Three Buddy Problem

(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 Offensive AI Con: Luta Security chief Katie Moussouris makes the case for an NTSB-style board for AI incidents, with subpoena power and full-time investigators, after OpenAI's DNS tunneling escape and the 52 days it took to notice a model had wandered into Australian government systems.

Along the way, we chat about her work on the Cyber Safety Review Board (CSRB), AI model refusals that leave defenders stuck, and why she still bets on hackers to bend this technology their way.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Katie Moussouris.

Timestamps:

0:00 Intros at Offensive AI Con

1:00 OpenAI's DNS tunneling incident and slow monitoring

4:36 Treating AI like malware in a sandbox

9:01 The business model is the misalignment

13:37 Log4j, SBOMs and an NTSB for AI

18:00 Trading liability protection for honest disclosure

22:13 Accountability and "once you become aware"

26:18 The Australia notification timeline

28:19 A blank-check administration and the Anthropic phaseout

34:35 Powerful models in the right hands

38:42 Kill switch bills and regulatory capture

42:36 EU fines as a tariff on American tech

48:03 Reasons for optimism

54:13 Bring back "information security"

1:01:57 Katie's last word

(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 Offensive AI Con: Ollie Whitehouse, CTO of the UK's National Cyber Security Centre, joins us to explain how Britain is preparing for an AI-driven patch wave and why the NCSC is pressing edge-device vendors to finally ship real telemetry.

Plus, we dig into rogue AI agents wandering into a Five Eyes network, along with his forecast that small, capable models could revive self-spreading worms around 2030, all part of what he calls the biggest forced correction of technical debt the industry will ever see.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Ollie Whitehouse.

Timestamps:

0:00 Live from Offensive AI Con: meet Ollie Whitehouse

2:46 Why the NCSC is a model for the US

6:48 What a "national technical authority" does

7:49 The Huawei analysis and the push for passkeys

10:50 Independent AI model testing

13:12 Open-weight vs. closed models and AI sovereignty

19:02 Capability density and AI worms by 2030

23:09 Robotics security and lessons from Japan

26:49 Preparing for the patch wave

31:06 Architecture fixes: OT, cross domain, privileged access

32:28 Telecoms security and Salt Typhoon

38:59 Minimum telemetry standards for edge devices

41:55 Market incentives and the EU Cyber Resilience Act

46:05 Rogue agents and the forced correction of technical debt

(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 Offensive AI Con: Umbriel AI's Aaron Grattafiori breaks down the new offensive-security playbook, using LLMs for patch variant analysis, why the vuln apocalypse hasn't become an exploit apocalypse, and how the death of security through obscurity puts closed-source binaries and firmware within reach.

Plus, we discuss rogue agents escaping sandboxes, the eval-driven loop behind recursive self-improvement, and the brutal cost asymmetry that makes offense cheap and defense almost unaffordable.

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

Timestamps:

0:00 Introductory banter

1:12 Umbriel AI pitch: "Smart people in a place to cook”

3:08 Weird, exhausting, exciting time in security

4:00 What AI really changed: speed (and a 30-minute reimplementation)

6:36 Incomplete fixes and the variant-analysis pipeline

9:21 Uplifting, abstraction, and representing vulnerabilities

11:48 Experimentation and the new shape of security companies

14:46 The vuln apocalypse vs. the exploit apocalypse

16:36 Triage, verification, and reward hacking

18:08 Do models reintroduce bugs? Is vuln-free code possible?

24:22 Specialized models and the rise of Jev-style classifiers

26:47 Binaries, firmware, and the death of security through obscurity

31:15 Open source as a requirement and corporate contracting

33:54 Rogue agents: Hugging Face, OpenAI, and lab escapes

39:17 Why defense is so expensive, and running the rig

(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 Offensive AI Con: Former US intelligence and national security official Joel Todoroff joins us live from OffensiveAIcon to explain why his new startup Phyle is building AI for the recon and targeting work that happens long before anyone fires an exploit.

We get into bribable sysadmins, the military framing that boxes in Western cyber operations, letters of marque, AI doomerism, and what happens when a frontier model decides mid-project that your use case is off-limits.

Cast: Juan Andres Guerrero-Saade, Ryan Naraine and Joel Todoroff.

Timestamps:

0:00 Live from OffensiveAIcon in Oceanside

1:23 What Phyle builds for governments

3:02 Skepticism of the AI 0-day factory

5:57 Paying a sysadmin vs. burning tokens

9:30 Recon gets less love than weaponization

12:41 Exploit shelf life and target No. 1,000

17:30 Why attacker costs will keep rising

22:23 What HUMINT looks like in 2026

27:06 Why intelligence stovepipes persist

32:16 Cyber as statecraft beyond the military frame

41:23 People will keep making dumb mistakes

48:03 The White House memo and letters of marque

54:06 Doomerism vs. near-term AI harms

1:04:20 PSOA concerns and building guardrails in

1:26:03 Open models, guardrails and zero data retention

(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 Offensive AI Con: Live from OAIC, IBM X-Force's Valentina Palmiotti (chompie) walks us through the autonomous Windows kernel exploit pipeline she built on older Claude models, which landed within a hair of Mythos for about $180 a chain.

Plus, the Pwn2Own bug Claude called unexploitable, why her Pwn2Own bugs still sit unpatched, disappearing exploit techniques, the dread of being a defender, and how Phrack found its way back into print.

Timestamps:

0:00 Intro and Pwn2Own war stories

3:46 What vibe hacking means

8:16 When long agent runs go sideways

10:31 Self-verification in an n-day kernel pipeline

16:11 Matching Mythos for $180 a chain

18:42 The bug Claude called unexploitable

21:49 Unpatched bugs and the defender gap

25:37 Mythos arrives through CVP

27:00 Models only know public techniques

32:01 Testing models on held-back bugs

37:45 Inside chompie's daily workflow

46:07 Where's the exploitpocalypse?

50:07 Pixel drops MTE

53:40 Advice for defenders: design for containment

58:34 Phrack is back