diff --git a/Modules/_ssl.c b/Modules/_ssl.c
index 986ec46..3047d97 100644
--- a/Modules/_ssl.c
+++ b/Modules/_ssl.c
@@ -1347,7 +1347,7 @@
 
 static PyObject *PySSL_SSLshutdown(PySSLObject *self)
 {
-	int err;
+	int err, ssl_err, sockstate;
 
 	/* Guard against closed socket */
 	if (self->Socket->sock_fd < 0) {
@@ -1356,13 +1356,42 @@
 		return NULL;
 	}
 
-	PySSL_BEGIN_ALLOW_THREADS
-	err = SSL_shutdown(self->ssl);
-	if (err == 0) {
-		/* we need to call it again to finish the shutdown */
+	while (1) {
+		PySSL_BEGIN_ALLOW_THREADS
 		err = SSL_shutdown(self->ssl);
+		if (err == 0) {
+			/* we need to call it again to finish the shutdown */
+			err = SSL_shutdown(self->ssl);
+		}
+		PySSL_END_ALLOW_THREADS
+		if (err >= 0)
+			break;
+		/* Possibly retry shutdown until timeout or failure */
+		ssl_err = SSL_get_error(self->ssl, err);
+		if (ssl_err == SSL_ERROR_WANT_READ)
+			sockstate = check_socket_and_wait_for_timeout(self->Socket, 0);
+		else if (ssl_err == SSL_ERROR_WANT_WRITE)
+			sockstate = check_socket_and_wait_for_timeout(self->Socket, 1);
+		else
+			break;
+		if (sockstate == SOCKET_HAS_TIMED_OUT) {
+			if (ssl_err == SSL_ERROR_WANT_READ)
+				PyErr_SetString(PySSLErrorObject,
+		                                "The read operation timed out");
+			else
+				PyErr_SetString(PySSLErrorObject,
+		                                "The write operation timed out");
+			return NULL;
+		}
+		else if (sockstate == SOCKET_TOO_LARGE_FOR_SELECT) {
+			PyErr_SetString(PySSLErrorObject,
+	                                "Underlying socket too large for select().");
+			return NULL;
+		}
+		else if (sockstate != SOCKET_OPERATION_OK)
+			/* Retain the SSL error code */
+			break;
 	}
-	PySSL_END_ALLOW_THREADS
 
 	if (err < 0)
 		return PySSL_SetError(self, err, __FILE__, __LINE__);