diff --git a/Doc/library/ssl.rst b/Doc/library/ssl.rst
index 7371024..5d5232e 100644
--- a/Doc/library/ssl.rst
+++ b/Doc/library/ssl.rst
@@ -831,6 +831,15 @@
 
    .. versionadded:: 3.3
 
+.. data:: OP_ENABLE_MIDDLEBOX_COMPAT
+
+   Send dummy Change Cipher Spec (CCS) messages in TLS 1.3 handshake to make
+   a TLS 1.3 connection look more like a TLS 1.2 connection.
+
+   This option is only available with OpenSSL 1.1.1 and later.
+
+   .. versionadded:: 3.8
+
 .. data:: OP_NO_COMPRESSION
 
    Disable compression on the SSL channel.  This is useful if the application
diff --git a/Doc/whatsnew/3.7.rst b/Doc/whatsnew/3.7.rst
index c924f6d..10aed52 100644
--- a/Doc/whatsnew/3.7.rst
+++ b/Doc/whatsnew/3.7.rst
@@ -669,6 +669,9 @@
 than the U-label form (``"pythön.org"``). (Contributed by
 Nathaniel J. Smith and Christian Heimes in :issue:`28414`.)
 
+The ssl module has preliminary and experimental support for TLS 1.3 and
+OpenSSL 1.1.1. (Contributed by Christian Heimes in :issue:`32947`,
+:issue:`20995`, :issue:`29136`, and :issue:`30622`)
 
 string
 ------
diff --git a/Lib/test/test_asyncio/utils.py b/Lib/test/test_asyncio/utils.py
index 96dfe2f..711085f 100644
--- a/Lib/test/test_asyncio/utils.py
+++ b/Lib/test/test_asyncio/utils.py
@@ -74,6 +74,8 @@
     server_context.load_cert_chain(ONLYCERT, ONLYKEY)
     server_context.check_hostname = False
     server_context.verify_mode = ssl.CERT_NONE
+    # TODO: fix TLSv1.3 support
+    server_context.options |= ssl.OP_NO_TLSv1_3
     return server_context
 
 
diff --git a/Lib/test/test_ftplib.py b/Lib/test/test_ftplib.py
index 32aab04..1a8e2f9 100644
--- a/Lib/test/test_ftplib.py
+++ b/Lib/test/test_ftplib.py
@@ -312,6 +312,8 @@
 
         def secure_connection(self):
             context = ssl.SSLContext()
+            # TODO: fix TLSv1.3 support
+            context.options |= ssl.OP_NO_TLSv1_3
             context.load_cert_chain(CERTFILE)
             socket = context.wrap_socket(self.socket,
                                          suppress_ragged_eofs=False,
@@ -908,6 +910,8 @@
     def test_context(self):
         self.client.quit()
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
+        # TODO: fix TLSv1.3 support
+        ctx.options |= ssl.OP_NO_TLSv1_3
         ctx.check_hostname = False
         ctx.verify_mode = ssl.CERT_NONE
         self.assertRaises(ValueError, ftplib.FTP_TLS, keyfile=CERTFILE,
@@ -940,6 +944,8 @@
     def test_check_hostname(self):
         self.client.quit()
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
+        # TODO: fix TLSv1.3 support
+        ctx.options |= ssl.OP_NO_TLSv1_3
         self.assertEqual(ctx.verify_mode, ssl.CERT_REQUIRED)
         self.assertEqual(ctx.check_hostname, True)
         ctx.load_verify_locations(CAFILE)
diff --git a/Lib/test/test_poplib.py b/Lib/test/test_poplib.py
index 4d7a439..fd0db79 100644
--- a/Lib/test/test_poplib.py
+++ b/Lib/test/test_poplib.py
@@ -153,6 +153,8 @@
             if self.tls_active is False:
                 self.push('+OK Begin TLS negotiation')
                 context = ssl.SSLContext()
+                # TODO: fix TLSv1.3 support
+                context.options |= ssl.OP_NO_TLSv1_3
                 context.load_cert_chain(CERTFILE)
                 tls_sock = context.wrap_socket(self.socket,
                                                server_side=True,
@@ -356,6 +358,8 @@
     def test_stls_context(self):
         expected = b'+OK Begin TLS negotiation'
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
+        # TODO: fix TLSv1.3 support
+        ctx.options |= ssl.OP_NO_TLSv1_3
         ctx.load_verify_locations(CAFILE)
         self.assertEqual(ctx.verify_mode, ssl.CERT_REQUIRED)
         self.assertEqual(ctx.check_hostname, True)
@@ -396,6 +400,8 @@
 
