self._call(given_command), (stderr, stdout))
+                self.assertEqual(self._call(given_name, given_command), (stderr, stdout))
 
         executed_command = mock_popen.call_args[1].get(
             "args", mock_popen.call_args[0][0])
         self.assertEqual(executed_command, given_command)
 
+        mock_logger.info.assert_any_call("Running %s command: %s",
+                                         given_name, given_command)
         if stdout:
-            self.assertTrue(mock_logger.info.called)
+            mock_logger.info.assert_any_call(mock.ANY, mock.ANY,
+                                             mock.ANY, stdout)
         if stderr or returncode:
             self.assertTrue(mock_logger.error.called)
 
diff --git a/certbot/tests/lock_test.py b/certbot/tests/lock_test.py
index aa82701f3..6379693ae 100644
--- a/certbot/tests/lock_test.py
+++ b/certbot/tests/lock_test.py
@@ -3,6 +3,12 @@ import functools
 import multiprocessing
 import os
 import unittest
+try:
+    import fcntl  # pylint: disable=import-error,unused-import
+except ImportError:
+    POSIX_MODE = False
+else:
+    POSIX_MODE = True
 
 import mock
 
@@ -10,7 +16,6 @@ from certbot import errors
 from certbot.tests import util as test_util
 
 
-@test_util.broken_on_windows
 class LockDirTest(test_util.TempDirTestCase):
     """Tests for certbot.lock.lock_dir."""
     @classmethod
@@ -25,7 +30,6 @@ class LockDirTest(test_util.TempDirTestCase):
         test_util.lock_and_call(assert_raises, lock_path)
 
 
-@test_util.broken_on_windows
 class LockFileTest(test_util.TempDirTestCase):
     """Tests for certbot.lock.LockFile."""
     @classmethod
@@ -37,6 +41,7 @@ class LockFileTest(test_util.TempDirTestCase):
         super(LockFileTest, self).setUp()
         self.lock_path = os.path.join(self.tempdir, 'test.lock')
 
+    @test_util.broken_on_windows
     def test_acquire_without_deletion(self):
         # acquire the lock in another process but don't delete the file
         child = multiprocessing.Process(target=self._call,
@@ -54,6 +59,7 @@ class LockFileTest(test_util.TempDirTestCase):
             self.assertRaises, errors.LockError, self._call, self.lock_path)
         test_util.lock_and_call(assert_raises, self.lock_path)
 
+    @test_util.broken_on_windows
     def test_locked_repr(self):
         lock_file = self._call(self.lock_path)
         locked_repr = repr(lock_file)
@@ -71,6 +77,8 @@ class LockFileTest(test_util.TempDirTestCase):
         self.assertTrue(lock_file.__class__.__name__ in lock_repr)
         self.assertTrue(self.lock_path in lock_repr)
 
+    @test_util.skip_on_windows(
+        'Race conditions on lock are specific to the non-blocking file access approach on Linux.')
     def test_race(self):
         should_delete = [True, False]
         stat = os.stat
@@ -86,32 +94,42 @@ class LockFileTest(test_util.TempDirTestCase):
             self._call(self.lock_path)
         self.assertFalse(should_delete)
 
+    @test_util.broken_on_windows
     def test_removed(self):
         lock_file = self._call(self.lock_path)
         lock_file.release()
         self.assertFalse(os.path.exists(self.lock_path))
 
-    @mock.patch('certbot.compat.fcntl.lockf')
-    def test_unexpected_lockf_err(self, mock_lockf):
+    def test_unexpected_lockf_or_locking_err(self):
+        if POSIX_MODE:
+            mocked_function = 'certbot.lock.fcntl.lockf'
+        else:
+            mocked_function = 'certbot.lock.msvcrt.locking'
         msg = 'hi there'
-        mock_lockf.side_effect = IOError(msg)
-        try:
-            self._call(self.lock_path)
-        except IOError as err:
-            self.assertTrue(msg in str(err))
-        else:  # pragma: no cover
-            self.fail('IOError not raised')
+        with mock.patch(mocked_function) as mock_lock:
+            mock_lock.side_effect = IOError(msg)
+            try:
+                self._call(self.lock_path)
+            except IOError as err:
+                self.assertTrue(msg in str(err))
+            else:  # pragma: no cover
+                self.fail('IOError not raised')
 
