I don't know if this is appropriate or not. I am seeking a way to find out if my company has security holes. My boss does NOT want to install Microsoft 2003 patches (believe me I've recommended it stronglyy). Is there a book where I can try to 'hack' our server from another IP address to show if there is vulnerability of not. I swear I am not a hacker, but I need to see if our network is secure. he is under the impression that if you are not trying to get in from a specific IP address, it's absolutely safe. i wanted to mention that even microsoft.com has been hacked but held my tongue. I need something nitty gritty. The lowest of the low tricks.
If this is an inappropriate request, please let me know. I don't mean to offend.