Risky Business

Latest Episodes:

Risky Business #829 -- Sneaky lobsters: Why AI is the new insider threat Mar 18, 2026

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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 beautiful .txt files…)

This week’s episode is sponsored by browser-based detection and response company, Push Security. Researcher Dan Green and Field CTO Mark Orlando join Pat to talk through the InstallFix variant of the *Fix attack technique.

This episode is also available on Youtube.

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Risky Biz Soap Box: It took a decade, but allowlisting is cool again Mar 13, 2026

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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 chasing the latest attacker TTPs and writing detection rules for them.

This episode is also available on Youtube.

Show notes

Risky Business #828 -- The Coruna exploits are truly exquisite Mar 11, 2026

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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 episode is sponsored by open source cloud security scanner Prowler. Creator and CEO Toni de la Fuente talks to Pat about some of the enterprise features Prowler is growing, while remaining true to its open source roots.

This episode is also available on Youtube.

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Risky Business #827 -- Iranian cyber threat actors are down but not out Mar 04, 2026

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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
ASD’s Cisco SD-WAN threat hunting guide is clearly borne of … experience

This week’s episode is sponsored by AI threat hunting platform Nebulock. Sydney Marrone joins to talk about how useful AI models are on the hunt, and her work building out an open source framework and maturity model. It’s methodology agnostic, so you can adapt it for your environment, and the github link is in the show notes!

This episode is also available on Youtube.

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Risky Business #826 -- A week of AI mishaps and skulduggery Feb 25, 2026

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On this week’s show, Patrick Gray, Adam Boileau and James WIlson discuss the week’s cybersecurity news. They cover:

Low skill actors compromise 600 Fortinets with AI-generated playbooks
Anthropic calls out Chinese AI firms over model distillation
Meta’s director of AI safety tells her ClawdBot not to delete her mail… so of course it does
Peter Williams cops 7 years in jail for selling L3 Harris Trenchant’s exploits to Russia
Ivanti got hacked in 2021 via… bugs in Ivanti

This episode is sponsored by line-rate network capture system Corelight. CEO Brian Dye joins to discuss what AI can do for defenders, and what it can’t.

This episode is also available on Youtube.

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Risky Biz Soap Box: The lethal trifecta of AI risks Feb 20, 2026

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There’s a lethal trifecta of AI risks: access to private data, exposure to untrusted content, and external communication. In this conversation, Risky Business host Patrick Gray chats with Josh Devon, the co-founder of Sondera, about how to best address these risks.

There is no magic solution to this problem. AI models mix code and data, are non-deterministic, and are crawling around all over your enterprise data and APIs as you read this.

But in this sponsored interview, Josh outlines how we can start to wrap our hands around the problem.

This episode is also available on Youtube.

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Risky Business #825 -- Palo Alto Networks blames it on the boogie Feb 18, 2026

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On this week’s show, Patrick Gray, Adam Boileau and James WIlson discuss the week’s cybersecurity news. They cover:

Palo Alto threat researchers want to attribute to China, but management says shush
An increasing proportion of ransomware is data extortion. Is this good?
Cambodia says it’s going to dismantle scam compounds
CISA sufferers through yet another shutdown
Google Gemini’s training secrets are being systematically harvested to improve other LLMs
Academics assess SaaS password managers’ resilience against a malicious server

This episode is sponsored by SSO-firewall integration vendor Knocknoc. Chief exec Adam Pointon joins to talk about the latest in defences… which is to say Knocknoc for Solaris/Sparc and HPUX on PA-RISC?! Okay also that other little known OS… Windows.

This episode is also available on Youtube.

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Risky Business #824 -- Microsoft's Secure Future is looking a bit wobbly Feb 11, 2026

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On this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news, including:

Microsoft reshuffles security leadership. It doesn’t spark joy.
Russia is hacking the Winter Olympics. Again. But y tho?
China-linked groups are keeping busy, hacking telcos in Norway, Singapore and dozens of others
Campaigns underway targeting Ivanti, BeyondTrust and SolarWinds products
An unknown hero blocks 23/tcp on the US internet backbone
And James Wilson pops into talk about Claude’s go at a C compiler

This week’s episode is sponsored by Ent.AI, an AI startup that isn’t quite ready to tell us all what they’re doing. But nevertheless, founder Brandon Dixon joins to discuss AI’s role in security. Where does language-based understanding take us that previous methods couldn’t?

This episode is also available on Youtube.

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Risky Business #823 -- Humans impersonate clawdbots impersonating humans Feb 04, 2026

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Patrick Gray and Adam Boileau are joined by the newest guy on the Risky Business Media team, James WIlson. They discuss the week’s cybersecurity news, including:

Notepad++ update supply chain attack has been attributed to China
The AI agent future is even more stupid than expected; behold the OpenClaw/Clawdbot/Moltbook mess
The Epstein files claim he had a personal hacker?
Microsoft is finally getting ready to (think about starting to begin to) disable NTLM by default
The usual bugs in the usual things! Ivanti, Fortinet, and Solarwinds. Again.
Telco hides a free trip in its privacy policy, someone actually reads it and wins!

This weeks’s episode is sponsored by opensource IDP platform Authentik. CEO Fletcher Heisler talks to Pat about their new endpoint agent that can enforce device posture policies during login.

This episode is also available on Youtube.

Show notes

Risky Business #822 -- France will ditch American tech over security risks Jan 28, 2026

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In this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news. They discuss:

La France is tres sérieux about ditching US productivity software
China’s Salt Typhoon was snooping on Downing Street
Trump wields the mighty DISCOMBOBULATOR
ESET says the Polish power grid wiper was Russia’s GRU Sandworm crew
US cyber institutions CISA and NIST are struggling
Voice phishing for MFA bypass is getting even more polished

This episode is sponsored by Sublime Security. Brian Baskin is one of the team behind Sublime’s 2026 Email Threat Research report. He joins to talk through what they see of attackers’ use of AI, as well as the other trends of the year.

This episode is also available on Youtube.