Episode 266 - Live from BlackHat and DEFCON 34, Telegram Gets Extorted, Vegas Enshitification Redux, Bartender's Corporate Handcuffs

Welcome to this week's episode of the PEBCAK Podcast!  We’ve got four amazing stories this week so sit back, relax, and keep being awesome!  Be sure to stick around for our Dad Joke of the Week. (DJOW)

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Telegram's App Store Scare

Apple briefly yanked Telegram from the App Store after an extortionist planted AI-doctored illegal content in a public group by editing an old message, exploiting a blind spot in moderation visibility.

• https://x.com/durov/status/2084686326540996625
• Telegram founder Pavel Durov revealed Apple pulled Telegram from the App Store overnight and restored it within hours, after an attacker identified as a "takedown extortionist" who demands ransom from group owners under threat of triggering platform bans used automated accounts to insert AI-modified illegal pornographic content by editing an old message in an active public chat, effectively backdating and hiding it from members' view/report tools; Durov argues Apple removed the app before contacting Telegram, exposing a systemic risk that any app with over a billion users hosting user-generated content could face sudden removal from coordinated reporting attacks, and warns other platforms may be less prepared than Telegram to detect these evolving tactics.

 

Black Hat 2026

Black Hat 2026 rolled out a dedicated AI Summit track and an even bigger startup floor — but ask the vendors a follow-up question and half of them read straight back off the slide.

• Chris Louie, Tyson Kindler, and Brian Weber clocked Black Hat 2026's floor as noticeably bigger than any pre-COVID year, with a new standalone AI Summit track (badge-visible attendees) and Chris estimating roughly 40-46% of startup names were unfamiliar to a 20-year industry veteran; the crew roasted booth reps who couldn't get past their slide deck when pressed ("tell me more" met with dead air), pivoted into DEF CON 34 deepfake territory, referencing last year's "real or AI-generated?" quiz booth that stumped a surprising number of attendees, and their own AI-manipulated group photo from Black Hat 2025

 

Enshitification of Vegas Check-In

Vegas's cab lobby is apparently still out here physically rerouting Ubers — and yes, Cory Doctorow's favorite term made its annual appearance.

• In a recurring bit referencing Cory Doctorow (who coined "enshittification" and recently discussed platform decay on Jon Stewart's podcast), Chris described a traffic marshal at Mandalay Bay physically blocking his rideshare from a taxi-only pickup lane, forcing a 20-minute detour through an underground garage, while Uber/Lyft surge pricing hit $33-43 for trips that walk-up cabs covered for $10-13 during the same conference window; the group debated whether the taxi lobby's friction tactics (echoes of NYC's collapsed medallion cartel) count as fair pushback against rideshare, landing on the broader point that Uber, Lyft, and Airbnb, no longer VC-subsidized and now under pressure to actually turn a profit, quietly stopped being cheaper than the thing they set out to disrupt.

 

Vegas Bartenders Ditch the Free Pour

Vegas bartenders have quietly swapped free-pouring for measuring cups this year

• The crew (including self-described 6-year bartending veteran Brian Weber) noticed nearly every bartender working on The Strip now measures pours with jiggers/measuring cups instead of the traditional four-count free pour by sight, time, or feel, chalking it up to corporate liability policy amid $20 cocktails and joking about inevitable "shrinkflation" via smaller cups; the tangent detoured into a plug for the Cocktail Party app, road-tested across 16 years of DEF CON parties as a "here's what I have, what can I make" tool, as the lower-effort alternative to repeatedly asking ChatGPT the same question.

 

Dad Joke of the Week (DJOW)

 

Find the hosts on LinkedIn:

Chris - https://www.linkedin.com/in/chlouie/

Tyson - https://www.linkedin.com/in/tyson-kindler-910658101/

Brian - https://www.linkedin.com/in/brianweber1122/