diff --git a/letsencrypt-apache/letsencrypt_apache/configurator.py b/letsencrypt-apache/letsencrypt_apache/configurator.py
index 9ccb3ca1f..16e8dd606 100644
--- a/letsencrypt-apache/letsencrypt_apache/configurator.py
+++ b/letsencrypt-apache/letsencrypt_apache/configurator.py
@@ -182,6 +182,7 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
 
         """
         vhost = self.choose_vhost(domain)
+        self._clean_vhost(vhost)
 
         # This is done first so that ssl module is enabled and cert_path,
         # cert_key... can all be parsed appropriately
@@ -205,16 +206,27 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
                 "Unable to find cert and/or key directives")
 
         logger.info("Deploying Certificate to VirtualHost %s", vhost.filep)
+        logger.debug("Apache version is %s",
+                     ".".join(str(i) for i in self.version))
 
-        # Assign the final directives; order is maintained in find_dir
-        self.aug.set(path["cert_path"][-1], cert_path)
-        self.aug.set(path["cert_key"][-1], key_path)
-        if chain_path is not None:
-            if not path["chain_path"]:
-                self.parser.add_dir(
-                    vhost.path, "SSLCertificateChainFile", chain_path)
+        if self.version < (2, 4, 8) or (chain_path and not fullchain_path):
+            # install SSLCertificateFile, SSLCertificateKeyFile,
+            # and SSLCertificateChainFile directives
+            set_cert_path = cert_path
+            self.aug.set(path["cert_path"][-1], cert_path)
+            self.aug.set(path["cert_key"][-1], key_path)
+            if chain_path is not None:
+                self.parser.add_dir(vhost.path,
+                                    "SSLCertificateChainFile", chain_path)
             else:
-                self.aug.set(path["chain_path"][-1], chain_path)
+                raise errors.PluginError("--chain-path is required for your version of Apache")
+        else:
+            if not fullchain_path:
+                raise errors.PluginError("Please provide the --fullchain-path\
+ option pointing to your full chain file")
+            set_cert_path = fullchain_path
+            self.aug.set(path["cert_path"][-1], fullchain_path)
+            self.aug.set(path["cert_key"][-1], key_path)
 
         # Save notes about the transaction that took place
         self.save_notes += ("Changed vhost at %s with addresses of %s\n"
@@ -222,7 +234,7 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
                             "\tSSLCertificateKeyFile %s\n" %
                             (vhost.filep,
                              ", ".join(str(addr) for addr in vhost.addrs),
-                             cert_path, key_path))
+                             set_cert_path, key_path))
         if chain_path is not None:
             self.save_notes += "\tSSLCertificateChainFile %s\n" % chain_path
 
@@ -663,6 +675,25 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
 
         return ssl_addrs
 
+    def _clean_vhost(self, vhost):
+        # remove duplicated or conflicting ssl directives
+        self._deduplicate_directives(vhost.path,
+            ["SSLCertificateFile", "SSLCertificateKeyFile"])
+        # remove all problematic directives
+        self._remove_directives(vhost.path, ["SSLCertificateChainFile"])
+
+    def _deduplicate_directives(self, vh_path, directives):
+        for directive in directives:
+            while len(self.parser.find_dir(directive, None, vh_path, False)) > 1:
+                directive_path = self.parser.find_dir(directive, None, vh_path, False)
+                self.aug.remove(re.sub(r"/\w*$", "", directive_path[0]))
+
+    def _remove_directives(self, vh_path, directives):
+        for directive in directives:
+            while len(self.parser.find_dir(directive, None, vh_path, False)) > 0:
+                directive_path = self.parser.find_dir(directive, None, vh_path, False)
+                self.aug.remove(re.sub(r"/\w*$", "", directive_path[0]))
+
     def _add_dummy_ssl_directives(self, vh_path):
         self.parser.add_dir(vh_path, "SSLCertificateFile",
                             "insert_cert_file_path")
diff --git a/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py b/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
index 0350a32ec..442229e8d 100644
--- a/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
+++ b/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
@@ -236,6 +236,64 @@ class TwoVhost80Test(util.ApacheTest):
             self.config.enable_site,
             obj.VirtualHost("asdf", "afsaf", set(), False, False))
 
