I'm posting from the IRC chat what as happening for posterity's sake:
<oana> sugarcakes, ok. What is happening is that the handler in NIB has a higher priority than regexroute.
<oana> that handler, if it doesnt recognize the number as a registered user, it will try to route it to a gateway
<oana> and the route messages never reaches regexroute. If you want to be able to call to tone/* set a higher priority to the regexroute handler
<oana> what you need to do is to set something like route=75 in the [priorities] section in regexroute.conf
<oana> it's commented by default in the conf, so uncomment it too