diff --git a/certbot-nginx/certbot_nginx/configurator.py b/certbot-nginx/certbot_nginx/configurator.py
index fe27dbc4b..98990664f 100644
--- a/certbot-nginx/certbot_nginx/configurator.py
+++ b/certbot-nginx/certbot_nginx/configurator.py
@@ -117,6 +117,9 @@ class NginxConfigurator(common.Installer):
         # Files to save
         self.save_notes = ""
 
+        # For creating new vhosts if no names match
+        self.new_vhost = None
+
         # Add number of outstanding challenges
         self._chall_out = 0
 
@@ -191,9 +194,11 @@ class NginxConfigurator(common.Installer):
                 "The nginx plugin currently requires --fullchain-path to "
                 "install a cert.")
 
-        vhost = self.choose_vhost(domain)
-        cert_directives = [['\n', 'ssl_certificate', ' ', fullchain_path],
-                           ['\n', 'ssl_certificate_key', ' ', key_path]]
+        vhost = self.choose_vhost(domain, raise_if_no_match=False)
+        if vhost is None:
+            vhost = self._vhost_from_duplicated_default(domain)
+        cert_directives = [['\n    ', 'ssl_certificate', ' ', fullchain_path],
+                           ['\n    ', 'ssl_certificate_key', ' ', key_path]]
 
         self.parser.add_server_directives(vhost,
                                           cert_directives, replace=True)
@@ -209,7 +214,7 @@ class NginxConfigurator(common.Installer):
     #######################
     # Vhost parsing methods
     #######################
-    def choose_vhost(self, target_name):
+    def choose_vhost(self, target_name, raise_if_no_match=True):
         """Chooses a virtual host based on the given domain name.
 
         .. note:: This makes the vhost SSL-enabled if it isn't already. Follows
@@ -223,6 +228,8 @@ class NginxConfigurator(common.Installer):
             hostname. Currently we just ignore this.
 
         :param str target_name: domain name
+        :param bool raise_if_no_match: True iff not finding a match is an error;
+                                       otherwise, return None
 
         :returns: ssl vhost associated with name
         :rtype: :class:`~certbot_nginx.obj.VirtualHost`
@@ -233,13 +240,16 @@ class NginxConfigurator(common.Installer):
         matches = self._get_ranked_matches(target_name)
         vhost = self._select_best_name_match(matches)
         if not vhost:
-            # No matches. Raise a misconfiguration error.
-            raise errors.MisconfigurationError(
-                        ("Cannot find a VirtualHost matching domain %s. "
-                         "In order for Certbot to correctly perform the challenge "
-                         "please add a corresponding server_name directive to your "
-                         "nginx configuration: "
-                         "https://nginx.org/en/docs/http/server_names.html") % (target_name))
+            if raise_if_no_match:
+                # No matches. Raise a misconfiguration error.
+                raise errors.MisconfigurationError(
+                            ("Cannot find a VirtualHost matching domain %s. "
+                             "In order for Certbot to correctly perform the challenge "
+                             "please add a corresponding server_name directive to your "
+                             "nginx configuration: "
+                             "https://nginx.org/en/docs/http/server_names.html") % (target_name))
+            else:
+                return None
         else:
             # Note: if we are enhancing with ocsp, vhost should already be ssl.
             if not vhost.ssl:
@@ -247,6 +257,65 @@ class NginxConfigurator(common.Installer):
 
         return vhost
 
+
+    def ipv6_info(self, port):
+        """Returns tuple of booleans (ipv6_active, ipv6only_present)
+        ipv6_active is true if any server block listens ipv6 address in any port
+
+        ipv6only_present is true if ipv6only=on option exists in any server
+        block ipv6 listen directive for the specified port.
+
+        :param str port: Port to check ipv6only=on directive for
+
+        :returns: Tuple containing information if IPv6 is enabled in the global
+            configuration, and existence of ipv6only directive for specified port
+        :rtype: tuple of type (bool, bool)
+        """
+        vhosts = self.parser.get_vhosts()
+        ipv6_active = False
+        ipv6only_present = False
+        for vh in vhosts:
+            for addr in vh.addrs:
+                if addr.ipv6:
+                    ipv6_active = True
+                if addr.ipv6only and addr.get_port() == port:
+                    ipv6only_present = True
+        return (ipv6_active, ipv6only_present)
+
+    def _vhost_from_duplicated_default(self, domain):
+        if self.new_vhost is None:
+            default_vhost = self._get_default_vhost()
+            self.new_vhost = self.parser.create_new_vhost_from_default(default_vhost)
+            if not self.new_vhost.ssl:
+                self._make_server_ssl(self.new_vhost)
+            self.new_vhost.names = set()
+
+        self.new_vhost.names.add(domain)
+        name_block = [['\n    ', 'server_name']]
+        for name in self.new_vhost.names:
+            name_block[0].append(' ')
+            name_block[0].append(name)
+        self.parser.add_server_directives(self.new_vhost, name_block, replace=True)
+        return self.new_vhost
+
+    def _get_default_vhost(self):
+        vhost_list = self.parser.get_vhosts()
+        # if one has default_server set, return that one
+        default_vhosts = []
+        for vhost in vhost_list:
+            for addr in vhost.addrs:
+                if addr.default:
+                    default_vhosts.append(vhost)
+                    break
+
+        if len(default_vhosts) == 1:
+            return default_vhosts[0]
+
+        # TODO: present a list of vhosts for user to choose from
+
+        raise errors.MisconfigurationError("Could not automatically find a matching server"
+            " block. Set the `server_name` directive to use the Nginx installer.")
+
     def _get_ranked_matches(self, target_name):
         """Returns a ranked list of vhosts that match target_name.
         The ranking gives preference to SSL vhosts.
@@ -405,9 +474,12 @@ class NginxConfigurator(common.Installer):
                     all_names.add(host)
                 elif not common.private_ips_regex.match(host):
                     # If it isn't a private IP, do a reverse DNS lookup
-                    # TODO: IPv6 support
                     try:
-                        socket.inet_aton(host)
+                        if addr.ipv6:
+                            host = addr.get_ipv6_exploded()
+                            socket.inet_pton(socket.AF_INET6, host)
+                        else:
+                            socket.inet_pton(socket.AF_INET, host)
                         all_names.add(socket.gethostbyaddr(host)[0])
                     except (socket.error, socket.herror, socket.timeout):
                         continue
@@ -443,16 +515,38 @@ class NginxConfigurator(common.Installer):
         :type vhost: :class:`~certbot_nginx.obj.VirtualHost`
 