-    @mock.patch('certbot.lock.os.stat')
-    def test_unexpected_stat_err(self, mock_stat):
+    def test_unexpected_os_err(self):
+        if POSIX_MODE:
+            mock_function = 'certbot.lock.os.stat'
+        else:
+            mock_function = 'certbot.lock.msvcrt.locking'
+        # The only expected errno are ENOENT and EACCES in lock module.
         msg = 'hi there'
-        mock_stat.side_effect = OSError(msg)
-        try:
-            self._call(self.lock_path)
-        except OSError as err:
-            self.assertTrue(msg in str(err))
-        else:  # pragma: no cover
-            self.fail('OSError not raised')
+        with mock.patch(mock_function) as mock_os:
+            mock_os.side_effect = OSError(msg)
+            try:
+                self._call(self.lock_path)
+            except OSError as err:
+                self.assertTrue(msg in str(err))
+            else:  # pragma: no cover
+                self.fail('OSError not raised')
 
 
 if __name__ == "__main__":
diff --git a/certbot/tests/util.py b/certbot/tests/util.py
index 8c5db2c2f..4c0c66a42 100644
--- a/certbot/tests/util.py
+++ b/certbot/tests/util.py
@@ -3,14 +3,15 @@
 .. warning:: This module is not part of the public API.
 
 """
-import multiprocessing
+import logging
 import os
 import pkg_resources
 import shutil
+import stat
 import tempfile
 import unittest
 import sys
-import warnings
+from multiprocessing import Process, Event
 
 from cryptography.hazmat.backends import default_backend
 from cryptography.hazmat.primitives import serialization
@@ -23,8 +24,9 @@ from six.moves import reload_module  # pylint: disable=import-error
 from certbot import constants
 from certbot import interfaces
 from certbot import storage
-from certbot import util
 from certbot import configuration
+from certbot import lock
+from certbot import util
 
 from certbot.display import util as display_util
 
@@ -211,7 +213,7 @@ class FreezableMock(object):
 
     """
     def __init__(self, frozen=False, func=None, return_value=mock.sentinel.DEFAULT):
-        self._frozen_set = set() if frozen else set(('freeze',))
+        self._frozen_set = set() if frozen else {'freeze', }
         self._func = func
         self._mock = mock.MagicMock()
         if return_value != mock.sentinel.DEFAULT:
@@ -328,22 +330,25 @@ class TempDirTestCase(unittest.TestCase):
 
     def tearDown(self):
         """Execute after test"""
-        # 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 the tempdir {0}'
-                           ' for path {1} during tearDown process: {2}'
-                           .format(self.tempdir, path, str(excinfo)))
-                warnings.warn(message)
-        shutil.rmtree(self.tempdir, onerror=onerror_handler)
+        # 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.
+        logging.shutdown()
+        # Remove logging handlers that have been closed so they won't be
+        # accidentally used in future tests.
+        logging.getLogger().handlers = []
+        util._release_locks()  # pylint: disable=protected-access
+
+        def handle_rw_files(_, path, __):
+            """Handle read-only files, that will fail to be removed on Windows."""
+            os.chmod(path, stat.S_IWRITE)
+            os.remove(path)
+        shutil.rmtree(self.tempdir, onerror=handle_rw_files)
+
 
 class ConfigTestCase(TempDirTestCase):
-    """Test class which sets up a NamespaceConfig object.
-
-    """
+    """Test class which sets up a NamespaceConfig object."""
     def setUp(self):
         super(ConfigTestCase, self).setUp()
         self.config = configuration.NamespaceConfig(
@@ -358,47 +363,51 @@ class ConfigTestCase(TempDirTestCase):
         self.config.chain_path = constants.CLI_DEFAULTS['auth_chain_path']
         self.config.server = "https://example.com"
 
