Fixing pentesting, Meta is destroying its engineering org, the weekly news - Adriel Desautels - ESW #465
Enterprise Security Weekly (Audio)
Release Date: 06/29/2026
Sandbox Escapes with Rubrik's Zero Labs, AI recorders eroding privacy, and the news - Joe Hladik - ESW #472
Enterprise Security Weekly (Audio)
Interview with Jon Hladik - ChatMate Imagine a user asks an LLM a question about a document. An attacker then gains an interactive prompt on the user’s chat session, enabling the attacker to instruct the AI assistant to take actions on behalf of the victim. That is exactly the capability researchers at Rubrik Zero Labs were able to demonstrate in a recent study designed to test the bounds of LLM security. Join Joe Hladik, Head of Rubrik Zero Labs, as he breaks down the discovery of "Remote Prompt Execution," a novel vulnerability class that enabled full takeovers of Microsoft Copilot...
info_outline
Three interviews: system fragility, operational clarity, and Identity for AI agents - Todd Thiemann, Robin Macfarlane, Kyle Sandy - ESW #471
Enterprise Security Weekly (Audio)
Interview 1: Robin Macfarlane from RRMac Associats The Mattress Money Principle: What a 50-Year Veteran Knows About System Fragility In this interview, Robin and Adrian discuss how technology has evolved over the past 50 years. Despite massive technological changes over the decades: the PC revolution, the Internet, smartphones, the Cloud, and now Generative AI - the majority of financial institutions still use mainframes and midrange machines. Why? We explore the reasons why older technology persists alongside the new and the lessons retiring technologists can pass on to new generations...
info_outline
AppSec, Shopify-Style; State of Mobile Security; the News - Kern Smith, Andrew Dunbar - ESW #470
Enterprise Security Weekly (Audio)
Interview with Andrew Dunbar, CISO at Shopify After 13 years at Shopify, Andrew has some valuable insights to share on application security. In this episode, we discuss how AI has changed application security processes where bug bounty now fits in a post-Mythos, post-AI harness world. Andrew's Resources: Interview with Kern Smith Kern Smith, VP of Global Solutions at Zimperium, joins us to talk about the state of mobile security. This was a great conversation, talking about the history of mobile devices in the enterprise and how challenging securing mobile apps is in the age of vibe-coding....
info_outline
Exploring AI Network Protocols; Vulnerability Truths and Guarantees; and the News - Jeremiah Grossman, O'Shea Bowens - ESW #469
Enterprise Security Weekly (Audio)
Segment 1 - Interview with O'Shea Bowens What do we really know about "AI Network Protocols"? Network security is about to get popular all over again. Generative AI caused a disruptive explosion across all of tech and every company’s roadmap. The move from chatbots to AI agents doubled down on that disruption. Now agents need to talk to each other? Boom: we have MCP. A2A. Universal Commerce Protocol. General purpose and specialized protocols for agent communication. What does this look like from the network perspective, though? O’Shea Bowen joins us to answer this question, and he thinks...
info_outline
AI Security at Scale, CMMC phase II paused, and the Weekly Enterprise News - Keith Hollender - ESW #468
Enterprise Security Weekly (Audio)
Interview with Keith Hollender, CEO and Co-Founder of Arcova Why AI Security Is Becoming an Execution Problem, Not Just a Governance Problem As enterprises move from AI experimentation to adoption at scale, security leaders are under pressure to enable innovation without introducing unmanaged risk. The challenge is no longer whether organizations should pursue AI, but how they can govern it, secure it, and operationalize it in ways that stand up to real-world business and threat conditions. In this conversation, Keith Hollender discusses what Arcova is seeing across enterprise environments as...
info_outline
Hungry? We talk Smoked Meat, Poutine, and Bagel - also, Identiverse Interviews! - John Pritchard, Cassie Christensen, Jaime Lewis-Gross, François Proulx, Kim Brown - ESW #467
Enterprise Security Weekly (Audio)
Interview with François Proulx from Boost Security Software Supply Chain Security: Build Pipeline (CI/CD) Exploitation Boost Security is the creator of some very popular build pipeline security tools, like Bagel and Poutine. Today, we discuss their latest tool, Smoked Meat. They describe it as "Like Metasploit, but for CI/CD pipelines". Segment Resources: Smoked Meat Smoked Meat Smoked with Guillaume and François Identiverse Interview with Dr. John Prichard from Radiant Logic The Three Identity Problem: Surviving Identity Security's Chaotic Era Identity security has entered its chaotic...
