Hacker Jeopardy Format and Teams

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Three teams took the stage for the 31st annual Hacker Jeopardy at DEF CON 33. Pandemonium arrived covered in felt from the night before. Something Chalupa entered from the blue corner. Only Lands rounded out the field. The format ran two rounds, single and double Jeopardy, with a final round. Six categories for round one covered pre-quantum cryptography, RFC 1925, urban thesaurus, DFIU clue crew questions, Win Actually, and Gmarks.

Single Jeopardy: Cipher History and Security Fundamentals

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Pre-quantum cryptography covered Caesar’s cipher, the 1467 Vigenère cipher that resisted frequency analysis for 300 years until Kasiski found repeating key patterns, the Spartan skytale, and the Playfair 5x5 keyword grid. The Enigma’s reflector, sharing its name with a bicycle safety feature, gave Turing the flaw he needed. Open-source security questions identified OWASP ZAP for web vulnerability scanning. Session fixation, bearer tokens, reflective injection, SS7 telecom routing, and SPF DNS records filled the security categories.

EFF Charity Auction and Double Jeopardy

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Between rounds, Win Schwartz ran a charity auction for the EFF using old Hacker Jeopardy coins and pins found at home. A DEF CON 29 challenge coin sold for $800. Two original 2012 serial-numbered coins with beer openers sold for $750 each. A season 30 pin went for $600. Double Jeopardy doubled point values and added categories covering Linux terminal outputs, hacker spelling bee, SE soft skills (IMSI, bearer tokens, SS7), and notorious hackers including Edward Snowden, LulzSec, and The Mentor.

Final Jeopardy and a Message to the Community

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Before final Jeopardy, the host told the crowd that things look bleak for many right now and urged the audience to take hacker skills back to communities, workplaces, and friend groups. The final category was “OG Physical Hacks in Three Parts,” showing an image contestants had to identify with three specific answers. Only Lands bet everything and got it wrong, dropping to zero. Pandemonium wagered nothing, staying at 7,600. The Chalupas also wagered zero and won.

Notable Quotes

Defcon community, I I love you guys. Lintile · ▶ 1:28:56

There’s never been a problem that I have ever heard of that hackers can’t solve. Lintile · ▶ 1:29:45

600 sold to some guy I can’t see. Win Schwartz · ▶ 37:56

Key Takeaways

  • Hacker Jeopardy reached its 31st edition across 33 DEF CON conferences, missing two years in between.
  • The EFF charity auction raised several thousand dollars from attendees bidding on rare DEF CON collector coins.
  • The Chalupas won by wagering zero in final Jeopardy after Only Lands lost everything on the wrong answer.

About the Speaker(s)

Jeff “The Dark Tangent” Moss is an internet security expert and the founder of both the Black Hat Briefings and DEF CON Hacking conferences.