         """
+        ipv6info = self.ipv6_info(self.config.tls_sni_01_port)
+        ipv6_block = ['']
+        ipv4_block = ['']
+
         # If the vhost was implicitly listening on the default Nginx port,
         # have it continue to do so.
         if len(vhost.addrs) == 0:
             listen_block = [['\n    ', 'listen', ' ', self.DEFAULT_LISTEN_PORT]]
             self.parser.add_server_directives(vhost, listen_block, replace=False)
 
+        if vhost.ipv6_enabled():
+            ipv6_block = ['\n    ',
+                          'listen',
+                          ' ',
+                          '[::]:{0} ssl'.format(self.config.tls_sni_01_port)]
+            if not ipv6info[1]:
+                # ipv6only=on is absent in global config
+                ipv6_block.append(' ')
+                ipv6_block.append('ipv6only=on')
+
+        if vhost.ipv4_enabled():
+            ipv4_block = ['\n    ',
+                          'listen',
+                          ' ',
+                          '{0} ssl'.format(self.config.tls_sni_01_port)]
+
+
         snakeoil_cert, snakeoil_key = self._get_snakeoil_paths()
 
         ssl_block = ([
-            ['\n    ', 'listen', ' ', '{0} ssl'.format(self.config.tls_sni_01_port)],
+            ipv6_block,
+            ipv4_block,
             ['\n    ', 'ssl_certificate', ' ', snakeoil_cert],
             ['\n    ', 'ssl_certificate_key', ' ', snakeoil_key],
             ['\n    ', 'include', ' ', self.mod_ssl_conf],
diff --git a/certbot-nginx/certbot_nginx/nginxparser.py b/certbot-nginx/certbot_nginx/nginxparser.py
index 20aeeb554..14481e298 100644
--- a/certbot-nginx/certbot_nginx/nginxparser.py
+++ b/certbot-nginx/certbot_nginx/nginxparser.py
@@ -7,6 +7,7 @@ from pyparsing import (
     Literal, White, Forward, Group, Optional, OneOrMore, QuotedString, Regex, ZeroOrMore, Combine)
 from pyparsing import stringEnd
 from pyparsing import restOfLine
+import six
 
 logger = logging.getLogger(__name__)
 
@@ -71,7 +72,7 @@ class RawNginxDumper(object):
         """Iterates the dumped nginx content."""
         blocks = blocks or self.blocks
         for b0 in blocks:
-            if isinstance(b0, str):
+            if isinstance(b0, six.string_types):
                 yield b0
                 continue
             item = copy.deepcopy(b0)
@@ -88,7 +89,7 @@ class RawNginxDumper(object):
                 yield '}'
             else: # not a block - list of strings
                 semicolon = ";"
-                if isinstance(item[0], str) and item[0].strip() == '#': # comment
+                if isinstance(item[0], six.string_types) and item[0].strip() == '#': # comment
                     semicolon = ""
                 yield "".join(item) + semicolon
 
@@ -145,7 +146,7 @@ def dump(blocks, _file):
     return _file.write(dumps(blocks))
 
