In this talk Tyler discusses the highlights from another year of penetration testing. This includes the most direct challenge he has ever received when a CSO told him ‘You wont be able to hack our mainframe’ and the steps he took to gain root access to said mainframe. Tyler will discuss several tools written during the year as well as make public releases of the unpublished tools. Tyler will also discuss the surprising failures he had and what can be learned from those failures. Filled with war stories of social engineering- physical infiltration- internal and external network penetration tests and more this talk will not only be educational but very entertaining.