-def lock_and_call(func, lock_path):
-    """Grab a lock for lock_path and call func.
-
-    :param callable func: object to call after acquiring the lock
-    :param str lock_path: path to file or directory to lock
 
+def _handle_lock(event_in, event_out, path):
     """
-    # Reload module to reset internal _LOCKS dictionary
+    Acquire a file lock on given path, then wait to release it. This worker is coordinated
+    using events to signal when the lock should be acquired and released.
+    :param multiprocessing.Event event_in: event object to signal when to release the lock
+    :param multiprocessing.Event event_out: event object to signal when the lock is acquired
+    :param path: the path to lock
+    """
+    if os.path.isdir(path):
+        my_lock = lock.lock_dir(path)
+    else:
+        my_lock = lock.LockFile(path)
+    try:
+        event_out.set()
+        assert event_in.wait(timeout=20), 'Timeout while waiting to release the lock.'
+    finally:
+        my_lock.release()
+
+
+def lock_and_call(callback, path_to_lock):
+    """
+    Grab a lock on path_to_lock from a foreign process then execute the callback.
+    :param callable callback: object to call after acquiring the lock
+    :param str path_to_lock: path to file or directory to lock
+    """
+    # Reload certbot.util module to reset internal _LOCKS dictionary.
     reload_module(util)
 
-    # start child and wait for it to grab the lock
-    cv = multiprocessing.Condition()
-    cv.acquire()
-    child_args = (cv, lock_path,)
-    child = multiprocessing.Process(target=hold_lock, args=child_args)
-    child.start()
-    cv.wait()
+    emit_event = Event()
+    receive_event = Event()
+    process = Process(target=_handle_lock, args=(emit_event, receive_event, path_to_lock))
+    process.start()
 
-    # call func and terminate the child
-    func()
-    cv.notify()
-    cv.release()
-    child.join()
-    assert child.exitcode == 0
+    # Wait confirmation that lock is acquired
+    assert receive_event.wait(timeout=10), 'Timeout while waiting to acquire the lock.'
+    # Execute the callback
+    callback()
+    # Trigger unlock from foreign process
+    emit_event.set()
 
-def hold_lock(cv, lock_path):  # pragma: no cover
-    """Acquire a file lock at lock_path and wait to release it.
+    # Wait for process termination
+    process.join(timeout=10)
+    assert process.exitcode == 0
 
-    :param multiprocessing.Condition cv: condition for synchronization
-    :param str lock_path: path to the file lock
-
-    """
-    from certbot import lock
-    if os.path.isdir(lock_path):
-        my_lock = lock.lock_dir(lock_path)
-    else:
-        my_lock = lock.LockFile(lock_path)
-    cv.acquire()
-    cv.notify()
-    cv.wait()
-    my_lock.release()
 
 def skip_on_windows(reason):
     """Decorator to skip permanently a test on Windows. A reason is required."""
@@ -407,6 +416,7 @@ def skip_on_windows(reason):
         return unittest.skipIf(sys.platform == 'win32', reason)(function)
     return wrapper
 
+
 def broken_on_windows(function):
     """Decorator to skip temporarily a broken test on Windows."""
     reason = 'Test is broken and ignored on windows but should be fixed.'
@@ -415,9 +425,10 @@ def broken_on_windows(function):
         and os.environ.get('SKIP_BROKEN_TESTS_ON_WINDOWS', 'true') == 'true',
         reason)(function)
 
