diff --git a/Doc/library/ssl.rst b/Doc/library/ssl.rst
index 08824feeb3958f..78d44a23a83bf0 100644
--- a/Doc/library/ssl.rst
+++ b/Doc/library/ssl.rst
@@ -823,6 +823,13 @@ Constants
 
    .. versionadded:: 3.12
 
+.. data:: OP_LEGACY_SERVER_CONNECT
+
+   Allow legacy insecure renegotiation between OpenSSL and unpatched servers
+   only.
+
+   .. versionadded:: 3.12
+
 .. data:: HAS_ALPN
 
    Whether the OpenSSL library has built-in support for the *Application-Layer
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index e926fc5e88e584..d4eb2d2e81fe0f 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -1461,6 +1461,8 @@ def _assert_context_options(self, ctx):
         if OP_CIPHER_SERVER_PREFERENCE != 0:
             self.assertEqual(ctx.options & OP_CIPHER_SERVER_PREFERENCE,
                              OP_CIPHER_SERVER_PREFERENCE)
+        self.assertEqual(ctx.options & ssl.OP_LEGACY_SERVER_CONNECT,
+                         0 if IS_OPENSSL_3_0_0 else ssl.OP_LEGACY_SERVER_CONNECT)
 
     def test_create_default_context(self):
         ctx = ssl.create_default_context()
@@ -3815,6 +3817,20 @@ def test_compression_disabled(self):
                                    sni_name=hostname)
         self.assertIs(stats['compression'], None)
 
+    def test_legacy_server_connect(self):
+        client_context, server_context, hostname = testing_context()
+        client_context.options |= ssl.OP_LEGACY_SERVER_CONNECT
+        server_params_test(client_context, server_context,
+                                   chatty=True, connectionchatty=True,
+                                   sni_name=hostname)
+
+    def test_no_legacy_server_connect(self):
+        client_context, server_context, hostname = testing_context()
+        client_context.options &= ~ssl.OP_LEGACY_SERVER_CONNECT
+        server_params_test(client_context, server_context,
+                                   chatty=True, connectionchatty=True,
+                                   sni_name=hostname)
+
     @unittest.skipIf(Py_DEBUG_WIN32, "Avoid mixing debug/release CRT on Windows")
     def test_dh_params(self):
         # Check we can get a connection with ephemeral Diffie-Hellman
diff --git a/Misc/NEWS.d/next/Core and Builtins/2022-06-17-08-00-34.gh-issue-89051.yP4Na0.rst b/Misc/NEWS.d/next/Core and Builtins/2022-06-17-08-00-34.gh-issue-89051.yP4Na0.rst
new file mode 100644
index 00000000000000..5c8164863b8192
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2022-06-17-08-00-34.gh-issue-89051.yP4Na0.rst	
@@ -0,0 +1 @@
+Add :data:`ssl.OP_LEGACY_SERVER_CONNECT`
diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index 591eb91dd0f340..8f03a846aed089 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -5845,6 +5845,8 @@ sslmodule_init_constants(PyObject *m)
                             SSL_OP_CIPHER_SERVER_PREFERENCE);
     PyModule_AddIntConstant(m, "OP_SINGLE_DH_USE", SSL_OP_SINGLE_DH_USE);
     PyModule_AddIntConstant(m, "OP_NO_TICKET", SSL_OP_NO_TICKET);
+    PyModule_AddIntConstant(m, "OP_LEGACY_SERVER_CONNECT",
+                            SSL_OP_LEGACY_SERVER_CONNECT);
 #ifdef SSL_OP_SINGLE_ECDH_USE
     PyModule_AddIntConstant(m, "OP_SINGLE_ECDH_USE", SSL_OP_SINGLE_ECDH_USE);
 #endif