     def test_context(self):
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
+        # TODO: fix TLSv1.3 support
+        ctx.options |= ssl.OP_NO_TLSv1_3
         ctx.check_hostname = False
         ctx.verify_mode = ssl.CERT_NONE
         self.assertRaises(ValueError, poplib.POP3_SSL, self.server.host,
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 3b34fc0..d978a9e 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -30,7 +30,8 @@
 PROTOCOLS = sorted(ssl._PROTOCOL_NAMES)
 HOST = support.HOST
 IS_LIBRESSL = ssl.OPENSSL_VERSION.startswith('LibreSSL')
-IS_OPENSSL_1_1 = not IS_LIBRESSL and ssl.OPENSSL_VERSION_INFO >= (1, 1, 0)
+IS_OPENSSL_1_1_0 = not IS_LIBRESSL and ssl.OPENSSL_VERSION_INFO >= (1, 1, 0)
+IS_OPENSSL_1_1_1 = not IS_LIBRESSL and ssl.OPENSSL_VERSION_INFO >= (1, 1, 1)
 PY_SSL_DEFAULT_CIPHERS = sysconfig.get_config_var('PY_SSL_DEFAULT_CIPHERS')
 
 def data_file(*name):
@@ -54,6 +55,7 @@
 BYTES_CAPATH = os.fsencode(CAPATH)
 CAFILE_NEURONIO = data_file("capath", "4e1295a3.0")
 CAFILE_CACERT = data_file("capath", "5ed36f99.0")
+WRONG_CERT = data_file("wrongcert.pem")
 
 CERTFILE_INFO = {
     'issuer': ((('countryName', 'XY'),),
@@ -124,6 +126,7 @@
 OP_SINGLE_DH_USE = getattr(ssl, "OP_SINGLE_DH_USE", 0)
 OP_SINGLE_ECDH_USE = getattr(ssl, "OP_SINGLE_ECDH_USE", 0)
 OP_CIPHER_SERVER_PREFERENCE = getattr(ssl, "OP_CIPHER_SERVER_PREFERENCE", 0)
+OP_ENABLE_MIDDLEBOX_COMPAT = getattr(ssl, "OP_ENABLE_MIDDLEBOX_COMPAT", 0)
 
 
 def handle_error(prefix):
@@ -232,6 +235,7 @@
 
     server_context = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER)
     server_context.load_cert_chain(server_cert)
+    client_context.load_verify_locations(SIGNING_CA)
 
     return client_context, server_context, hostname
 
@@ -1016,7 +1020,8 @@
         default = (ssl.OP_ALL | ssl.OP_NO_SSLv2 | ssl.OP_NO_SSLv3)
         # SSLContext also enables these by default
         default |= (OP_NO_COMPRESSION | OP_CIPHER_SERVER_PREFERENCE |
-                    OP_SINGLE_DH_USE | OP_SINGLE_ECDH_USE)
+                    OP_SINGLE_DH_USE | OP_SINGLE_ECDH_USE |
+                    OP_ENABLE_MIDDLEBOX_COMPAT)
         self.assertEqual(default, ctx.options)
         ctx.options |= ssl.OP_NO_TLSv1
         self.assertEqual(default | ssl.OP_NO_TLSv1, ctx.options)
@@ -1778,6 +1783,8 @@
         der = ssl.PEM_cert_to_DER_cert(pem)
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS)
         ctx.verify_mode = ssl.CERT_REQUIRED
+        # TODO: fix TLSv1.3 support
+        ctx.options |= ssl.OP_NO_TLSv1_3
         ctx.load_verify_locations(cadata=pem)
         with ctx.wrap_socket(socket.socket(socket.AF_INET)) as s:
             s.connect(self.server_addr)
@@ -1787,6 +1794,8 @@
         # same with DER
         ctx = ssl.SSLContext(ssl.PROTOCOL_TLS)
         ctx.verify_mode = ssl.CERT_REQUIRED
+        # TODO: fix TLSv1.3 support
+        ctx.options |= ssl.OP_NO_TLSv1_3
         ctx.load_verify_locations(cadata=der)
         with ctx.wrap_socket(socket.socket(socket.AF_INET)) as s:
             s.connect(self.server_addr)
@@ -2629,7 +2638,10 @@
     def test_ecc_cert(self):
         client_context = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
         client_context.load_verify_locations(SIGNING_CA)
-        client_context.set_ciphers('ECDHE:ECDSA:!NULL:!aRSA')
+        client_context.set_ciphers(
+            'TLS13-AES-128-GCM-SHA256:TLS13-CHACHA20-POLY1305-SHA256:'
+            'ECDHE:ECDSA:!NULL:!aRSA'
+        )
         hostname = SIGNED_CERTFILE_ECC_HOSTNAME
 
