diff --git a/letsencrypt-apache/letsencrypt_apache/configurator.py b/letsencrypt-apache/letsencrypt_apache/configurator.py
index 0b40a7e38..f72492ac2 100644
--- a/letsencrypt-apache/letsencrypt_apache/configurator.py
+++ b/letsencrypt-apache/letsencrypt_apache/configurator.py
@@ -1,7 +1,6 @@
 """Apache Configuration based off of Augeas Configurator."""
 # pylint: disable=too-many-lines
 import filecmp
-import itertools
 import logging
 import os
 import re
@@ -26,6 +25,7 @@ from letsencrypt_apache import tls_sni_01
 from letsencrypt_apache import obj
 from letsencrypt_apache import parser
 
+from collections import defaultdict
 
 logger = logging.getLogger(__name__)
 
@@ -904,15 +904,33 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
                         "redirection")
             self._create_redirect_vhost(ssl_vhost)
         else:
-            # Check if redirection already exists
-            self._verify_no_redirects(general_vh)
+            # Check if LetsEncrypt redirection already exists
+            self._verify_no_letsencrypt_redirect(general_vh)
+
+
+            # Note: if code flow gets here it means we didn't find the exact
+            # letsencrypt RewriteRule config for redirection. Finding
+            # another RewriteRule is likely to be fine in most or all cases,
+            # but redirect loops are possible in very obscure cases; see #1620
+            # for reasoning.
+            if self._is_rewrite_exists(general_vh):
+                logger.warn("Added an HTTP->HTTPS rewrite in addition to "
+                            "other RewriteRules; you may wish to check for "
+                            "overall consistency.")
 
             # Add directives to server
             # Note: These are not immediately searchable in sites-enabled
             #     even with save() and load()
-            self.parser.add_dir(general_vh.path, "RewriteEngine", "on")
-            self.parser.add_dir(general_vh.path, "RewriteRule",
+            if not self._is_rewrite_engine_on(general_vh):
+                self.parser.add_dir(general_vh.path, "RewriteEngine", "on")
+
+            if self.get_version() >= (2, 3, 9):
+                self.parser.add_dir(general_vh.path, "RewriteRule",
+                                constants.REWRITE_HTTPS_ARGS_WITH_END)
+            else:
+                self.parser.add_dir(general_vh.path, "RewriteRule",
                                 constants.REWRITE_HTTPS_ARGS)
+
             self.save_notes += ("Redirecting host in %s to ssl vhost in %s\n" %
                                 (general_vh.filep, ssl_vhost.filep))
             self.save()
@@ -920,40 +938,67 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
             logger.info("Redirecting vhost in %s to ssl vhost in %s",
                         general_vh.filep, ssl_vhost.filep)
 
-    def _verify_no_redirects(self, vhost):
-        """Checks to see if existing redirect is in place.
+    def _verify_no_letsencrypt_redirect(self, vhost):
+        """Checks to see if a redirect was already installed by letsencrypt.
 
-        Checks to see if virtualhost already contains a rewrite or redirect
-        returns boolean, integer
+        Checks to see if virtualhost already contains a rewrite rule that is
+        identical to Letsencrypt's redirection rewrite rule.
 
         :param vhost: vhost to check
         :type vhost: :class:`~letsencrypt_apache.obj.VirtualHost`
 
         :raises errors.PluginEnhancementAlreadyPresent: When the exact
                 letsencrypt redirection WriteRule exists in virtual host.
-
-                errors.PluginError: When there exists directives that may hint
-                other redirection. (TODO: We should not throw a PluginError,
-                    but that's for an other PR.)
         """
         rewrite_path = self.parser.find_dir(
-            "RewriteRule", None, start=vhost.path)
-        redirect_path = self.parser.find_dir("Redirect", None, start=vhost.path)
+                "RewriteRule", None, start=vhost.path)
 
