diff --git a/certbot-apache/certbot_apache/configurator.py b/certbot-apache/certbot_apache/configurator.py
index c433c5159..f7c27bf76 100644
--- a/certbot-apache/certbot_apache/configurator.py
+++ b/certbot-apache/certbot_apache/configurator.py
@@ -23,6 +23,7 @@ from certbot import interfaces
 from certbot import util
 
 from certbot.achallenges import KeyAuthorizationAnnotatedChallenge  # pylint: disable=unused-import
+from certbot.compat import filesystem
 from certbot.compat import os
 from certbot.plugins import common
 from certbot.plugins.util import path_surgery
@@ -895,7 +896,7 @@ class ApacheConfigurator(common.Installer):
                 if not new_vhost:
                     continue
                 internal_path = apache_util.get_internal_aug_path(new_vhost.path)
-                realpath = os.path.realpath(new_vhost.filep)
+                realpath = filesystem.realpath(new_vhost.filep)
                 if realpath not in file_paths:
                     file_paths[realpath] = new_vhost.filep
                     internal_paths[realpath].add(internal_path)
@@ -1221,11 +1222,11 @@ class ApacheConfigurator(common.Installer):
         """
 
         if self.conf("vhost-root") and os.path.exists(self.conf("vhost-root")):
-            fp = os.path.join(os.path.realpath(self.option("vhost_root")),
+            fp = os.path.join(filesystem.realpath(self.option("vhost_root")),
                               os.path.basename(non_ssl_vh_fp))
         else:
             # Use non-ssl filepath
-            fp = os.path.realpath(non_ssl_vh_fp)
+            fp = filesystem.realpath(non_ssl_vh_fp)
 
         if fp.endswith(".conf"):
             return fp[:-(len(".conf"))] + self.option("le_vhost_ext")
diff --git a/certbot-apache/certbot_apache/override_debian.py b/certbot-apache/certbot_apache/override_debian.py
index 5706ce760..58492bd01 100644
--- a/certbot-apache/certbot_apache/override_debian.py
+++ b/certbot-apache/certbot_apache/override_debian.py
@@ -7,6 +7,7 @@ import zope.interface
 from certbot import errors
 from certbot import interfaces
 from certbot import util
+from certbot.compat import filesystem
 from certbot.compat import os
 
 from certbot_apache import apache_util
@@ -65,7 +66,7 @@ class DebianConfigurator(configurator.ApacheConfigurator):
         try:
             os.symlink(vhost.filep, enabled_path)
         except OSError as err:
-            if os.path.islink(enabled_path) and os.path.realpath(
+            if os.path.islink(enabled_path) and filesystem.realpath(
                enabled_path) == vhost.filep:
                 # Already in shape
                 vhost.enabled = True
diff --git a/certbot-apache/certbot_apache/tests/centos_test.py b/certbot-apache/certbot_apache/tests/centos_test.py
index 5d16c2b55..dddbf489e 100644
--- a/certbot-apache/certbot_apache/tests/centos_test.py
+++ b/certbot-apache/certbot_apache/tests/centos_test.py
@@ -4,6 +4,7 @@ import unittest
 import mock
 
 from certbot import errors
+from certbot.compat import filesystem
 from certbot.compat import os
 
 from certbot_apache import obj
@@ -160,7 +161,7 @@ class MultipleVhostsTestCentOS(util.ApacheTest):
         """Make sure we read the sysconfig OPTIONS variable correctly"""
         # Return nothing for the process calls
         mock_cfg.return_value = ""
-        self.config.parser.sysconfig_filep = os.path.realpath(
+        self.config.parser.sysconfig_filep = filesystem.realpath(
             os.path.join(self.config.parser.root, "../sysconfig/httpd"))
         self.config.parser.variables = {}
 
diff --git a/certbot-apache/certbot_apache/tests/configurator_test.py b/certbot-apache/certbot_apache/tests/configurator_test.py
index f9b6fb186..1eafae982 100644
--- a/certbot-apache/certbot_apache/tests/configurator_test.py
+++ b/certbot-apache/certbot_apache/tests/configurator_test.py
@@ -675,8 +675,7 @@ class MultipleVhostsTest(util.ApacheTest):
     def test_make_vhost_ssl_nonexistent_vhost_path(self):
         ssl_vhost = self.config.make_vhost_ssl(self.vh_truth[1])
         self.assertEqual(os.path.dirname(ssl_vhost.filep),
-                            os.path.dirname(os.path.realpath(
-                                self.vh_truth[1].filep)))
+                         os.path.dirname(filesystem.realpath(self.vh_truth[1].filep)))
 
