Risky Business

Weekly information-security news and analysis for security leaders.

Episodes (40)

Software Development

Snake Oilers: Minimal.dev, Request Rocket and TRM Labs

In this edition of the Snake Oilers podcast, three vendors drop by to pitch their products. Minimal.dev: A sandbox for AI agents! Co-Founder and CEO Jake King explains what the company is and how it works. Request Rocket: Runtime access control for AI agents and APIs. Founder and CTO Alex Ferguson drops by to talk about the problem the company is trying to solve. TRM Labs: All-source threat intelligence. Global Strategic Accounts Director Simon Warren talks about the company’s platform Ardence.

44 min

Series: Risky Business

Software Development

Risky Business #857 -- AI FUD intensifies

On this week’s show Patrick Gray and James Wilson are joined by special guest co-host Alex Stamos to talk through the week’s cybersecurity news, including: Everyone’s still panicking about “misbehaving” AI models that are pretty much just doing what they’re being told to do Americans are giving AI agents unfettered access to their bank accounts. What could go wrong? Last week’s PHP meteor seems to have missed Earth This week’s Brotli HTTP/2 critical flaw is this week’s meteor The private key is

66 min

Series: Risky Business

Software Development

Risky Business #856 -- 8-bit encryption, PHP megabugs and more

On this week’s show Patrick Gray and James Wilson are joined by special guest co-host security engineer Mark El-Khoury to talk through the week’s cybersecurity news, including: The PHP foundation is about to release patches for a couple of critical bugs… We’re watching to see if the internet burns down 8 private keys underpinning some CA certs got compromised. The keys only had 8 bits of entropy! Is the breach-polcalypse upon us? OpenAI’s inside spy, Anthropic’s safety bill and election influenc

64 min

Series: Risky Business

Software Development

Risky Business #855 -- ShinyHunters done sowing, enters reaping phase

On this week’s show Patrick Gray and James Wilson are joined by special guest co-host Brad Arkin to talk through the week’s cybersecurity news, including: Sacré bleu! Hackers turn up the heat at French supermarket freezers ShinyHunters enters “find out” stage Netscaler, Zimbra, SharePoint, Atlassian…. So many bugs exploited in the wild More models “behave badly” (by… doing exactly what we’re telling them to do) Ukraine hit another Yandex data centre in Russia and all those Texan patriots with nu

66 min

Series: Risky Business

Software Development

Soap Box: HD Moore talks OT security, frontier fearmongering and more

In this sponsored Soap Box edition of the Risky Business podcast Patrick Gray chats with industry legend HD Moore about how his company runZero wound up being used heavily to discover OT devices in enterprise networks. They also talk about the vulnpocalypse and how frontier lab fearmongering is reminiscent of the collective freakout when HD released the Metasploit exploit framework back in 2003. This episode is also available on YouTube.

34 min

Series: Risky Business

Software Development

Risky Business #854 -- We're Jevpilled

THE RISKY BUSINESS WEEKLY SHOW IS NOW ON HIATUS FOR TWO WEEKS AND WILL RETURN OCTOBER 14 On this week’s show Patrick Gray and James Wilson are joined by Adam Boileau to talk through the week’s news, including: Google’s Gemini finally did some crimes OpenAI admits more agents did silly things because “alignment” US Treasury’s Scott Bessent rules out a liability waiver for the frontier labs, saying, roughly: “Lol. Lmao even.” Jev is Silicon Valley’s “hot dog/not hotdog” app brought to life, and it

54 min

Series: Risky Business

Software Development

Risky Business #853 -- We're all gonna die, apparently

On this week’s show Patrick Gray and James Wilson are joined by former US Cyber Command executive director turned PwC’s Cyber, Data & Technology Risk leader Morgan Adamski to talk through the week’s news, including: More tech guys penned more open letters and AI will destroy us all! Another Wednesday, another congregation of OpenAI agents on wikis… yawn OpenAI agents were behind the headscratching RubyGems hacking campaign in May The FBI will disrupt more adversary operations, NSA is creating mo

59 min

Series: Risky Business

Software Development

Snake Oilers: watchTowr, XBOW and CoreView

In this edition of the Snake Oilers podcast three vendors stop by to pitch the audience on their products: watchTowr: We’re all familiar with watchTowr’s research, but what do they actually do? XBOW: The AI pentesting company pitches its approach CoreView: Your M365 tenant is probably a security disaster. Tame it with CoreView! This episode is also available on YouTube.

