pfSense

As it is today route-to in pf(4) does not check for any static routes before sending the packet.
In 1.2.3 there were rules added to avoid this but they bring problems since you cannot do anymore reply-to or traffic shaping or follow some other policies.(Possibly not more relevant with the match action?)

The best solution would be for pf(4) to check static route before applying reply-to but there might be performance implications.
Reference:http://forum.pfsense.org/index.php/topic,36710.0.html