Three Buddy Problem

(Presented by Ent.ai: Ent delivers intent-aware security that protects every action, adapts to every workflow, and works for every user. Enterprise threat detection, reimagined.)

Three Buddy Problem - Episode 99: Microsoft is now threatening legal action against researchers who drop zero-days. We debate whether it's a fair line against extortion, or amateur-hour PR from a company that already torched its own research community? Costin plays reluctant defender, JAGS says the damage was done years ago, and Ryan reopens the long history of silent fixes and stolen bounties.

Plus, on the 10th anniversary of the Shadow Brokers leak, we discuss some enduring mysteries, theories on attribution and an interesting trail that leads to Edward Snowden.

We also unpack Rob Joyce's warning that China's cyber explosives are already planted in US infrastructure, and the Pope's warnings about around artificial intelligence.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Costin Raiu.

Timestamps:

0:00 - Introductory banter

2:03 - The Pope's AI paper

3:35 - New sponsor: Brandon Dixon's Ent Security

9:34 - Costin's Chinese-model OSINT rabbit hole

13:34 - Codex, GPT-5.5, and the "American AI welfare state"

23:20 - Microsoft threatens vulnerability researchers

27:06 - Is it extortion or retribution? The disclosure fight

40:48 - How Microsoft's consultant class broke MSRC and MSTIC

48:42 - Silent fixes, stolen bounties, and the marketing machine

1:02:29 - Ten years of the Shadow Brokers

1:14:20 - The Snowden theory

1:32:34 - Rob Joyce: China's cyber explosives are in place

1:53:26 - Shout-outs

(Presented by TLPBLACK: A cybersecurity intelligence platform focused on sharing curated, high-sensitivity threat insights and research with trusted security professionals.)

Three Buddy Problem x Ekoparty Miami: Aaron Portnoy (Zero Day Initiative alum, early Pwn2Own organizer, and now at Mindgard) joins us at Ekoparty Miami to reminisce on the early days of the hacking contest, where vulnerabilities actually live (the boundaries between systems, not inside them), why LLMs will take out the trash but can't dream up the next speculative-execution-class bug, and the coming patching apocalypse when discovery 10x's overnight.

Plus, why your SOC is a forensic historian, the promise of hijacking an attacker's reward loop with deception tech, and the legendary story of carrying a Walmart "fat stack" of cash to bootstrap Ekoparty in Buenos Aires.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Aaron Portnoy.

Timestamps:

0:00 — Introductory banter

1:17 — Dropping out, iDefense, and getting good at reversing everything

2:19 — How Pwn2Own got started

4:15 — The most impressive Pwn2Own ever: Nils, VUPEN, and exploit "art"

5:59 — "iPhone hacked in 30 seconds" — and the 18 months behind it

6:41 — Does Pwn2Own still have a place in the AI era?

9:16 — Why LLMs take out the trash but can't invent the next bug class

12:48 — Will LLMs deliver new mitigation classes? Aaron's skeptical

18:34 — The place of the human when the easy bugs run dry

21:08 — Cognitive offloading, Halvar's warning, and skill rot

22:39 — Decompiling 800k functions: Aaron's LLM "holy shit" moment

25:26 — The patching apocalypse and why "assume breach" breaks

28:15 — Compounding asymmetries: why offense just transcended defense

(Presented by TLPBLACK: A cybersecurity intelligence platform focused on sharing curated, high-sensitivity threat insights and research with trusted security professionals.)

Three Buddy Problem x Ekoparty Miami: Perri Adams of DARPA AIxCC fame joins the show to chat about proof engines, formal methods, and why LLMs just made a once-niche corner of computer science suddenly essential.

We get into why verifiers and proof engines are the key to effective AI, why vulnerability research is so far ahead of threat intel, and the case for baking security checks directly into code generation tools like Claude Code and Codex.

Plus, designing a multi-million dollar challenge that's allowed to fail, the Mythos "too dangerous to release" debate, and musings on every LLM-discovered bug being a public bug by default.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Perri Adams.

Timestamps:

0:00 — Introductory banter

1:09 — Why LLMs just made formal methods relevant again

4:03 — Proof engines, explained

8:43 — Can a layman grab this fire? The calculus problem

11:58 — Vuln researchers are scrappy kids with a trust fund

14:55 — Pitching AIxCC inside DARPA: hard sell or easy sell?

18:00 — Designing a challenge that's allowed to fail

22:06 — Inside Team Atlanta's 150-page winning system

24:00 — Why this is bigger for defense than for offense

31:49 — Mythos, safeguards, and "every LLM bug is a public bug"

(Presented by TLPBLACK: A cybersecurity intelligence platform focused on sharing curated, high-sensitivity threat insights and research with trusted security professionals.)

Three Buddy Problem x Ekoparty Miami: SentinelLabs researcher Gabriel Bernadett-Shapiro hops on the mic to unpack who gets to define what "security" even means in the age of AI, why venture capital keeps funding the wrong things, and how the frontier labs quietly ate everyone's coding harness.

Plus, how AI actually contributed to cracking the FAST 16 research, overcoming the guardrails, and why your domain expertise is the only thing keeping you out of full-blown rabbit-hole psychosis.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Gabriel Bernadett-Shapiro.

Timestamps:

0:00 Introductory banter

4:55 Gabe returns: how the models got scary-good at code

8:45 Bay Area short-termism and the "10x in 18 months" trap

11:35 VCs as tastemakers, and why that's broken

13:00 The unpaid-labor pipeline into the AI labs

18:00 The real misunderstanding about security's moat

20:18 Bug bounties: a net negative for the industry?

22:20 The great vuln fire sale — find 50,000, fix zero

27:28 Who will maintain vetted open-source libraries?

29:29 FAST 16: how AI actually broke the case open

35:05 The rabbit-holing machine and the path to "AI psychosis"

41:05 Stuxnet, Kim Zetter, and the story we'll never be told

(Presented by TLPBLACK: A cybersecurity intelligence platform focused on sharing curated, high-sensitivity threat insights and research with trusted security professionals.)

Three Buddy Problem x Ekoparty Miami: Federico Kirschbaum, founder of Ekoparty and now head of Security Lab at XBOW, talks about what happens to offensive security when an autonomous AI hacker can find and exploit real vulnerabilities. Fede walks through XBOW's "Tales from the Trace," the surreal experience of watching a non-human adversary reason its way to an ASLR bypass, and why he believes pen-testing isn't dying but finally becoming accessible to far more than the world's biggest companies.

Plus, where humans still matter in the loop, whether an LLM-discovered bug is public by definition, the looming reckoning over software liability, and Halvar Flake's very honest fear of getting lazy.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Federico Kirschbaum.

Timestamps:

0:00 Fede's move to XBOW

2:20 What's XBOW building? An AI hacker for real vulnerabilities

5:53 Where the human stays in the loop

6:35 The Exim bug: a craftsman races the LLM to an ASLR bypass

10:49 Does bug discovery still need a human asking the right question?

16:24 A short history: Satan, CORE, Metasploit, bug bounties

18:48 An LLM-discovered bug is public by definition

24:12 Halvar Flake's laziness worry & the assembly-to-C parallel

29:47 Rising tides: script kiddies get the full gamut

41:02 The economics: does pentesting get cheap?

43:18 Argentina, Ekoparty, and an untapped talent pipeline