You will know that I am a regular listener to the Security Now! podcasts, but I was recently reminded of the really useful utilities that are on Steve’s website.
Whenever I configure a new machine I always run ‘Shields Up!’ (top of the ‘services’ menu at grc.com) to check that none of the ports are vulnerable. It’s not a substitute for a full penetration test but it’s a very useful starting point and can signpost areas that you need to consider.
Steve has other great utilities there too, and of course every IT person ought to have a copy of Spinrite.