+
 def temp_join(path):
     """
     Return the given path joined to the tempdir path for the current platform
     Eg.: 'cert' => /tmp/cert (Linux) or 'C:\\Users\\currentuser\\AppData\\Temp\\cert' (Windows)
     """
-    return  os.path.join(tempfile.gettempdir(), path)
+    return os.path.join(tempfile.gettempdir(), path)
diff --git a/certbot/tests/util_test.py b/certbot/tests/util_test.py
index 6685b88c6..cac587995 100644
--- a/certbot/tests/util_test.py
+++ b/certbot/tests/util_test.py
@@ -2,7 +2,6 @@
 import argparse
 import errno
 import os
-import shutil
 import unittest
 
 import mock
@@ -88,7 +87,6 @@ class LockDirUntilExit(test_util.TempDirTestCase):
         import certbot.util
         reload_module(certbot.util)
 
-    @test_util.broken_on_windows
     @mock.patch('certbot.util.logger')
     @mock.patch('certbot.util.atexit_register')
     def test_it(self, mock_register, mock_logger):
@@ -100,11 +98,15 @@ class LockDirUntilExit(test_util.TempDirTestCase):
 
         self.assertEqual(mock_register.call_count, 1)
         registered_func = mock_register.call_args[0][0]
-        shutil.rmtree(subdir)
-        registered_func()  # exception not raised
-        # logger.debug is only called once because the second call
-        # to lock subdir was ignored because it was already locked
-        self.assertEqual(mock_logger.debug.call_count, 1)
+
+        from certbot import util
+        # Despite lock_dir_until_exit has been called twice to subdir, its lock should have been
+        # added only once. So we expect to have two lock references: for self.tempdir and subdir
+        self.assertTrue(len(util._LOCKS) == 2)  # pylint: disable=protected-access
+        registered_func()  # Exception should not be raised
+        # Logically, logger.debug, that would be invoked in case of unlock failure,
+        # should never been called.
+        self.assertEqual(mock_logger.debug.call_count, 0)
 
 
 class SetUpCoreDirTest(test_util.TempDirTestCase):
@@ -191,7 +193,12 @@ class CheckPermissionsTest(test_util.TempDirTestCase):
 
     def test_wrong_mode(self):
         os.chmod(self.tempdir, 0o400)
-        self.assertFalse(self._call(0o600))
+        try:
+            self.assertFalse(self._call(0o600))
+        finally:
+            # Without proper write permissions, Windows is unable to delete a folder,
+            # even with admin permissions. Write access must be explicitly set first.
+            os.chmod(self.tempdir, 0o700)
 
 
 class UniqueFileTest(test_util.TempDirTestCase):
@@ -277,20 +284,9 @@ class UniqueLineageNameTest(test_util.TempDirTestCase):
         for f, _ in items:
             f.close()
 
-    @mock.patch("certbot.util.os.fdopen")
-    def test_failure(self, mock_fdopen):
-        err = OSError("whoops")
-        err.errno = errno.EIO
-        mock_fdopen.side_effect = err
-        self.assertRaises(OSError, self._call, "wow")
-
-    @mock.patch("certbot.util.os.fdopen")
-    def test_subsequent_failure(self, mock_fdopen):
-        self._call("wow")
-        err = OSError("whoops")
-        err.errno = errno.EIO
-        mock_fdopen.side_effect = err
-        self.assertRaises(OSError, self._call, "wow")
+    def test_failure(self):
+        with mock.patch("certbot.util.os.open", side_effect=OSError(errno.EIO)):
+            self.assertRaises(OSError, self._call, "wow")
 
 
 class SafelyRemoveTest(test_util.TempDirTestCase):
diff --git a/certbot/util.py b/certbot/util.py
index d7c542465..416075ce8 100644
--- a/certbot/util.py
+++ b/certbot/util.py
@@ -142,6 +142,7 @@ def _release_locks():
         except:  # pylint: disable=bare-except
             msg = 'Exception occurred releasing lock: {0!r}'.format(dir_lock)
             logger.debug(msg, exc_info=True)
+    _LOCKS.clear()
 
