Risky BusinessRanked number 6 in the Top 15
Risky Business Media
Show details
- Cadence
- Weekly
- Typical episode
- ~1 hr
- Established
- Since 2007
- Latest episode
- Oct 21, 2026
Risky Business is a weekly information security podcast featuring news and in-depth interviews with industry luminaries. Launched in February 2007, Risky Business is a must-listen digest for information security pros. With a running time of approximately 50-60 minutes, Risky Business is pacy; a security podcast without the waffle.
Classification
Level
IntermediatelevelLatest episodes
- Risky Business #856 -- 8-bit encryption, PHP megabugs and moreOct 21, 2026Episode length: · 1:04:58On 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…
- Risky Business #855 -- ShinyHunters done sowing, enters reaping phaseOct 14, 2026Episode length: · 1:06:27On 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…
- Soap Box: HD Moore talks OT security, frontier fearmongering and moreSep 29, 2026Episode length: · 34:01In 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
- Risky Business #854 -- We're JevpilledSep 23, 2026Episode length: · 54:49THE 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…
- Risky Business #853 -- We're all gonna die, apparentlySep 16, 2026Episode length: · 59:08On 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…
- Snake Oilers: watchTowr, XBOW and CoreViewSep 11, 2026Episode length: · 42:00In this edition of the Snake Oilers podcast three vendors stop by to pitch the audience on their products: watchTowr
- Risky Business #852 -- Cyber Command wants to buy shellsSep 9, 2026Episode length: · 1:03:29On 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…
- Risky Business #851 -- Agents are just ones and zeros, and tigers are just atomsSep 2, 2026Episode length: · 58:38On 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……
- Risky Business #850 -- Widespread AI-enabled attacks target Siemens PLCsAug 26, 2026Episode length: · 1:02:53On 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…
- Risky Business #849 -- Trump will unleash contractors on cybercriminalsAug 19, 2026Episode length: · 59:06On 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…
- Soap Box: Zero Trust(ish) NetworksAug 14, 2026Episode length: · 29:04In 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…
- Risky Business #848 -- OpenAI comes cleanAug 12, 2026Episode length: · 59:47On 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…
- Risky Business #847 -- Oops! Claude's accidental hacking spreeAug 5, 2026Episode length: · 1:08:22On 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…
- Risky Business #846 -- OpenAI built a fireplace out of woodJul 29, 2026Episode length: · 1:02:00On 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…
- Risky Business #845 -- OpenAI's Skynet momentJul 22, 2026Episode length: · 1:09:31On 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…
- Soap Box: Using threat hunting to drive detectionJul 8, 2026Episode length: · 35:16In 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…
- Risky Business #844 -- China closes AI vulndev gap as USA lifts Fable banJul 1, 2026Episode length: · 1:00:11On 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…
- Risky Business #843 -- Fortibleed is kinda awesome, actuallyJun 24, 2026Episode length: · 1:03:35On 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…
- Risky Business #842 -- Anthropic needs an adult in the C suiteJun 17, 2026Episode length: · 59:59On 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…
- Risky Business #841 -- Microsoft gets owned and 0day'dJun 10, 2026Episode length: · 1:03:02On 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…
- Soap Box: Detection and response in the AI ageJun 5, 2026Episode length: · 36:35In 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…
- Risky Business #840 -- Microsoft walks back researcher threatsJun 3, 2026Episode length: · 1:06:03On 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…
- Risky Business #839 -- TeamPCP stole GitHub's internal reposMay 27, 2026Episode length: · 1:00:23On 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…
- Risky Business #838 -- GitHub investigates possible breachMay 20, 2026Episode length: · 1:02:49On 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…
- Soap Box: Where does AI fit into cloud security?May 15, 2026Episode length: · 33:37In 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…
Hosts
- Patrick Gray
- Adam Boileau@Metlstorm
Show account
@riskydotbizFor the show’s team
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