This talk will be an enjoyable conversation with good beer, great bourbon, and terrific friends who are reliving the journey of infosec maturity from the perspective of both a penetration testing company and their client over a three year period. Details of various engagements will be discussed along with post-mortem analysis, lessons learned, as well as resulting mitigation tactics and defensive strategies. We will discuss the outcomes at each stage of rendered service and how both client and vendor adjusted their approach to re-engage again and again. The engagement culminates in Red Team exercises that clearly demonstrate the infosec evolution of the client. The talk will leave the defensive audience with a sense of hope, a list of achievable goals, and several tactics. The red team with get a glimpse into the maw of the blue future and the value of their tradecraft. Special brief guest appearances and commentary are expected from others in the community that assisted the client along the way as well.