diff --git a/certbot-nginx/certbot_nginx/configurator.py b/certbot-nginx/certbot_nginx/configurator.py
index afa8b8087..5e415bce6 100644
--- a/certbot-nginx/certbot_nginx/configurator.py
+++ b/certbot-nginx/certbot_nginx/configurator.py
@@ -341,7 +341,7 @@ class NginxConfigurator(common.Plugin):
         options_subblock = self.parser.loc["ssl_options"]
         # the options file doesn't have a newline at the beginning, but there
         # needs to be one when it's dropped into the file
-        if "\n" not in options_subblock[0]:
+        if options_subblock and "\n" not in options_subblock[0]:
             options_subblock[0].insert(0, "\n")
         ssl_block = (
             [['\n    ', 'listen', ' ', '{0} ssl'.format(self.config.tls_sni_01_port)],
diff --git a/certbot-nginx/certbot_nginx/parser.py b/certbot-nginx/certbot_nginx/parser.py
index cf1f3c1db..73224ea1f 100644
--- a/certbot-nginx/certbot_nginx/parser.py
+++ b/certbot-nginx/certbot_nginx/parser.py
@@ -179,7 +179,7 @@ class NginxParser(object):
                 with open(ssl_options) as _file:
                     return nginxparser.load(_file).spaced
             except IOError:
-                logger.debug("Could not open file: %s", ssl_options)
+                logger.warn("Missing NGINX TLS options file: %s", ssl_options)
             except pyparsing.ParseException:
                 logger.debug("Could not parse file: %s", ssl_options)
         return []