         server_context = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER)
@@ -2650,6 +2662,9 @@
     def test_dual_rsa_ecc(self):
         client_context = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
         client_context.load_verify_locations(SIGNING_CA)
+        # TODO: fix TLSv1.3 once SSLContext can restrict signature
+        #       algorithms.
+        client_context.options |= ssl.OP_NO_TLSv1_3
         # only ECDSA certs
         client_context.set_ciphers('ECDHE:ECDSA:!NULL:!aRSA')
         hostname = SIGNED_CERTFILE_ECC_HOSTNAME
@@ -2676,6 +2691,8 @@
 
         server_context = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER)
         server_context.load_cert_chain(IDNSANSFILE)
+        # TODO: fix TLSv1.3 support
+        server_context.options |= ssl.OP_NO_TLSv1_3
 
         context = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
         context.verify_mode = ssl.CERT_REQUIRED
@@ -2738,15 +2755,22 @@
         Launch a server with CERT_REQUIRED, and check that trying to
         connect to it with a wrong client certificate fails.
         """
-        certfile = os.path.join(os.path.dirname(__file__) or os.curdir,
-                                   "wrongcert.pem")
-        server = ThreadedEchoServer(CERTFILE,
-                                    certreqs=ssl.CERT_REQUIRED,
-                                    cacerts=CERTFILE, chatty=False,
-                                    connectionchatty=False)
+        client_context, server_context, hostname = testing_context()
+        # load client cert
+        client_context.load_cert_chain(WRONG_CERT)
+        # require TLS client authentication
+        server_context.verify_mode = ssl.CERT_REQUIRED
+        # TODO: fix TLSv1.3 support
+        # With TLS 1.3, test fails with exception in server thread
+        server_context.options |= ssl.OP_NO_TLSv1_3
+
+        server = ThreadedEchoServer(
+            context=server_context, chatty=True, connectionchatty=True,
+        )
+
         with server, \
-                socket.socket() as sock, \
-                test_wrap_socket(sock, certfile=certfile) as s:
+                client_context.wrap_socket(socket.socket(),
+                                           server_hostname=hostname) as s:
             try:
                 # Expect either an SSL error about the server rejecting
                 # the connection, or a low-level connection reset (which
@@ -3400,7 +3424,9 @@
                 self.assertIs(s.version(), None)
                 self.assertIs(s._sslobj, None)
                 s.connect((HOST, server.port))
-                if ssl.OPENSSL_VERSION_INFO >= (1, 0, 2):
+                if ssl.OPENSSL_VERSION_INFO >= (1, 1, 1):
+                    self.assertEqual(s.version(), 'TLSv1.3')
+                elif ssl.OPENSSL_VERSION_INFO >= (1, 0, 2):
                     self.assertEqual(s.version(), 'TLSv1.2')
                 else:  # 0.9.8 to 1.0.1
                     self.assertIn(s.version(), ('TLSv1', 'TLSv1.2'))
@@ -3412,18 +3438,18 @@
     def test_tls1_3(self):
         context = ssl.SSLContext(ssl.PROTOCOL_TLS)
         context.load_cert_chain(CERTFILE)
-        # disable all but TLS 1.3
         context.options |= (
             ssl.OP_NO_TLSv1 | ssl.OP_NO_TLSv1_1 | ssl.OP_NO_TLSv1_2
         )
         with ThreadedEchoServer(context=context) as server:
             with context.wrap_socket(socket.socket()) as s:
                 s.connect((HOST, server.port))
-                self.assertIn(s.cipher()[0], [
+                self.assertIn(s.cipher()[0], {
                     'TLS13-AES-256-GCM-SHA384',
                     'TLS13-CHACHA20-POLY1305-SHA256',
                     'TLS13-AES-128-GCM-SHA256',
-                ])
+                })
+                self.assertEqual(s.version(), 'TLSv1.3')
 
     @unittest.skipUnless(ssl.HAS_ECDH, "test requires ECDH-enabled OpenSSL")
     def test_default_ecdh_curve(self):
@@ -3452,58 +3478,54 @@
         if support.verbose:
             sys.stdout.write("\n")
 
