Pen Testing has evolved greatly over the years, but it is still more an art than a science. Tests performed by different professionals often yield wildly varied results. Even the same person or team repeating the same test can end up with different outcomes. This may cause a mess, and limits the value which can be derived from a Pen Test. To move our field forward we need to be able to produce measurable and consistent results. This talk will cover the art of Pen Testing and suggest a line we can draw to move this art form into the 21st century as a science.