TechnologyNewsTech NewsNews Commentary

Breach Please

Breach Please Team

Cybersecurity has a nonsense problem. Vendors overpromise, headlines overhype, and half the "experts" in your feed have never actually responded to an incident at 3 a.m.

Breach Please is the antidote — cybersecurity news, analysis, and unfiltered commentary from two people who have actually done the work: breaking into networks, defending them, and cleaning up after the breaches everyone else only tweets about.

Every episode, Jake Williams and Jess Hebenstreit break down the stories that matter, call out the nonsense that doesn't, and translate the never-ending chaos into something you can actually use — whether you're in the SOC, the boardroom, or somewhere pretending to understand both.

No fear-mongering. No vendor scripts. No "synergizing our threat posture." Just two seasoned practitioners, the news that matters, and the takes your CISO wishes they could say out loud.

Breach? Please. Pull up a chair.

Play

Open in

63 episodes
daily
Avg 35 min
English

Episodes 63

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

#22
August 27 · 47 min
S0:E22. We go a little long discussing the OpenAI post-mortem on Hugging Face.
In today's episode of Breach Please, Jake and Jess talk through the OpenAI post-mortem on the Hugging Face hack. It's a doozy. There's little doubt in either of our minds that the facts as presented don't exonerate OpenAI - they make it look far worse. We cut through the hype and conclude that there's no way OpenAI was following even the most basic of security best practices, even accounting for hindsight bias. Jake closes by reading a passage from one of Sam Altman's tweets from December 2025, which made clear he knew the dangers of AI - the kind of thing that is likely to haunt him in the future. https://openai.com/index/hugging-face-incident-and-the-road-ahead/ https://x.com/sama/status/2004939524216910323
#21
August 26 · 37 min
S0E21: Alabama Comes for OpenAI, WebLogic Comes for Everyone
Fifteen state attorneys general, led by Alabama, just subpoenaed OpenAI over the Hugging Face breach, demanding the company preserve all evidence related to the intrusion. Jess and Jake break down what that legal hold actually requires, why "mark it ACP" doesn't make a Slack channel privileged, and why the discovery list's question about internal safety concerns might be the part that burns OpenAI hardest. Then: a perfect-10 WebLogic vulnerability, patched back in January, just landed on CISA's Known Exploited Vulnerabilities list, eight months after active exploitation began. Jess and Jake talk through why "patch applied" isn't the finish line and what a post-patch threat hunt should actually look like. In this episode: Fifteen states subpoena OpenAI over the Hugging Face hack and order evidence preservation What a legal hold actually requires (and what evidence spoliation means) Why marking a channel "ACP" doesn't make it attorney-client privileged The discovery request digging into internal safety concerns and model testing A perfect-10 WebLogic CVE, patched in January, added to CISA's KEV eight months later Why "patch applied" doesn't mean "threat hunt done"
#20
August 25 · 41 min
S0:E20 Multi-Agent AI Systems Turn Into Turf Wars
AI just became a cybersecurity governance problem in public. Jess Hebenstreit and Jake Williams break down Anthropic’s multi-agent research, where AI agents with conflicting goals start negotiating, forcing, or trucing their way through “collaboration.”What does it mean when one model settles by force and another settles by truce? Jess and Jake unpack what that means for real-world agent deployments, human-in-the-loop approvals, and the danger of letting “AI says so” become the final word. You’ll learn why multi-agent systems can spiral into turf wars, why governance gets harder once agents are involved, and how to build controls that still let humans say no.
#19
August 24 · 40 min
S0:E19: Cloud Platform Vulnerabilities and Vendor Transparency
In this episode, Jake and Jess talk about vulnerabilities in cloud platforms and how vulnerabilities should be disclosed. We discussed this in the context of recent Microsoft vulnerabilities in Entra, Azure Arc, Exchange Online, and Managed Apache Casandra. All of these had vulnerabilities with minimal details from Microsoft. We generally agree that this isn't what transparency looks like. We also discuss a patch from April that is now actively exploited in the wild.
#18
August 21 · 42 min