     def test_make_vhost_ssl(self):
         ssl_vhost = self.config.make_vhost_ssl(self.vh_truth[0])
@@ -1336,7 +1335,7 @@ class MultipleVhostsTest(util.ApacheTest):
         self.config.parser.modules.add("ssl_module")
         self.config.parser.modules.add("mod_ssl.c")
         self.config.parser.modules.add("socache_shmcb_module")
-        tmp_path = os.path.realpath(tempfile.mkdtemp("vhostroot"))
+        tmp_path = filesystem.realpath(tempfile.mkdtemp("vhostroot"))
         filesystem.chmod(tmp_path, 0o755)
         mock_p = "certbot_apache.configurator.ApacheConfigurator._get_ssl_vhost_path"
         mock_a = "certbot_apache.parser.ApacheParser.add_include"
diff --git a/certbot-apache/certbot_apache/tests/debian_test.py b/certbot-apache/certbot_apache/tests/debian_test.py
index f1d5843a5..54ced2d0b 100644
--- a/certbot-apache/certbot_apache/tests/debian_test.py
+++ b/certbot-apache/certbot_apache/tests/debian_test.py
@@ -79,9 +79,9 @@ class MultipleVhostsTestDebian(util.ApacheTest):
 
     def test_enable_site_failure(self):
         self.config.parser.root = "/tmp/nonexistent"
-        with mock.patch("os.path.isdir") as mock_dir:
+        with mock.patch("certbot.compat.os.path.isdir") as mock_dir:
             mock_dir.return_value = True
-            with mock.patch("os.path.islink") as mock_link:
+            with mock.patch("certbot.compat.os.path.islink") as mock_link:
                 mock_link.return_value = False
                 self.assertRaises(
                     errors.NotSupportedError,
diff --git a/certbot-apache/certbot_apache/tests/fedora_test.py b/certbot-apache/certbot_apache/tests/fedora_test.py
index 67533fe1d..4d3f3a313 100644
--- a/certbot-apache/certbot_apache/tests/fedora_test.py
+++ b/certbot-apache/certbot_apache/tests/fedora_test.py
@@ -4,6 +4,7 @@ import unittest
 import mock
 
 from certbot import errors
+from certbot.compat import filesystem
 from certbot.compat import os
 
 from certbot_apache import obj
@@ -160,7 +161,7 @@ class MultipleVhostsTestFedora(util.ApacheTest):
         """Make sure we read the sysconfig OPTIONS variable correctly"""
         # Return nothing for the process calls
         mock_cfg.return_value = ""
-        self.config.parser.sysconfig_filep = os.path.realpath(
+        self.config.parser.sysconfig_filep = filesystem.realpath(
             os.path.join(self.config.parser.root, "../sysconfig/httpd"))
         self.config.parser.variables = {}
 
diff --git a/certbot-apache/certbot_apache/tests/gentoo_test.py b/certbot-apache/certbot_apache/tests/gentoo_test.py
index dd01e9170..d0d3ba0dd 100644
--- a/certbot-apache/certbot_apache/tests/gentoo_test.py
+++ b/certbot-apache/certbot_apache/tests/gentoo_test.py
@@ -4,6 +4,7 @@ import unittest
 import mock
 
 from certbot import errors
+from certbot.compat import filesystem
 from certbot.compat import os
 