42 min

Series: Risky Business

Software Development

Risky Business #852 -- Cyber Command wants to buy shells

On this week’s show Patrick Gray and James Wilson are joined by guest co-host Robby Winchester from SpecterOps to talk through the week’s news, including: ID verification company IDScan was breached and 153m driver licenses wound up for sale online. Cue the barrage of lawsuits The US government plans to pay private contractors to conduct military hacks The US accuses China of distillation attacks, a.k.a. forbidden training It’s Wednesday, so OpenAI’s agents escaped sandboxes again and passed not

63 min

Series: Risky Business

Software Development

Risky Business #851 -- Agents are just ones and zeros, and tigers are just atoms

On this week’s show Patrick Gray and James Wilson are joined by guest co-host The Grugq to talk through the week’s news, including: Two alleged TeamPCP hackers got arrested in Australia The White House has a plan to boost security for water facilities, but we can’t see it working OpenAI keeps the ol’ Hugging Face discourse going for another week with an incident debrief Tech companies write another open letter about AI… we’re getting CISA Shields Up flashbacks, but for robots Much, much more… Th

58 min

Series: Risky Business

Software Development

Risky Business #850 -- Widespread AI-enabled attacks target Siemens PLCs

On this week’s show Patrick Gray and James Wilson are joined by guest co-host Ollie Whitehouse, the CTO of the UK’s NCSC, to talk through the week’s news, including: Iranian hackers take down a small-scale power generator in the UK Siemens PLCs in critical US sectors are also being targeted… We’re stumped on who could be behind that one, too. Microsoft fixed a CVSS 10 deserialisation bug in Entra before someone else found it and owned the planet Prompt injection isn’t going away LLMs are deceivi

62 min

Series: Risky Business

Software Development

Risky Business #849 -- Trump will unleash contractors on cybercriminals

On this week’s show Patrick Gray and James Wilson are joined by guest co-host Dmitri Alperovitch to talk through the week’s news, including: Trump’s memo authorising the private sector to release the cyber hounds is fine, don’t worry! OpenAI finally decides to add a few safety measures after the whole “oopsie we committed some felonies” thing Anthropic’s models start a turf war when given the same task, surprising… nobody We can’t figure out whether a device that can hack a 737 is showboating st

59 min

Series: Risky Business

Software Development

Soap Box: Zero Trust(ish) Networks

In this Soap Box edition of the Risky Business podcast host Patrick Gray chats with Adam Pointon, CEO of Knocknoc, about the failure of Zero Trust as a comprehensive architecture. Most networks look like they were designed in 1999, and most Zero Trust products look like they were designed for 2049. Instead, Patrick and Adam pitch something in the middle: Zero Trust(ish) networks, where Zero Trust principles are applied selectively where possible. Instead of trying to re-architect entire networks

29 min

Series: Risky Business

Software Development

Risky Business #848 -- OpenAI comes clean

On this week’s show Patrick Gray and James Wilson are joined by guest co-host Brad Arkin to talk through the week’s news, including: The AI-agent-hacks-stuff saga continues. This week we have one booting gymgoers from full classes to nab its owner a spot Somehow OpenAI’s legal team allowed the company to spill all the Hugging Face tea at BlackHat and it’s hot and delicious More details emerge about Iran’s hacking campaign against US water utilities, but Brad is unimpressed It turns out TeamPCP h

59 min

Series: Risky Business

Software Development

Risky Business #847 -- Oops! Claude's accidental hacking spree

On this week’s show Patrick Gray, and James Wilson are joined by bearded man of leisure Adam Boileau to discuss the week’s cybersecurity news, including: Accidental AI agent hacking sprees have the world’s media freaking out, but we think it’s all pretty funny The bugpocalypse is so chaotic, Microsoft can’t patch fast enough A ColdCard wallet flaw led to millions in Bitcoin theft, but the back story behind the bug is bonkers Iran hacks and disrupts water infrastructure in multiple American state

68 min

Series: Risky Business

Software Development

Risky Business #846 -- OpenAI built a fireplace out of wood

On this week’s show special guest co-host Pete Ranks, the former director of the CIA’s Centre for Cyber Intelligence, joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. They cover: Everyone signs the open weights open letter, except Anthropic… of course. OpenAI had no idea it had hacked Hugging Face Kimi K3 open weights released and they’re massive! Why a more aggressive response is needed to cyber attacks on OT And much, much more! This week’s show is brought to you b

