Testing your IT Security defenses

The best way to make sure your infrastructure is secure, is to test its defenses. Just like with backups, you don't know if your system is fully functional until you've attempted a restore and succeeded. No matter how thorough you may be with your firewalls and network systems, we all make mistakes. Not only could you have missed something, but there are constant exploits & holes being released and tested on systems everywhere.
Hence, we need to try Hacking into your own system(s). This technique is commonly referred to as Pen-Testing (Penetration Testing). This is a deep field to go into, so I will just point you in a direction to start off with, by listing some of the common tools used in this field. That being said, the tools required for Pen-Testing, are the same used by hackers, so use caution.