 
-spacey = lambda x: (isinstance(x, str) and x.isspace()) or x == ''
+spacey = lambda x: (isinstance(x, six.string_types) and x.isspace()) or x == ''
 
 class UnspacedList(list):
     """Wrap a list [of lists], making any whitespace entries magically invisible"""
@@ -189,13 +190,15 @@ class UnspacedList(list):
         item, spaced_item = self._coerce(x)
         slicepos = self._spaced_position(i) if i < len(self) else len(self.spaced)
         self.spaced.insert(slicepos, spaced_item)
-        list.insert(self, i, item)
+        if not spacey(item):
+            list.insert(self, i, item)
         self.dirty = True
 
     def append(self, x):
         item, spaced_item = self._coerce(x)
         self.spaced.append(spaced_item)
-        list.append(self, item)
+        if not spacey(item):
+            list.append(self, item)
         self.dirty = True
 
     def extend(self, x):
@@ -226,7 +229,8 @@ class UnspacedList(list):
             raise NotImplementedError("Slice operations on UnspacedLists not yet implemented")
         item, spaced_item = self._coerce(value)
         self.spaced.__setitem__(self._spaced_position(i), spaced_item)
-        list.__setitem__(self, i, item)
+        if not spacey(item):
+            list.__setitem__(self, i, item)
         self.dirty = True
 
     def __delitem__(self, i):
@@ -235,8 +239,8 @@ class UnspacedList(list):
         self.dirty = True
 
     def __deepcopy__(self, memo):
-        l = UnspacedList(self[:])
-        l.spaced = copy.deepcopy(self.spaced, memo=memo)
+        new_spaced = copy.deepcopy(self.spaced, memo=memo)
+        l = UnspacedList(new_spaced)
         l.dirty = self.dirty
         return l
 
diff --git a/certbot-nginx/certbot_nginx/obj.py b/certbot-nginx/certbot_nginx/obj.py
index 849cefe1f..5816c5571 100644
--- a/certbot-nginx/certbot_nginx/obj.py
+++ b/certbot-nginx/certbot_nginx/obj.py
@@ -34,10 +34,13 @@ class Addr(common.Addr):
     UNSPECIFIED_IPV4_ADDRESSES = ('', '*', '0.0.0.0')
     CANONICAL_UNSPECIFIED_ADDRESS = UNSPECIFIED_IPV4_ADDRESSES[0]
 
-    def __init__(self, host, port, ssl, default):
+    def __init__(self, host, port, ssl, default, ipv6, ipv6only):
+        # pylint: disable=too-many-arguments
         super(Addr, self).__init__((host, port))
         self.ssl = ssl
         self.default = default
+        self.ipv6 = ipv6
+        self.ipv6only = ipv6only
         self.unspecified_address = host in self.UNSPECIFIED_IPV4_ADDRESSES
 
     @classmethod
@@ -46,6 +49,8 @@ class Addr(common.Addr):
         parts = str_addr.split(' ')
         ssl = False
         default = False
+        ipv6 = False
+        ipv6only = False
         host = ''
         port = ''
 
@@ -56,15 +61,25 @@ class Addr(common.Addr):
         if addr.startswith('unix:'):
             return None
 
-        tup = addr.partition(':')
-        if re.match(r'^\d+$', tup[0]):
-            # This is a bare port, not a hostname. E.g. listen 80
-            host = ''
-            port = tup[0]
+        # IPv6 check
+        ipv6_match = re.match(r'\[.*\]', addr)
+        if ipv6_match:
+            ipv6 = True
+            # IPv6 handling
+            host = ipv6_match.group()
+            # The rest of the addr string will be the port, if any
+            port = addr[ipv6_match.end()+1:]
         else:
-            # This is a host-port tuple. E.g. listen 127.0.0.1:*
-            host = tup[0]
-            port = tup[2]
+            # IPv4 handling
+            tup = addr.partition(':')
+            if re.match(r'^\d+$', tup[0]):
+                # This is a bare port, not a hostname. E.g. listen 80
+                host = ''
+                port = tup[0]
+            else:
+                # This is a host-port tuple. E.g. listen 127.0.0.1:*
+                host = tup[0]
+                port = tup[2]
 
         # The rest of the parts are options; we only care about ssl and default
         while len(parts) > 0:
@@ -73,8 +88,10 @@ class Addr(common.Addr):
                 ssl = True
             elif nextpart == 'default_server':
                 default = True
+            elif nextpart == "ipv6only=on":
+                ipv6only = True
 
-        return cls(host, port, ssl, default)
+        return cls(host, port, ssl, default, ipv6, ipv6only)
 
     def to_string(self, include_default=True):
         """Return string representation of Addr"""
@@ -114,8 +131,6 @@ class Addr(common.Addr):
                                 self.tup[1]), self.ipv6) == \
                    common.Addr((other.CANONICAL_UNSPECIFIED_ADDRESS,
                                 other.tup[1]), other.ipv6)
-        # Nginx plugin currently doesn't support IPv6 but this will
-        # future-proof it
         return super(Addr, self).__eq__(other)
 
     def __eq__(self, other):
@@ -195,10 +210,24 @@ class VirtualHost(object):  # pylint: disable=too-few-public-methods
                 return True
         return False
 