-        server = ThreadedEchoServer(CERTFILE,
-                                    certreqs=ssl.CERT_NONE,
-                                    ssl_version=ssl.PROTOCOL_TLS_SERVER,
-                                    cacerts=CERTFILE,
+        client_context, server_context, hostname = testing_context()
+        # TODO: fix TLSv1.3 support
+        client_context.options |= ssl.OP_NO_TLSv1_3
+
+        server = ThreadedEchoServer(context=server_context,
                                     chatty=True,
                                     connectionchatty=False)
+
         with server:
-            s = test_wrap_socket(socket.socket(),
-                                server_side=False,
-                                certfile=CERTFILE,
-                                ca_certs=CERTFILE,
-                                cert_reqs=ssl.CERT_NONE,
-                                ssl_version=ssl.PROTOCOL_TLS_CLIENT)
-            s.connect((HOST, server.port))
-            # get the data
-            cb_data = s.get_channel_binding("tls-unique")
-            if support.verbose:
-                sys.stdout.write(" got channel binding data: {0!r}\n"
-                                 .format(cb_data))
+            with client_context.wrap_socket(
+                    socket.socket(),
+                    server_hostname=hostname) as s:
+                s.connect((HOST, server.port))
+                # get the data
+                cb_data = s.get_channel_binding("tls-unique")
+                if support.verbose:
+                    sys.stdout.write(
+                        " got channel binding data: {0!r}\n".format(cb_data))
 
-            # check if it is sane
-            self.assertIsNotNone(cb_data)
-            self.assertEqual(len(cb_data), 12) # True for TLSv1
+                # check if it is sane
+                self.assertIsNotNone(cb_data)
+                self.assertEqual(len(cb_data), 12) # True for TLSv1
 
-            # and compare with the peers version
-            s.write(b"CB tls-unique\n")
-            peer_data_repr = s.read().strip()
-            self.assertEqual(peer_data_repr,
-                             repr(cb_data).encode("us-ascii"))
-            s.close()
+                # and compare with the peers version
+                s.write(b"CB tls-unique\n")
+                peer_data_repr = s.read().strip()
+                self.assertEqual(peer_data_repr,
+                                 repr(cb_data).encode("us-ascii"))
 
             # now, again
-            s = test_wrap_socket(socket.socket(),
-                                server_side=False,
-                                certfile=CERTFILE,
-                                ca_certs=CERTFILE,
-                                cert_reqs=ssl.CERT_NONE,
-                                ssl_version=ssl.PROTOCOL_TLS_CLIENT)
-            s.connect((HOST, server.port))
-            new_cb_data = s.get_channel_binding("tls-unique")
-            if support.verbose:
-                sys.stdout.write(" got another channel binding data: {0!r}\n"
-                                 .format(new_cb_data))
-            # is it really unique
-            self.assertNotEqual(cb_data, new_cb_data)
-            self.assertIsNotNone(cb_data)
-            self.assertEqual(len(cb_data), 12) # True for TLSv1
-            s.write(b"CB tls-unique\n")
-            peer_data_repr = s.read().strip()
-            self.assertEqual(peer_data_repr,
-                             repr(new_cb_data).encode("us-ascii"))
-            s.close()
+            with client_context.wrap_socket(
+                    socket.socket(),
+                    server_hostname=hostname) as s:
+                s.connect((HOST, server.port))
+                new_cb_data = s.get_channel_binding("tls-unique")
+                if support.verbose:
+                    sys.stdout.write(
+                        "got another channel binding data: {0!r}\n".format(
+                            new_cb_data)
+                    )
+                # is it really unique
+                self.assertNotEqual(cb_data, new_cb_data)
+                self.assertIsNotNone(cb_data)
+                self.assertEqual(len(cb_data), 12) # True for TLSv1
+                s.write(b"CB tls-unique\n")
+                peer_data_repr = s.read().strip()
+                self.assertEqual(peer_data_repr,
+                                 repr(new_cb_data).encode("us-ascii"))
 
     def test_compression(self):
         client_context, server_context, hostname = testing_context()
@@ -3528,8 +3550,11 @@
     def test_dh_params(self):
         # Check we can get a connection with ephemeral Diffie-Hellman
         client_context, server_context, hostname = testing_context()
+        # test scenario needs TLS <= 1.2
+        client_context.options |= ssl.OP_NO_TLSv1_3
         server_context.load_dh_params(DHFILE)
         server_context.set_ciphers("kEDH")
+        server_context.options |= ssl.OP_NO_TLSv1_3
         stats = server_params_test(client_context, server_context,
                                    chatty=True, connectionchatty=True,
                                    sni_name=hostname)
@@ -3539,9 +3564,11 @@
             self.fail("Non-DH cipher: " + cipher[0])
 
