It might not be the safest (outpost should still recognise a different program, using the web shield localhost loopback), but first get it working, and then you can tweak it if required. If you have it as partially allowed, you will obviously get more queries from Outpost, you might try the grc.com leak test and see if it gets through. I tried a while ago and it didn’t get through, so it was being checked by outpost. The problem is I can’t remember if I was using the beta version of ashwebsv.exe.

I haven’t seen anything on the outpost forum recently, if you have a link I would be interested to see what it is about and if this would relate to web shield.