+    def test_deploy_cert_newssl(self):
+        self.config = util.get_apache_configurator(
+            self.config_path, self.config_dir, self.work_dir, version=(2, 4, 16))
+
+        self.config.parser.modules.add("ssl_module")
+        self.config.parser.modules.add("mod_ssl.c")
+
+        # Get the default 443 vhost
+        self.config.assoc["random.demo"] = self.vh_truth[1]
+        self.config.deploy_cert(
+            "random.demo", "example/cert.pem", "example/key.pem",
+            "example/cert_chain.pem", "example/fullchain.pem")
+        self.config.save()
+
+        # Verify ssl_module was enabled.
+        self.assertTrue(self.vh_truth[1].enabled)
+        self.assertTrue("ssl_module" in self.config.parser.modules)
+
+        loc_cert = self.config.parser.find_dir(
+            "sslcertificatefile", "example/fullchain.pem", self.vh_truth[1].path)
+        loc_key = self.config.parser.find_dir(
+            "sslcertificateKeyfile", "example/key.pem", self.vh_truth[1].path)
+
+        # Verify one directive was found in the correct file
+        self.assertEqual(len(loc_cert), 1)
+        self.assertEqual(configurator.get_file_path(loc_cert[0]),
+                         self.vh_truth[1].filep)
+
+        self.assertEqual(len(loc_key), 1)
+        self.assertEqual(configurator.get_file_path(loc_key[0]),
+                         self.vh_truth[1].filep)
+
+    def test_deploy_cert_newssl_no_fullchain(self):
+        self.config = util.get_apache_configurator(
+            self.config_path, self.config_dir, self.work_dir, version=(2, 4, 16))
+
+        self.config.parser.modules.add("ssl_module")
+        self.config.parser.modules.add("mod_ssl.c")
+
+        # Get the default 443 vhost
+        self.config.assoc["random.demo"] = self.vh_truth[1]
+        self.assertRaises(errors.PluginError,
+                          lambda: self.config.deploy_cert(
+                              "random.demo", "example/cert.pem", "example/key.pem"))
+
+    def test_deploy_cert_old_apache_no_chain(self):
+        self.config = util.get_apache_configurator(
+            self.config_path, self.config_dir, self.work_dir, version=(2, 4, 7))
+
+        self.config.parser.modules.add("ssl_module")
+        self.config.parser.modules.add("mod_ssl.c")
+
+        # Get the default 443 vhost
+        self.config.assoc["random.demo"] = self.vh_truth[1]
+        self.assertRaises(errors.PluginError,
+                          lambda: self.config.deploy_cert(
+                              "random.demo", "example/cert.pem", "example/key.pem"))
+
     def test_deploy_cert(self):
         self.config.parser.modules.add("ssl_module")
         self.config.parser.modules.add("mod_ssl.c")
@@ -353,6 +411,65 @@ class TwoVhost80Test(util.ApacheTest):
 
         self.assertEqual(len(self.config.vhosts), 6)
 
+    def test_clean_vhost_ssl(self):
+        # pylint: disable=protected-access
+        for directive in ["SSLCertificateFile", "SSLCertificateKeyFile",
+                          "SSLCertificateChainFile", "SSLCACertificatePath"]:
+            for _ in range(10):
+                self.config.parser.add_dir(self.vh_truth[1].path, directive, ["bogus"])
+        self.config.save()
+
+        self.config._clean_vhost(self.vh_truth[1])
+        self.config.save()
+
+        loc_cert = self.config.parser.find_dir(
+            'SSLCertificateFile', None, self.vh_truth[1].path, False)
+        loc_key = self.config.parser.find_dir(
+            'SSLCertificateKeyFile', None, self.vh_truth[1].path, False)
+        loc_chain = self.config.parser.find_dir(
+            'SSLCertificateChainFile', None, self.vh_truth[1].path, False)
+        loc_cacert = self.config.parser.find_dir(
+            'SSLCACertificatePath', None, self.vh_truth[1].path, False)
+
+        self.assertEqual(len(loc_cert), 1)
+        self.assertEqual(len(loc_key), 1)
+
+        self.assertEqual(len(loc_chain), 0)
+
+        self.assertEqual(len(loc_cacert), 10)
+
+    def test_deduplicate_directives(self):
+        # pylint: disable=protected-access
+        DIRECTIVE = "Foo"
+        for _ in range(10):
+            self.config.parser.add_dir(self.vh_truth[1].path, DIRECTIVE, ["bar"])
+        self.config.save()
+
+        self.config._deduplicate_directives(self.vh_truth[1].path, [DIRECTIVE])
+        self.config.save()
+
+        self.assertEqual(
+                         len(self.config.parser.find_dir(
+                             DIRECTIVE, None, self.vh_truth[1].path, False)),
+                         1)
+
+    def test_remove_directives(self):
+        # pylint: disable=protected-access
+        DIRECTIVES = ["Foo", "Bar"]
+        for directive in DIRECTIVES:
+            for _ in range(10):
+                self.config.parser.add_dir(self.vh_truth[1].path, directive, ["baz"])
+        self.config.save()
+
+        self.config._remove_directives(self.vh_truth[1].path, DIRECTIVES)
+        self.config.save()
+
+        for directive in DIRECTIVES:
+            self.assertEqual(
+                             len(self.config.parser.find_dir(
+                                 directive, None, self.vh_truth[1].path, False)),
+                             0)
+
     def test_make_vhost_ssl_extra_vhs(self):
         self.config.aug.match = mock.Mock(return_value=["p1", "p2"])
         self.assertRaises(