def handshake(
        self,
        server_hostname,
        verify,
        trust_bundle,
        min_version,
        max_version,
        client_cert,
        client_key,
        client_key_passphrase,
    ):
        """
        Actually performs the TLS handshake. This is run automatically by
        wrapped socket, and shouldn't be needed in user code.
        """
        # First, we do the initial bits of connection setup. We need to create
        # a context, set its I/O funcs, and set the connection reference.
        self.context = Security.SSLCreateContext(
            None, SecurityConst.kSSLClientSide, SecurityConst.kSSLStreamType
        )
        result = Security.SSLSetIOFuncs(
            self.context, _read_callback_pointer, _write_callback_pointer
        )
        _assert_no_error(result)

        # Here we need to compute the handle to use. We do this by taking the
        # id of self modulo 2**31 - 1. If this is already in the dictionary, we
        # just keep incrementing by one until we find a free space.
        with _connection_ref_lock:
            handle = id(self) % 2147483647
            while handle in _connection_refs:
                handle = (handle + 1) % 2147483647
            _connection_refs[handle] = self

        result = Security.SSLSetConnection(self.context, handle)
        _assert_no_error(result)

        # If we have a server hostname, we should set that too.
        if server_hostname:
            if not isinstance(server_hostname, bytes):
                server_hostname = server_hostname.encode("utf-8")

            result = Security.SSLSetPeerDomainName(
                self.context, server_hostname, len(server_hostname)
            )
            _assert_no_error(result)

        # Setup the ciphers.
        self._set_ciphers()

        # Set the minimum and maximum TLS versions.
        result = Security.SSLSetProtocolVersionMin(self.context, min_version)
        _assert_no_error(result)

        result = Security.SSLSetProtocolVersionMax(self.context, max_version)
        _assert_no_error(result)

        # If there's a trust DB, we need to use it. We do that by telling
        # SecureTransport to break on server auth. We also do that if we don't
        # want to validate the certs at all: we just won't actually do any
        # authing in that case.
        if not verify or trust_bundle is not None:
            result = Security.SSLSetSessionOption(
                self.context, SecurityConst.kSSLSessionOptionBreakOnServerAuth, True
            )
            _assert_no_error(result)

        # If there's a client cert, we need to use it.
        if client_cert:
            self._keychain, self._keychain_dir = _temporary_keychain()
            self._client_cert_chain = _load_client_cert_chain(
                self._keychain, client_cert, client_key
            )
            result = Security.SSLSetCertificate(self.context, self._client_cert_chain)
            _assert_no_error(result)

        while True:
            with self._raise_on_error():
                result = Security.SSLHandshake(self.context)

                if result == SecurityConst.errSSLWouldBlock:
                    raise socket.timeout("handshake timed out")
                elif result == SecurityConst.errSSLServerAuthCompleted:
                    self._custom_validate(verify, trust_bundle)
                    continue
                else:
                    _assert_no_error(result)
                    break

        Actually performs the TLS handshake. This is run automatically by
        wrapped socket, and shouldn't be needed in user code.
        
product/gradle-plugin/src/main/python/pip/_vendor/urllib3/contrib/securetransport.py