diff --git a/deps/cares/cares.gyp b/deps/cares/cares.gyp
index 053cdf8c8286ad..d654a896f56ffd 100644
--- a/deps/cares/cares.gyp
+++ b/deps/cares/cares.gyp
@@ -21,6 +21,8 @@
       'src/lib/ares__htable_strvp.h',
       'src/lib/ares__htable_szvp.c',
       'src/lib/ares__htable_szvp.h',
+      'src/lib/ares__htable_vpvp.c',
+      'src/lib/ares__htable_vpvp.h',
       'src/lib/ares__iface_ips.c',
       'src/lib/ares__iface_ips.h',
       'src/lib/ares__llist.c',
@@ -46,6 +48,7 @@
       'src/lib/ares_dns_record.c',
       'src/lib/ares_dns_private.h',
       'src/lib/ares_dns_write.c',
+      'src/lib/ares_event_configchg.c',
       'src/lib/ares_event.h',
       'src/lib/ares_event_win32.h',
       'src/lib/ares_event_epoll.c',
@@ -113,6 +116,11 @@
       'src/tools/ares_getopt.c',
       'src/tools/ares_getopt.h',
     ],
+    'cares_sources_mac': [
+      'config/darwin/ares_config.h',
+      'src/lib/ares_sysconfig_mac.c',
+      'src/lib/thirdparty/apple/dnsinfo.h',
+    ],
     'cares_sources_win': [
       'src/lib/config-win32.h',
       'src/lib/windows_port.c',
@@ -206,7 +214,9 @@
         }],
         [ 'OS=="mac" or OS=="ios"', {
           'include_dirs': [ 'config/darwin' ],
-          'sources': [ 'config/darwin/ares_config.h' ]
+          'sources': [
+            '<@(cares_sources_mac)',
+          ]
         }],
         [ 'OS=="freebsd" or OS=="dragonflybsd"', {
           'include_dirs': [ 'config/freebsd' ],
diff --git a/deps/cares/src/lib/thirdparty/apple/dnsinfo.h b/deps/cares/src/lib/thirdparty/apple/dnsinfo.h
new file mode 100644
index 00000000000000..d51c546f2f58ce
--- /dev/null
+++ b/deps/cares/src/lib/thirdparty/apple/dnsinfo.h
@@ -0,0 +1,128 @@
+/*
+ * Copyright (c) 2004-2006, 2008, 2009, 2011-2013, 2015-2018 Apple Inc. All rights reserved.
+ *
+ * @APPLE_LICENSE_HEADER_START@
+ *
+ * This file contains Original Code and/or Modifications of Original Code
+ * as defined in and that are subject to the Apple Public Source License
+ * Version 2.0 (the 'License'). You may not use this file except in
+ * compliance with the License. Please obtain a copy of the License at
+ * http://www.opensource.apple.com/apsl/ and read it before using this
+ * file.
+ *
+ * The Original Code and all software distributed under the License are
+ * distributed on an 'AS IS' basis, WITHOUT WARRANTY OF ANY KIND, EITHER
+ * EXPRESS OR IMPLIED, AND APPLE HEREBY DISCLAIMS ALL SUCH WARRANTIES,
+ * INCLUDING WITHOUT LIMITATION, ANY WARRANTIES OF MERCHANTABILITY,
+ * FITNESS FOR A PARTICULAR PURPOSE, QUIET ENJOYMENT OR NON-INFRINGEMENT.
+ * Please see the License for the specific language governing rights and
+ * limitations under the License.
