diff --git a/CHANGELOG.md b/CHANGELOG.md
index c1af9ffb3..d80f1baa5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,9 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
   `malformed` error to be received from the ACME server.
 * Linode DNS plugin now supports api keys created from their new panel
   at [cloud.linode.com](https://cloud.linode.com)
+* Adding a warning noting that future versions of Certbot will automatically configure the
+  webserver so that all requests redirect to secure HTTPS access. You can control this
+  behavior and disable this warning with the --redirect and --no-redirect flags.
 
 ### Fixed
 
diff --git a/certbot/client.py b/certbot/client.py
index 5ec3c4d92..3c4a894ae 100644
--- a/certbot/client.py
+++ b/certbot/client.py
@@ -549,6 +549,11 @@ class Client(object):
                 if ask_redirect:
                     if config_name == "redirect" and config_value is None:
                         config_value = enhancements.ask(enhancement_name)
+                        if not config_value:
+                            logger.warning("Future versions of Certbot will automatically "
+                                "configure the webserver so that all requests redirect to secure "
+                                "HTTPS access. You can control this behavior and disable this "
+                                "warning with the --redirect and --no-redirect flags.")
                 if config_value:
                     self.apply_enhancement(domains, enhancement_name, option)
                     enhanced = True
diff --git a/certbot/tests/client_test.py b/certbot/tests/client_test.py
index 711346dbb..844758ad5 100644
--- a/certbot/tests/client_test.py
+++ b/certbot/tests/client_test.py
@@ -564,6 +564,21 @@ class EnhanceConfigTest(ClientTestCommon):
         self.assertEqual(mock_log.warning.call_args[0][1],
                           'redirect')
 
+    @mock.patch("certbot.client.logger")
+    def test_config_set_no_warning_redirect(self, mock_log):
+        self.config.redirect = False
+        self._test_with_already_existing()
+        self.assertFalse(mock_log.warning.called)
+
+    @mock.patch("certbot.client.enhancements.ask")
+    @mock.patch("certbot.client.logger")
+    def test_warn_redirect(self, mock_log, mock_ask):
+        self.config.redirect = None
+        mock_ask.return_value = False
+        self._test_with_already_existing()
+        self.assertTrue(mock_log.warning.called)
+        self.assertTrue("disable" in mock_log.warning.call_args[0][0])
+
     def test_no_ask_hsts(self):
         self.config.hsts = True
         self._test_with_all_supported()