In this talk, Kevin Tackett takes attendees on an expedition through the tangled ruins of modern application architecture. Drawing from real-world penetration testing engagements, he will share stories of uncovering forgotten API endpoints still connected to production data, third-party integrations that outlived their original purpose but retained their access, and AI components bolted onto legacy systems with little consideration for the attack surface they introduced. Like any good archaeologist, a security tester must piece together fragments of understanding while avoiding the traps left behind by those who built before them.