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In this episode, Ashu Savani, co-founder of TryHackMe, explains how the company's Live Breach product puts teams inside fully-executed, realistic breach simulations built around the threat actors and tech stacks they face, building the reflexes and reporting security leaders need before a real incident hits. Joining him are Roland Toussaint, Senior Director of Incident Response and Security Engineering at ChenMed, and Heather Hinton, CISO at Sitecore. Want to know: How can a simulated environment realistically reflect a security team's actual tech stack and the threat actors they care about? Can TryHackMe's reporting help security leaders prove upskilling progress to auditors and cyber insurance carriers? How does TryHackMe help teams train for incidents caused by their own people, not just outside attackers? How granular can training get: can a team run a meaningful exercise in just 15 to 20 minutes? How are TryHackMe's custom exercises tiered and packaged across its plans? What's TryHackMe's track record getting cyber insurance carriers to accept its exercises as sufficient proof of readiness? Does TryHackMe offer anything built specifically around HIPAA for healthcare organizations? Why is crisis communication often more under-rehearsed than technical response, and how does TryHackMe help teams practice it? Check out the episode for the answers you need. Huge thanks to our sponsor, TryHackMe Live Breach challenges security teams to test their incident response against a rogue AI agent in a realistic, three-hour exercise. The campaign uses a compelling AI-driven attack scenario to create urgency, while highlighting the low-risk setup, actionable readiness insights and practical value of testing teams before a real incident occurs. Business applicants only, 18+. Applications open 7 October 2026 and close 18 October 2026 at 23:59 EST time. Six companies are selected by a TryHackMe panel from eligible applications, against published criteria; each receives one complimentary simulated Live Breach exercise. No purchase necessary. Full terms: http://tryhackme.com/legal/live-breach-giveaway-terms

In this episode, Joseph Perla, founder and CEO at TrustedRouter, explains how his company's confidential-computing-based LLM router lets teams send prompts to hundreds of AI models while cryptographically verifying, rather than simply trusting, that no one, including TrustedRouter itself, can see the data passing through. Joining him are TC Niedzialkowski, former head of IT & security at Opendoor, and Keith McCartney, svp of security and IT at DNAnexus. Want to know: Why hasn't the AI privacy problem already been solved, given how many tools and architectures already exist? What's wrong with the "zero data retention" promises most AI providers offer today? How does a confidential virtual machine let a company verify, instead of just trust, that its own router isn't looking at its prompts? For a use case like HIPAA-covered medical data, does TrustedRouter provide one complete, auditable path from a user's machine to the model and back? How does remote attestation confirm end-to-end encryption down to the chip level? Does TrustedRouter's SOC 2 Type 2 attestation cover the AI workload itself, or just its own SaaS interface? Can customers restrict which data centers or jurisdictions their AI workloads run in? What happens to a company's existing AI usage monitoring once it starts routing through TrustedRouter? Check out the episode for the answers you need. Huge thanks to our sponsor, TrustedRouter TrustedRouter is the open-source AI gateway for teams that need privacy with proof. It routes hundreds of models through attested confidential compute, keeps prompts and outputs out of logs, verifies the code handling each request, and adds provider failover, spend controls, and OpenAI-compatible APIs for production AI systems.

In this episode, Dean Shroll, senior director of sales engineering at ThreatDown, explains how the company's Nebula and OneView consoles simplify protection across Mac, Linux, and Windows endpoints while its managed detection and response team absorbs the 24/7 monitoring that resource-constrained teams can't staff on their own. Joining him are Jonathan Waldrop, CISO at Acoustic, and Arif Hameed, CISO at C&R Software. Want to know: Why is managing security for resource-constrained organizations suddenly getting more attention? How does ThreatDown keep its console simple without sacrificing depth across Windows, Mac, Linux, and cloud environments? Where does ThreatDown draw the line between what it automates and what still needs a human analyst? How does the platform distinguish suspicious behavior from normal DevOps activity without drowning teams in false positives? What guardrails exist to stop overly broad exclusions from opening up a device? Who owns what when an MDR provider is involved, and where does that responsibility actually end? How should a CISO justify an MDR investment to the board when nothing bad happens? Check out the episode for the answers you need. Huge thanks to our sponsor, ThreatDown ThreatDown delivers elite Managed Detection and Response purpose-built for resource-constrained teams with high-efficacy protection without complexity. Combining artificial intelligence and expert analyst judgment, ThreatDown intercepts sophisticated attacks with speed and accuracy, scaling security effortlessly. Recognized by MRG Effitas, AVLab, and G2, ditch fragmented tools for fast, 24/7 protection without overhead.