 from certbot_apache import obj
@@ -81,7 +82,7 @@ class MultipleVhostsTestGentoo(util.ApacheTest):
         """Make sure we read the Gentoo APACHE2_OPTS variable correctly"""
         defines = ['DEFAULT_VHOST', 'INFO',
                    'SSL', 'SSL_DEFAULT_VHOST', 'LANGUAGE']
-        self.config.parser.apacheconfig_filep = os.path.realpath(
+        self.config.parser.apacheconfig_filep = filesystem.realpath(
             os.path.join(self.config.parser.root, "../conf.d/apache2"))
         self.config.parser.variables = {}
         with mock.patch("certbot_apache.override_gentoo.GentooParser.update_modules"):
diff --git a/certbot-apache/local-oldest-requirements.txt b/certbot-apache/local-oldest-requirements.txt
index a959ad44f..da509406e 100644
--- a/certbot-apache/local-oldest-requirements.txt
+++ b/certbot-apache/local-oldest-requirements.txt
@@ -1,3 +1,3 @@
 # Remember to update setup.py to match the package versions below.
 acme[dev]==0.29.0
-certbot[dev]==0.36.0
+-e .[dev]
diff --git a/certbot-apache/setup.py b/certbot-apache/setup.py
index 1003ad678..98b7382db 100644
--- a/certbot-apache/setup.py
+++ b/certbot-apache/setup.py
@@ -10,7 +10,7 @@ version = '0.37.0.dev0'
 # acme/certbot version.
 install_requires = [
     'acme>=0.29.0',
-    'certbot>=0.36.0',
+    'certbot>=0.37.0.dev0',
     'mock',
     'python-augeas',
     'setuptools',
diff --git a/certbot/compat/_path.py b/certbot/compat/_path.py
new file mode 100644
index 000000000..fe2d2d1d2
--- /dev/null
+++ b/certbot/compat/_path.py
@@ -0,0 +1,31 @@
+"""This compat module wraps os.path to forbid some functions."""
+# pylint: disable=function-redefined
+from __future__ import absolute_import
+
+# First round of wrapping: we import statically all public attributes exposed by the os.path
+# module. This allows in particular to have pylint, mypy, IDEs be aware that most of os.path
+# members are available in certbot.compat.path.
+from os.path import *  # type: ignore  # pylint: disable=wildcard-import,unused-wildcard-import,redefined-builtin,os-module-forbidden
+
+# Second round of wrapping: we import dynamically all attributes from the os.path module that have
+# not yet been imported by the first round (static star import).
+import os.path as std_os_path  # pylint: disable=os-module-forbidden
+import sys as std_sys
+
+ourselves = std_sys.modules[__name__]
+for attribute in dir(std_os_path):
+    # Check if the attribute does not already exist in our module. It could be internal attributes
+    # of the module (__name__, __doc__), or attributes from standard os.path already imported with
+    # `from os.path import *`.
+    if not hasattr(ourselves, attribute):
+        setattr(ourselves, attribute, getattr(std_os_path, attribute))
+
+# Clean all remaining importables that are not from the core os.path module.
+del ourselves, std_os_path, std_sys
+
+
+# Function os.path.realpath is broken on some versions of Python for Windows.
+def realpath(*unused_args, **unused_kwargs):
+    """Method os.path.realpath() is forbidden"""
+    raise RuntimeError('Usage of os.path.realpath() is forbidden. '
+                       'Use certbot.compat.filesystem.realpath() instead.')
diff --git a/certbot/compat/filesystem.py b/certbot/compat/filesystem.py
index d0d1c262d..e2757eb2f 100644
--- a/certbot/compat/filesystem.py
+++ b/certbot/compat/filesystem.py
@@ -207,13 +207,22 @@ def replace(src, dst):
         os.rename(src, dst)
 
