diff --git a/library/ssl_tls.c b/library/ssl_tls.c
index c64036c0c..38690fa66 100644
--- a/library/ssl_tls.c
+++ b/library/ssl_tls.c
@@ -3201,8 +3201,10 @@ int mbedtls_ssl_write_handshake_msg( mbedtls_ssl_context *ssl )
         }
     }
 
-    if( ssl->out_msgtype == MBEDTLS_SSL_MSG_HANDSHAKE &&
-        hs_type != MBEDTLS_SSL_HS_HELLO_REQUEST &&
+    /* Whenever we send anything different from a
+     * HelloRequest we should be in a handshake - double check. */
+    if( ! ( ssl->out_msgtype == MBEDTLS_SSL_MSG_HANDSHAKE &&
+            hs_type          == MBEDTLS_SSL_HS_HELLO_REQUEST ) &&
         ssl->handshake == NULL )
     {
         MBEDTLS_SSL_DEBUG_MSG( 1, ( "should never happen" ) );
@@ -3296,8 +3298,8 @@ 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 &&
-        ( ssl->out_msgtype != MBEDTLS_SSL_MSG_HANDSHAKE ||
-          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 )
         {