+    def ipv6_enabled(self):
+        """Return true if one or more of the listen directives in vhost supports
+        IPv6"""
+        for a in self.addrs:
+            if a.ipv6:
+                return True
+
+    def ipv4_enabled(self):
+        """Return true if one or more of the listen directives in vhost are IPv4
+        only"""
+        for a in self.addrs:
+            if not a.ipv6:
+                return True
+
 def _find_directive(directives, directive_name):
     """Find a directive of type directive_name in directives
     """
-    if not directives or isinstance(directives, str) or len(directives) == 0:
+    if not directives or isinstance(directives, six.string_types) or len(directives) == 0:
         return None
 
     if directives[0] == directive_name:
diff --git a/certbot-nginx/certbot_nginx/parser.py b/certbot-nginx/certbot_nginx/parser.py
index 158cb9929..3eb6264aa 100644
--- a/certbot-nginx/certbot_nginx/parser.py
+++ b/certbot-nginx/certbot_nginx/parser.py
@@ -6,6 +6,8 @@ import os
 import pyparsing
 import re
 
+import six
+
 from certbot import errors
 
 from certbot_nginx import obj
@@ -312,6 +314,32 @@ class NginxParser(object):
         except errors.MisconfigurationError as err:
             raise errors.MisconfigurationError("Problem in %s: %s" % (filename, str(err)))
 
+    def create_new_vhost_from_default(self, vhost_template):
+        """Duplicate the default vhost in the configuration files.
+
+        :param :class:`~certbot_nginx.obj.VirtualHost` vhost_template: The vhost
+            whose information we copy
+
+        :returns: A vhost object for the newly created vhost
+        :rtype: :class:`~certbot_nginx.obj.VirtualHost`
+        """
+        # TODO: https://github.com/certbot/certbot/issues/5185
+        # put it in the same file as the template, at the same level
+        enclosing_block = self.parsed[vhost_template.filep]
+        for index in vhost_template.path[:-1]:
+            enclosing_block = enclosing_block[index]
+        new_location = vhost_template.path[-1] + 1
+        raw_in_parsed = copy.deepcopy(enclosing_block[vhost_template.path[-1]])
+        enclosing_block.insert(new_location, raw_in_parsed)
+        new_vhost = copy.deepcopy(vhost_template)
+        new_vhost.path[-1] = new_location
+        for addr in new_vhost.addrs:
+            addr.default = False
+        for directive in enclosing_block[new_vhost.path[-1]][1]:
+            if len(directive) > 0 and directive[0] == 'listen' and 'default_server' in directive:
+                del directive[directive.index('default_server')]
+        return new_vhost
+
 def _parse_ssl_options(ssl_options):
     if ssl_options is not None:
         try:
@@ -444,7 +472,7 @@ def _is_include_directive(entry):
     """
     return (isinstance(entry, list) and
             len(entry) == 2 and entry[0] == 'include' and
-            isinstance(entry[1], str))
+            isinstance(entry[1], six.string_types))
 
 def _is_ssl_on_directive(entry):
     """Checks if an nginx parsed entry is an 'ssl on' directive.
@@ -561,7 +589,8 @@ def _add_directive(block, directive, replace):
     directive_name = directive[0]
     def can_append(loc, dir_name):
         """ Can we append this directive to the block? """
-        return loc is None or (isinstance(dir_name, str) and dir_name in REPEATABLE_DIRECTIVES)
+        return loc is None or (isinstance(dir_name, six.string_types)
+            and dir_name in REPEATABLE_DIRECTIVES)
 
     err_fmt = 'tried to insert directive "{0}" but found conflicting "{1}".'
 
diff --git a/certbot-nginx/certbot_nginx/tests/configurator_test.py b/certbot-nginx/certbot_nginx/tests/configurator_test.py
index f4fe16924..996bd238b 100644
--- a/certbot-nginx/certbot_nginx/tests/configurator_test.py
+++ b/certbot-nginx/certbot_nginx/tests/configurator_test.py
@@ -45,7 +45,7 @@ class NginxConfiguratorTest(util.NginxTest):
 
     def test_prepare(self):
         self.assertEqual((1, 6, 2), self.config.version)
-        self.assertEqual(8, len(self.config.parser.parsed))
+        self.assertEqual(10, len(self.config.parser.parsed))
 
     @mock.patch("certbot_nginx.configurator.util.exe_exists")
     @mock.patch("certbot_nginx.configurator.subprocess.Popen")
@@ -89,7 +89,7 @@ class NginxConfiguratorTest(util.NginxTest):
         self.assertEqual(names, set(
             ["155.225.50.69.nephoscale.net", "www.example.org", "another.alias",
              "migration.com", "summer.com", "geese.com", "sslon.com",
-             "globalssl.com", "globalsslsetssl.com"]))
+             "globalssl.com", "globalsslsetssl.com", "ipv6.com", "ipv6ssl.com"]))
 
     def test_supported_enhancements(self):
         self.assertEqual(['redirect', 'staple-ocsp'],
@@ -131,6 +131,7 @@ class NginxConfiguratorTest(util.NginxTest):
         server_conf = set(['somename', 'another.alias', 'alias'])
         example_conf = set(['.example.com', 'example.*'])
         foo_conf = set(['*.www.foo.com', '*.www.example.com'])
+        ipv6_conf = set(['ipv6.com'])
 
