diff --git a/certbot-compatibility-test/certbot_compatibility_test/test_driver.py b/certbot-compatibility-test/certbot_compatibility_test/test_driver.py
index c07586d8c..928870f66 100644
--- a/certbot-compatibility-test/certbot_compatibility_test/test_driver.py
+++ b/certbot-compatibility-test/certbot_compatibility_test/test_driver.py
@@ -177,8 +177,15 @@ def test_enhancements(plugin, domains):
                      "enhancements")
         return False
 
-    for domain in domains:
+    domains_and_info = [(domain, []) for domain in domains]
+
+    for domain, info in domains_and_info:
         try:
+            verify = functools.partial(validator.Validator().any_redirect,
+                                       "localhost", plugin.http_port,
+                                       headers={"Host": domain})
+            previous_redirect = _try_until_true(verify)
+            info.append(previous_redirect)
             plugin.enhance(domain, "redirect")
             plugin.save()  # Needed by the Apache plugin
         except le_errors.PluginError as error:
@@ -194,12 +201,14 @@ def test_enhancements(plugin, domains):
         return False
 
     success = True
-    for domain in domains:
-        verify = functools.partial(validator.Validator().redirect, "localhost",
-                                   plugin.http_port, headers={"Host": domain})
-        if not _try_until_true(verify):
-            logger.error("*** Improper redirect for domain %s", domain)
-            success = False
+    for domain, info in domains_and_info:
+        previous_redirect = info[0]
+        if not previous_redirect:
+            verify = functools.partial(validator.Validator().redirect, "localhost",
+                                       plugin.http_port, headers={"Host": domain})
+            if not _try_until_true(verify):
+                logger.error("*** Improper redirect for domain %s", domain)
+                success = False
 
     if success:
         logger.info("Enhancements test succeeded")
diff --git a/certbot-compatibility-test/certbot_compatibility_test/validator.py b/certbot-compatibility-test/certbot_compatibility_test/validator.py
index 62dd466a1..0fd6efab5 100644
--- a/certbot-compatibility-test/certbot_compatibility_test/validator.py
+++ b/certbot-compatibility-test/certbot_compatibility_test/validator.py
@@ -45,19 +45,12 @@ class Validator(object):
         else:
             response = requests.get(url, allow_redirects=False)
 
-        if response.status_code not in (301, 303):
-            return False
-
         redirect_location = response.headers.get("location", "")
         # We're checking that the redirect we added behaves correctly.
         # It's okay for some server configuration to redirect to an
         # http URL, as long as it's on some other domain.
         if not redirect_location.startswith("https://"):
-            if not redirect_location.startswith("http://"):
-                return False
-            else:
-                if redirect_location[len("http://"):] == name:
-                    return False
+            return False
 
         if response.status_code != 301:
             logger.error("Server did not redirect with permanent code")
@@ -65,6 +58,16 @@ class Validator(object):
 
         return True
 
+    def any_redirect(self, name, port=80, headers=None):
+        """Test whether webserver redirects."""
+        url = "http://{0}:{1}".format(name, port)
+        if headers:
+            response = requests.get(url, headers=headers, allow_redirects=False)
+        else:
+            response = requests.get(url, allow_redirects=False)
+
+        return response.status_code in xrange(300, 309)
+
     def hsts(self, name):
         """Test for HTTP Strict Transport Security header"""
         headers = requests.get("https://" + name).headers
diff --git a/tox.ini b/tox.ini
index 5d6de5730..39218651c 100644
--- a/tox.ini
+++ b/tox.ini
@@ -151,7 +151,7 @@ passenv = DOCKER_*
 commands =
     docker build -t certbot-compatibility-test -f certbot-compatibility-test/Dockerfile .
     docker build -t nginx-compat -f certbot-compatibility-test/Dockerfile-nginx .
-    docker run --rm -it nginx-compat -c nginx.tar.gz -vvvv -ai
+    docker run --rm -it nginx-compat -c nginx.tar.gz -vvvv -aie
 whitelist_externals =
     docker
 passenv = DOCKER_*