diff --git a/certbot/compat.py b/certbot/compat.py
index e3e1bc4e1..d42febe81 100644
--- a/certbot/compat.py
+++ b/certbot/compat.py
@@ -65,6 +65,30 @@ def os_geteuid():
         # Windows specific
         return 0
 
+def os_rename(src, dst):
+    """
+    Rename a file to a destination path and handles situations where the destination exists.
+
+    :param str src: The current file path.
+    :param str dst: The new file path.
+    """
+    try:
+        os.rename(src, dst)
+    except OSError as err:
+        # Windows specific, renaming a file on an existing path is not possible.
+        # On Python 3, the best fallback with atomic capabilities we have is os.replace.
+        if err.errno != errno.EEXIST:
+            # Every other error is a legitimate exception.
+            raise
+        if not hasattr(os, 'replace'):  # pragma: no cover
+            # We should never go on this line. Either we are on Linux and os.rename has succeeded,
+            # either we are on Windows, and only Python >= 3.4 is supported where os.replace is
+            # available.
+            raise RuntimeError('Error: tried to run os_rename on Python < 3.3. '
+                               'Certbot supports only Python 3.4 >= on Windows.')
+        getattr(os, 'replace')(src, dst)
+
+
 def readline_with_timeout(timeout, prompt):
     """
     Read user input to return the first line entered, or raise after specified timeout.
diff --git a/certbot/reverter.py b/certbot/reverter.py
index 5d56615fd..919037358 100644
--- a/certbot/reverter.py
+++ b/certbot/reverter.py
@@ -576,7 +576,7 @@ class Reverter(object):
             timestamp = self._checkpoint_timestamp()
             final_dir = os.path.join(self.config.backup_dir, timestamp)
             try:
-                os.rename(self.config.in_progress_dir, final_dir)
+                compat.os_rename(self.config.in_progress_dir, final_dir)
                 return
             except OSError:
                 logger.warning("Extreme, unexpected race condition, retrying (%s)", timestamp)
diff --git a/certbot/storage.py b/certbot/storage.py
index c16ea35b8..4b8110072 100644
--- a/certbot/storage.py
+++ b/certbot/storage.py
@@ -14,6 +14,7 @@ import six
 
 import certbot
 from certbot import cli
+from certbot import compat
 from certbot import constants
 from certbot import crypto_util
 from certbot import errors
@@ -188,7 +189,7 @@ def update_configuration(lineagename, archive_dir, target, cli_config):
     # Save only the config items that are relevant to renewal
     values = relevant_values(vars(cli_config.namespace))
     write_renewal_config(config_filename, temp_filename, archive_dir, target, values)
-    os.rename(temp_filename, config_filename)
+    compat.os_rename(temp_filename, config_filename)
 
     return configobj.ConfigObj(config_filename)
 
diff --git a/certbot/tests/compat_test.py b/certbot/tests/compat_test.py
new file mode 100644
index 000000000..552aa5645
--- /dev/null
+++ b/certbot/tests/compat_test.py
@@ -0,0 +1,21 @@
+"""Tests for certbot.compat."""
+import os
+
+from certbot import compat
+import certbot.tests.util as test_util
+
+class OsReplaceTest(test_util.TempDirTestCase):
+    """Test to ensure consistent behavior of os_rename method"""
+
+    def test_os_rename_to_existing_file(self):
+        """Ensure that os_rename will effectively rename src into dst for all platforms."""
+        src = os.path.join(self.tempdir, 'src')
+        dst = os.path.join(self.tempdir, 'dst')
+        open(src, 'w').close()
+        open(dst, 'w').close()
+
+        # On Windows, a direct call to os.rename will fail because dst already exists.
+        compat.os_rename(src, dst)
+
+        self.assertFalse(os.path.exists(src))
+        self.assertTrue(os.path.exists(dst))
diff --git a/certbot/tests/reverter_test.py b/certbot/tests/reverter_test.py
index 999c6225c..d04e3c641 100644
--- a/certbot/tests/reverter_test.py
+++ b/certbot/tests/reverter_test.py
@@ -356,7 +356,7 @@ class TestFullCheckpointsReverter(test_util.ConfigTestCase):
         self.assertRaises(
             errors.ReverterError, self.reverter.finalize_checkpoint, "Title")
 
-    @mock.patch("certbot.reverter.os.rename")
+    @mock.patch("certbot.reverter.compat.os_rename")
     def test_finalize_checkpoint_no_rename_directory(self, mock_rename):
 
         self.reverter.add_to_checkpoint(self.sets[0], "perm save")