Enterprise Security Weekly (Audio)
News, analysis, and insights into enterprise security. We put security vendors under the microscope, and explore the latest trends that can help defenders succeed. Hosted by Adrian Sanabria. Co hosts: Katie Teitler-Santullo, Ayman Elsawah, Jason Wood, Jackie McGuire, Sean Metcalf.
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Sandbox Escapes with Rubrik's Zero Labs, AI recorders eroding privacy, and the news - Joe Hladik - ESW #472
08/17/2026
Sandbox Escapes with Rubrik's Zero Labs, AI recorders eroding privacy, and the news - Joe Hladik - ESW #472
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 sessions through sandbox escapes. He explores the technical journey behind the eight critical CVEs uncovered by Rubrik Zero Labs and discusses the broader implications for securing generative AI assistants within enterprise environments. This interview highlights the groundbreaking research that earned a $48,000 bounty and featured as a premier briefing at Black Hat USA. Segment Resources: Find from Rubrik Zero Labs' Demo of the ChatMate attack This segment is sponsored by Rubrik. Visit to learn more about them! Topic Segment - AI Notetakers and Recorders AI notetakers are built into everything now, and hardware-based AI recorders are becoming mainstream as well. Is privacy over in the workplace? Adrian, Jackie, Katie, and Tyler discuss. Questions enterprises should be asking: Are employees recording or transcribing meetings? Does this policy change if non-employees (external parties) are present? Is consent asked for/given? Is the context of the conversation taken into consideration? Is the geographic/legal/political context of the external party taken into account? Have you done your due diligence on third parties hosting/storing these recordings and transcriptions? Was your due diligence a SOC 2, or real, actual evidence-based due diligence? Do these third parties have an option to allow you to store/manage your own recordings in a place of your choosing, or does it have to be hosted by the AI recording/transcription company? News Segment Finally, in the enterprise security news, we check the vibes and the funding, and the acquisitions seriously, don’t mess with the wifi on planes 181,000 meetings were left wide open the sandbox escapes are getting ridiculous research on how reliable AI-generated patches are research on what attackers do after they get a shell research on how cybercriminals are using AI agents research on how vulnerable datacenters are and finally, what’s a “mouthpad”? Stick around till the end of the news segment to find out! All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Three interviews: system fragility, operational clarity, and Identity for AI agents - Todd Thiemann, Robin Macfarlane, Kyle Sandy - ESW #471
08/10/2026
Three interviews: system fragility, operational clarity, and Identity for AI agents - Todd Thiemann, Robin Macfarlane, Kyle Sandy - ESW #471
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 inheriting an increasingly diverse tech landscape. Interview 2 with Kyle Sandy from Logically Operational Clarity as the New Customer Experience Kyle Sandy joins Adrian to discuss how prioritizing resilience affects how organizations should plan for incident response. In the past, security teams were focused on prevention and limiting breach damage. Today, boards want to know how long it will take to recover operations. The interview wraps up with a discussion of the right and wrong way to handle a breach and the three most important things every company must get right in order to handle an incident well. Interview 3 with Todd Thiemann from Omdia AI Agents and Identity Security: How Enterprises Are Rewriting the Rules Todd joins ESW with some eye-opening survey insights on the topic of IAM for AI agents. While cybersecurity conversations about internal AI use often revolve around the SOC and security operations, Omdia surveyed identity professionals for a more holistic enterprise perspective. Unsurprisingly, AI agent use is as diverse as enterprise business units. The surprises are around where the budget comes from for these AI projects, and how authentication is handled. Visit for all the latest episodes! Show Notes:
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AppSec, Shopify-Style; State of Mobile Security; the News - Kern Smith, Andrew Dunbar - ESW #470
08/03/2026
AppSec, Shopify-Style; State of Mobile Security; the News - Kern Smith, Andrew Dunbar - ESW #470
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. Segment Resources Enterprise Security News Finally, in the enterprise security news, Pre-black hat funding goes nuts we have 4 new cybersecurity unicorns! Cyera acquires Oasis for one BILLION dollars Lots of new product announcements with hacker summer camp next week Hugging Face got hacked by a competitor’s agent and are cool with it? Finding out that wiping a burner phone is illegal the week before DEF CON is not ideal Are open, local models the future of AI? AI isn’t coming for your job lots of vendor reports bad cybersecurity takes are apparently mainstream memes now??? All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Exploring AI Network Protocols; Vulnerability Truths and Guarantees; and the News - Jeremiah Grossman, O'Shea Bowens - ESW #469
07/27/2026
Exploring AI Network Protocols; Vulnerability Truths and Guarantees; and the News - Jeremiah Grossman, O'Shea Bowens - ESW #469
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 the results are interesting enough to spark a resurgence of interest in network security tooling. Segment Resources: Segment 2 - Interview with Jeremiah Grossman Jeremiah Grossman on why we've been measuring cyber risk wrong for 20 years After decades helping shape modern web security, and building companies that were ultimately acquired by Synopsys and Tenable, Jeremiah Grossman believes cybersecurity has arrived at an inflection point. His argument is a provocative one: for years, the industry has optimized around the wrong metrics. His latest venture, Root Evidence, aims to help security teams identify which risks are most likely to cause meaningful business loss, and he has the evidence - real-world breach data, cyber insurance claims, digital forensics intelligence, attack surface intelligence, and observed attacker behavior - to back it up. Find all of CyberRisk TV's Black Hat 2026 coverage at: Segment 3 - Weekly Enterprise News Finally, in the enterprise security news, We vibe check the AI model situation hidden devices in California cars causes concerns OpenAI’s models escape sandboxes and breaches another AI company, totally by accident, they promise! Grok Build uploads all your files, totally by accident, they promise! Eclipsium debuts a firmware version of patch tuesday! HTTP gets a new method common problems with incident response Which one of the security weekly hosts would consider switching to a “dumb phone”? All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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AI Security at Scale, CMMC phase II paused, and the Weekly Enterprise News - Keith Hollender - ESW #468
07/20/2026
AI Security at Scale, CMMC phase II paused, and the Weekly Enterprise News - Keith Hollender - ESW #468
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 organizations work to connect cybersecurity, AI governance, resilience, and broader transformation priorities. He explores where companies are getting stuck, why traditional siloed approaches are falling short, and what it takes to move from strategy decks to secure execution. Keith also shares how Arcova’s practitioner-led, relationship-driven model helps organizations turn complexity into clarity by embedding with client teams, solving urgent problems hands-on, and building capabilities designed to last. The conversation also covers Arcova’s continued growth, including expansion into the Middle East, and what global demand signals reveal about the next phase of cybersecurity and AI consulting. Segment Resources: For more information about Arcova and how they can help your enterprise shape what's next, please visit: Topic: CMMC Pause creating chaos among federal contractors This one sent some shockwaves through the CMMC community, particularly the hundreds or thousands of folks gearing up to assist with the validation that phase 2 aimed to provide. The TL;DR - defense contractors have been required to comply with CMMC controls for years, but self-attestation means that many probably haven't been meeting the requirements. Perhaps, rather than have tons of defense contractors fail the test, they just suspended the requirement for the test itself. I think Howard Holton nails it here when he says: "100,000 defense contractors needed third-party assessments. Roughly 100 authorized assessors exist. That's 