         results = {'localhost': localhost_conf,
                    'alias': server_conf,
@@ -139,7 +140,8 @@ class NginxConfiguratorTest(util.NginxTest):
                    'www.example.com': example_conf,
                    'test.www.example.com': foo_conf,
                    'abc.www.foo.com': foo_conf,
-                   'www.bar.co.uk': localhost_conf}
+                   'www.bar.co.uk': localhost_conf,
+                   'ipv6.com': ipv6_conf}
 
         conf_path = {'localhost': "etc_nginx/nginx.conf",
                    'alias': "etc_nginx/nginx.conf",
@@ -148,7 +150,8 @@ class NginxConfiguratorTest(util.NginxTest):
                    'www.example.com': "etc_nginx/sites-enabled/example.com",
                    'test.www.example.com': "etc_nginx/foo.conf",
                    'abc.www.foo.com': "etc_nginx/foo.conf",
-                   'www.bar.co.uk': "etc_nginx/nginx.conf"}
+                   'www.bar.co.uk': "etc_nginx/nginx.conf",
+                   'ipv6.com': "etc_nginx/sites-enabled/ipv6.com"}
 
         bad_results = ['www.foo.com', 'example', 't.www.bar.co',
                        '69.255.225.155']
@@ -159,11 +162,24 @@ class NginxConfiguratorTest(util.NginxTest):
 
             self.assertEqual(results[name], vhost.names)
             self.assertEqual(conf_path[name], path)
+            # IPv6 specific checks
+            if name == "ipv6.com":
+                self.assertTrue(vhost.ipv6_enabled())
+                # Make sure that we have SSL enabled also for IPv6 addr
+                self.assertTrue(
+                    any([True for x in vhost.addrs if x.ssl and x.ipv6]))
 
         for name in bad_results:
             self.assertRaises(errors.MisconfigurationError,
                               self.config.choose_vhost, name)
 
+    def test_ipv6only(self):
+        # ipv6_info: (ipv6_active, ipv6only_present)
+        self.assertEquals((True, False), self.config.ipv6_info("80"))
+        # Port 443 has ipv6only=on because of ipv6ssl.com vhost
+        self.assertEquals((True, True), self.config.ipv6_info("443"))
+
+
     def test_more_info(self):
         self.assertTrue('nginx.conf' in self.config.more_info())
 
@@ -558,6 +574,145 @@ class NginxConfiguratorTest(util.NginxTest):
         self.assertTrue(util.contains_at_depth(
             generated_conf, ['ssl_stapling_verify', 'on'], 2))
 