In this episode, Leo Taddeo, CEO and President at AppGate, explains how the company's zero trust network access platform cloaks internet-facing infrastructure from discovery, uses direct-routed architecture instead of cloud-routed hairpinning to avoid the latency tax, and layers in continuous, context-aware policy checks that go beyond device posture and MFA. Joining him are Ross Young, co-host of CISO Tradecraft, and Derek Fisher, Director of the Cyber Defense and Information Assurance Program at Temple University. Want to know: Why does securing remote access remain one of the top attack vectors year after year? How does AppGate's direct-routed architecture avoid the latency and throughput limits of cloud-routed competitors? What happens to a user's access when the circumstances that justified it change, like a closed service ticket? How does cloaking network infrastructure stop an adversary's reconnaissance before it starts? What's the fallback when a controller hosted in a customer's own data center goes down? How does AppGate defend against credential replay and man-in-the-middle attacks that bypass MFA entirely? What does AppGate's per-user licensing model mean for organizations managing multiple devices and enclaves? Check out the episode for the answers you need. Huge thanks to our sponsor, AppGate AppGate secures and protects an organization's most valuable assets with its high performance Zero Trust Network Access (ZTNA) solution. AppGate ZTNA is the only direct-routed Zero Trust solution built for peak performance, superior protection and seamless interoperability. AppGate safeguards enterprises and government agencies worldwide. Learn more at appgate.com.

In this episode, Sagar Batchu, CEO of Speakeasy, explains how the Speakeasy AI control plane lets organizations adopt AI everywhere and still prove it's governed — putting every agent, tool, and MCP server behind a single security layer that authenticates each action, enforces policy, and inspects every session for prompt injection and data exfiltration. Pressure-testing the approach are George Finney, CISO at The University of Texas System, and Nick Espinosa, host of The Deep Dive Radio Show. Want to know: Why is knowing what your AI agent can access still an unsolved problem, and how much of it traces back to the identity and data governance we never fixed for humans? Should an AI agent ever be allowed to take an action no individual can fully understand, even when it's statistically more effective than the human alternative? Where's the line between legitimate governance and surveillance, and how do you assure employees you're not building a panopticon? Are there decisions and departments that should stay permanently in human hands, off-limits to agents entirely? When an agent acts through a company's API and something goes wrong, who's actually responsible: the employee, the company, the model developer, the API provider, or the governance platform? Could a control plane have flagged the week's biggest AI incident before it escalated? Is adopting this really as simple as switching on enterprise settings and plugging in an API, whether you're an SMB or the Fortune 1? What is "cognitive surrender," and why does Speakeasy's CEO think it's the one quality companies most need to protect? Check out the episode for the answers you need. A huge thanks to our sponsor, Speakeasy. Speakeasy is the enterprise AI control plane. It governs every AI agent, tool, and MCP server from one place. Every connection is authenticated, every policy enforced, and every agentic action inspected and logged. So organizations can scale AI adoption with visibility and control. Copy for below Banner: AI usage is outgrowing your enterprise controls. Speakeasy is the AI control plane that governs every agent, assistant, and MCP server from one layer. Each connection is authenticated, each policy enforced, and every action recorded. So you stay in control as AI adoption scales."