S0:E18. Student stops AI supply chain attack and prompt injection is still a thing...
In this episode of Breach Please, we talk about the details that emerged about the Anthropic agent that tried to social engineer a college student into committing a supply chain attack. The whole thing feels very xz-utils 'esque, only with an agent - and a malfunctioning one at that. Then we cover some interesting reporting by Dan Goodin showing how Grok's guardrails can be bypassed through passing it encrypted data along with the instructios to decrypt it. We reinforce that prompt injection is a feature of LLMs, not a bug. We then talk about informed consent of the risks and applicable guardrails based on a viewer note. We even tee up the question of what cyber insurance is likely to cover costs of AI agent activity. Finally, we opine on whether orgs should consider including the inevitable costs of incidents in AI deployment budgets. Show links: https://www.reuters.com/world/how-texas-student-blew-whistle-rogue-ai-hacking-attempt-2026-08-20/ https://arstechnica.com/security/2026/08/grok-exfiltrates-user-data-when-malicious-instructions-are-encrypted/
#17
August 20 · 40 min
S0E17: Amazon vs Perplexity Reveals the First Big AI Agent Liability Test
AI agents are about to test the limits of who gets blamed when they act on your behalf. A new Ninth Circuit ruling in the Amazon vs. Perplexity fight could reshape how enterprises think about autonomous tools, non-human identities, and legal exposure - and the takeaway is more unsettling than most vendors will admit. Jake Williams and Jess Hebenstreit break down what happened when Amazon pushed back against Perplexity’s AI browser, why the CFAA and California’s CDFAA matter here, and how the court’s reasoning could shift responsibility from the agent publisher to the organization that deploys it. They also dig into what this means for legal teams, risk registers, and why every AI agent needs its own identity instead of borrowing a human user’s. You’ll also hear how this ruling fits into the bigger enterprise governance problem: who owns AI risk, who should be accountable when an agent crosses a line, and why security teams can’t be expected to carry every line-of-business risk themselves. Jake and Jess make the case for splitting cybersecurity risk from business risk, naming a real owner, and making legal counsel aware before your agent does something expensive. Then the conversation pivots to another cautionary tale: a 3M expert witness who allegedly used ChatGPT to generate a report aimed at proving the company was 0% at fault in a gas detector explosion case. That story opens up a bigger discussion about leading prompts, hallucinated conclusions, discoverability, and why AI-generated work product can become evidence against you. Perfect for security leaders, legal teams, incident responders, and anyone deploying AI agents in the enterprise.
#16
August 19 · 30 min
S0:E16. OpenAI Highlights Security Basics and Hopes We Won't Notice
In this episode of Breach Please, Jake and Jess talk through OpenAI's recent blog on "pacing model development." The blog reads pretty poorly and really just covers security best practices, apparently hoping readers won't notice that OpenAI is just recommending basics it should have been doing all along (monitoring, sandboxing, etc.). One significant takeaway is that OpenAI has probably raised the bar for agentic logging, owing to the apparent requirement to analyze reasoning traces. We talk about why this is difficult, at least in part because these will contain sensitive data not appropriate for most SIEMs. Show links: https://openai.com/index/pacing-model-development-cyber-capabilities/ https://www.custody-framework.org/
#15
August 18 · 35 min
S0E15 Faking out Famous Chollima and is in-car infotainment advertising a threat?
In this episode of Breach Please Jake and Jess talk about Famous Chollima getting faked out and tricked into revealing TTPs. We discuss our own experience with DPRK workers and share actionable tips for not hiring them or discovering them after they've been hired. Jake may or may not have gone on a rant about cryptocurrency more generally and how it facilitates lots of crime (inspired by talking about DPRK using it for sanctions evasion). Then we talk about in-car advertising on infotainment systems. These won't be patched reliably. Do we need regulation here? Jake thinks it's a right to repair issue. Jake's class Friday August 21, 2026: https://learning.antisyphontraining.com/courses/assessing-ai-security-model-context-protocol Jake's class at Wild West Hackin' Fest in October: https://www.antisyphontraining.com/product/hands-on-ai-security-risk-assessment-with-jake-williams/ Show notes: https://any.run/cybersecurity-blog/lazarus-group-it-workers-investigation-part-two/ https://disconnect.blog/bmws-in-car-spider-man-ad-is-a-warning-sign/