1,000 assessments each, with the deadline in November." PCI already created a model that works for a scenario like this. If you're small, you self-assess. If you're big enough, an independent auditor comes to check you out once a year. I'm sure they were probably aware of this and chose not to go down that path for some reasons. I'm not aware of those reasons. What this means: Phase II is paused Phase I self-assessments still in place (note, however, that phase II existed, because self-attestation didn't work) NIST SP 800-171 Rev 2 and DFARS 252.204-7012 compliance still required 60-day review aims to reform CMMC DoW opened an RFI for industry perspectives on what they should do CMMC characterized as a "compliance burden" and "red tape" False Claims Act and DOJ's cyber-fraud enforcement are still on the table More resources: CIO Davies' post on Twitter Administrator of the Small Business Administration, Kelly Loeffler's post A useful LinkedIn post that breaks down a lot of what this really means (and doesn't) Weekly Enterprise News Finally, in the enterprise security news, will AI eliminate more cybersecurity jobs than it creates? Linus’s law, amended the biggest patch Tuesday ever AI context bombs AI workflows are a security disaster people using AI in areas they don’t understand ransomware crews are hitting legal firms hard lessons learned from CISA’s recent github leak demystify your USB cables! All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Hungry? We talk Smoked Meat, Poutine, and Bagel - also, Identiverse Interviews! - John Pritchard, Cassie Christensen, Jaime Lewis-Gross, François Proulx, Kim Brown - ESW #467
07/13/2026
Hungry? We talk Smoked Meat, Poutine, and Bagel - also, Identiverse Interviews! - John Pritchard, Cassie Christensen, Jaime Lewis-Gross, François Proulx, Kim Brown - ESW #467
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 era. Human, non-human, and agentic AI identities no longer just coexist. They form an uncontrolled inheritance chain in which a human creates an agent, the agent spins up service principals, OAuth grants, and role assignments, and that whole chain keeps running long after the human changes roles or leaves. Most of these chains are being spawned by business users on low-code and enterprise AI platforms, outside traditional identity controls and largely invisible to security. In this segment, Radiant Logic CEO Dr. John Pritchard joins us to unpack why this is no longer a visibility problem. It is an observability problem. And it is shifting the center of gravity in identity security from authentication to authorization. Listeners will leave with a clearer view of where their current IAM, IGA, and NHI programs fall short, and a practical lens for governing the rapidly expanding population of AI agents already inside their environments. To go deeper on what John discussed today, watch Radiant Logic's on-demand webinar Identities Under Attack: How Adversaries Exploit the Human-Machine-Agent Divide at . Identiverse Interview with Cassie Christensen from Saviynt Everyone Wants an AI Assistant. Few Are Ready to Govern One Explore a growing reality many professionals can relate to: the appeal of using AI agents to handle the work that keeps piling up - from inbox management to research and logistics - and the governance challenges that quickly follow. The real barrier to scaling personal or enterprise AI agents isn’t the technology itself, but defining clear roles, access boundaries, oversight, and lifecycle management. As organizations deploy more autonomous AI agents, the same identity frameworks used to govern workforce and non-employee identities must now evolve to manage AI-driven access before scale and risk outpace control. This segment is sponsored by Saviynt. Learn more or get a free demo at Identiverse Interview with Jaime Lewis-Gross from Saviynt From Sales Engineer to Forward Deployed Engineer: The Rise of Hybrid Technical Roles As technology organizations evolve, technical roles are becoming increasingly fluid - particularly at the intersection of product, engineering, and customer success. This conversation explores what it means to be a modern sales engineer and how the role is increasingly expanding into responsibilities often associated with forward deployed engineers: translating complex technical capabilities into real-world outcomes, solving customer challenges in real time, and serving as a critical bridge between product teams and end users. At the center of this evolution is a customer-first mindset - one that prioritizes listening, adaptability, and long-term partnership. As organizations race to innovate, the companies that stand out will be those that remain deeply focused on customer needs while empowering technical teams to operate beyond traditional role boundaries. This segment is sponsored by Saviynt. Learn more or get a free demo at Identiverse Interview with Kim Brown from LexisNexis Stop Identity Fraud: Modern Strategies for Insurance and Healthcare Identity fraud is growing more sophisticated across both insurance and healthcare, making identity management a critical line of defense. In this executive interview, Kim Brown, VP of Product Management, will explore how organizations can strengthen identity verification, authentication, and risk assessment to reduce fraud while improving user experiences. The discussion will highlight emerging threats, evolving regulatory expectations, and practical strategies for deploying identity solutions at scale. Attendees will gain actionable insights to protect customers, patients, and their organizations without adding friction. This segment is sponsored by LexisNexis Risk Solutions. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Mastering agent permissions and Identiverse interviews - Howard Ting, Ajay Gupta, Sandy Bird, Amir Ofek - ESW #466
07/06/2026
Mastering agent permissions and Identiverse interviews - Howard Ting, Ajay Gupta, Sandy Bird, Amir Ofek - ESW #466
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 finds and how Sonrai goes about addressing them. This segment is sponsored by Sonrai Security. Visit to learn more about them! Segment Resources AWS Bedrock agent permissions: Making Enterprise AI Agents Accountable with Amir Ofek, CEO and Co-Founder of aizome Organizations looking to unlock the power of Enterprise AI Agents, and in a controlled and safe way at the speed of AI. Identity is at the heart of it. However, NHI Governance Is Not Enough for Enterprise AI Agents. The identity industry has responded to the rise of AI agents the same way it responds to every new identity challenge: extend existing frameworks. Map agents to human owners. Enforce least privilege. Govern them like non-human identities. It is a reasonable instinct. It is also insufficient in ways that matter enormously. Non-human identity security was built for a deterministic world - service accounts, API keys, bots. These identities do what they are configured to do. Their behavior is predictable enough that static governance models work. Enterprise AI agents are categorically different. Not in degree - in kind. They don't execute fixed instructions. They reason, plan, and adapt in response to context. Their scope shifts with every task. Their behavior at runtime can diverge significantly from anything true at provisioning time. Unlike any identity that came before them, they frequently change their intent, at a pace no governance model built for human movers or machine credentials was designed to handle. Wrapping them in the same framework you use for a service account isn't wrong. It's just insufficient in precisely the places where risk accumulates. Download the This segment is sponsored by aizome. Visit to learn more about them! The Human Authorized. The Agent Acted. Who's Accountable? Interview with Howard Ting - CEO - Opal Security A self-driving car still has a license plate The accountability didn't change just because the driver did. The same has to be true for AI agents, but most environments can't trace an agent action back through the layers of delegation to the human who authorized it. Howard Ting, CEO of Opal Security, joins Security Weekly to discuss what the accountability model looks like when employees run swarms of agents, and what has to be in place before that accountability chain is tested. This segment is sponsored by Opal Security. Visit to learn more about them! Next Evolution of Identity Security: AI for Lower Cost, Efficiency & Governance with Ajay Gupta - President & CEO - SDG Organizations have invested heavily in identity platforms, but many still struggle to maximize security, efficiency, and governance outcomes. As AI transforms both cyber defense and cyber threats, Identity Security is emerging as a critical foundation for securing human and non-human identities alike. In this discussion, we explore how AI is helping organizations reduce costs, improve operations, defend against AI-powered attacks, and address the governance challenges created by AI agents—highlighting the convergence of Identity Security, AI Security, and AI Governance. This segment is sponsored by SDG. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Fixing pentesting, Meta is destroying its engineering org, the weekly news - Adriel Desautels - ESW #465