In this episode, Curtis Simpson, CSO at Gambit Security, explains how Gambit moves organizations past that guesswork by continuously mapping a company's minimally viable business capabilities and validating whether the infrastructure, backups, and recovery processes behind them can actually deliver within the timeframes the business requires. Joining him to pressure-test the approach are Howard Holton, former CEO of GigaOm, and Adam Palmer, CISO at First Hawaiian Bank. Want to know: Why do so many disaster recovery plans hold up on paper but fail the moment they're actually needed? What's the real difference between having something backed up and proving you can recover it? What is a "minimally viable company," and how much of mapping it is automated versus built on human input? What happens when your infrastructure fails today, versus what Gambit's roadmap has planned for tomorrow? What should actually land in front of your CEO or board to demonstrate recovery confidence? Is there an organization too small, or too mature, to get value from this kind of resilience assessment? Why does decades-old infrastructure like the mainframe often cause the longest, most damaging outages? Why is now the moment for security to finally move from a "trust but trust" model to "trust but verify" on recoverability? Check out the episode for the answers you need. Huge thanks to our sponsor, Gambit Security Gambit is the AI-native cyber resilience platform for enterprises that can't afford downtime. It continuously maps your live environment, backups, security tools, and infrastructure-as-code, then validates whether your entire stack can actually recover from disruption. Gambit gives security and infrastructure leaders proof of recoverability on demand, so the business keeps running. Balens maps, controls, and proves your recoverability across every layer of your stack - against infrastructure failures, human and AI errors, and cyber threats. One live view of your cloud, IaC, and backups that updates as your environment evolves. Agentless deployment in 15 minutes. Learn more at gambit.security

In this episode, Andrea Sivieri, Chief Product and Technology Officer at CoreView, explains how CoreView secures that overlooked layer, the configuration, permissions, and structure of a Microsoft 365 tenant rather than just the data flowing through it. Joining him are Davi Ottenheimer, principal at Flying Penguin, and Will Gregorian, CISO at Galileo Medical. Want to know: Why does Microsoft's own admin console give you roughly a thousand ways to configure a single setting? What's the actual difference between securing your Microsoft 365 data and securing your Microsoft 365 configuration? How does a "virtual tenant" stop one compromised admin account from exposing your entire company? How do you stay ahead of a vendor that can change its APIs or shut off access without warning? How do you catch a change to your tenant that you had no way of seeing in the first place? How far back can you rewind a tenant's configuration history, and why does that number matter? What does managing a 2.7 million-user tenant reveal about resilience that a small business never has to think about? Check out the episode for the answers you need. A huge thanks to our sponsor, CoreView

In this episode, Abby Kearns, CEO of ActiveState, explains how her company closes that gap by rebuilding open-source packages from verified sources before they ever reach a developer's pipeline, rather than scanning for problems after the fact. Joining her are Doug Mayer, vp and CISO at WCG, and Howard Holton, former CEO at GigaOM. Want to know: Why is AI increasing exploitability on both the attacker side and the developer side of the open source supply chain? How does a package catalog replace your package manager without slowing developers down or pushing them around the process? What does ActiveState do differently than upstream scanning tools like JFrog Artifactory or Sonatype Nexus? What happens when a developer needs a package that isn't in the catalog yet? How is ActiveState thinking about shadow AI and SBOM coverage beyond language libraries? What upcoming regulatory deadlines, like the EU Cyber Resilience Act, should security teams have on their radar? What happens to open source security when AI produces more CVEs and patches than the maintainers behind these projects can process? Huge thanks to our sponsor, ActiveState ActiveState gives security and engineering teams a single governed source for open source software. With 79 million components built from source, continuously remediated, and delivered directly into the tools teams already use, ActiveState eliminates the CVE backlog and the developer toil that comes with it. Companies see a 60 to 99% reduction in CVEs and reclaim up to 30% of developer time.  Curate a private, vetted repository of open source components from the ActiveState Library that developers use safely without scouring the internet. A Curated Catalog provides your security team total control over what enters their environments while giving engineering teams a fast, secure way to build, onboard, and start new projects.

