diff --git a/library/ssl_tls.c b/library/ssl_tls.c
index e54bb0e50..cceb96fd0 100644
--- a/library/ssl_tls.c
+++ b/library/ssl_tls.c
@@ -3256,7 +3256,8 @@ int mbedtls_ssl_write_handshake_msg( mbedtls_ssl_context *ssl )
     /* Either send now, or just save to be sent (and resent) later */
 #if defined(MBEDTLS_SSL_PROTO_DTLS)
     if( ssl->conf->transport == MBEDTLS_SSL_TRANSPORT_DATAGRAM &&
-        hs_type != MBEDTLS_SSL_HS_HELLO_REQUEST )
+        ( ssl->out_msgtype != MBEDTLS_SSL_MSG_HANDSHAKE ||
+          hs_type != MBEDTLS_SSL_HS_HELLO_REQUEST ) )
     {
         if( ( ret = ssl_flight_append( ssl ) ) != 0 )
         {