62 min

Series: Risky Business

Software Development

Risky Business #845 -- OpenAI's Skynet moment

On this week’s show special guest co-host Chris Krebs joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. They cover: Oopsie daisy! OpenAI agents went rogue and hacked Hugging Face US and China trade AI model ban threats Iran has been using SS7 queries to locate and target US troops Scattered Spider is having a hard time, not just because of Microsoft’s GDID And much, much more! This week’s show is brought to you by Push Security. Luke Jennings joins Patrick this week t

69 min

Series: Risky Business

Software Development

Soap Box: Using threat hunting to drive detection

In this wholly sponsored Soap Box edition of the podcast Patrick Gray chats with Damien Lewke, the CEO and founder of Nebulock, about the future of threat hunting and detection. Damien spent a decade in the EDR and MDR space before founding Nebulock in 2024. It started off as an AI-powered threat hunt platform but has evolved into a broader security data platform that can answer questions, drive hunts and drive detections. This product is engineered around the idea that a lot of security is a da

35 min

Series: Risky Business

Software Development

Risky Business #844 -- China closes AI vulndev gap as USA lifts Fable ban

On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Anthropic’s Fable 5 returning while OpenAI’s GPT-5.6 gets thrown in model jail Distillation, cheap tokens, and AI chat harvesting is an industry in China Edge becomes a lolbin via a new malicious extension An Iranian APT boss’s vacation in a beautiful place goes wrong Much, much more! In this week’s sponsor interview Daf Stuttard and Katie Warren from Portswigger pop along to talk a

60 min

Series: Risky Business

Software Development

Risky Business #843 -- Fortibleed is kinda awesome, actually

On this week’s show special guest co-host Rob Joyce joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. Rob served as an advisor to Donald Trump during his first term as president and also served at NSA for 34 years. While at the agency, Joyce led Tailored Access Operations (TAO), and later became NSA’s Director of Cybersecurity. They cover: The surprisingly well done Fortibleed campaign Stolen Klue OAuth tokens lead to Salesforce data theft OpenAI wants to patch the pl

63 min

Series: Risky Business

Software Development

Risky Business #842 -- Anthropic needs an adult in the C suite

On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Anthropic’s Fable 5 and Mythos 5 get nuked by the US government four days after launch “because security” Why “guardrails” won’t keep the world safe from your AI doomsday machine The FISA 702 statute expired, but the spying can (probably) continue! NPM v12 delivers some protection against supply chain attacks, but not enough. Microsoft has a series of bugs that prevent Windows Updat

59 min

Series: Risky Business

Software Development

Risky Business #841 -- Microsoft gets owned and 0day'd

On this week’s show special guest co-host Chris Wade, the founder of Corellium turned Cellebrite CTO, joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. They cover: Microsoft has repos owned, GitHub tokens popped, and a new 0day dropped on them Meanwhile, researchers are choosing full disclosure instead of engaging MSRC Meta’s AI support agent allowed a staggering 20,000 accounts to be stolen! Apple pulls Russia’s MAX messenger from the App Store and disables notificat

63 min

Series: Risky Business

Software Development

Soap Box: Detection and response in the AI age

In this sponsored Soap Box edition of the Risky Business podcast Patrick Gray chats with Edward Wu, founder of Dropzone, about what AI is doing to detection, response and the SOC more generally. Dropzone makes AI agents that conduct alert investigations in your SOC, but will the SOC as we know it even exist in the future? Ed has a deep expertise in SOC tech, having previously led AI/ML detection engineering at Extrahop. This interview is a fantastic look at what the future may bring for detectio

36 min

Series: Risky Business

Software Development

Risky Business #840 -- Microsoft walks back researcher threats

On this week’s show special guest co-host Andy Boyd joins Patrick Gray and James Wilson to discuss the week’s cybersecurity news. Andy is the CEO of REDLattice, which makes the Paragon “intelligence collection and reconnaissance” solution. They cover: Adversaries are tracking US troop locations with commercially available location data A new Signal phishing campaign is going after message backups 404 Media is suing ICE to get its spyware contract with REDLattice (lol) Microsoft’s tone-deaf respo

