diff --git a/letsencrypt-apache/letsencrypt_apache/configurator.py b/letsencrypt-apache/letsencrypt_apache/configurator.py
index 3e6881739..d67e7bc18 100644
--- a/letsencrypt-apache/letsencrypt_apache/configurator.py
+++ b/letsencrypt-apache/letsencrypt_apache/configurator.py
@@ -1119,6 +1119,12 @@ class ApacheConfigurator(augeas_configurator.AugeasConfigurator):
         """
 
         enabled_dir = os.path.join(self.parser.root, "sites-enabled")
+        if not os.path.isdir(enabled_dir):
+            error_msg = ("Directory '{0}' does not exist. Please ensure "
+                         "that the values for --apache-handle-sites and "
+                         "--apache-server-root are correct for your "
+                         "environment.".format(enabled_dir))
+            raise errors.ConfigurationError(error_msg)
         for entry in os.listdir(enabled_dir):
             try:
                 if filecmp.cmp(avail_fp, os.path.join(enabled_dir, entry)):
diff --git a/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py b/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
index e16dff173..064111d4a 100644
--- a/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
+++ b/letsencrypt-apache/letsencrypt_apache/tests/configurator_test.py
@@ -219,6 +219,10 @@ class TwoVhost80Test(util.ApacheTest):
         self.assertFalse(self.config.is_site_enabled(self.vh_truth[1].filep))
         self.assertTrue(self.config.is_site_enabled(self.vh_truth[2].filep))
         self.assertTrue(self.config.is_site_enabled(self.vh_truth[3].filep))
+        with mock.patch("os.path.isdir") as mock_isdir:
+            mock_isdir.return_value = False
+            with (self.assertRaises(errors.ConfigurationError)):
+                self.config.is_site_enabled("irrelevant")
 
     @mock.patch("letsencrypt.le_util.run_script")
     @mock.patch("letsencrypt.le_util.exe_exists")