-        if redirect_path:
-            # "Existing Redirect directive for virtualhost"
-            raise errors.PluginError("Existing Redirect present on HTTP vhost.")
-        if rewrite_path:
-            # "No existing redirection for virtualhost"
-            if len(rewrite_path) != len(constants.REWRITE_HTTPS_ARGS):
-                raise errors.PluginError("Unknown Existing RewriteRule")
-            for match, arg in itertools.izip(
-                    rewrite_path, constants.REWRITE_HTTPS_ARGS):
-                if self.aug.get(match) != arg:
-                    raise errors.PluginError("Unknown Existing RewriteRule")
+        # There can be other RewriteRule directive lines in vhost config.
+        # rewrite_args_dict keys are directive ids and the corresponding value
+        # for each is a list of arguments to that directive.
+        rewrite_args_dict = defaultdict(list)
+        pat = r'.*(directive\[\d+\]).*'
+        for match in rewrite_path:
+            m = re.match(pat, match)
+            if m:
+                dir_id = m.group(1)
+                rewrite_args_dict[dir_id].append(match)
 
-            raise errors.PluginEnhancementAlreadyPresent(
-                "Let's Encrypt has already enabled redirection")
+        if rewrite_args_dict:
+            redirect_args = [constants.REWRITE_HTTPS_ARGS,
+                constants.REWRITE_HTTPS_ARGS_WITH_END]
+
+            for matches in rewrite_args_dict.values():
+                if [self.aug.get(x) for x in matches] in redirect_args:
+                    raise errors.PluginEnhancementAlreadyPresent(
+                    "Let's Encrypt has already enabled redirection")
+
+    def _is_rewrite_exists(self, vhost):
+        """Checks if there exists a RewriteRule directive in vhost
+
+        :param vhost: vhost to check
+        :type vhost: :class:`~letsencrypt_apache.obj.VirtualHost`
+
+        :returns: True if a RewriteRule directive exists.
+        :rtype: bool
+
+        """
+        rewrite_path = self.parser.find_dir(
+                "RewriteRule", None, start=vhost.path)
+        return bool(rewrite_path)
+
+    def _is_rewrite_engine_on(self, vhost):
+        """Checks if a RewriteEngine directive is on
+
+        :param vhost: vhost to check
+        :type vhost: :class:`~letsencrypt_apache.obj.VirtualHost`
+
+        """
+        rewrite_engine_path = self.parser.find_dir("RewriteEngine", "on",
+                start=vhost.path)
+        if rewrite_engine_path:
+            return self.parser.get_arg(rewrite_engine_path[0])
+        return False
 
     def _create_redirect_vhost(self, ssl_vhost):
         """Creates an http_vhost specifically to redirect for the ssl_vhost.
@@ -990,6 +1035,13 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
         if ssl_vhost.aliases:
             serveralias = "ServerAlias " + " ".join(ssl_vhost.aliases)
 
+        rewrite_rule_args = []
+        if self.get_version() >= (2, 3, 9):
+            rewrite_rule_args = constants.REWRITE_HTTPS_ARGS_WITH_END
+        else:
+            rewrite_rule_args = constants.REWRITE_HTTPS_ARGS
+
+
         return ("<VirtualHost %s>\n"
                 "%s \n"
                 "%s \n"
@@ -1003,7 +1055,7 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
                 "</VirtualHost>\n"
                 % (" ".join(str(addr) for addr in self._get_proposed_addrs(ssl_vhost)),
                    servername, serveralias,
-                   " ".join(constants.REWRITE_HTTPS_ARGS)))
+                   " ".join(rewrite_rule_args)))
 
     def _write_out_redirect(self, ssl_vhost, text):
         # This is the default name
diff --git a/letsencrypt-apache/letsencrypt_apache/constants.py b/letsencrypt-apache/letsencrypt_apache/constants.py
index 202fc3e21..eb004b975 100644
--- a/letsencrypt-apache/letsencrypt_apache/constants.py
+++ b/letsencrypt-apache/letsencrypt_apache/constants.py
@@ -25,8 +25,12 @@ AUGEAS_LENS_DIR = pkg_resources.resource_filename(
 