+ *
+ * @APPLE_LICENSE_HEADER_END@
+ */
+
+#ifndef __DNSINFO_H__
+#define __DNSINFO_H__
+
+/*
+ * These routines provide access to the systems DNS configuration
+ */
+
+#include <os/availability.h>
+#include <sys/cdefs.h>
+#include <stdint.h>
+#include <sys/types.h>
+#include <sys/socket.h>
+#include <netinet/in.h>
+
+#define DNSINFO_VERSION   20170629
+
+#define DEFAULT_SEARCH_ORDER    200000   /* search order for the "default" resolver domain name */
+
+#define DNS_PTR(type, name)       \
+  union {           \
+    type    name;     \
+    uint64_t  _ ## name ## _p;  \
+  }
+
+#define DNS_VAR(type, name)       \
+  type  name
+
+
+#pragma pack(4)
+typedef struct {
+  struct in_addr  address;
+  struct in_addr  mask;
+} dns_sortaddr_t;
+#pragma pack()
+
+
+#pragma pack(4)
+typedef struct {
+  DNS_PTR(char *,     domain);  /* domain */
+  DNS_VAR(int32_t,    n_nameserver);  /* # nameserver */
+  DNS_PTR(struct sockaddr **, nameserver);
+  DNS_VAR(uint16_t,   port);    /* port (in host byte order) */
+  DNS_VAR(int32_t,    n_search);  /* # search */
+  DNS_PTR(char **,    search);
+  DNS_VAR(int32_t,    n_sortaddr);  /* # sortaddr */
+  DNS_PTR(dns_sortaddr_t **,  sortaddr);
+  DNS_PTR(char *,     options); /* options */
+  DNS_VAR(uint32_t,   timeout); /* timeout */
+  DNS_VAR(uint32_t,   search_order);  /* search_order */
+  DNS_VAR(uint32_t,   if_index);
+  DNS_VAR(uint32_t,   flags);
+  DNS_VAR(uint32_t,   reach_flags); /* SCNetworkReachabilityFlags */
+  DNS_VAR(uint32_t,   service_identifier);
+  DNS_PTR(char *,     cid);   /* configuration identifer */
+  DNS_PTR(char *,     if_name); /* if_index interface name */
+} dns_resolver_t;
+#pragma pack()
+
+
+#define DNS_RESOLVER_FLAGS_REQUEST_A_RECORDS  0x0002    /* always requesting for A dns records in queries */
+#define DNS_RESOLVER_FLAGS_REQUEST_AAAA_RECORDS 0x0004    /* always requesting for AAAA dns records in queries */
+
+#define DNS_RESOLVER_FLAGS_REQUEST_ALL_RECORDS  \
+  (DNS_RESOLVER_FLAGS_REQUEST_A_RECORDS | DNS_RESOLVER_FLAGS_REQUEST_AAAA_RECORDS)
+
+#define DNS_RESOLVER_FLAGS_SCOPED   0x1000    /* configuration is for scoped questions */
+#define DNS_RESOLVER_FLAGS_SERVICE_SPECIFIC 0x2000    /* configuration is service-specific */
+#define DNS_RESOLVER_FLAGS_SUPPLEMENTAL   0x4000    /* supplemental match configuration */
+
+
+#pragma pack(4)
+typedef struct {
+  DNS_VAR(int32_t,    n_resolver);    /* resolver configurations */
+  DNS_PTR(dns_resolver_t **,  resolver);
+  DNS_VAR(int32_t,    n_scoped_resolver); /* "scoped" resolver configurations */
+  DNS_PTR(dns_resolver_t **,  scoped_resolver);
+  DNS_VAR(uint64_t,   generation);
+  DNS_VAR(int32_t,    n_service_specific_resolver);
+  DNS_PTR(dns_resolver_t **,  service_specific_resolver);
+  DNS_VAR(uint32_t,   version);
+} dns_config_t;
+#pragma pack()
+
+
+__BEGIN_DECLS
+
+/*
+ * DNS configuration access APIs
+ */
+const char *
+dns_configuration_notify_key    (void)        API_AVAILABLE(macos(10.4), ios(2.0));
+
+dns_config_t *
+dns_configuration_copy    (void)        API_AVAILABLE(macos(10.4), ios(2.0));
+
+void
+dns_configuration_free    (dns_config_t *config)  API_AVAILABLE(macos(10.4), ios(2.0));
+
+void
+_dns_configuration_ack    (dns_config_t *config,
+         const char *bundle_id) API_AVAILABLE(macos(10.8), ios(6.0));
+
+__END_DECLS
+
+#endif  /* __DNSINFO_H__ */