In this episode, Grant Oviatt, vp of product and co-founder at Prophet Security, explains how his platform deploys AI agents to investigate and respond to alerts the way a skilled analyst would, using REST API integrations across existing security tools rather than absorbing all your data into another SIEM. Joining him are Will Gregorian, CISO at Galileo Medical, and Howard Holton, CEO at GigaOm. Want to know: Why are AI-powered SOC tools adding to analyst frustration rather than reducing it? When an AI agent makes a bad call on an investigation, who actually owns that failure? How does Prophet Security's audit trail let you trace every query, piece of evidence, and reasoning step an agent used? Why is Prophet Security using frontier models rather than training its own, and how does security-specific context change the outcome? What does giving an AI agent remediation authority look like in practice, and where does Prophet Security draw the line? How long does it realistically take to go from contract to running Prophet Security against live alerts? Check out the episode for the answers you need. Huge thanks to our episode sponser, Prophet Security Prophet AI is an Agentic AI SOC Platform that investigates and responds with context, shows its reasoning, and elevates every part of your SOC. Prophet AI SOC Analyst investigates and responds to alerts in minutes; Threat Hunter streamlines threat hunts with a natural language interface; and Detection Advisor provides insights on detection quality and coverage.

In this episode, Venkat Siva, co-founder and CEO at CompFly AI, explains how his platform gives security, engineering, and business teams a control plane for autonomous AI agents across their full lifecycle. CompFly discovers agents, assigns each one a verifiable distributed identity, runs adversarial and safety simulations before launch, enforces deterministic policies at runtime through a gateway, and produces immutable audit logs for compliance teams after the fact. Joining him are Mike Lockhart, CISO at EagleView, and Gary Chan, System VP and CISO at SSM Health. Huge thank you to our sponsor, CompFly AI CompFly is the control plane for the agentic enterprise. We make autonomous AI agents governable at scale discovering them, evaluating their risk, and enforcing real-time guardrails before execution. Enterprises deploy CompFly to move agents from sandbox to production with the evidence trail their boards/management require.

In this episode, Nico Waisman, CISO at XBOW, explains how XBOW uses autonomous AI agents to run continuous, incremental penetration testing without triggering false-positive avalanches or taking down production systems. Joining him are Jacob Combs, CISO at Tandem Diabetes Care, and Davi Ottenheimer, president at Flying Penguin. Want to know: Why can't traditional pen tests keep up with modern attack surfaces? How XBOW's attack credit model maps to the way security teams already size testing effort? What stops an autonomous pen testing agent from causing real damage in production? How incremental testing works when a new pull request changes the application? Where XBOW is headed on prompt injection and LLM-specific vulnerabilities? How you audit what the AI actually did during an assessment? What novel vulnerability chains are emerging as AI reasoning models get more capable? Check out the episode for the answers you need. Huge thanks to our sponsor, XBOW

In this episode, Cassio Goldschmidt, co-founder and CTO at Reflex Security, explains how Reflex replaces static, script-driven tabletops with adaptive AI-driven simulations that fight back, measure real human behavior under pressure, and surface the gaps that scripted exercises never reach. Joining him are Nick Espinosa, host of the nationally syndicated Deep Dive Radio Show, and Jay Wilson, CISO and CIO at Insurity. Want to know: Why do traditional tabletops train teams to know the plan rather than execute under pressure? What's the difference between a team that panics and a team that chokes, and why does it matter? How does Reflex use AI agents to adapt the simulation based on what the team actually does? Can you run separate tabletops for technical, legal, and executive audiences without multiplying the workload? Is there a risk that security leaders optimize for the AI's score rather than genuine preparedness? How does an AI agent joining a video conference change the way a tabletop runs? How hard should training be relative to the real thing? Check out the episode for the answers you need. Huge thanks to our sponsor, Reflex Security Most tabletop exercises are static, predictable, and easy to pass. Reflex Security built the first tabletop that fights back, throwing teams into dynamic simulations against intelligent AI adversaries that adapt to your every move. With Reflex, your team can move from checkbox exercises to real crisis readiness.