06/29/2026
Fixing pentesting, Meta is destroying its engineering org, the weekly news - Adriel Desautels - ESW #465
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 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 for all the latest episodes! Show Notes:
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Navigating Shadow AI in the Enterprise, Verizon's SECOND 2026 report, and the news - Ankita Gupta - ESW #464
06/22/2026
Navigating Shadow AI in the Enterprise, Verizon's SECOND 2026 report, and the news - Ankita Gupta - ESW #464
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: YouTube: This segment is sponsored by Akto. Visit to secure your AI agents before attackers do. Topic Segment: Verizon's Breach Impact Study The same team that delivers the DBIR every year gave us a bonus, based on over 70,000 insurance claims! Some of my favorite insights: Cost of breaches, broken out by SMB, mid-sized enterprise, and large The claim amount as a percentage of the company's revenue Losses broken down by loss TYPE This data validates something I think everyone in cyber needs to understand: cyber events are rarely business-ending events. Every cybersecurity professional and vendor, frustrated by companies "not taking security seriously enough" now have data explaining why: breaches don't hurt as much as you thought they did. Maybe you think they should hurt more? Push for regulation/fines/etc. With that said, the report also shows breach costs increasing significantly over the past 6 years and the quantity of incidents shooting up. Specifically, the median impact has almost doubled. Security failures aren't getting any cheaper. Weekly Enterprise News Finally, in the enterprise security news, A $100M seed round! Accenture acquires 3 security vendors Some thoughts on the government takedown of Fable and Mythos One of the craziest security mistakes I’ve ever seen, in the software FIFA uses to manage World Cup streams! A Critical Copilot vulnerability 75,000 Fortinet Firewalls get compromised Remediation is broken Using guardrails to evade detection All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Safe AI at scale, what happens after initial access, and the weekly enterprise news - Albert Estevez Polo, Shiva Pillay - ESW #463
06/15/2026
Safe AI at scale, what happens after initial access, and the weekly enterprise news - Albert Estevez Polo, Shiva Pillay - ESW #463
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 for Zero Networks (a community guest, not a podcast sponsor). Zero Networks just released some very interesting data on what attackers are doing after they gain access to victim's environments and how they're doing it. Segment Resources: Weekly Enterprise Security News Finally, in the enterprise security news, Funding and acquisitions Good news, Mythos isn’t dangerous anymore! An excellent breach analysis Cyber insurance rates are dropping, but there’s a catch CISA updates vulnerability remediation guidance Zoom calls are worse than you think, and maybe not for the reasons you think Remember when it was illegal to rip DVDs? All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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The State of AI in SecOps, the Unintended Consequences of Vulnmaxxing, and the News - Filip Stojkovski - ESW #462
06/08/2026
The State of AI in SecOps, the Unintended Consequences of Vulnmaxxing, and the News - Filip Stojkovski - ESW #462
Interview with Filip Stojkovski on the State of AI in SecOps Filip joins us to talk through the 2+ year rollercoaster that Security Operations tooling has been on since AI entered the chat. We discuss the AI SecOps market, which Filip closely tracks through his project. We also discuss how most of the market has traditionally been focused on the "middle" of the process, which is effectively alert management. Where the conversation really gets interesting is shifting left to discuss . Segment Resources: Be sure to check out - it has more than just vendor information: there are articles, frameworks, podcast episodes, research, and articles/thought leadership Topic: The Unintended Consequences of Vulnmaxxing We discuss where I share a theory that perhaps Project Glasswing is a clever exclusive freemium tier, where Anthropic is hoping to ensnare the world's largest producers of software into using its most expensive model to fix their code for the foreseeable future, creating a much needed new revenue stream for the AI giant with a Trillion dollar valuation. There are some potential unintended consequences that come along with an expensive vulnerability discovery/remediation process that threatens to raise the security poverty line and leave less wealthy companies behind. The Weekly Enterprise News Finally, in the enterprise security news, If you were starting a cybersecurity company today, which category would you pick? layoffs funding the White House AI executive order OpenAI’s frontier governance framework Anthropic’s Zero Trust for AI agents guide IBM’s vulnmaxxing efforts RICO as a service for job seekers Instagram had possibly the most embarrassing hack ever All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Helping defense's use of AI catch up with offense, cost of the vulnpocalypse, news - Evan Powell - ESW #461
06/01/2026
Helping defense's use of AI catch up with offense, cost of the vulnpocalypse, news - Evan Powell - ESW #461
Interview with Evan Powell - Generative and agentic AI are improving cyberattacks faster than they're improving cyber defenses. Offensive folks have been having the most luck with AI so far, which is further eroding any advantage defenders might have had. Evan Powell joins us to share some ideas on how defenders can get some benefits from AI as well, and why open source is important with this approach. Topic For this week’s topic segment, we’ve got two very interesting data sources. The first is Anthropic’s first update on Project Glasswing, where they’re absolutely tearing through codebases with ultra premium Mythos tokens, but then hitting a human-shaped bottleneck as they attempt to validate all the findings. The second is the first report from Root Evidence, the latest startup from Jeremiah Grossman and Robert Hansen (aka RSnake), which aims to help organizations filter out all the vulnerabilities that don’t matter. Where these two reports meet in the middle is my concern that the use of AI to scour every last bug out of code is going to be the most Sisyphean task the cybersecurity industry has ever come up with (and we have some deep experience here). The Weekly Enterprise News Finally, in the enterprise security news, Less funding, more acquisition the AI SOC startup space is CROWDED your CEO is suffering from AI psychosis Some CISOs are done with the job, IT can have it detecting and removing dangerous secrets from dev workstations 230,000 security advisories roll up to 6 attacker behaviors The FBI’s 2025 IC3 report is out When tech billionaires make predictions, they’re actually sales pitches All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Visibility with EDR/MDR is still important, 'the basics' are impossible, and the news - Rob Allen - ESW #460
05/25/2026
Visibility with EDR/MDR is still important, 'the basics' are impossible, and the news - Rob Allen - ESW #460
Interview with Rob Allen from Threatlocker This week, Rob Allen from Threatlocker is with us to discuss the importance of EDR and MDR visibility. We discuss some real world attacks and anecdotes where EDR was able to save the day when threats were missed by other controls. Topic: Do the basics, they said. Easier said than done. Guillaume and Adrian discuss the futility of attempting to do all the foundational work standards, best practices, and regulations expect of organizations. Adrian has given up. Fortunately, Guillaume has some excellent advice and hope to share on this front. The weekly enterprise news Finally, in the enterprise security news, a really interesting vibe check funding acquisitions the verizon DBIR we give a tutorial on how to leak AWS keys on github OH NEVERMIND, SOMEONE AT CISA ALREADY MADE THE TUTORIAL agents versus agents exploitbench the vulnpocalypse robot dogs are SO EASY to take out, we don’t need to be too scared of them yet All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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AI Has a data problem, cascading breaches, and the weekly news - Dimitri Sirota - ESW #459