info_outline
Mastering agent permissions and Identiverse interviews - Howard Ting, Ajay Gupta, Sandy Bird, Amir Ofek - ESW #466
Enterprise Security Weekly (Audio)
Interview with Sandy Bird, co-founder of Sonrai Security In this week's interview, we kick off the conversation with how Sonrai's expertise in securing cloud identity permissions had the company well placed to address the explosion of AI agents and the clear risks they represented. On the surface, this looks like a cloud/hyperscaler permissions challenge, but it isn't that simple. As agents like Claude Code, Codex, and Hermes are connected to enterprise cloud agents, the risk spreads outside VPCs and onto endpoints. Check out the episode to learn more about some of the most common risks Sandy...
info_outline
Fixing pentesting, Meta is destroying its engineering org, the weekly news - Adriel Desautels - ESW #465
Enterprise Security Weekly (Audio)
Interview with Adriel Desautels - the pentest is broken Adriel joins us for a discussion on the state of penetration testing, why it hasn't done much to help security teams over the last 20 years, and why AI won't save it. Segment Resources: Topic: Why Meta is destroying its engineering organization The titular essay: A very interesting analysis of what's going on inside big tech companies as they try to dogfood their own AI hype and tokenmaxx themselves into oblivion. There have been a LOT of stories on this, but this is the most comprehensive and enlightening. A few more are linked...
info_outline
Navigating Shadow AI in the Enterprise, Verizon's SECOND 2026 report, and the news - Ankita Gupta - ESW #464
Enterprise Security Weekly (Audio)
Interview with Ankita Gupta, CEO of Akto How to Navigate Shadow AI Risk in the enterprise This week, we discuss AI governance in the enterprise, starting with the nuts and bolts of how to discover and understand shadow AI. Following that, we dive into what security and tech leaders should do next with this information: apply guardrails? Limit vendor options? Ankita has a wealth of experience and anecdotes to share here, from years of working with customers and seeing all the unexpected things that happen with AI in today's workplace. Segment Resources: Website: Book a Free Demo: LinkedIn: ...
info_outline
Safe AI at scale, what happens after initial access, and the weekly enterprise news - Albert Estevez Polo, Shiva Pillay - ESW #463
Enterprise Security Weekly (Audio)
Interview with Shiva Pillay from Veeam Safe AI at Scale AI investment is exploding, yet nearly 90% of enterprise initiatives fail because the data powering AI cannot be trusted. That’s the uncomfortable truth the industry is facing right now. Safe AI at scale requires more than just great models—it demands trusted, governed, and recoverable data. This segment is sponsored by Veeam. Visit to learn more about them! Segment resources: Topic: Sure, we know how initial access works, but what about lateral movement? A special topic segment where we're joined by Albert Estevez Polo, field CTO...
info_outlineInterview with Adriel Desautels - the pentest is broken
Adriel joins us for a discussion on the state of penetration testing, why it hasn't done much to help security teams over the last 20 years, and why AI won't save it.
Segment Resources:
- https://hbr.org/2026/04/boards-are-falling-short-on-cybersecurity
- https://www.scworld.com/perspective/how-to-build-a-breach-ready-security-posture-without-the-enterprise-price-tag
- https://netragard.com/blog/what-is-penetration-testing/
Topic: Why Meta is destroying its engineering organization
The titular essay: https://newsletter.pragmaticengineer.com/p/why-is-meta-destroying-its-engineering
A very interesting analysis of what's going on inside big tech companies as they try to dogfood their own AI hype and tokenmaxx themselves into oblivion. There have been a LOT of stories on this, but this is the most comprehensive and enlightening. A few more are linked below.
This is relevant to security, because heavier AI use appears to be linked to a much higher occurrence of availability and security issues.
- ‘Tell Him He’s a Piece of Shit’: Meta’s New AI Unit Is a Total Mess
- The Newest Instagram "Exploit" is the Goofiest I've Seen
- Meta CTO Andrew Bosworth Admits the Company’s AI Reorg Was ‘Atrocious’
- Meta’s months-old AI unit is a soul-crushing gulag, say the engineers stuck inside it
The Weekly Enterprise News
Finally, in the enterprise security news,
- an AI vibe check
- An AI SOC vendor shuts down
- Cybersecurity vendor layoffs
- funding & acquisitions
- cascading breaches
- digital estate management
- criminals don’t trust AI either
- some devs won’t code without AI, even if you pay them to
- Midjourney is now a healthcare company?
All that and more, on this episode of Enterprise Security Weekly.
Visit https://www.securityweekly.com/esw for all the latest episodes!
Show Notes: https://securityweekly.com/esw-465