 
 def set_up_core_dir(directory, mode, uid, strict):
@@ -225,9 +226,8 @@ def safe_open(path, mode="w", chmod=None, buffering=None):
     fdopen_args = ()  # type: Union[Tuple[()], Tuple[int]]
     if buffering is not None:
         fdopen_args = (buffering,)
-    return os.fdopen(
-        os.open(path, os.O_CREAT | os.O_EXCL | os.O_RDWR, *open_args),
-        mode, *fdopen_args)
+    fd = os.open(path, os.O_CREAT | os.O_EXCL | os.O_RDWR, *open_args)
+    return os.fdopen(fd, mode, *fdopen_args)
 
 
 def _unique_file(path, filename_pat, count, chmod, mode):
diff --git a/setup.py b/setup.py
index 14fef37f3..26a1c4293 100644
--- a/setup.py
+++ b/setup.py
@@ -1,8 +1,10 @@
 import codecs
 import os
 import re
+import sys
 
 from setuptools import find_packages, setup
+from setuptools.command.test import test as TestCommand
 
 # Workaround for http://bugs.python.org/issue8876, see
 # http://bugs.python.org/issue8876#msg208792
@@ -77,6 +79,22 @@ docs_extras = [
     'sphinx_rtd_theme',
 ]
 
+
+class PyTest(TestCommand):
+    user_options = []
+
+    def initialize_options(self):
+        TestCommand.initialize_options(self)
+        self.pytest_args = ''
+
+    def run_tests(self):
+        import shlex
+        # import here, cause outside the eggs aren't loaded
+        import pytest
+        errno = pytest.main(shlex.split(self.pytest_args))
+        sys.exit(errno)
+
+
 setup(
     name='certbot',
     version=version,
@@ -123,6 +141,8 @@ setup(
     # to test all packages run "python setup.py test -s
     # {acme,certbot_apache,certbot_nginx}"
     test_suite='certbot',
+    tests_require=["pytest"],
+    cmdclass={"test": PyTest},
 
     entry_points={
         'console_scripts': [
diff --git a/tests/display.py b/tests/display.py
deleted file mode 100644
index 1f548e33d..000000000
--- a/tests/display.py
+++ /dev/null
@@ -1,22 +0,0 @@
-"""Manual test of display functions."""
-import sys
-
-from certbot.display import util
-from certbot.tests.display import util_test
-
-
-def test_visual(displayer, choices):
-    """Visually test all of the display functions."""
-    displayer.notification("Random notification!")
-    displayer.menu("Question?", choices,
-                   ok_label="O", cancel_label="Can", help_label="??")
-    displayer.menu("Question?", [choice[1] for choice in choices],
-                   ok_label="O", cancel_label="Can", help_label="??")
-    displayer.input("Input Message")
-    displayer.yesno("YesNo Message", yes_label="Yessir", no_label="Nosir")
-    displayer.checklist("Checklist Message", [choice[0] for choice in choices])
-
-
-if __name__ == "__main__":
-    displayer = util.FileDisplay(sys.stdout, False)
-    test_visual(displayer, util_test.CHOICES)
diff --git a/tests/letstest/multitester.py b/tests/letstest/multitester.py
index 8babc67b3..b8ae937ad 100644
--- a/tests/letstest/multitester.py
+++ b/tests/letstest/multitester.py
@@ -564,6 +564,11 @@ try:
         ii, target, status = outq
         print('%d %s %s'%(ii, target['name'], status))
         results_file.write('%d %s %s\n'%(ii, target['name'], status))
+    if len(outputs) != num_processes:
+        failure_message = 'FAILURE: Some target machines failed to run and were not tested. ' +\
+            'Tests should be rerun.'
+        print(failure_message)
+        results_file.write(failure_message + '\n')
     results_file.close()
 