05/18/2026
AI Has a data problem, cascading breaches, and the weekly news - Dimitri Sirota - ESW #459
Interview with Dimitri Sirota from BigID Most organizations think AI risk lives in the model – or the identity. It doesn’t. It lives in the data. In this episode, BigID’s CEO reframes the conversation: why legacy access controls are breaking down, why visibility into sensitive data is the missing foundation, and what it takes to govern humans and machines under a single, accountable framework. Segment Resources: BigID's BigID's podcast, This Week's Topic: Cascading Breaches We’re seeing more and more 3rd and 4th party attacks that chain through multiple layers of compromised tools and services. In this topic segment, we discuss the two main aspects of this trend: How we can stop the chain of breaches from a third party library, vendor, or service provider How this might get handled at the legal, contractual, and organizational levels We discuss two big recent examples: Sonicwall's 2025 breach of their cloud firewall configuration backup service The compromise of Aqua Security's widely used Trivy open source tool The Weekly Enterprise News Finally, in the enterprise security news, Funding and M&A courtesy of the Security, Funded newsletter We have evidence that attackers are leveraging AI now (this sounds like old news, but there was little to no evidence before, when people were claiming this) The Angry admin problem emerges again Vulnerability information is getting crazy to keep up with Breach information is getting crazy to keep up with You can give your Agents an allowance now - don’t spend it all in one place Are vulnerabilities sparse or dense? Mythos, as a model, isn’t all that special Deploy your own deception sensors! Japan made something weird. Again. All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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The impact of Mythos and Florida Man, confidence gaps, phishing, & AI adoption - Chris Wallis, Deepen Desai, Erich Kron - ESW #458
05/11/2026
The impact of Mythos and Florida Man, confidence gaps, phishing, & AI adoption - Chris Wallis, Deepen Desai, Erich Kron - ESW #458
The Weekly Enterprise News This week, in the enterprise security news, Copy Fail The hits keep coming for CVE, NIST and NVD Cyber attacks on breathalyzers insurance carriers pulling support for AI Florida Man pleads guilty ignore the humanities at your own peril offense and defense don’t scale the same is it okay to be left behind? scientists gave cocaine to salmon Mind the Gap: Confidence, AI, and the Future of Exposure Management Former ethical hacker, now founder and CEO of Intruder, Chris Wallis explores whether AI can bridge the divide between finding vulnerabilities and understanding real-world attack context as exploit windows continue to shrink. This conversation dives into the structural "confidence gap" uncovered in Intruder’s 2026 Security Middle Child Report, where executive risk appetite is increasingly decoupled from front-line operational reality. Check out Intruder’s Security Middle Child Report at . Modern Phishing Attacks Are Under Multi-Channel Siege Recently, there has been a shift in cybercriminals’ behavior, marked by a surge in total phishing attack volume. These attacks are fueled by high-scale automation and a coordinated multi-channel siege targeting corporate collaboration tools. Trusted platforms such as email, Teams, calendars and others are in the cross-hairs, bypassing traditional phishing methods that have worked in the past. This segment is sponsored by KnowBe4. Visit to learn more about them! AI is Now Default Enterprise Accelerator The Zscaler ThreatLabz 2026 AI Security Report reveals that enterprise AI adoption has surged by up to 93% year-over-year, yet 100% of tested AI environments remain vulnerable to breaches that can occur in as little as 16 minutes. It highlights a dangerous shift toward "machine-speed" threats, where attackers use generative AI to automate data exfiltration and create sophisticated deepfakes. To combat these risks, the report urges organizations to move beyond simple blocking and instead implement a Zero Trust architecture for safe, AI-native data protection. This segment is sponsored by Zscaler. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Post Quantum Migration Struggles, AI Threats, and Modern Defenses - HD Moore, Ramin Farassat, Eyal Benishti, Daniel dos Santos, Bobby Ford - ESW #457
05/04/2026
Post Quantum Migration Struggles, AI Threats, and Modern Defenses - HD Moore, Ramin Farassat, Eyal Benishti, Daniel dos Santos, Bobby Ford - ESW #457
Interview with Daniel dos Santos: Post-Quantum Cryptography and the Risks No One Is Talking About Post-quantum cryptography (PQC) is quickly shifting from theory to inevitability. In this segment, Daniel dos Santos, VP of Research at Forescout, explains why PQC isn’t the most immediate threat today—but still demands early attention as standards solidify and timelines accelerate. The discussion highlights overlooked risks beyond encrypted traffic, including digital signatures, firmware integrity, and blockchain systems. Daniel also emphasizes the real challenge: migration. While client-side adoption is already underway, organizations face major hurdles identifying and upgrading servers, legacy systems, and unmanaged assets like IoT and OT. The bottom line: PQC migration is unavoidable. Starting early—especially with crypto inventory and planning—will make the transition far less painful. RSAC Interview: Multi-Channel Impersonation: Why Legacy Controls Are Failing As social engineering expands past just email to include text messages, chat apps, social platforms, and live video calls, traditional point solutions are struggling to keep up. In this segment, Bobby Ford explains how AI-powered impersonation and deepfake-enabled campaigns are exposing critical gaps in legacy defenses, and why organizations must evolve toward a unified social engineering defense platform that connects Digital Risk Management and Human Risk Management. He’ll outline what modern security programs need: real-time cross-channel visibility, behavior-driven detection, and strategies designed around how people actually communicate and make decisions today. Visit to learn how Doppel helps organizations defend against AI-powered impersonation, phishing, and multi-channel social engineering threats with a modern Human Risk Management approach. RSAC Interview: OT: Segmented Today, Breached Tomorrow As the worlds of IT and OT converge, traditional network segmentation falls short, exposing risks in the critical environments that keep energy flowing and shelves stocked. Conventional security tools fail to identify these gaps, with serious repercussions for operators. At runZero, we empower defenders to win by default through comprehensive discovery, rapid detection of critical exposures, and unique segmentation analysis that does not depend on span ports, credentials, or on-device agents. runZero provides real-time insights into even the most sensitive environments — quickly, safely, and securely. This segment is sponsored by runZero. Visit to learn more about them! RSAC Interview: Securing the Next Billion Users: Why the Browser is the Front Line for Agentic AI The enterprise is facing a fundamental shift: the next billion knowledge workers will not be human, they will be AI agents. While these agents offer exponential productivity, they operate at machine speed without human guardrails like MFA or skepticism, creating a massive security blind spot. Ramin Farassat discusses the "Agentic Paradox" and how a new approach to browser security is required to provide architectural immunity for the modern, hybrid workforce of both humans and agents. Learn more about how Menlo Security protects both humans and agents at . RSAC Interview: The Threat Curve Has Reset: Why AI Made “Solved” Attacks Dangerous Again AI hasn’t just evolved cyberattacks—it has reset the threat curve entirely. New research shows that even “solved” problems like phishing and business email compromise are immature and dangerous again, with attackers using AI and autonomous agents to launch hyper-personalized, multi-channel attacks at scale. This session explores what Phishing 3.0 really means for security leaders—and why defending trust now requires a fundamentally new approach. This segment is sponsored by IRONSCALES. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Rethinking Security from the OS Up in the Age of AI and more RSAC 2026 Interviews - Karen Heart, Sachin Jade, Phil Calvin, Craig Sanderson, Travis Wong - ESW #456
04/27/2026
Rethinking Security from the OS Up in the Age of AI and more RSAC 2026 Interviews - Karen Heart, Sachin Jade, Phil Calvin, Craig Sanderson, Travis Wong - ESW #456
