This paper was originally written in 2003 after working one of my first pentest assignments. I was green and mainly there to watch and learn. On this assignment the lead pentester took a random IP based on the network information conveniently labeled on each station. The results of his actions quickly caused problems (the IP address belonged to the printer of an executive) Once I returned home at the end of the week, I started working on an idea on how to allocate addresses. Yes there are many tools and devices (Ettercap and Fluke) to name a few that can do this, but they are noisy to say the least, my goal during pentesting was stealth and leaving a minimal footprint on the network. This paper is a result of those efforts.