In this episode, Ryan Lloyd, Chief Product Officer at Guardsquare, explains how the platform combines code obfuscation, runtime integrity checks, and real-time threat monitoring to secure mobile apps at the binary level, integrated directly into the CI/CD pipeline. Joining him are TC Niedzialkowski, Head of IT & Security at Opendoor, and Montez Fitzpatrick, CISO at Navvis. Want to know: Why does organizational apathy around mobile app security persist even as mobile becomes the primary customer channel? What's the difference between app integrity and code integrity, and why does it matter for defending against repackaging attacks? How does obfuscation function as a real security control rather than just security through obscurity? How does Guardsquare fit into the CI/CD pipeline, and what does the actual build overhead look like for development teams? What API and webhook capabilities exist for routing threat monitoring data into your existing security stack? How does Guardsquare's mobile app attestation model bind server-side APIs to verified legitimate app instances — and why does that matter for stopping bots and credential theft? Huge thanks to our sponsor, Guardsquare Guardsquare delivers mobile app security without compromise, providing advanced protections for both Android and iOS apps. From app security testing to code hardening to real-time visibility into the threat landscape, Guardsquare solutions provide enhanced mobile application security from early in the development process through publication. Learn more about how to protect your app at Guardsquare.com.

In this episode, Ori Eisen, founder and CEO at Trusona, makes a case for getting out of the AI detection arms race entirely. He argues that trying to catch AI-generated fakes with AI detection is the antivirus playbook, and we know how that ends. Trusona instead anchors verification to authoritative sources, DMV records and physical-world signals, things AI can mimic on screen but can't actually own. No pre-registered devices required. And it works in both directions: attackers calling your help desk, and attackers calling your employees while pretending to be IT. Joining him are Eduardo Ortiz, VP and Global Head of Cybersecurity at Techtronic Industries, and Mandy Huth, SVP and CISO at Ultra Clean Technology. Want to know: Why do MFA and SSO still leave gaps attackers walk right through? How Trusona verifies identity with no pre-registered devices or tokens? Why building AI detection on top of AI fakes is a losing strategy? How is a false rejection rate of zero achievable without locking out real employees? What deployment actually looks like, and how fast you can be live? Which departments beyond IT need identity verification, and where do you start? How to measure the business value of this beyond just counting blocked account takeovers? Why is a solid help desk protocol still not enough on its own? Huge thanks to our sponsor, Trusona GenAI supercharges identity impersonation and social engineering attacks – rendering legacy identity verification methods obsolete, especially in high-risk workflows like IT Help Desk password/MFA resets, vendor payment changes, remote employee hiring, or customer account access. Trusona ATO Protect empowers your team to thwart these attacks across business units and channels. GenAI supercharges identity impersonation and social engineering. It's rapidly eroding traditional authentication, especially in high-risk workflows like help desk password or MFA resets, vendor payment changes, remote employee hiring, and customer account access.   Trusona's ATO Protect addresses deepfakes and social engineering directly—without adding friction or relying on legacy MFA.

All links and images can be found on CISO Series. In this episode, Raj Patil, CTO at enQase, explains how enQase's full-stack platform helps enterprises implement quantum-safe security through a structured, integrated approach. This covers everything from cryptographic asset discovery and governance to out-of-band key generation for network appliances, without requiring organizations to rip and replace existing infrastructure. Joining him are Ross Young, co-host at CISO Tradecraft, and Adam Palmer, CISO at First Hawaiian Bank. Want to know: Why is the post-quantum cryptography transition harder than simply implementing new standards? What three factors should frame every CEO conversation about quantum risk? Where should a highly regulated enterprise start, and what can reasonably wait three to five years? Why should we be planning for "harvest now, decrypt later" attacks right now? How do you build and track a cryptographic bill of materials across hundreds of applications and devices? Why is crypto agility more important than picking the perfect algorithm? Huge thanks to our sponsor, enQase The enQase Platform empowers enterprises, defense organizations, cloud providers, and critical infrastructure operators to seamlessly adopt quantum-safe technologies while achieving crypto agility across their ecosystems.  By combining quantum-grade hardware with software-defined control and interoperability, enQase ensures alignment with NIST standards, delivers unmatched flexibility and compliance readiness, and reduces risk across data, network, and compute layers, all while maintaining business continuity and operational resilience in an evolving cryptographic landscape. Learn more at enqase.com.