+    def test_deploy_no_match_default_set(self):
+        default_conf = self.config.parser.abs_path('sites-enabled/default')
+        foo_conf = self.config.parser.abs_path('foo.conf')
+        del self.config.parser.parsed[foo_conf][2][1][0][1][0] # remove default_server
+        self.config.version = (1, 3, 1)
+
+        self.config.deploy_cert(
+            "www.nomatch.com",
+            "example/cert.pem",
+            "example/key.pem",
+            "example/chain.pem",
+            "example/fullchain.pem")
+        self.config.save()
+
+        self.config.parser.load()
+
+        parsed_default_conf = util.filter_comments(self.config.parser.parsed[default_conf])
+
+        self.assertEqual([[['server'],
+                           [['listen', 'myhost', 'default_server'],
+                            ['listen', 'otherhost', 'default_server'],
+                            ['server_name', 'www.example.org'],
+                            [['location', '/'],
+                             [['root', 'html'],
+                              ['index', 'index.html', 'index.htm']]]]],
+                          [['server'],
+                           [['listen', 'myhost'],
+                            ['listen', 'otherhost'],
+                            ['server_name', 'www.nomatch.com'],
+                            [['location', '/'],
+                             [['root', 'html'],
+                              ['index', 'index.html', 'index.htm']]],
+                            ['listen', '5001', 'ssl'],
+                            ['ssl_certificate', 'example/fullchain.pem'],
+                            ['ssl_certificate_key', 'example/key.pem'],
+                            ['include', self.config.mod_ssl_conf],
+                            ['ssl_dhparam', self.config.ssl_dhparams]]]],
+                         parsed_default_conf)
+
+        self.config.deploy_cert(
+            "nomatch.com",
+            "example/cert.pem",
+            "example/key.pem",
+            "example/chain.pem",
+            "example/fullchain.pem")
+        self.config.save()
+
+        self.config.parser.load()
+
+        parsed_default_conf = util.filter_comments(self.config.parser.parsed[default_conf])
+
+        self.assertTrue(util.contains_at_depth(parsed_default_conf, "nomatch.com", 3))
+
+    def test_deploy_no_match_default_set_multi_level_path(self):
+        default_conf = self.config.parser.abs_path('sites-enabled/default')
+        foo_conf = self.config.parser.abs_path('foo.conf')
+        del self.config.parser.parsed[default_conf][0][1][0]
+        del self.config.parser.parsed[default_conf][0][1][0]
+        self.config.version = (1, 3, 1)
+
+        self.config.deploy_cert(
+            "www.nomatch.com",
+            "example/cert.pem",
+            "example/key.pem",
+            "example/chain.pem",
+            "example/fullchain.pem")
+        self.config.save()
+
+        self.config.parser.load()
+
+        parsed_foo_conf = util.filter_comments(self.config.parser.parsed[foo_conf])
+
+        self.assertEqual([['server'],
+                          [['listen', '*:80', 'ssl'],
+                          ['server_name', 'www.nomatch.com'],
+                          ['root', '/home/ubuntu/sites/foo/'],
+                          [['location', '/status'], [[['types'], [['image/jpeg', 'jpg']]]]],
+                          [['location', '~', 'case_sensitive\\.php$'], [['index', 'index.php'],
+                           ['root', '/var/root']]],
+                          [['location', '~*', 'case_insensitive\\.php$'], []],
+                          [['location', '=', 'exact_match\\.php$'], []],
+                          [['location', '^~', 'ignore_regex\\.php$'], []],
+                          ['ssl_certificate', 'example/fullchain.pem'],
+                          ['ssl_certificate_key', 'example/key.pem']]],
+                         parsed_foo_conf[1][1][1])
+
+    def test_deploy_no_match_no_default_set(self):
+        default_conf = self.config.parser.abs_path('sites-enabled/default')
+        foo_conf = self.config.parser.abs_path('foo.conf')
+        del self.config.parser.parsed[default_conf][0][1][0]
+        del self.config.parser.parsed[default_conf][0][1][0]
+        del self.config.parser.parsed[foo_conf][2][1][0][1][0]
+        self.config.version = (1, 3, 1)
+
+        self.assertRaises(errors.MisconfigurationError, self.config.deploy_cert,
+            "www.nomatch.com", "example/cert.pem", "example/key.pem",
+            "example/chain.pem", "example/fullchain.pem")
+
+    def test_deploy_no_match_fail_multiple_defaults(self):
+        self.config.version = (1, 3, 1)
+        self.assertRaises(errors.MisconfigurationError, self.config.deploy_cert,
+            "www.nomatch.com", "example/cert.pem", "example/key.pem",
+            "example/chain.pem", "example/fullchain.pem")
+
+    def test_deploy_no_match_add_redirect(self):
+        default_conf = self.config.parser.abs_path('sites-enabled/default')
+        foo_conf = self.config.parser.abs_path('foo.conf')
+        del self.config.parser.parsed[foo_conf][2][1][0][1][0] # remove default_server
+        self.config.version = (1, 3, 1)
+
+        self.config.deploy_cert(
+            "www.nomatch.com",
+            "example/cert.pem",
+            "example/key.pem",
+            "example/chain.pem",
+            "example/fullchain.pem")
+
+        self.config.deploy_cert(
+            "nomatch.com",
+            "example/cert.pem",
+            "example/key.pem",
+            "example/chain.pem",
+            "example/fullchain.pem")
+
+        self.config.enhance("www.nomatch.com", "redirect")
+
+        self.config.save()
+
+        self.config.parser.load()
+
+        expected = [
+            ['if', '($scheme', '!=', '"https")'],
+            [['return', '301', 'https://$host$request_uri']]
+        ]
+
+        generated_conf = self.config.parser.parsed[default_conf]
+        self.assertTrue(util.contains_at_depth(generated_conf, expected, 2))
+
+
 class InstallSslOptionsConfTest(util.NginxTest):
     """Test that the options-ssl-nginx.conf file is installed and updated properly."""
 
diff --git a/certbot-nginx/certbot_nginx/tests/parser_test.py b/certbot-nginx/certbot_nginx/tests/parser_test.py
index e655bc3e3..ca5de7ff6 100644
--- a/certbot-nginx/certbot_nginx/tests/parser_test.py
+++ b/certbot-nginx/certbot_nginx/tests/parser_test.py
@@ -50,7 +50,9 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
                                'sites-enabled/example.com',
                                'sites-enabled/migration.com',
                                'sites-enabled/sslon.com',
-                               'sites-enabled/globalssl.com']]),
+                               'sites-enabled/globalssl.com',
+                               'sites-enabled/ipv6.com',
+                               'sites-enabled/ipv6ssl.com']]),
                          set(nparser.parsed.keys()))
         self.assertEqual([['server_name', 'somename', 'alias', 'another.alias']],
                          nparser.parsed[nparser.abs_path('server.conf')])
@@ -74,7 +76,7 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
         parsed = nparser._parse_files(nparser.abs_path(
             'sites-enabled/example.com.test'))
         self.assertEqual(3, len(glob.glob(nparser.abs_path('*.test'))))
-        self.assertEqual(5, len(
+        self.assertEqual(7, len(
             glob.glob(nparser.abs_path('sites-enabled/*.test'))))
         self.assertEqual([[['server'], [['listen', '69.50.225.155:9000'],
                                         ['listen', '127.0.0.1'],
@@ -110,7 +112,8 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
         vhosts = nparser.get_vhosts()
 