Rethinking Security from the OS Up in the Age of AI Karen Heart discusses a file-system–first approach to security, arguing that most modern attacks—including ransomware and supply chain compromises—succeed because they inherit user permissions and operate inside overly trusted system structures. She explains how limiting file access, socket (network) access, and privilege escalation at the operating system level can reduce entire classes of attacks. Rather than relying on reactive detection, her approach emphasizes immutable, allowlisted controls embedded close to the kernel layer, designed to prevent both data exfiltration and malicious code execution at the source. The conversation also explores how AI agents and contractors expand the attack surface, reinforcing the need for strict isolation, backup protection, and deterministic system boundaries. Segment Resources: The New Era of DNS Resilience: Breaking down the newly finalized NIST SP 800-81 Craig Sanderson from Infoblox will dive into the newly finalized NIST SP 800-81 as it marks a pivotal shift in DNS security, emphasizing resilience through modernized practices tailored for today’s distributed, cloud-driven, and threat-laden environments. This update provides actionable guidance for organizations to strengthen DNS infrastructure against evolving threats like ransomware and data exfiltration, while prioritizing initiatives like DNSSEC, encryption, and protective DNS for immediate risk reduction. This segment is sponsored by Infoblox. Visit to learn more about them! Agentic AI and the Future of Threat Intelligence Operations Security teams collect large volumes of threat intelligence but often struggle to translate that information into coordinated operational response. This discussion explores how organizations are embedding intelligence directly into security workflows and introducing AI agents to support investigation, enrichment and response. Sachin will discuss Cyware’s Agentic Fabric approach and the evolution toward an agent-centric model, where a portfolio of specialized agents assists analysts across threat intelligence, detection engineering and response workflows. The conversation will focus on how AI can support security teams while maintaining human oversight and operational control. This segment is sponsored by Cyware. Visit to learn more about them! Beyond the Audit: Making Cyber Risk Continuous, Quantified, and Actionable Most companies assess cyber risk once a year and call it done — but for organizations managing dozens of subsidiaries or portfolio companies, that's a costly blind spot. In this RSA interview, Resilience's VP of Customer Engagement explores why measuring risk in dollars (not color-coded charts) changes the conversation at the board level, and why the organizations best positioned to prevent losses are the ones treating cyber risk as a continuous discipline rather than an annual exercise. See it in action. Request a demo at . Delinea: Redefining Identity Security for the Agentic AI Era As enterprises scale agentic AI and automation, privileged access is increasingly required by non-human identities (NHIs) that operate autonomously across hybrid and cloud-native environments, introducing risks that static, credential-based models were never designed to govern. Delinea's recent of acquisition of StrongDM. This segment is sponsored by Delinea. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Making AI actually work in the enterprise and more RSAC Conference 2026 interviews - Camellia Chan, Aamir Lakhani, Jim Spignardo, Jody Brazil, Ely Abramovitch - ESW #455
04/20/2026
Making AI actually work in the enterprise and more RSAC Conference 2026 interviews - Camellia Chan, Aamir Lakhani, Jim Spignardo, Jody Brazil, Ely Abramovitch - ESW #455
Interview with Jim Spignardo What does it take to build AI workflows that work? Why do so many fail? Jim isn’t a typical ESW guest. I think it’s essential for security folks to regularly step outside the security bubble and understand other perspectives and mindsets. That’s what we’re doing today with Jim. He specializes in building custom AI architecture and workflows for his clients. We discuss the state of AI in the enterprise and why so many of these efforts fail. We’ll discuss the elements of AI success and whether security plays a role in helping AI efforts succeed or contribute to failures. Segment Resources: RSAC Exec Interviews, Part 1 Trends Revealed in Fortinet’s FortiGuard Labs 2026 Global Threat Landscape Report Fortinet’s Global Director of Threat Intelligence and Adversarial AI Research explores the trends revealed in the latest Global Threat Landscape Report from FortiGuard Labs, including a surge in AI-enabled cybercrime. As AI optimizes and accelerates attack techniques, here’s how cyber defenders should respond. This segment is sponsored by Fortinet . Visit to learn more about them! X-PHY Delivers Hardware-Enforced Security for the Age of AI Agents Camellia Chan, CEO and Co-Founder of X-PHY, discusses how Model Context Protocol (MCP) is making it easier for AI agents to plug into enterprise apps and operate with elevated permissions—creating new opportunities for attacks and data exfiltration. She explains how X-PHY’s hardware-enforced monitoring and detection sit beyond the OS trust boundary to enforce immutable limits on what agents can do and stop threats before data is lost, so organizations can adopt agentic AI with confidence. Security leaders looking to deploy AI agents safely can request a demo or briefing with X-PHY at . RSAC Exec Interviews, Part 2 Introducing Legion Investigator: Goal-Oriented AI Investigations Traditional security playbooks often fail because they cannot capture the fluid, context-dependent reasoning required when a routine investigation hits a non-scripted "judgment point." Legion Investigator addresses this gap by employing goal-oriented AI agents that move beyond rigid scripts to interpret findings and execute complex, multi-step investigations based on your team's unique environment and expertise. By bridging the divide between automated execution and human-level reasoning, the platform ensures that every alert (no matter how unpredictable) is handled with the depth and consistency of a senior analyst. This segment is sponsored by Legion Security. Visit to learn more about them! The Missing Layer in Zero Trust: The Security Policy Control Plane Zero Trust has become the dominant security architecture for hybrid and cloud environments, but many organizations are discovering that deploying enforcement technologies alone does not deliver operational control. Firewalls, cloud security groups, and microsegmentation platforms enforce access decisions, yet the policies behind those controls are often fragmented, difficult to validate, and constantly changing. In this conversation, FireMon CEO Jody Brazil discusses why modern security architectures increasingly require a security policy control plane: a layer that continuously validates how policy is enforced across firewalls, cloud networks, and segmentation platforms. The discussion explores why policy drift occurs in real environments, how enforcement systems become difficult to coordinate at scale, and what organizations must do to ensure Zero Trust policies remain consistent as infrastructure evolves. This segment is sponsored by FireMon. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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We catch up on the news, including AI vuln hunting; also more RSAC interviews! - John Wilson, Mark Lambert, Georges Bossert, Samuel Hassine - ESW #454
04/13/2026
We catch up on the news, including AI vuln hunting; also more RSAC interviews! - John Wilson, Mark Lambert, Georges Bossert, Samuel Hassine - ESW #454