 
-def _apply_win_mode(file_path, mode):
+def realpath(file_path):
     """
-    This function converts the given POSIX mode into a Windows ACL list, and applies it to the
-    file given its path. If the given path is a symbolic link, it will resolved to apply the
-    mode on the targeted file.
+    Find the real path for the given path. This method resolves symlinks, including
+    recursive symlinks, and is protected against symlinks that creates an infinite loop.
     """
     original_path = file_path
+
+    if POSIX_MODE:
+        path = os.path.realpath(file_path)
+        if os.path.islink(path):
+            # If path returned by realpath is still a link, it means that it failed to
+            # resolve the symlink because of a loop.
+            # See realpath code: https://github.com/python/cpython/blob/master/Lib/posixpath.py
+            raise RuntimeError('Error, link {0} is a loop!'.format(original_path))
+        return path
+
     inspected_paths = []  # type: List[str]
     while os.path.islink(file_path):
         link_path = file_path
@@ -223,6 +232,17 @@ def _apply_win_mode(file_path, mode):
         if file_path in inspected_paths:
             raise RuntimeError('Error, link {0} is a loop!'.format(original_path))
         inspected_paths.append(file_path)
+
+    return os.path.abspath(file_path)
+
+
+def _apply_win_mode(file_path, mode):
+    """
+    This function converts the given POSIX mode into a Windows ACL list, and applies it to the
+    file given its path. If the given path is a symbolic link, it will resolved to apply the
+    mode on the targeted file.
+    """
+    file_path = realpath(file_path)
     # Get owner sid of the file
     security = win32security.GetFileSecurity(file_path, win32security.OWNER_SECURITY_INFORMATION)
     user = security.GetSecurityDescriptorOwner()
diff --git a/certbot/compat/os.py b/certbot/compat/os.py
index 6d3c7bb02..bb0e02eb3 100644
--- a/certbot/compat/os.py
+++ b/certbot/compat/os.py
@@ -26,7 +26,9 @@ for attribute in dir(std_os):
     if not hasattr(ourselves, attribute):
         setattr(ourselves, attribute, getattr(std_os, attribute))
 
-# Similar to os.path, allow certbot.compat.os.path to behave as a module
+# Import our internal path module, then allow certbot.compat.os.path
+# to behave as a module (similarly to os.path).
+from certbot.compat import _path as path  # type: ignore  # pylint: disable=wrong-import-position
 std_sys.modules[__name__ + '.path'] = path
 
 # Clean all remaining importables that are not from the core os module.
diff --git a/certbot/main.py b/certbot/main.py
index 6bd47cee3..50470438f 100644
--- a/certbot/main.py
+++ b/certbot/main.py
@@ -31,6 +31,7 @@ from certbot import reporter
 from certbot import storage
 from certbot import updater
 from certbot import util
+from certbot.compat import filesystem
 from certbot.compat import misc
 from certbot.compat import os
 from certbot.display import util as display_util, ops as display_ops
@@ -841,12 +842,12 @@ def _populate_from_certname(config):
     return config
 
 def _check_certificate_and_key(config):
-    if not os.path.isfile(os.path.realpath(config.cert_path)):
+    if not os.path.isfile(filesystem.realpath(config.cert_path)):
         raise errors.ConfigurationError("Error while reading certificate from path "
-                                       "{0}".format(config.cert_path))
-    if not os.path.isfile(os.path.realpath(config.key_path)):
+                                        "{0}".format(config.cert_path))
+    if not os.path.isfile(filesystem.realpath(config.key_path)):
         raise errors.ConfigurationError("Error while reading private key from path "
-                                       "{0}".format(config.key_path))
+                                        "{0}".format(config.key_path))
 def plugins_cmd(config, plugins):
     """List server software plugins.
 
diff --git a/certbot/plugins/common.py b/certbot/plugins/common.py
index 2e2e0f64c..5c292bfad 100644
--- a/certbot/plugins/common.py
+++ b/certbot/plugins/common.py
@@ -486,7 +486,7 @@ def dir_setup(test_dir, pkg):  # pragma: no cover
         link, (ex: OS X) such plugins will be confused. This function prevents
         such a case.
         """
-        return os.path.realpath(tempfile.mkdtemp(prefix))
+        return filesystem.realpath(tempfile.mkdtemp(prefix))
 