 REWRITE_HTTPS_ARGS = [
     "^", "https://%{SERVER_NAME}%{REQUEST_URI}", "[L,QSA,R=permanent]"]
-"""Apache rewrite rule arguments used for redirections to https vhost"""
+"""Apache version<2.3.9 rewrite rule arguments used for redirections to https vhost"""
 
+REWRITE_HTTPS_ARGS_WITH_END = [
+    "^", "https://%{SERVER_NAME}%{REQUEST_URI}", "[END,QSA,R=permanent]"]
+"""Apache version >= 2.3.9 rewrite rule arguments used for redirections to
+    https vhost"""
 
 HSTS_ARGS = ["always", "set", "Strict-Transport-Security",
     "\"max-age=31536000; includeSubDomains\""]
diff --git a/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py b/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
index 991704144..f2bf89d2c 100644
--- a/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
+++ b/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
@@ -653,6 +653,19 @@ class TwoVhost80Test(util.ApacheTest):
     def test_supported_enhancements(self):
         self.assertTrue(isinstance(self.config.supported_enhancements(), list))
 
+
+    @mock.patch("letsencrypt.le_util.exe_exists")
+    def test_enhance_unknown_vhost(self, mock_exe):
+        self.config.parser.modules.add("rewrite_module")
+        mock_exe.return_value = True
+        ssl_vh = obj.VirtualHost(
+            "fp", "ap", set([obj.Addr(("*", "443")), obj.Addr(("satoshi.com",))]),
+            True, False)
+        self.config.vhosts.append(ssl_vh)
+        self.assertRaises(
+            errors.PluginError,
+            self.config.enhance, "satoshi.com", "redirect")
+
     def test_enhance_unknown_enhancement(self):
         self.assertRaises(
             errors.PluginError,
@@ -741,6 +754,8 @@ class TwoVhost80Test(util.ApacheTest):
     def test_redirect_well_formed_http(self, mock_exe, _):
         self.config.parser.update_runtime_variables = mock.Mock()
         mock_exe.return_value = True
+        self.config.get_version = mock.Mock(return_value=(2, 2))
+
         # This will create an ssl vhost for letsencrypt.demo
         self.config.enhance("letsencrypt.demo", "redirect")
 
@@ -760,6 +775,55 @@ class TwoVhost80Test(util.ApacheTest):
 
         self.assertTrue("rewrite_module" in self.config.parser.modules)
 