Segment 1: We cover the weekly enterprise news! Segment 2: RSAC interviews from ArmorCode and Filigran ArmorCode: AI Exposure Management and Governing Shadow AI AI is moving faster than most governance models can keep up. As organizations race to adopt new AI tools, developer workflows, agents and MCP servers, security leaders must enable innovation without losing control over risk, accountability and oversight. In this segment, ArmorCode will discuss its new AI Exposure Management (AIEM) solution, as part of the ArmorCode Agentic AI Platform. ArmorCode will highlight how AIEM gives enterprises clearer visibility into where AI is being used, who owns it and the potential risks it introduces across heterogeneous environments. By turning AI usage and signals from existing security and IT systems into governed, auditable outcomes, AIEM helps organizations reduce shadow AI risk, assign accountability and accelerate AI adoption with stronger control and board-ready governance. ArmorCode will also share findings from its new 2026 State of AI Risk Management report, developed in partnership with The Purple Book Community and based on responses from more than 650 enterprise security leaders. The discussion will connect ArmorCode’s latest product innovation to the broader industry need for scalable, enterprise-ready AI risk governance. ArmorCode AI Exposure Management is available now as a solution deployed on the ArmorCode Agentic AI Platform. To learn more, visit . Beyond IOCs: A Framework for High-Impact Cyber Threat Intelligence In a time where the ability to turn intelligence into decisive action is a true competitive advantage, organizations must move beyond reactive alert triage to a proactive, threat-informed defense. This segment explores how unifying threat intelligence with adversarial attack simulation enables a Continuous Threat Exposure Management (CTEM) framework that replaces hype with measurable outcomes. We will discuss why these are no longer just technical security conversations, but critical business strategies that provide the board and C-suite with the clarity and confidence to reduce risk and focus resources where they matter most. This segment is sponsored by Filigran. Visit to learn more about them! Segment 3: RSAC interviews with Sekioa and Fortra Agentic AI: Don't Make Your SOC Faster at Being Wrong Adding AI agents to an unprepared SOC doesn't make it smarter; it just makes it "faster at being wrong." Georges Bossert challenges the industry hype to explain why true autonomy relies on reliable context and structured runbooks, not just prompts. He will discuss how to build the necessary foundations to automate rapidly without losing control. This segment is sponsored by Sekoia.io. Visit to discover their AI SOC Platform! Scripted Sparrow: A Prolific BEC Group In December, Fortra Intelligence and Research Experts (FIRE) released a major report exposing Scripted Sparrow, one of the most active Business Email Compromise (BEC) collectives operating today. The group sends an estimated 6 million highly targeted scam emails each month, impersonating executive coaching firms and leveraging spoofed reply chains, missing attachment lures, and evolving multilingual campaigns. FIRE’s investigation links the collective to 119 domains, 245 webmail accounts, and 256 bank accounts, with members operating across three continents and continually refining their fraud techniques at scale. This segment is sponsored by Fortra. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Battling payment fraud with tokenization and executive interviews from RSAC 2026 - Jimmy White, Thyaga Vasudevan, Brian Oh, Mickey Bresman, Ashish Jain - ESW #453
04/06/2026
Battling payment fraud with tokenization and executive interviews from RSAC 2026 - Jimmy White, Thyaga Vasudevan, Brian Oh, Mickey Bresman, Ashish Jain - ESW #453
Interview with Brian Oh from FIS Global Merchant-Specific Tokenization: Making Embedded Finance More Fraud-Resistant Payment fraud has not gone away. It has evolved into a largely social engineering-driven problem that increasingly lands on security leaders’ desks. In this episode, Brian Oh from FIS Global explains how merchant-specific tokenization and virtual cards work, why embedded finance raises the stakes, and how approaches like behavioral biometrics and tokenized payments can reduce fraud while keeping checkout experiences fast and seamless. Segment Resources: FIS Global - PYMNTS Article - FIS Global Blog - FIS Global Blog - Interviews with Mickey Bresman from Semperis and Ashish Jain from OneSpan The Making of Midnight in the War Room Semperis is producing , a full length feature film on cyberwar and CISO heroism and their work defending their companies against the onslaught of cyberattacks. Midnight in the War Room puts a human face on the front lines of cyber defense and will reveal the weight carried by defenders every day and why resilience must be built not only into systems, but into people and institutions. This segment is sponsored by Semperis! Visit to learn more. Why Passkeys Are Ready for Prime Time in Modern Banking Authentication has long required an uneasy tradeoff between strong security and smooth user experience. This interview segment explores why passkeys are ready now for even the highest risk banking use cases, why banks should be moving quickly to adopt them, and how OneSpan delivers the most complete, secure, and enterprise ready passkey solution on the market. This segment is sponsored by OneSpan. Visit to learn more about them! Interviews with Jimmy White from F5 and Thyaga Vasudevan from SkyHigh Security Securing AI Agents: Managing Runtime Risk in Enterprise AI Systems As organizations deploy AI agents and automated workflows, security challenges are increasingly emerging once these systems interact with APIs, enterprise data, and business processes in production. For more information about F5, please visit . AI’s Security Inflection Point: Hybrid, Browser Security, and Data Compliance The rapid adoption of AI applications is reshaping enterprise security architectures. As organizations integrate AI copilots, agentic workflows, and cloud-native platforms, traditional network-centric security models are proving insufficient. This segment is sponsored by Skyhigh Security. Visit to learn more about them! Visit for all the latest episodes! Show Notes:
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Oops, all Interviews: Switching to Cyber, CISO Reflections, and the State of TPCRM - Alexandre Sieira, Lenny Zeltser, Helen Patton - ESW #452
03/30/2026
Oops, all Interviews: Switching to Cyber, CISO Reflections, and the State of TPCRM - Alexandre Sieira, Lenny Zeltser, Helen Patton - ESW #452
Interview with Helen Patton about her new book, Switching to Cyber Helen joins us to discuss her second book, "Switching to Cyber." Her first book discussed strategies for handling various stages of the cybersecurity career, while this one, co-written with Josiah Dykstra, provides a guide for switching to cyber mid-career. Check out her book, Switching to Cyber: The Mid-Career Guide to Launching a Cybersecurity Career: and on the publisher's Interview with Lenny Zeltzer: Reflections on Being a CISO After a cybersecurity career in various roles, doing everything from product management to malware analysis training, Lenny spent 6 years in the CISO seat at Axonius, from near the inception of the company through its growth from its modest Series A stage in 2019 to the present, with nearly a billion in funding today. Lenny's CISO Essays: Interview with Alexandre Sieira: The state of TPCRM is shifting The gold standard for third party cyber risk management has long been the humble questionnaire. While we've seen security rating services companies generate scores by scanning a company's external resources. Both approaches are for either creating trust relationships or determining the true risk of doing business with a third party. Every analysis of this problem comes to the same conclusion: without internal data about the state of systems and the security program, TPCRM can't improve substantially. Most this believe this to be an impossible problem: third parties would never share data this sensitive with a customer and first parties assume the same. What if they did? That's exactly the premise behind Tenchi Security, and Alexandre joins us to talk about how they've accomplished the 'impossible' in Brazil and aim to expand their success to the US. Resources: Thoughts from a panel discussion at a recent FS-ISAC event, Predicts 2026: (Gartner Subscribers only, sorry) Visit for all the latest episodes! Show Notes:
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Can AI help critical infrastructure, the state of the cyber market, and weekly news - Mike Privette, Kara Sprague - ESW #451
03/23/2026
Can AI help critical infrastructure, the state of the cyber market, and weekly news - Mike Privette, Kara Sprague - ESW #451
Interview with Kara Sprague - The AI Fix for Infrastructure’s Oldest Security Risks. Critical infrastructure, often built on decades-old systems and legacy code, remains vulnerable to cyberattacks. From pipelines and energy grids to transportation networks, we break down where critical infrastructure is vulnerable and how AI could potentially help strengthen defenses. Interview with Mike Privette - The State of the Cybersecurity Market Here at ESW, we use Mike Privette's Security, Funded newsletter to prepare for every news segment. His covers the latest fundings, acquisitions, public market performance, layoffs, and other pertinent market details every week. We particularly enjoy the weekly Vibe Check. In this interview, he joins us for the third year in a row, to discuss the most interesting insights from his annual . Post recording Adrian here: Whooooo, so this conversation was SO good, I decided to punt the news segment in favor of a part 2 with Mike, so enjoy! Also, though I punted the news segment, I did collect these stories and annotated them, so I think there's still some value in leaving them in the show notes. Scroll down for the links and my comments on each of these! Weekly Enterprise News Finally, in the enterprise security news, funding announcements seem to be ramping up before RSA Should security architects be shifting right? How McKinsley’s AI platform got hacked… by AI Amazon is having a bad time with AI lately Europe announces a Google Workspace/Microsoft 365 replacement Robot dogs are apparently guarding datacenters now Some much needed security humor in our squirrel stories before we all fly to San Francisco and lose our minds for a week All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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AI Governance, new book (Code War) from Allie Mellen, and the weekly news! - Jeremy Snyder, Allie Mellen - ESW #450