66 min

Series: Risky Business

Software Development

Risky Business #839 -- TeamPCP stole GitHub's internal repos

On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: TeamPCP breached GitHub’s internal repos. Now what? Some absolute plonker glued Coruna to a hijacked npm package CISA is worried about about open source and wants third party submissions for KEV AI infrastructure is “systemically” insecure Much, much more This week’s episode is sponsored by allowlisting vendor Airlock Digital. Airlock’s founders David Cottingham and Daniel Schell jo

60 min

Series: Risky Business

Software Development

Risky Business #838 -- GitHub investigates possible breach

On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: GitHub announced a possible breach CISA leaks important creds, keys in public repo Awful vulnerability in Bitlocker renders it useless without a PIN So. Many. Patches. Polish Government urges officials to ditch Signal for mSzyfr Much, much more This week’s show is brought to you by Thinkst Canary. Thinkst’s founder, Haroon Meer, is this week’s sponsor guest. He joined James Wilson t

62 min

Series: Risky Business

Software Development

Soap Box: Where does AI fit into cloud security?

In this sponsored soap box edition of the Risky Business podcast Patrick Gray chats with Toni de la Fuente, the founder of Prowler. Prowler started off as a bunch of scripts in a trenchcoat, then became an open source cloud security tool, and it’s now a venture-funded cloud security business. In this interview Toni talks us through how AI is changing the game for him as an open source project owner, and as a vendor. In short, reports of the death of IT and security tooling at the hands of fronti

33 min

Series: Risky Business

Cloud & Infrastructure

Risky Business #837 -- GitHub Actions footgun claims TanStack

On this week’s show Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Mini Shai-Hulud and the TanStack compromise using Github Actions Instructure pays Canvas elearning platform data extortionists More Linux privilege escalation 0days! CISA helping critical infrastructure operators rearchitect their networks so they work offline This week’s episode is sponsored by email security platform Sublime Security. Bobby Filar chats with Patrick about how agent

65 min

Series: Risky Business

Software Development

Risky Business #836 -- You can't patch the bugpocalypse

On this week’s show, Patrick Gray and James Wilson are joined by special guest co-host Brad Arkin. They discuss the week’s cybersecurity news, including: The US Government says we just have to patch faster, but… Bugs in cPanel, MoveIt and all Linux distributions this week show that patching alone isn’t enough James gets mad about lame AI Agent adoption advice from the US and Australian Governments James Kettle and Niels Provos both showed us that any model can find 0day like Mythos And the cyber

61 min

Series: Risky Business

Software Development

Snake Oilers: Ent AI, Spacewalk and Mondoo

In this edition of the Snake Oilers podcast three vendors stop by to pitch the audience on their products: Ent AI: Co-founder Brandon Dixon pitched Ent, an intent-aware, AI-powered endpoint security control. Spacewalk AI: Founders Chris Fuller and Tim Wenzlau pitch Spacewalk, an AI-powered incident response platform. Mondoo: Co-founder Dominik Richter pitches Mondoo, an AI-powered “service as software” in the vulnerability management space. This episode is also available on YouTube.

43 min

Series: Risky Business

Software Development

Risky Business #835 -- Why the Fast16 malware is badass

On this week’s show, Patrick Gray and James Wilson are joined by special guest-host Dmitri Alperovitch. They discuss the week’s cybersecurity news, including: The US government is mad as hell about Chinese firms stealing American AI technology Dmitri has an opinion or two about the US selling Nvidia chips to China Speaking of Chinese AI, Kimi’s new 2.6 is very interesting The US sanctions a Cambodian senator for earning mega bucks through scam compounds And a ransomware family is promoting itsel

66 min

Series: Risky Business

Software Development

Risky Business #834 -- Vercel gets owned, Mozilla dumps hundreds of Mythos bugs

On this week’s show, Patrick Gray and James Wilson are joined by special guest The Grugq. They discuss the week’s cybersecurity news, including: Vercel got owned, and there’s a few infostealer and compromised employee dots to connect Mozilla used Mythos to find 271 bugs, which feels like a sign of the bug-pocalypse Speaking of the bug-pocalypse, is that why NIST is noping out of enriching a bunch of bugs? The NSA is using Mythos even though the government did that whole Anthropic blacklisting th

60 min

Series: Risky Business

Software Development

Risky Business #833 -- The Great Mythos Freakout of 2026

On this week’s show, Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Everyone has an opinion about Claude Mythos… even though almost nobody has used it yet CISA adds a 2009 Excel bug to the KEV list, u wot? Adobe also parties like it’s the 2000s, and fixes an Acrobat Reader bug Disgraced former Trenchant exec Peter Williams’ sob story fails to resonate with … anyone Remember those crosswalk buttons hacked to play audio mocking Trump and Zuck? They w