     temp_dir = expanded_tempdir("temp")
     config_dir = expanded_tempdir("config")
diff --git a/certbot/plugins/storage_test.py b/certbot/plugins/storage_test.py
index f72e69d4b..9d08cc7ef 100644
--- a/certbot/plugins/storage_test.py
+++ b/certbot/plugins/storage_test.py
@@ -31,7 +31,7 @@ class PluginStorageTest(test_util.ConfigTestCase):
         self.plugin.storage.storagepath = os.path.join(self.config.config_dir,
                                                        ".pluginstorage.json")
         with mock.patch("six.moves.builtins.open", mock_open):
-            with mock.patch('os.path.isfile', return_value=True):
+            with mock.patch('certbot.compat.os.path.isfile', return_value=True):
                 with mock.patch("certbot.reverter.util"):
                     self.assertRaises(errors.PluginStorageError,
                                       self.plugin.storage._load)  # pylint: disable=protected-access
diff --git a/certbot/tests/cert_manager_test.py b/certbot/tests/cert_manager_test.py
index 30ca6f099..b4cd946ee 100644
--- a/certbot/tests/cert_manager_test.py
+++ b/certbot/tests/cert_manager_test.py
@@ -97,8 +97,8 @@ class UpdateLiveSymlinksTest(BaseCertManagerTest):
                 for kind in ALL_FOUR:
                     os.chdir(os.path.dirname(self.config_files[domain][kind]))
                     self.assertEqual(
-                        os.path.realpath(os.readlink(self.config_files[domain][kind])),
-                        os.path.realpath(archive_paths[domain][kind]))
+                        filesystem.realpath(os.readlink(self.config_files[domain][kind])),
+                        filesystem.realpath(archive_paths[domain][kind]))
         finally:
             os.chdir(prev_dir)
 
diff --git a/certbot/tests/compat/filesystem_test.py b/certbot/tests/compat/filesystem_test.py
index 27c48c19a..5d112b652 100644
--- a/certbot/tests/compat/filesystem_test.py
+++ b/certbot/tests/compat/filesystem_test.py
@@ -48,18 +48,6 @@ class WindowsChmodTests(TempDirTestCase):
         self.assertFalse(filesystem._compare_dacls(ref_dacl_probe, cur_dacl_probe))  # pylint: disable=protected-access
         self.assertTrue(filesystem._compare_dacls(ref_dacl_link, cur_dacl_link))  # pylint: disable=protected-access
 
-    def test_symlink_loop_mitigation(self):
-        link1_path = os.path.join(self.tempdir, 'link1')
-        link2_path = os.path.join(self.tempdir, 'link2')
-        link3_path = os.path.join(self.tempdir, 'link3')
-        os.symlink(link1_path, link2_path)
-        os.symlink(link2_path, link3_path)
-        os.symlink(link3_path, link1_path)
-
-        with self.assertRaises(RuntimeError) as error:
-            filesystem.chmod(link1_path, 0o755)
-        self.assertTrue('link1 is a loop!' in str(error.exception))
-
     def test_world_permission(self):
         everybody = win32security.ConvertStringSidToSid(EVERYBODY_SID)
 
@@ -320,7 +308,6 @@ class CopyOwnershipTest(test_util.TempDirTestCase):
 
 class OsReplaceTest(test_util.TempDirTestCase):
     """Test to ensure consistent behavior of rename method"""
-
     def test_os_replace_to_existing_file(self):
         """Ensure that replace will effectively rename src into dst for all platforms."""
         src = os.path.join(self.tempdir, 'src')
@@ -335,6 +322,46 @@ class OsReplaceTest(test_util.TempDirTestCase):
         self.assertTrue(os.path.exists(dst))
 
 
+class RealpathTest(test_util.TempDirTestCase):
+    """Tests for realpath method"""
+    def setUp(self):
+        super(RealpathTest, self).setUp()
+        self.probe_path = _create_probe(self.tempdir)
+
+    def test_symlink_resolution(self):
+        # Absolute resolution
+        link_path = os.path.join(self.tempdir, 'link_abs')
+        os.symlink(self.probe_path, link_path)
+
+        self.assertEqual(self.probe_path, filesystem.realpath(self.probe_path))
+        self.assertEqual(self.probe_path, filesystem.realpath(link_path))
+
+        # Relative resolution
+        curdir = os.getcwd()
+        link_path = os.path.join(self.tempdir, 'link_rel')
+        probe_name = os.path.basename(self.probe_path)
+        try:
+            os.chdir(os.path.dirname(self.probe_path))
+            os.symlink(probe_name, link_path)
+
+            self.assertEqual(self.probe_path, filesystem.realpath(probe_name))
+            self.assertEqual(self.probe_path, filesystem.realpath(link_path))
+        finally:
+            os.chdir(curdir)
+
+    def test_symlink_loop_mitigation(self):
+        link1_path = os.path.join(self.tempdir, 'link1')
+        link2_path = os.path.join(self.tempdir, 'link2')
+        link3_path = os.path.join(self.tempdir, 'link3')
+        os.symlink(link1_path, link2_path)
+        os.symlink(link2_path, link3_path)
+        os.symlink(link3_path, link1_path)
+
+        with self.assertRaises(RuntimeError) as error:
+            filesystem.realpath(link1_path)
+        self.assertTrue('link1 is a loop!' in str(error.exception))
+
+
 def _get_security_dacl(target):
     return win32security.GetFileSecurity(target, win32security.DACL_SECURITY_INFORMATION)
 