03/16/2026
AI Governance, new book (Code War) from Allie Mellen, and the weekly news! - Jeremy Snyder, Allie Mellen - ESW #450
Interview with Jeremy Snyder from FireTail about AI Governance Death by a thousand cuts: the AI shadow IT problem I think the best description of the AI governance problem during this interview was the title of the award-winning movie, Everything, Everywhere, All At Once. Generative AI has been disrupting businesses, products, and vendor risk management for a few years now. FireTail is one of the companies trying to address this problem for enterprises, so we check in with Jeremy Snyder to see how things are going. Segment 1 Resources: Interview with Allie Mellen about her new book, Code War: How Nations Hack, Spy, and Shape the Digital Battlefield We're VERY excited to check out Allie's new book, which will be released on St. Patrick's Day 2026! The timing could not be better, as her book is perfectly positioned to provide some much needed perspective on the cyber aspects of the ongoing war in Iran. Is it normal to see the use of wipers on healthcare companies in the midst of the conflict? Is there any precedent for hyperscaler datacenters getting targeted (some of AWS's EMEA regions are still recovering)? Check out the conversation to find out! Pick up the book! from from from Allie's The Weekly Enterprise News Finally, in the enterprise security news, Vibes and funding! Starting to see some disruption in the vuln mgmt space (finally!) Tons of new free tools lots of essays lots of reports logs of breaches the talks our hosts are giving at RSAC conference and someone is selling an actual cone of silence??? All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Breaking in with CrashFix, supply chain security, and CMMC phase 1 - David Zendzian, Anna Pham, Jacob Horne - ESW #449
03/09/2026
Breaking in with CrashFix, supply chain security, and CMMC phase 1 - David Zendzian, Anna Pham, Jacob Horne - ESW #449
Interview with Anna Pham Breaking in with ClickFix: Anatomy of a modern endpoint attack Cybersecurity company Huntress just published a report on a new ClickFix variant they’ve discovered, which they’ve dubbed CrashFix. This technique was developed by KongTuke to serve as the primary lure within a new custom malicious browser extension also created by the group. In short, the team observed the threat actors using KongTuke’s malicious browser extension to display a fake security warning, claiming the browser had “stopped abnormally” and prompting users to run a “scan” to remediate the threats. Upon “running the scan,” the user is presented with a fake “Security issues detected” alert and instructed to manually “fix” the issue by opening the Windows Run dialog, pasting from their clipboard, and pressing Enter. The malicious extension silently copies a PowerShell command to the clipboard, disguised as a legitimate repair command. From there, they execute the malicious command. Segment Resources: BLOG - Interview with David Zendzian Continuous compliance and real security lifecycle management Supply chain attacks are not just on the rise; attackers are learning from the past, making these attacks even more effective and dangerous than before. It was just over a month ago when the Shai-Hulud attack first impacted NPM packages, forcing enterprises around the world into lockdown. While only 187 packages were compromised in that initial incident, it served as a wake-up call for many: an accurate inventory of systems is good, but a clear, real-time Software Bill of Materials (SBOM) for applications is non-negotiable. In this world of manifest based infrastructure and container based applications with (real) "devsecops", the dream of continuous upgrades of OS/Runtime/Stack/App and App Dependencies is very mature and there are solid examples of companies and federal entities managing this at scale without thousands of teams and people. Segment Resources: BLOG - Interview with Jacob Horne CMMC Phase 1 Enforcement — What the November 10 Deadline Means for the Defense Supply Chain With the upcoming CMMC Phase 1 enforcement on November 10, cybersecurity teams across the defense and federal supply chain are facing new compliance requirements that directly affect contract eligibility and data-protection standards. Jacob Horne, Chief Cybersecurity Evangelist at Summit 7, can break down what this milestone means for enterprise security leaders, MSPs/MSSPs, and contractors preparing for audits. Visit for all the latest episodes! Show Notes:
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OT Security/business resilience, lack of incentives for securing software & the news - Ben Worthy - ESW #448
03/02/2026
OT Security/business resilience, lack of incentives for securing software & the news - Ben Worthy - ESW #448
Interview - Ben Worthy from Airbus Protect The current state of OT security and business resilience In this episode of Enterprise Security Weekly, we sit down with Ben Worthy, OT Security Specialist at Airbus Protect, to explore the evolving landscape of business resilience in safety-critical sectors. With over 25 years of experience across aerospace, nuclear, water, oil & gas, and other industries, Ben shares insights on how organizations are adapting to the surge in disruptive cyberattacks—from ransomware targeting operational technology to GPS spoofing and supply chain incidents. We discuss major cases including the Boeing/LockBit ransom demand, the Jaguar Land Rover production shutdown, and the SITA passenger data breach, examining how aviation and other critical infrastructure sectors are separating safety risk from business continuity risk. Ben also breaks down the regulatory changes reshaping the industry, including EASA's October 2025 and February 2026 deadlines that tie cyber assurance directly to safety oversight, and what ENISA's latest numbers reveal about hacktivism and ransomware trends. Whether you're in aviation, nuclear, or any safety-critical sector, this conversation offers practical lessons on building resilience that keeps operations moving while addressing threats in real time. This segment is sponsored by Airbus Protect. Visit to learn more about them! Topic: Where are the business incentives to build secure products and software? "It's the right thing to do," so of course businesses will make their products secure, right? Well, it turns out that breaches and vulnerabilities don't traditionally hurt financial performance all that much. Stocks recover, insurance covers the bulks of the losses, fines are paid, and lawsuits are settled. Most businesses can comfortably absorb the impact, so the threat of reputational harm or financial losses just aren't slowing them down. In the case of Ivanti, where the reputational harm was extreme, the company's companies continue to get hacked as critical vulnerabilities keep getting discovered in their products. In this topic segment, we don't aim to provide solutions to this problem, just the awareness that ethics, doing the right thing, and even signing the Secure by Design pledge don't seem to be enough to change vendor behavior when it comes to securing products. The Weekly Enterprise Security News Finally, in the enterprise security news, RSA Innovation Sandbox hot takes Did AI solve cyber? fundings and acquisitions a free app to warn you about smart glasses deep thoughts about OpenClaw replacing US tech with EU equivalents is hard should you turn off dependabot? accidentally taking over 7000 robot vacuums the director of AI Safety at Meta loses her email somehow should you go back to using a blackberry? All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Bringing intelligence to assets, new White House cybersecurity strategy, and the news - Tim Morris - ESW #447
02/23/2026
Bringing intelligence to assets, new White House cybersecurity strategy, and the news - Tim Morris - ESW #447
