When you fire up Claude Code, Cursor, or any AI coding agent, it launches with your full system permissions, your SSH keys, cloud credentials, browser passwords, every file on your machine. Most developers never think twice about it.

Luke Hinds did. And then he built something about it.

Luke is the creator of Sigstore, the cryptographic signing infrastructure now used by PyPI, Homebrew, GitHub, and Google as the industry standard for software supply chain security. In this episode, he joins Chris to talk about why he's watching the industry make the exact same mistake it made a decade ago, and what he built to try to stop it.

We cover the full picture: why application-layer guardrails and system prompts fundamentally fail as security boundaries for AI agents (and what kernel-level enforcement actually means), the .md file as an emerging control plane attack surface, the OpenClaw wake-up call and what the skills marketplace ecosystem gets structurally wrong about trust and provenance, the approval fatigue problem and Anthropic's 17% false negative rate on Claude Code's auto-mode classifier, extending SLSA and Sigstore attestation frameworks to AI-generated code, and why LLM-as-a-judge may not be the silver bullet many are hoping for.

Luke also makes a broader argument about where this is all heading — volumes of AI-generated code growing faster than human capacity to review it, junior engineers being priced out of the industry, and an aging cohort of engineers who can actually read and reason about code at depth. It's a candid, technically grounded conversation from someone who's been in open source security for 20+ years and has seen this movie before.

nono is at nono.sh, one line to install, one line to run. No excuse not to

Show Description

Joe Levy is the CEO of Sophos and a 30-year cybersecurity veteran who has held technical and executive roles across some of the industry's most recognizable brands. In this episode, we dig into a stat that should reframe how the entire industry thinks about its mission: out of roughly 359 million businesses worldwide, fewer than 32,000 have a CISO. That's less than one in 10,000 organizations with a security strategy leader — and it's a number Joe worked with Cybersecurity Ventures to quantify for the first time.

We explore what that structural gap means for how vendors build products, why the cybersecurity market is a 40-year-old market failure where spending goes up every year but outcomes don't improve, and how Sophos is betting that agentic AI can deliver CISO-level intuition to the hundreds of millions of organizations that could never conceive of hiring one. Joe breaks down where AI is genuinely delivering in security operations — and where the industry is overselling — drawing from Sophos's experience running the world's largest MDR service with 36,000 customers.

We also get into Sophos's Pacific Rim disclosure, a five-year engagement with a Chinese nation-state actor targeting their firewalls that Joe calls the highest form of threat intelligence sharing. He walks through the calculus of going public with that story, including the kernel-level monitoring they deployed on a handful of devices to stay one step ahead of the attacker. Plus, we discuss the SecureWorks acquisition, the CTO-to-CEO transition, competing with hyperscalers like Microsoft, and what the next chapter looks like for a billion-dollar PE-backed security company approaching maturity with Thoma Bravo.

Show Notes

• The cybersecurity poverty line quantified: out of 359 million businesses worldwide, fewer than 32,000 have a CISO — less than one in 10,000 — and this leadership gap compounds with the skills shortage and what Joe calls an "AI-enhanced market for lemons" where information asymmetry between buyers and vendors is getting worse
• The real problem isn't missing technology — most organizations already have endpoints and firewalls — it's misconfigurations, ignored alerts, undeployed agents, and no SOC to respond, which is why secure-by-default design and hybrid product-service models like MDR create more predictable outcomes than tools alone
• AI in the SOC is overhyped but not hype: Sophos runs 36,000 MDR customers and says the vast majority of Tier 1 (triage, false positive management) and Tier 2 (investigation, response) can now be performed by agents — but the industry lacks standard vocabulary for metrics like MTTR, letting vendors be "intentionally opaque" about what "response" actually means
• Joe introduces the concept of "humans as the accountability API" in an agentic world — AI can approximate analyst intuition, but someone still needs to be held accountable for remediation decisions, and a fully autonomous SOC may just be "a protection product with a very long data pipeline"
• The Pacific Rim story: Sophos spent five years engaged with a Chinese nation-state actor targeting their firewalls, deployed a kernel implant on fewer than a handful of attacker-controlled devices to observe exploit development in real time, and concealed targeted fixes among 150 other patches to avoid tipping off the adversary
• Sophos's CISO Advantage program aims to deliver the intuitions of a skilled security leader to the hundreds of millions of organizations that could never hire one — Joe calls it fixing a 40-year-old market failure and says they're shipping it this year

Show Description

The Zero Day Clock is ticking — and the numbers should make every security leader uncomfortable. In this episode, I sit down with Sergej Epp, CISO at a leading security firm, who built the Zero Day Clock after a weekend experiment using AI to discover vulnerabilities firsthand. What he found shocked him: with no professional vulnerability research background and just a few hours of work, he was successfully finding zero days across major security projects using AI models and basic scaffolding.

Sergej breaks down his concept of the "Verifier's Law" — the idea that offense has the cheapest verifier in cybersecurity because feedback is binary and instant (you either popped a shell or you didn't), while defense operates in a space where validation is expensive, ambiguous, and slow. We dig into what this asymmetry means for the industry, why 20 years of warnings from Ross Anderson, Bruce Schneier, Halvar Flake, and others have gone unheeded, and whether coordinated disclosure models are broken now that AI can reverse engineer a patch into a working exploit in minutes.

We also discuss the tension between regulation and deregulation playing out in the U.S. and EU, why the answer might be outcome-based accountability rather than prescriptive compliance, and what a realistic defensible posture actually looks like when the mean time to exploit for actively exploited vulnerabilities is under two days — while most organizations are still operating on 30-day patch cycles.

Show Notes

• Sergej shares how a weekend AI experiment led him to discover multiple zero days across major security projects with no professional vulnerability research experience — and why that should alarm the entire industry
• The "Verifier's Law" explained: offense has cheap, deterministic validators (pop a shell, exfiltrate data, trigger an XSS) while defense faces expensive, ambiguous validation (parsing SIM alerts, measuring security posture), giving AI-accelerated offense a structural advantage
• The Zero Day Clock synthesizes 3,500+ CVE-exploit pairs and shows the mean time to exploit for actively exploited vulnerabilities is now under two days — while organizations still operate on 14-to-30-day patch cycles
• 20 years of ignored warnings: from Ross Anderson's 2001 economics paper through Bruce Schneier, Halvar Flake's "the patch is the advisory" insight, and DARPA's Cyber Grand Challenge — the industry has consistently failed to act on clear signals
• AI can now reverse engineer patches to identify underlying flaws and generate working exploits in minutes, potentially breaking coordinated disclosure models and compressing the window between patch release and active exploitation to near zero
• The regulation paradox: the EU risks overregulating AI in ways that hamper defenders while attackers face no such constraints, while the U.S. is pushing deregulation that may remove the only forcing function for vendor accountability — Sergej and Chris discuss outcome-based regulation as a potential middle path
• Defenders have a data advantage: by understanding their own environments, infrastructure, and processes, security teams can detect AI-driven attacks through behavioral anomalies like hallucinated API calls, non-existent user accounts, and other artifacts of AI-generated attack playbooks
• The Zero Day Clock's real power is as a board-level communication tool — a single slide that translates the patching gap into a number executives and policymakers can't ignore, shifting the conversation from "are we compliant?" to "are we fast enough?"