diff --git a/Doc/library/ssl.rst b/Doc/library/ssl.rst
index 25ecfaec256..e12cfc6af0e 100644
--- a/Doc/library/ssl.rst
+++ b/Doc/library/ssl.rst
@@ -821,6 +821,15 @@ Constants
 
    .. 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:: 3.6.7
+
 .. data:: OP_NO_COMPRESSION
 
    Disable compression on the SSL channel.  This is useful if the application
diff --git a/Lib/test/test_asyncio/test_events.py b/Lib/test/test_asyncio/test_events.py
index 548a4610f77..bd62897b6a5 100644
--- a/Lib/test/test_asyncio/test_events.py
+++ b/Lib/test/test_asyncio/test_events.py
@@ -1187,7 +1187,11 @@ class EventLoopTestsMixin:
                     self.loop.run_until_complete(f_c)
 
         # close connection
-        proto.transport.close()
+        # transport may be None with TLS 1.3, because connection is
+        # interrupted, server is unable to send session tickets, and
+        # transport is closed.
+        if proto.transport is not None:
+            proto.transport.close()
         server.close()
 
     def test_legacy_create_server_ssl_match_failed(self):
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 9785a59a7e4..6b3cd5b6e37 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -89,6 +89,7 @@ OP_NO_COMPRESSION = getattr(ssl, "OP_NO_COMPRESSION", 0)
 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):
@@ -181,8 +182,8 @@ class BasicSocketTests(unittest.TestCase):
         ssl.OP_NO_TLSv1
         ssl.OP_NO_TLSv1_3
     if ssl.OPENSSL_VERSION_INFO >= (1, 0, 1):
-            ssl.OP_NO_TLSv1_1
-            ssl.OP_NO_TLSv1_2
+        ssl.OP_NO_TLSv1_1
+        ssl.OP_NO_TLSv1_2
 
     def test_str_for_enums(self):
         # Make sure that the PROTOCOL_* constants have enum-like string
@@ -899,12 +900,13 @@ class ContextTests(unittest.TestCase):
 
     @skip_if_broken_ubuntu_ssl
     def test_options(self):
-        ctx = ssl.SSLContext(ssl.PROTOCOL_TLSv1)
+        ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_CLIENT)
         # OP_ALL | OP_NO_SSLv2 | OP_NO_SSLv3 is the default value
         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)
@@ -1857,11 +1859,23 @@ if _have_threads:
                         self.sock, server_side=True)
                     self.server.selected_npn_protocols.append(self.sslconn.selected_npn_protocol())
                     self.server.selected_alpn_protocols.append(self.sslconn.selected_alpn_protocol())
-                except (ssl.SSLError, ConnectionResetError, OSError) as e:
+                except (ConnectionResetError, BrokenPipeError) as e:
                     # We treat ConnectionResetError as though it were an
                     # SSLError - OpenSSL on Ubuntu abruptly closes the
                     # connection when asked to use an unsupported protocol.
                     #
+                    # BrokenPipeError is raised in TLS 1.3 mode, when OpenSSL
+                    # tries to send session tickets after handshake.
+                    # https://github.com/openssl/openssl/issues/6342
+                    self.server.conn_errors.append(str(e))
+                    if self.server.chatty:
+                        handle_error(
+                            "\n server:  bad connection attempt from " + repr(
+                                self.addr) + ":\n")
+                    self.running = False
+                    self.close()
+                    return False
+                except (ssl.SSLError, OSError) as e:
                     # OSError may occur with wrong protocols, e.g. both
                     # sides use PROTOCOL_TLS_SERVER.
                     #
@@ -3042,7 +3056,7 @@ if _have_threads:
                 # Block on the accept and wait on the connection to close.
                 evt.set()
                 remote, peer = server.accept()
-                remote.recv(1)
+                remote.send(remote.recv(4))
 
             t = threading.Thread(target=serve)
             t.start()
@@ -3050,6 +3064,8 @@ if _have_threads:
             evt.wait()
             client = context.wrap_socket(socket.socket())
             client.connect((host, port))
+            client.send(b'data')
+            client.recv()
             client_addr = client.getsockname()
             client.close()
             t.join()
diff --git a/Misc/NEWS.d/next/Library/2018-08-14-08-57-01.bpo-32947.mqStVW.rst b/Misc/NEWS.d/next/Library/2018-08-14-08-57-01.bpo-32947.mqStVW.rst
new file mode 100644
index 00000000000..28de360c367
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2018-08-14-08-57-01.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 5e007da858b..e0c7dfbdaac 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -5486,6 +5486,10 @@ PyInit__ssl(void)
     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
 
 #if HAVE_SNI
     r = Py_True;