 finally:
diff --git a/tests/letstest/scripts/test_sdists.sh b/tests/letstest/scripts/test_sdists.sh
index 0b9a91ffd..260a0acfb 100755
--- a/tests/letstest/scripts/test_sdists.sh
+++ b/tests/letstest/scripts/test_sdists.sh
@@ -12,6 +12,8 @@ export VENV_ARGS="-p $PYTHON"
 # setup venv
 tools/_venv_common.py --requirement letsencrypt-auto-source/pieces/dependency-requirements.txt
 . ./venv/bin/activate
+# pytest is needed to run tests on some of our packages so we install a pinned version here.
+tools/pip_install.py pytest
 
 # build sdists
 for pkg_dir in acme . $PLUGINS; do
diff --git a/tests/letstest/scripts/test_tests.sh b/tests/letstest/scripts/test_tests.sh
index e6ab836b8..d5fd6e14a 100755
--- a/tests/letstest/scripts/test_tests.sh
+++ b/tests/letstest/scripts/test_tests.sh
@@ -1,18 +1,20 @@
 #!/bin/sh -xe
 
-LE_AUTO="letsencrypt/letsencrypt-auto-source/letsencrypt-auto"
+REPO_ROOT="letsencrypt"
+LE_AUTO="$REPO_ROOT/letsencrypt-auto-source/letsencrypt-auto"
 LE_AUTO="$LE_AUTO --debug --no-self-upgrade --non-interactive"
 MODULES="acme certbot certbot_apache certbot_nginx"
+PIP_INSTALL="$REPO_ROOT/tools/pip_install.py"
 VENV_NAME=venv
 
 # *-auto respects VENV_PATH
 $LE_AUTO --os-packages-only
 LE_AUTO_SUDO="" VENV_PATH="$VENV_NAME" $LE_AUTO --no-bootstrap --version
 . $VENV_NAME/bin/activate
+"$PIP_INSTALL" pytest
 
 # change to an empty directory to ensure CWD doesn't affect tests
 cd $(mktemp -d)
-pip install pytest==3.2.5
 
 for module in $MODULES ; do
     echo testing $module
diff --git a/tools/install_and_test.py b/tools/install_and_test.py
index b15c8eca5..288226527 100755
--- a/tools/install_and_test.py
+++ b/tools/install_and_test.py
@@ -15,7 +15,7 @@ import subprocess
 import re
 
 SKIP_PROJECTS_ON_WINDOWS = [
-    'certbot-apache', 'certbot-nginx', 'certbot-postfix', 'letshelp-certbot']
+    'certbot-apache', 'certbot-postfix', 'letshelp-certbot']
 
 
 def call_with_print(command, cwd=None):
diff --git a/tox.cover.py b/tox.cover.py
index 008424641..e323ba255 100755
--- a/tox.cover.py
+++ b/tox.cover.py
@@ -35,7 +35,8 @@ COVER_THRESHOLDS = {
 }
 
 SKIP_PROJECTS_ON_WINDOWS = [
-    'certbot-apache', 'certbot-nginx', 'certbot-postfix', 'letshelp-certbot']
+    'certbot-apache', 'certbot-postfix', 'letshelp-certbot']
+
 
 def cover(package):
     threshold = COVER_THRESHOLDS.get(package)['windows' if os.name == 'nt' else 'linux']
@@ -54,6 +55,7 @@ def cover(package):
         sys.executable, '-m', 'coverage', 'report', '--fail-under', str(threshold), '--include',
         '{0}/*'.format(pkg_dir), '--show-missing'])
 
+
 def main():
     description = """
 This script is used by tox.ini (and thus by Travis CI and AppVeyor) in order
@@ -77,5 +79,6 @@ Option -e makes sure we fail fast and don't submit to codecov."""
     for package in packages:
         cover(package)
 
+
 if __name__ == '__main__':
     main()