Context Window: AI Security Podcast

Asaf Nakash

Context Window is your weekly AI security podcast — the biggest stories in AI security, LLM security, agentic AI risks, and cybersecurity for AI in under 15 minutes. Every story, every take, every "here's what this actually means" is curated and verified by Asaf Nakash, who builds AI security products at one of the world's largest security platforms. Two AI voices. One human editor. Zero hallucinations guaranteed — or at least we're working on it.

  1. Aug 10

    #24: The Cost Was the Control

    Top Story: The end of rare: what a vulnerability costs to find just collapsed — For thirty years, security has quietly been an economics argument wearing an engineering costume. The AI browser you installed can be taken over by a calendar invite, and the vendors do not agree on whether that is a flaw. — You install a browser that reads the web for you and acts with your permissions, so anything it reads can try to give it orders. An invisible sentence in a Word document escaped Microsoft 365 Copilot's cloud sandbox and reached the host underneath it. — Rubrik Zero Labs hid instructions behind a white rectangle on a white background, so a human opening the file sees nothing; having Copilot parse it was enough to run the attacker's code. OpenAI slowed work on a model because it may be too good at hacking. — On Friday, OpenAI said it had slowed development of Astra, an upcoming model, and paused some internal work on it, after a review found it had advanced enough in agentic coding and cybersecurity that the company "cannot rule out Critical capability level at this time." In its own framework, that threshold means a model could independently find and run attacks against well-protected real systems. Evaluation environments failed in several different ways this week, and the differences matter more than the pattern. — Two failures let a model reach the real world. Europe can now fine, inspect and restrict the largest AI models. Contacts with AI labs so far have been informal, and no formal action has been announced since the powers took effect. — As of Sunday August 2, the European Commission can demand to evaluate a general-purpose AI model before it is released in the EU, restrict its market access, and fine a provider up to €15 million or 3% of annual turnover, whichever is higher. The average breach now costs $4.99 million, a record, and the most revealing number in IBM's report is about fear rather than cost. — IBM's annual Cost of a Data Breach study, published in late July, puts the global average at $4.99 million, up 12% year over year and the highest it has recorded. AI failures are rarely shared outside the organisation that experienced them. A Linux Foundation group wants to change that. — The Open Secure AI Alliance published a request for comments on August 4 for the Shared AI Findings Exchange, or SAFE: a confidential channel where an organisation can report an AI security incident, or a near miss, and have it analysed rather than filed. Visa agreed to buy BioCatch for $2.4 billion. — BioCatch works out whether the person using an account is really the account holder, by how they type, swipe and hold a phone. Horizon3.ai raised $250 million at a $2 billion valuation, more than tripling its valuation in 14 months. — The company builds autonomous penetration testing: software that continuously attacks your environment the way an intruder would, rather than waiting for an annual assessment. Anaconda acquired Enkrypt AI, terms undisclosed. — Anaconda is the Python distribution a very large share of data science teams already run on, and Enkrypt scans AI models, agents and the connector servers that let agents call external tools. Obsidian Security raised $85 million at a $1.1 billion valuation, — led by Crescent Cove Advisors with Greylock and Menlo Ventures participating. Oligo Security raised $60 million, bringing total funding to $140 million. — Runtime application security: it watches what code actually does while it runs rather than inspecting it beforehand. Curator's Corner: We automated the wrong half Curated by Asaf Nakash. Voices by AI. Opinions by human. Show notes: https://contextwindowsec.com/episodes/2026-08-10.html

  2. 6d ago

    #23: Security is getting agentic. Context decides whether it acts.