         vhost = obj.VirtualHost(nparser.abs_path('sites-enabled/globalssl.com'),
-                                [obj.Addr('4.8.2.6', '57', True, False)],
+                                [obj.Addr('4.8.2.6', '57', True, False,
+                                          False, False)],
                                 True, True, set(['globalssl.com']), [], [0])
 
         globalssl_com = [x for x in vhosts if 'globalssl.com' in x.filep][0]
@@ -121,34 +124,42 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
         vhosts = nparser.get_vhosts()
 
         vhost1 = obj.VirtualHost(nparser.abs_path('nginx.conf'),
-                                 [obj.Addr('', '8080', False, False)],
+                                 [obj.Addr('', '8080', False, False,
+                                           False, False)],
                                  False, True,
                                  set(['localhost',
                                       r'~^(www\.)?(example|bar)\.']),
                                  [], [10, 1, 9])
         vhost2 = obj.VirtualHost(nparser.abs_path('nginx.conf'),
-                                 [obj.Addr('somename', '8080', False, False),
-                                  obj.Addr('', '8000', False, False)],
+                                 [obj.Addr('somename', '8080', False, False,
+                                           False, False),
+                                  obj.Addr('', '8000', False, False,
+                                           False, False)],
                                  False, True,
                                  set(['somename', 'another.alias', 'alias']),
                                  [], [10, 1, 12])
         vhost3 = obj.VirtualHost(nparser.abs_path('sites-enabled/example.com'),
                                  [obj.Addr('69.50.225.155', '9000',
-                                           False, False),
-                                  obj.Addr('127.0.0.1', '', False, False)],
+                                           False, False, False, False),
+                                  obj.Addr('127.0.0.1', '', False, False,
+                                           False, False)],
                                  False, True,
                                  set(['.example.com', 'example.*']), [], [0])
         vhost4 = obj.VirtualHost(nparser.abs_path('sites-enabled/default'),
-                                 [obj.Addr('myhost', '', False, True)],
+                                 [obj.Addr('myhost', '', False, True,
+                                           False, False),
+                                  obj.Addr('otherhost', '', False, True,
+                                           False, False)],
                                  False, True, set(['www.example.org']),
                                  [], [0])
         vhost5 = obj.VirtualHost(nparser.abs_path('foo.conf'),
-                                 [obj.Addr('*', '80', True, True)],
+                                 [obj.Addr('*', '80', True, True,
+                                           False, False)],
                                  True, True, set(['*.www.foo.com',
                                                   '*.www.example.com']),
                                  [], [2, 1, 0])
 
-        self.assertEqual(10, len(vhosts))
+        self.assertEqual(12, len(vhosts))
         example_com = [x for x in vhosts if 'example.com' in x.filep][0]
         self.assertEqual(vhost3, example_com)
         default = [x for x in vhosts if 'default' in x.filep][0]
@@ -395,6 +406,29 @@ class NginxParserTest(util.NginxTest): #pylint: disable=too-many-public-methods
         ])
         self.assertTrue(server['ssl'])
 
+    def test_create_new_vhost_from_default(self):
+        nparser = parser.NginxParser(self.config_path)
+
+        vhosts = nparser.get_vhosts()
+        default = [x for x in vhosts if 'default' in x.filep][0]
+        new_vhost = nparser.create_new_vhost_from_default(default)
+        nparser.filedump(ext='')
+
+        # check properties of new vhost
+        self.assertFalse(next(iter(new_vhost.addrs)).default)
+        self.assertNotEqual(new_vhost.path, default.path)
+
+        # check that things are written to file correctly
+        new_nparser = parser.NginxParser(self.config_path)
+        new_vhosts = new_nparser.get_vhosts()
+        new_defaults = [x for x in new_vhosts if 'default' in x.filep]
+        self.assertEqual(len(new_defaults), 2)
+        new_vhost_parsed = new_defaults[1]
+        self.assertFalse(next(iter(new_vhost_parsed.addrs)).default)
+        self.assertEqual(next(iter(default.names)), next(iter(new_vhost_parsed.names)))
+        self.assertEqual(len(default.raw), len(new_vhost_parsed.raw))
+        self.assertTrue(next(iter(default.addrs)).super_eq(next(iter(new_vhost_parsed.addrs))))
+
 
 if __name__ == "__main__":
     unittest.main()  # pragma: no cover
diff --git a/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/default b/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/default
index 26f37020c..4f67fa7d1 100644
--- a/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/default
+++ b/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/default
@@ -1,5 +1,6 @@
 server {
     listen       myhost default_server;
+    listen       otherhost default_server;
     server_name www.example.org;
 
