I believe that this is the way it should be. Filters are processed in the order they are listed. It the Do not send is processed first it won't send the matched email, then the Send filter is process and all the matches are sent. If the Send is processed first the Matches get sent and the one in question won't be available to be held. Finally all emails that don't match any filters are processed and either sent or not sent depending on your no match settings.
Rcbjr: I have just tested it and it seems that you are right. The higher one on the list trumps the lower one.
How do you achieve the correct placement on the list? When I add a new filter it shows at the top and later moves to the bottom and I can't change the placement.
It doesn't seem like a very sophisticated system.
Can't help you with 2.0, but with 1.8, when I go to the Filter Page from the opening screen, I get a list of my filters and on the far right are up and down arrows beside each filter that allows me to move them up or down in the list. Just checked this out.