Segment 1 - Interview with Tim Morris Bringing intelligence to assets You’ve been through 6 CMDB projects in the last decade. None of them came close to the original goals, the CMDB was already out-of-date long before the project had any hopes of completing. Is building an asset inventory just too ambitious a project for most organizations, or is there a better way? Tim Morris shares a different approach with us today. It might require some convincing and some courage, but it seems much more likely to succeed than any of your past CMDB efforts… Segment Resources This segment is sponsored by Tanium. Visit to learn more about them! Segment 2 - Topic: the new White House cybersecurity strategy In this segment, we explore some early details about the White House's new, but yet unreleased cybersecurity strategy. It appears that drafts have been shared (or leaked) to the press, so there's here! Segment 3 - News Finally, in the enterprise security news, Massive amounts of funding and acquisitions as we get close to RSA Open source registries need help Microsoft Copilot reads email marked as DO NOT READ Don’t use an LLM to generate passwords is prompt injection a vulnerability defining risks AI changes the build versus buy equation the scammer’s perspective All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Hardware-level zero trust, don't trust AI with your employees, and the news - J Wolfgang Goerlich, Matias Katz - ESW #446
02/16/2026
Hardware-level zero trust, don't trust AI with your employees, and the news - J Wolfgang Goerlich, Matias Katz - ESW #446
Segment 1: Interview with Mathias Katz What if you had enterprise-grade network security protections traveling with your users' laptops? What if it could be built into the laptop, but still stay safe even if the laptop OS and firmware were entirely compromised? Mathias and his company, Byos have built such a thing, and BOY do we have some questions for him. Segment 2: Interview with Wolfgang Goerlich Addressing the nuanced, nefarious threats of AI Sure, we need to worry about AI prompt injection and AI data leakage, but what about the threats to our BRAINS? Seriously, as we start to have daily conversations with this technology, how are they going to shape how we think? What inherent biases in the training, fine tuning, guardrails, or lack of guardrails are going to affect our decisions or how we work? Wolfgang is concerned about this, so he performed a human/AI experiment. With almost 1000 people partaking in the experiment, the results are sure to be intriguing. Segment 3: This week's enterprise security news Finally, in the enterprise security news, survey results on how folks are feeling about openclaw some hidden drama discovered in KEV updates some new KEV tools is AI replacing traditional code scanning tools? remote code execution in notepad no, not notepad++, NOTEPAD.EXE you know, the one that ships preinstalled on Windows the RSAC innovation sandbox finalists dealing with legacy vulnerabilities Don't accept OpenClaw Mac Minis from strangers! All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Clickfixed, Zero Trust World, and OpenClaw is out of control - but that's the point - Rob Allen - ESW #445
02/09/2026
Clickfixed, Zero Trust World, and OpenClaw is out of control - but that's the point - Rob Allen - ESW #445
Interview Segment - Rob Allen - Clickfix "Clickfix" attacks aren't new, but they're certainly more common these days. Rob Allen joins us to help us understand what they are, why they work on your employees, and how to stop them! We tie it into infostealers and ransomware actors. Plenty of practical recommendations for how to spot and prevent these attacks in your environment, don't miss it! This segment is sponsored by ThreatLocker. Visit to learn more about them! Interview Segment - Rob Allen - Zero Trust World Threatlocker's 6th annual Zero Trust World event is happening next month! This three day event runs from March 4th through the 6th once again in sunny Orlando, Florida. This year's event is packed with hands-on hacking workshops, competitions, prizes, and keynotes from Marcus Hutchins, and Linus and Luke from Linus Tech Tips. Security Weekly will be there as well, doing live interviews and recording an episode of ESW live! This segment is sponsored by ThreatLocker's annual Zero Trust World. Visit to learn more about the conference and register with discount code ZTW26ESW! News Segment For this week's enterprise news, we discuss OpenClaw! funding! acquisitions! testing out AI models’ offensive security capabilities more openclaw! the need for more transparency and testing in the vendor space A photobooth service leaks drunken pictures of wedding parties The salty snack that helps server uptime All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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Initial entry to resilience: understanding modern attack flows and this week's news - Warwick Webb - ESW #444
02/02/2026
Initial entry to resilience: understanding modern attack flows and this week's news - Warwick Webb - ESW #444
Segment 1: Interview with Warwick Webb From Initial Entry to Resilience: Understanding Modern Attack Flows Modern cyberattacks don’t unfold as isolated alerts--they move as coordinated attack flows that exploit gaps between tools, teams, and time. In this episode, Warwick Webb, Vice President of Managed Detection and Response at SentinelOne, breaks down how today’s breaches often begin invisibly, progress undetected through siloed security stacks, and accelerate faster than human response alone can handle. He’ll discuss how unified platforms, machine-speed detection powered by global threat intelligence, and expert-led response change the equation--turning fragmented signals into clear attack narratives. The conversation concludes with how organizations can move beyond incident response to build resilience, readiness, and continuous improvement through post-attack analysis. Listeners will leave with a clearer understanding of how attacks actually unfold in the real world—and what it takes to move from reactive alert handling to true attack-flow-driven defense. Segment Resources: Wayfinder 451 Managed Defense Redefined This segment is sponsored by SentinelOne. Visit to learn more about them! Segments 2 and 3: The Weekly News In this week's enterprise security news, we’ve got funding free tools! the CISO’s craft agentic browsers tech companies are building cyber units? giving AI agents access to your entire life lots of dumpster fires in the industry today Cisco killed Kenna the state of AI in the SOC homemade EMP guns! don’t try this at home All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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The future of data control, why detection fails, and the weekly news - Thyaga Vasudevan - ESW #443
01/26/2026
The future of data control, why detection fails, and the weekly news - Thyaga Vasudevan - ESW #443
Segment 1: Interview with Thyaga Vasudevan Hybrid by Design: Zero Trust, AI, and the Future of Data Control AI is reshaping how work gets done, accelerating decision-making and introducing new ways for data to be created, accessed, and shared. As a result, organizations must evolve Zero Trust beyond an access-only model into an inline data governance approach that continuously protects sensitive information wherever it moves. Securing access alone is no longer enough in an AI-driven world. In this episode, we’ll unpack why real-time visibility and control over data usage are now essential for safe AI adoption, accurate outcomes, and regulatory compliance. From preventing data leakage to governing how data is used by AI systems, security teams need controls that operate in the moment - across cloud, browser, SaaS, and on-prem environments - without slowing the business. We’ll also explore how growing data sovereignty and regulatory pressures are driving renewed interest in hybrid architectures. By combining cloud agility with local control, organizations can keep sensitive data protected, governed, and compliant, regardless of where it resides or how AI is applied. This segment is sponsored by Skyhigh Security. Visit to learn more about them! Segment 2: Why detection fails Caleb Sima put together of the issues around detection engineering struggles that I thought worth discussing. Amélie Koran also and experiences. Segment 3: Weekly Enterprise News Finally, in the enterprise security news, Fundings and acquisitions are going strong can cyber insurance be profitable? some new free tools shared by the community RSAC gets a new CEO Large-scale enterprise AI initiatives aren’t going well LLM impacts on exploit development AI vulnerabilities global risk reports floppies are still used daily, but not for long? All that and more, on this episode of Enterprise Security Weekly. Visit for all the latest episodes! Show Notes:
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