     location / {
diff --git a/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/ipv6.com b/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/ipv6.com
new file mode 100644
index 000000000..7a7744b92
--- /dev/null
+++ b/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/ipv6.com
@@ -0,0 +1,5 @@
+server {
+    listen 80;
+    listen [::]:80;
+    server_name ipv6.com;
+}
diff --git a/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/ipv6ssl.com b/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/ipv6ssl.com
new file mode 100644
index 000000000..d8f7eff12
--- /dev/null
+++ b/certbot-nginx/certbot_nginx/tests/testdata/etc_nginx/sites-enabled/ipv6ssl.com
@@ -0,0 +1,5 @@
+server {
+    listen 443 ssl;
+    listen [::]:443 ssl ipv6only=on;
+    server_name ipv6ssl.com;
+}
diff --git a/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py b/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py
index 85db584b3..32a5ed7d2 100644
--- a/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py
+++ b/certbot-nginx/certbot_nginx/tests/tls_sni_01_test.py
@@ -66,7 +66,7 @@ class TlsSniPerformTest(util.NginxTest):
         self.sni.add_chall(self.achalls[1])
         mock_choose.return_value = None
         result = self.sni.perform()
-        self.assertTrue(result is None)
+        self.assertFalse(result is None)
 
     def test_perform0(self):
         responses = self.sni.perform()
@@ -125,10 +125,10 @@ class TlsSniPerformTest(util.NginxTest):
         self.sni.add_chall(self.achalls[0])
         self.sni.add_chall(self.achalls[2])
 
-        v_addr1 = [obj.Addr("69.50.225.155", "9000", True, False),
-                   obj.Addr("127.0.0.1", "", False, False)]
-        v_addr2 = [obj.Addr("myhost", "", False, True)]
-        v_addr2_print = [obj.Addr("myhost", "", False, False)]
+        v_addr1 = [obj.Addr("69.50.225.155", "9000", True, False, False, False),
+                   obj.Addr("127.0.0.1", "", False, False, False, False)]
+        v_addr2 = [obj.Addr("myhost", "", False, True, False, False)]
+        v_addr2_print = [obj.Addr("myhost", "", False, False, False, False)]
         ll_addr = [v_addr1, v_addr2]
         self.sni._mod_config(ll_addr)  # pylint: disable=protected-access
 
diff --git a/certbot-nginx/certbot_nginx/tls_sni_01.py b/certbot-nginx/certbot_nginx/tls_sni_01.py
index d6faa12be..7f597ac4a 100644
--- a/certbot-nginx/certbot_nginx/tls_sni_01.py
+++ b/certbot-nginx/certbot_nginx/tls_sni_01.py
@@ -51,19 +51,32 @@ class NginxTlsSni01(common.TLSSNI01):
         default_addr = "{0} ssl".format(
             self.configurator.config.tls_sni_01_port)
 
-        for achall in self.achalls:
-            vhost = self.configurator.choose_vhost(achall.domain)
-            if vhost is None:
-                logger.error(
-                    "No nginx vhost exists with server_name matching: %s. "
-                    "Please specify server_names in the Nginx config.",
-                    achall.domain)
-                return None
+        ipv6, ipv6only = self.configurator.ipv6_info(
+            self.configurator.config.tls_sni_01_port)
 
-            if vhost.addrs:
+        for achall in self.achalls:
+            vhost = self.configurator.choose_vhost(achall.domain, raise_if_no_match=False)
+
+            if vhost is not None and vhost.addrs:
                 addresses.append(list(vhost.addrs))
             else:
-                addresses.append([obj.Addr.fromstring(default_addr)])
+                if ipv6:
+                    # If IPv6 is active in Nginx configuration
+                    ipv6_addr = "[::]:{0} ssl".format(
+                        self.configurator.config.tls_sni_01_port)
+                    if not ipv6only:
+                        # If ipv6only=on is not already present in the config
+                        ipv6_addr = ipv6_addr + " ipv6only=on"
+                    addresses.append([obj.Addr.fromstring(default_addr),
+                                      obj.Addr.fromstring(ipv6_addr)])
+                    logger.info(("Using default addresses %s and %s for " +
+                                 "TLSSNI01 authentication."),
+                                default_addr,
+                                ipv6_addr)
+                else:
+                    addresses.append([obj.Addr.fromstring(default_addr)])
+                    logger.info("Using default address %s for TLSSNI01 authentication.",
+                                default_addr)
 
         # Create challenge certs
         responses = [self._setup_challenge_cert(x) for x in self.achalls]
@@ -117,7 +130,6 @@ class NginxTlsSni01(common.TLSSNI01):
             raise errors.MisconfigurationError(
                 'Certbot could not find an HTTP block to include '
                 'TLS-SNI-01 challenges in %s.' % root)
-
         config = [self._make_server_block(pair[0], pair[1])
                   for pair in six.moves.zip(self.achalls, ll_addrs)]
         config = nginxparser.UnspacedList(config)
diff --git a/certbot/plugins/common.py b/certbot/plugins/common.py
index f605eb751..420d15679 100644
--- a/certbot/plugins/common.py
+++ b/certbot/plugins/common.py
@@ -251,7 +251,7 @@ class Addr(object):
         """Normalized representation of addr/port tuple
         """
         if self.ipv6:
-            return (self._normalize_ipv6(self.tup[0]), self.tup[1])
+            return (self.get_ipv6_exploded(), self.tup[1])
         return self.tup
 
     def __eq__(self, other):