diff --git a/letsencrypt/client/plugins/nginx/configurator.py b/letsencrypt/client/plugins/nginx/configurator.py
index 47a732070..84588ffe8 100644
--- a/letsencrypt/client/plugins/nginx/configurator.py
+++ b/letsencrypt/client/plugins/nginx/configurator.py
@@ -378,9 +378,15 @@ class NginxConfigurator(object):
         sni_regex = re.compile(r"TLS SNI support enabled", re.IGNORECASE)
         sni_matches = sni_regex.findall(text)
 
+        ssl_regex = re.compile(r" --with-http_ssl_module")
+        ssl_matches = ssl_regex.findall(text)
+
         if not version_matches:
             raise errors.LetsEncryptConfiguratorError(
                 "Unable to find Nginx version")
+        if not ssl_matches:
+            raise errors.LetsEncryptConfiguratorError(
+                "Nginx build is missing SSL module (--with-http_ssl_module).")
         if not sni_matches:
             raise errors.LetsEncryptConfiguratorError(
                 "Nginx build doesn't support SNI")
@@ -388,9 +394,7 @@ class NginxConfigurator(object):
         nginx_version = tuple([int(i) for i in version_matches[0].split(".")])
 
         # nginx < 0.8.21 doesn't use default_server
-        if (nginx_version[0] == 0 and (nginx_version[1] < 8 or
-                                       (nginx_version[1] == 8 and
-                                        nginx_version[2] < 21))):
+        if nginx_version < (0, 8, 21):
             raise errors.LetsEncryptConfiguratorError(
                 "Nginx version must be 0.8.21+")
 
diff --git a/letsencrypt/client/plugins/nginx/tests/configurator_test.py b/letsencrypt/client/plugins/nginx/tests/configurator_test.py
index 225ab1610..0ac0fd8bc 100644
--- a/letsencrypt/client/plugins/nginx/tests/configurator_test.py
+++ b/letsencrypt/client/plugins/nginx/tests/configurator_test.py
@@ -200,21 +200,43 @@ class NginxConfiguratorTest(util.NginxTest):
                            "nginx/1.6.2 --with-http_ssl_module"]))
         self.assertEqual(self.config.get_version(), (1, 4, 2))
 
+        mock_popen().communicate.return_value = (
+            "", "\n".join(["nginx version: nginx/0.9",
+                           "built by clang 6.0 (clang-600.0.56)"
+                           " (based on LLVM 3.5svn)",
+                           "TLS SNI support enabled",
+                           "configure arguments: --with-http_ssl_module"]))
+        self.assertEqual(self.config.get_version(), (0, 9))
+
         mock_popen().communicate.return_value = (
             "", "\n".join(["blah 0.0.1",
+                           "built by clang 6.0 (clang-600.0.56)"
+                           " (based on LLVM 3.5svn)",
+                           "TLS SNI support enabled",
+                           "configure arguments: --with-http_ssl_module"]))
+        self.assertRaises(errors.LetsEncryptConfiguratorError,
+                          self.config.get_version)
+
+        mock_popen().communicate.return_value = (
+            "", "\n".join(["nginx version: nginx/1.4.2",
                            "TLS SNI support enabled"]))
         self.assertRaises(errors.LetsEncryptConfiguratorError,
                           self.config.get_version)
 
         mock_popen().communicate.return_value = (
             "", "\n".join(["nginx version: nginx/1.4.2",
-                           ""]))
+                           "built by clang 6.0 (clang-600.0.56)"
+                           " (based on LLVM 3.5svn)",
+                           "configure arguments: --with-http_ssl_module"]))
         self.assertRaises(errors.LetsEncryptConfiguratorError,
                           self.config.get_version)
 
         mock_popen().communicate.return_value = (
             "", "\n".join(["nginx version: nginx/0.8.1",
-                           ""]))
+                           "built by clang 6.0 (clang-600.0.56)"
+                           " (based on LLVM 3.5svn)",
+                           "TLS SNI support enabled",
+                           "configure arguments: --with-http_ssl_module"]))
         self.assertRaises(errors.LetsEncryptConfiguratorError,
                           self.config.get_version)