59 min

Series: Risky Business

Software Development

Risky Business #827 -- Iranian cyber threat actors are down but not out

On this week’s show, Patrick Gray, Adam Boileau and James WIlson discuss the week’s cybersecurity news. They cover: The US-Israeli attack on Iran had a whole lot of cyber. It’s clearly in the playbook now! The NSA Triangulation / L3 Harris Trenchant iOS exploit kit is on the loose, and being used by Chinese crypto scammers So long Maddhu Gottumukkala, but CISA’s annus horribilis continues Adam “humbug” Boileau complains about the Airsnitch wifi attack just being three ethernets in a trenchcoat A

61 min

Series: Risky Business

Software Development

Risky Business #828 -- The Coruna exploits are truly exquisite

On this week’s show, Patrick Gray, Adam Boileau and James WIlson discuss the week’s cybersecurity news. They cover: The Coruna exploits were L3 Harris, but it seems Triangulation… was not! Iran’s cyber HQ hit by Israeli (kinetic) strikes Trump’s cyber “strategy” is … well, all we’ve got is jokes cause there’s no serious content NSA and CyberCom finally get a leader after Lt Gen Joshua Rudd gets Senate nod DOGE (remember them?!) employee walked a social security database out on a USB stick This e

62 min

Series: Risky Business

Software Development

Risky Biz Soap Box: It took a decade, but allowlisting is cool again

In this Soap Box edition of the Risky Business podcast Patrick Gray sits down with Airlock Digital co-founders Daniel Schell and David Cottingham to talk about the role AI models could play in managing enterprise allowlists. They also talk about the durability of allowlisting as a control. After 12 years in business, the Airlock product hasn’t really changed all that much. That’s a good thing! It also means the Airlock team have been able to spend some time doing deep engineering instead of chas

27 min

Series: Risky Business

Software Development

Risky Business #829 -- Sneaky lobsters: Why AI is the new insider threat

On this week’s show, Patrick Gray, Adam Boileau and James WIlson discuss the week’s cybersecurity news. They discuss: Iran’s Intune-based wiper attack on medical device maker Stryker Qihoo 360’s AI publishes its own wildcard TLS cert private key Instagram is canning its end-to-end encrypted messaging What’s going on with mobile internet access in Moscow? The Xbox One’s bootloader gets voltage glitched into submission Oh Qualys! We love you! (At least, whoever is in the basement writing these bea

63 min

Series: Risky Business

Software Development

Risky Business #830 -- LiteLLM and security scanner supply chains compromised

On this week’s show, Patrick Gray, Adam Boileau and James WIlson discuss the week’s cybersecurity news. They talk through: TeamPCP’s supply chain attack on Github, and they threw in an anti-Iran wiper, because why not?! Anthropic hooks up its models to just… use your whole computer After Stryker’s Very Bad Day, CISA says maybe add some more controls around your Intune? Another iOS exploit kit shows up in the cyber bargain-bin The FTC decides to ban… all new home routers?! U wot m8?! Supermicro f

63 min

Series: Risky Business

Software Development

Soap Box: Red teaming AI systems with SpecterOps

In this sponsored Soap Box edition of the show, Patrick Gray and James Wilson talk about red teaming AI systems with Russel Van Tuyl, Vice President of Services at elite penetration testing firm SpecterOps. SpecterOps is the company behind attack path enumeration tool Bloodhound and Bloodhound Enterprise, but they’re also a pentest and red teaming shop with world class expertise in popping shells on all sorts of interesting systems in all sorts of interesting places. This episode is also availab

30 min

Series: Risky Business

Software Development

Risky Business #831 -- The AI bugpocalypse begins

On this week’s show, Patrick Gray, Adam Boileau and James Wilson discuss the week’s cybersecurity news. They cover: Those pesky North Koreans shim a backdoor into a 100M-downloads-a-week npm package TeamPCP appear to have ransacked Cisco’s source and cloud environments AI is getting legitimately good at being told to “just go find some 0day in this” Kaspersky says Coruna and Triangulation do share code lineage Iranian hackers dump Kash Patel’s gmail spool Oh, and of course there’s a Citrix Netsc

59 min

Series: Risky Business