Anatomy of a Hack
The folks at InformIT -- actually authors Steve Riley and Jesper Johansson -- have excerpted a chapter of their security book entitled, "Protect Your Windows Network: From Perimeter to Data". The chapter is an interesting discussion of the pros and cons of penetration testing. In it, they discuss the anatomy of a "typical" hacking attempt and how how black-hats take advantage of typical configuration errors. Their intent? Education in order to protect networks by omitting the most common mistakes.
InformIT: Anatomy of a Hack - Rise and Fall of your Network