     @unittest.skipUnless(HAVE_SECP_CURVES, "needs secp384r1 curve support")
+    @unittest.skipIf(IS_OPENSSL_1_1_1, "TODO: Test doesn't work on 1.1.1")
     def test_ecdh_curve(self):
         # server secp384r1, client auto
         client_context, server_context, hostname = testing_context()
+
         server_context.set_ecdh_curve("secp384r1")
         server_context.set_ciphers("ECDHE:!eNULL:!aNULL")
         server_context.options |= ssl.OP_NO_TLSv1 | ssl.OP_NO_TLSv1_1
@@ -3572,7 +3599,7 @@
             pass
         else:
             # OpenSSL 1.0.2 does not fail although it should.
-            if IS_OPENSSL_1_1:
+            if IS_OPENSSL_1_1_0:
                 self.fail("mismatch curve did not fail")
 
     def test_selected_alpn_protocol(self):
@@ -3616,7 +3643,7 @@
             except ssl.SSLError as e:
                 stats = e
 
-            if (expected is None and IS_OPENSSL_1_1
+            if (expected is None and IS_OPENSSL_1_1_0
                     and ssl.OPENSSL_VERSION_INFO < (1, 1, 0, 6)):
                 # OpenSSL 1.1.0 to 1.1.0e raises handshake error
                 self.assertIsInstance(stats, ssl.SSLError)
@@ -3823,6 +3850,8 @@
 
     def test_session(self):
         client_context, server_context, hostname = testing_context()
+        # TODO: sessions aren't compatible with TLSv1.3 yet
+        client_context.options |= ssl.OP_NO_TLSv1_3
 
         # first connection without session
         stats = server_params_test(client_context, server_context,
@@ -3881,7 +3910,7 @@
         client_context, server_context, hostname = testing_context()
         client_context2, _, _ = testing_context()
 
-        # TODO: session reuse does not work with TLS 1.3
+        # TODO: session reuse does not work with TLSv1.3
         client_context.options |= ssl.OP_NO_TLSv1_3
         client_context2.options |= ssl.OP_NO_TLSv1_3
 
diff --git a/Misc/NEWS.d/next/Library/2018-02-25-13-06-21.bpo-32947.mqStVW.rst b/Misc/NEWS.d/next/Library/2018-02-25-13-06-21.bpo-32947.mqStVW.rst
new file mode 100644
index 0000000..28de360
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2018-02-25-13-06-21.bpo-32947.mqStVW.rst
@@ -0,0 +1,2 @@
+Add OP_ENABLE_MIDDLEBOX_COMPAT and test workaround for TLSv1.3 for future
+compatibility with OpenSSL 1.1.1.
diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index 52695fe..f50823e 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -5681,6 +5681,10 @@
     PyModule_AddIntConstant(m, "OP_NO_COMPRESSION",
                             SSL_OP_NO_COMPRESSION);
 #endif
+#ifdef SSL_OP_ENABLE_MIDDLEBOX_COMPAT
+    PyModule_AddIntConstant(m, "OP_ENABLE_MIDDLEBOX_COMPAT",
+                            SSL_OP_ENABLE_MIDDLEBOX_COMPAT);
+#endif
 
 #ifdef X509_CHECK_FLAG_ALWAYS_CHECK_SUBJECT
     PyModule_AddIntConstant(m, "HOSTFLAG_ALWAYS_CHECK_SUBJECT",
diff --git a/Tools/ssl/multissltests.py b/Tools/ssl/multissltests.py
index 75874cf..70913c7 100755
--- a/Tools/ssl/multissltests.py
+++ b/Tools/ssl/multissltests.py
@@ -41,24 +41,20 @@
 log = logging.getLogger("multissl")
 
 OPENSSL_OLD_VERSIONS = [
-     # "0.9.8zh",
-     # "1.0.1u",
+    "1.0.2",
 ]
 
 OPENSSL_RECENT_VERSIONS = [
-     "1.0.2",
-     "1.0.2m",
-     "1.1.0g",
+    "1.0.2n",
+    "1.1.0g",
+    "1.1.1-pre1",
 ]
 
 LIBRESSL_OLD_VERSIONS = [
-    # "2.3.10",
-    # "2.4.5",
 ]
 
 LIBRESSL_RECENT_VERSIONS = [
-    "2.5.3",
-    "2.5.5",
+    # "2.6.5",
 ]
 
 # store files in ../multissl