#14
August 17 · 43 min
S0:E14 - CTI and Geopolitical Events
In this episode of Breach Please, we talk about whether CTI analysts can use changes in dwell times, cyber targeting, etc. as a leading indicator of impending geopolitical events. We generally think there's to much noise to be generally effective (especially for Taiwan). Then we talk about a Mac vuln that's being exploited in the wild, with a CVSS score of 9.8. Somehow it isn't in CISA's KEV, but hey, what's a little vulnerability enrichment delay between friends... Show links: https://www.tomshardware.com/tech-industry/cyber-security/macos-screen-sharing-flaw-exploited-to-root-macs-and-plant-monero-miners
#13
August 14 · 40 min
S0E13 - We talk about private companies conducting cyber ops and another AI oopsie.
In today's episode of Breach Please, Jake and Jess talk about cyber companies conducting cyber ops against transnational-criminal organizations, per the new Presidential directive. We also talk about a bug in how major AI platform providers encrypted their chain of thought traces for their frontier models. The vulnerability, when combined with jailbreaking of less powerful models, allowed the traces (previously claimed to be trade secrets) to be extracted. https://www.whitehouse.gov/presidential-actions/2026/08/expanding-capabilities-to-combat-transnational-cyber-enabled-crime/ https://cybersecuritynews.com/top-ai-models-apis-flaw-exposes-hidden-reasoning/
#12
August 13 · 39 min
S0E12 - Vulnerable edge devices, Fortinet exploitation, and whether firewalls belong in zero trust
This episode tackles why internet-facing edge devices keep showing up in major incidents and why that creates more than just patching work. Jess Hebenstreit and Jake Williams also dig into the real operational cost of keeping vulnerable gear in place, from constant incident response to the challenge of proving a device is actually clean. We discuss Fortinet exploitation tied to Gunra ransomware, why OT and IT environments make edge patching especially hard, and whether firewalls should be considered part of a zero trust architecture. Along the way, Jess and Jake compare the realities of vendor complexity, flat networks, and the limits of threat hunting after an exploit.
#11
August 11 · 38 min
S0E11 - Using AI for patching and inflight shenanigans.
In this episode of Breach Please, Jake and Jess talk about new research showing that AI isn't actually that good at generating patches, highlighting objective rates of failure. Turns out, frontier models only generate the correct patch without introducing issues in about 25% of cases. In almost 5% of cases, the AI introduces new vulnerabilities. We also talk about some shenanigans on a Delta flight home from DEFCON. We discuss how time is a flat circle and reminisce Chris Roberts' issues with in-flight hacking from 2015. Show links: https://1password.com/blog/why-ai-generated-patches-still-require-human-review https://www.defendersinitiative.com/p/reviewing-initial-research-on-using https://www.insideflyer.com/posts/hackers-spoofed-delta-wi-fi-on-las-vegas-flight/
#10
August 6 · 33 min
S0E10 - Commonalities in AI lab escapes and How to govern smart devices.
In this episode of Breach Please, Jake and Jess talk about governing smart devices in the enterprise, pivoting off some outstanding research work that Andy Greenberg covered (and was a subject in himself). Then we talk about a common player whose name keeps popping up in these "AI lab escape" disclosures (and who we saw *again* with the Meta disclosure). We bat around some actionable advice for those thinking of outsourcing AI lab containment. Jess is stress testing the Breach Please stickers propping up our banner behind us. Throughout the episode, we see that while they are objectively great stickers, they are not great for this task. Show links: https://www.wired.com/story/hackers-stalked-me-by-hijacking-a-smartwatch-for-kids/ https://www.bleepingcomputer.com/news/security/meta-ai-model-hacked-a-company-during-misconfigured-cyber-test/ https://www.custody-framework.org/
#9
August 5 · 38 min
S0E9 - AI social engineering & operational concerns with AI workflows.
