If you read the OPs reply #11, having reinstalled win7 and used the latest Outpost version 7, which is meant to be fully compatible with win7, this problem doesn't occur (so far).
So as I said I think it was a case of Outpost pro 2009 (version 6.x) not being fully compatible with win7, but then again it came out earlier than win7, so I wouldn't expect it to be fully compatible.