diff --git a/certbot/tests/compat/os_test.py b/certbot/tests/compat/os_test.py
index 9e25548f0..754e97a10 100644
--- a/certbot/tests/compat/os_test.py
+++ b/certbot/tests/compat/os_test.py
@@ -7,8 +7,12 @@ from certbot.compat import os
 class OsTest(unittest.TestCase):
     """Unit tests for os module."""
     def test_forbidden_methods(self):
+        # Checks for os module
         for method in ['chmod', 'chown', 'open', 'mkdir', 'makedirs', 'rename', 'replace']:
             self.assertRaises(RuntimeError, getattr(os, method))
+        # Checks for os.path module
+        for method in ['realpath']:
+            self.assertRaises(RuntimeError, getattr(os.path, method))
 
 
 if __name__ == "__main__":
diff --git a/certbot/tests/main_test.py b/certbot/tests/main_test.py
index ebd9a28e1..ff8a800ab 100644
--- a/certbot/tests/main_test.py
+++ b/certbot/tests/main_test.py
@@ -542,7 +542,7 @@ class MainTest(test_util.ConfigTestCase):  # pylint: disable=too-many-public-met
                     return True
                 return orig_open(fn)
 
-            with mock.patch("os.path.isfile") as mock_if:
+            with mock.patch("certbot.compat.os.path.isfile") as mock_if:
                 mock_if.side_effect = mock_isfile
                 with mock.patch('certbot.main.client') as client:
                     ret, stdout, stderr = self._call_no_clientmock(args, stdout)
diff --git a/certbot/tests/util_test.py b/certbot/tests/util_test.py
index 41b5cf71d..b96f8afd2 100644
--- a/certbot/tests/util_test.py
+++ b/certbot/tests/util_test.py
@@ -528,7 +528,7 @@ class OsInfoTest(unittest.TestCase):
         from certbot.util import (get_os_info, get_systemd_os_info,
                                   get_os_info_ua)
 
-        with mock.patch('os.path.isfile', return_value=True):
+        with mock.patch('certbot.compat.os.path.isfile', return_value=True):
             self.assertEqual(get_os_info(
                 test_util.vector_path("os-release"))[0], 'systemdos')
             self.assertEqual(get_os_info(
@@ -536,13 +536,13 @@ class OsInfoTest(unittest.TestCase):
             self.assertEqual(get_systemd_os_info(os.devnull), ("", ""))
             self.assertEqual(get_os_info_ua(
                 test_util.vector_path("os-release")), "SystemdOS")
-        with mock.patch('os.path.isfile', return_value=False):
+        with mock.patch('certbot.compat.os.path.isfile', return_value=False):
             self.assertEqual(get_systemd_os_info(), ("", ""))
 
     def test_systemd_os_release_like(self):
         from certbot.util import get_systemd_os_like
 
-        with mock.patch('os.path.isfile', return_value=True):
+        with mock.patch('certbot.compat.os.path.isfile', return_value=True):
             id_likes = get_systemd_os_like(test_util.vector_path(
                 "os-release"))
             self.assertEqual(len(id_likes), 3)
@@ -552,7 +552,7 @@ class OsInfoTest(unittest.TestCase):
     def test_non_systemd_os_info(self, popen_mock):
         from certbot.util import (get_os_info, get_python_os_info,
                                      get_os_info_ua)
-        with mock.patch('os.path.isfile', return_value=False):
+        with mock.patch('certbot.compat.os.path.isfile', return_value=False):
             with mock.patch('platform.system_alias',
                             return_value=('NonSystemD', '42', '42')):
                 self.assertEqual(get_os_info()[0], 'nonsystemd')