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The Only Way to Win Is by Learning: Deception Design, Read Through a Comedy Game Show
Sunday September 13, 2026 1:00pm - 1:50pm CDT
Swissôtel Chicago
Most deception technology fails the same way a bad magic trick fails: the audience can see the strings. A pristine honeypot, a too-obvious credential, a decoy environment without any of the messy human fingerprints of a real network — these tip off skilled attackers in the first thirty seconds of contact and then sit unused, generating no intelligence and no value.
This talk argues that the people who have already solved this design problem are, improbably, the writers of Dropout's Game Changer — a comedy game show where contestants don't know the rules, and where the host's entire job is to design environments that intelligent, adaptive people will inhabit fully while being watched. The parallels to defensive cyber deception turn out to be precise and useful.
Working through concepts including verisimilitude and "coherent imperfection," choice architecture and the path of least resistance, flow-state engineering for sustained engagement past the initial probe, nested observation layers modeled on the show's "Bingo" episode, and the counterintuitive Tularosa finding that announcing deception makes it more effective, this session translates game-design craft into practical honeypot, honeytoken, and deception-fabric architecture any defender can deploy.
Attendees will leave with a design checklist for building deceptive environments that sustain coherence under adversarial pressure, a vocabulary for evaluating commercial deception platforms against actual attacker psychology, and an argument for why the best deception operators are, in a real sense, game designers.
The talk is interactive. The audience is already playing.
Speakers
avatar for Dylan Shroll

Dylan Shroll

Security Engineer, Bankers Trust
Dylan is a cybersecurity engineer with six-plus years across healthcare, financial services, lottery, and logistics — everywhere the stakes are high and the regulations are higher still. She specializes in LLM-powered cyber deception operations and behavior-science-driven security... Read More →
Sunday September 13, 2026 1:00pm - 1:50pm CDT
Swissôtel Chicago 323 E Wacker Dr, Chicago, IL 60601, USA
  Talk Track 1

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