In this episode, Jake and Jess talk about more issues with AI agents escaping containment, this time actively using social engineering to compromise victims. We pose ethical questions about whether you have a duty to investigate your logs for agent breakouts. Then, we discuss how Grokipedia can serve as a cautionary tale in AI workflows silently breaking down. Show links: https://www.bleepingcomputer.com/news/security/openai-anthropic-ai-agents-targeted-real-people-and-systems-in-cyber-tests/ https://www.lawfaremedia.org/article/grokipedia-stopped-reviewing-edits-in-april.-it-didn-t-tell-anyone
#8
August 3 · 37 min
S0E8 - Anthropic ruins Jake's best laid plans, BMC controller vulns, and SentinelOne vs HJ
In this episode of Breach Please, Jake and Jess talk about Anthropic announcing they have lost control of their agents too (not to be outdone by OpenAI). OpenAI is in good company though, since Anthropic ALSO failed to notice their agents breaking out of their sandbox environments. Jake mentions CUSTODY, a framework he'd been planning to present on later this year until these irresponsible agentic containment issues forced him to release it today for the good of the community. Then we talk about BMC controller vulnerabilities that have their roots in weaknesses so old they can not only vote, but legally buy alcohol in all 50 states. Finally, we wrap up with some notes about vendor shenanigans at DEF CON, brought to you by Sentinel One. Hey friends, if you're planning on introducing a new vulnerability class like line hijacking, talk to the conference and/or the guy running the event first? Also, just don't. In a world where you can be anything, don't be a Sentinel One...
#7
July 31 · 56 min
S0E7 - HuggingFace Post Mortem Breakdown
Jake and Jess discuss the excellent post mortem Hugging Face released as a follow on to the OpenAI agent attack. We cover everything from should we call an Autonomous Agent a Threat Actor, to API Security, other lessons learned.
#6
July 30 · 55 min
S0E6 - Hacker Summer Camp Survival Guide
In this episode, Jake and Jess share their tips for doing Hacker Summer Camp (Black Hat, DEF CON, B-Sides, and SO MANY side conferences) the right way. If you've never been, things can be overwhelming and it's easy to overdo it. Even if you're an old hat, there's probably learnings here - plus Jess shows off some of the Breach Please swag we'll have with us.
#5
July 29 · 34 min
S0E5 - Probable alert fatigue endangers DHS collaborators and duress passwords.
In this episode, Jake and Jess talk DHS (twice). First, we talk about DHS dismissing real alarms as false positives in what Jake assesses was a probable watering hole attack nobody seems to be acknowledging. Then we talk about a #stopCopCity activist being charged for giving CBP a duress password that wiped his device. While I think we should all agree that's not a chargeable offense, are duress passwords appropriate for enterprise applications? Jake and Jess debate the use of these passwords for enterprise applications. https://www.nextgov.com/cybersecurity/2026/07/dhs-network-intrusion-was-twice-ruled-false-positive-breach-confirmed/414724/ https://boingboing.net/2026/07/25/grapheneos-duress-password-border-search.html
#4
July 28 · 23 min
S0E4 - Google indexes AI chats (again) and dump of PoC exploits
In this episode of Breach Please, Jake and Jess talk about how the story (again) about AI chats being indexed by search engines isn't really an AI story. This is a data security problem and a misalignment with enterprise tooling. We then talk about a relatively new GitHub repo with lots of zero day exploits. We agree it's academically interesting, but doesn't change anything for how we do enterprise security.
#3
July 27 · 40 min
S0E3 - OpenAI Lost Control of its Agents
In this episode, we talk a lot (too much, we went over on time) about the reports that OpenAI lost control of its agents and apparently only realized it after Hugging Face posted and someone said "yeah, that sounds a bit like us." Reuters article: https://www.reuters.com/business/its-ai-agent-spent-days-hacking-company-sources-say-openai-did-not-notice-week-2026-07-24/ Jake mentioned training. Here's an upcoming one-day seminar on MCP security: https://learning.antisyphontraining.com/courses/assessing-ai-security-model-context-protocol Here's Jake's two-day class covering AI security risk assessment: https://www.antisyphontraining.com/product/hands-on-ai-security-risk-assessment-with-jake-williams/

Showing 41–60 of 63 episodes