+    def test_rewrite_rule_exists(self):
+        # Skip the enable mod
+        self.config.parser.modules.add("rewrite_module")
+        self.config.get_version = mock.Mock(return_value=(2, 3, 9))
+        self.config.parser.add_dir(
+            self.vh_truth[3].path, "RewriteRule", ["Unknown"])
+        self.assertTrue(self.config._is_rewrite_exists(self.vh_truth[3])) # pylint: disable=protected-access
+
+    def test_rewrite_engine_exists(self):
+        # Skip the enable mod
+        self.config.parser.modules.add("rewrite_module")
+        self.config.get_version = mock.Mock(return_value=(2, 3, 9))
+        self.config.parser.add_dir(
+            self.vh_truth[3].path, "RewriteEngine", "on")
+        self.assertTrue(self.config._is_rewrite_engine_on(self.vh_truth[3])) # pylint: disable=protected-access
+
+
+    @mock.patch("letsencrypt.le_util.run_script")
+    @mock.patch("letsencrypt.le_util.exe_exists")
+    def test_redirect_with_existing_rewrite(self, mock_exe, _):
+        self.config.parser.update_runtime_variables = mock.Mock()
+        mock_exe.return_value = True
+        self.config.get_version = mock.Mock(return_value=(2, 2))
+
+        # Create a preexisting rewrite rule
+        self.config.parser.add_dir(
+            self.vh_truth[3].path, "RewriteRule", ["Unknown"])
+        self.config.save()
+
+        # This will create an ssl vhost for letsencrypt.demo
+        self.config.enhance("letsencrypt.demo", "redirect")
+
+        # These are not immediately available in find_dir even with save() and
+        # load(). They must be found in sites-available
+        rw_engine = self.config.parser.find_dir(
+            "RewriteEngine", "on", self.vh_truth[3].path)
+        rw_rule = self.config.parser.find_dir(
+            "RewriteRule", None, self.vh_truth[3].path)
+
+        self.assertEqual(len(rw_engine), 1)
+        # three args to rw_rule + 1 arg for the pre existing rewrite
+        self.assertEqual(len(rw_rule), 4)
+
+        self.assertTrue(rw_engine[0].startswith(self.vh_truth[3].path))
+        self.assertTrue(rw_rule[0].startswith(self.vh_truth[3].path))
+
+        self.assertTrue("rewrite_module" in self.config.parser.modules)
+
+
     def test_redirect_with_conflict(self):
         self.config.parser.modules.add("rewrite_module")
         ssl_vh = obj.VirtualHost(
@@ -774,43 +838,16 @@ class TwoVhost80Test(util.ApacheTest):
     def test_redirect_twice(self):
         # Skip the enable mod
         self.config.parser.modules.add("rewrite_module")
+        self.config.get_version = mock.Mock(return_value=(2, 3, 9))
+
         self.config.enhance("encryption-example.demo", "redirect")
         self.assertRaises(
             errors.PluginEnhancementAlreadyPresent,
             self.config.enhance, "encryption-example.demo", "redirect")
 
-    def test_unknown_rewrite(self):
-        # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
-        self.config.parser.add_dir(
-            self.vh_truth[3].path, "RewriteRule", ["Unknown"])
-        self.config.save()
-        self.assertRaises(
-            errors.PluginError,
-            self.config.enhance, "letsencrypt.demo", "redirect")
-
-    def test_unknown_rewrite2(self):
-        # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
-        self.config.parser.add_dir(
-            self.vh_truth[3].path, "RewriteRule", ["Unknown", "2", "3"])
-        self.config.save()
-        self.assertRaises(
-            errors.PluginError,
-            self.config.enhance, "letsencrypt.demo", "redirect")
-
-    def test_unknown_redirect(self):
-        # Skip the enable mod
-        self.config.parser.modules.add("rewrite_module")
-        self.config.parser.add_dir(
-            self.vh_truth[3].path, "Redirect", ["Unknown"])
-        self.config.save()
-        self.assertRaises(
-            errors.PluginError,
-            self.config.enhance, "letsencrypt.demo", "redirect")
-
     def test_create_own_redirect(self):
         self.config.parser.modules.add("rewrite_module")
+        self.config.get_version = mock.Mock(return_value=(2, 3, 9))
         # For full testing... give names...
         self.vh_truth[1].name = "default.com"
         self.vh_truth[1].aliases = set(["yes.default.com"])
@@ -818,6 +855,17 @@ class TwoVhost80Test(util.ApacheTest):
         self.config._enable_redirect(self.vh_truth[1], "")  # pylint: disable=protected-access
         self.assertEqual(len(self.config.vhosts), 7)
 
+    def test_create_own_redirect_for_old_apache_version(self):
+        self.config.parser.modules.add("rewrite_module")
+        self.config.get_version = mock.Mock(return_value=(2, 2))
+        # For full testing... give names...
+        self.vh_truth[1].name = "default.com"
+        self.vh_truth[1].aliases = set(["yes.default.com"])
+
+        self.config._enable_redirect(self.vh_truth[1], "")  # pylint: disable=protected-access
+        self.assertEqual(len(self.config.vhosts), 7)
+
+
     def get_achalls(self):
         """Return testing achallenges."""
         account_key = self.rsa512jwk