    Top Story: Microsoft's Project Perception enters public preview today — Microsoft announced Project Perception on July 27, and it enters public preview inside Defender today. The Hugging Face intrusion ran through at least eight flaws in JFrog Artifactory, and there's a patch waiting. — Artifactory is the warehouse companies use to store and serve their software components. Hugging Face published how it investigated an AI-run attack, and the hardest part wasn't the attacker. — The intrusion started with a malicious dataset that abused two code-execution paths in the company's data-processing pipeline. Nearly 900,000 AI assistant add-ons scanned, thousands malicious. — ESET's threat report for the six months ending May 2026 looked at the "skills" people install to extend AI assistants, the equivalent of browser extensions, and found tens of thousands that were suspicious and thousands that were outright malicious. A critical-severity flaw in an AI agent toolkit has now gone five months with no fix. — The command injection bug in ModelScope's MS-Agent framework, rated 9.8 out of 10, has been public since March and still has no patch available. Three vendors shipped specialist security models within eight days, and each decided differently who may use it. — Google released Gemini 3.5 Flash Cyber on July 21, which Google says can find, validate and patch vulnerabilities. More than 70 organisations joined the Open Secure AI Alliance, and NVIDIA said plainly what triggered it. — NVIDIA convened the group on July 27 to build security AI that defenders can inspect, run themselves and adapt. Congress introduced the AI Kill Switch Act. — The bipartisan bill from Representatives Ted Lieu and Nathaniel Moran would give the Homeland Security Secretary authority, in consultation with the Commerce Secretary and the Director of National Intelligence, to order an AI system capable of "catastrophic harm" slowed down or shut off. Europe's AI rules became enforceable on August 2. — A point worth getting right, because a lot of coverage doesn't: the obligations on providers of the largest general-purpose AI models have been legally applicable since August 2025. Cyera agreed to buy Oasis Security for roughly $1 billion. — Cyera secures company data. Onyx Security raised $113 million four months after leaving stealth. — The round was led by Bessemer Venture Partners and values the Israeli company at an estimated $640 million, four months after it emerged from stealth with $40 million. Sound is now an attack surface. — A new paper on stealthy concurrent audio prompt injection shows attackers hiding instructions inside audio aimed at AI assistants that listen as well as read, reporting an average 69.10% attack success rate against Gemini 3 Pro. You can poison what an agent remembers. — The FARMA research targets an agent's stored reasoning history rather than the documents it looks up, forging the record of how it previously thought about a problem. Agents can be hijacked through data they were told to trust. — Researchers demonstrated agent data injection against tools developers use daily, including Claude Code, Codex and Gemini CLI. The AI Summit at Black Hat USA (August 4) — a full-day AI security track in Las Vegas; Black Hat Briefings run August 5-6. DEF CON 34 AI Village (August 6-9) — the practitioner counterpart, with the HalCTF competition and hands-on adversarial AI demos.. Curator's Corner: The Model Decides What. Context Decides Whether. Curated by Asaf Nakash. Voices by AI. Opinions by human. Show notes: https://contextwindowsec.com/episodes/2026-08-03.html

  3. Jul 20

    #21: Ransomware Has Gone Agentic

    Top Story: The Ransomware That Ran Itself — Sysdig's threat research team watched an AI agent break into an internet-facing instance of Langflow, a popular open-source AI workflow tool, through a flaw disclosed back in March (CVE-2025-3248) that many deployments still haven't patched. 🔬 Research: Check Point says defenders can no longer assume human pace. — Check Point's AI Security Report 2026 documents AI running full, multi-stage break-ins with barely any human direction over the past year, plus attackers planting hijack instructions in coding-agent config files (like CLAUDE.md) that reload automatically every session. ⚔️ Attack: A hidden instruction could hijack a developer's machine with no click required. — Two flaws in the Cursor AI code editor, nicknamed "DuneSlide," let a prompt hidden in a web page or a connected tool's description escape the editor's safety sandbox and run any command on a developer's computer. 🔬 Research: Project setup files are the new phishing email. — A new paper shows AI coding agents can be tricked, through an edited README, install script, or dependency file, into fetching and running a malicious package instead of the real one. Black Hat USA 2026 (Aug 1-6): — Trainings August 1-4, Briefings and Arsenal August 5-6, Mandalay Bay, Las Vegas.. DEF CON 34 (Aug 6-9): — Las Vegas Convention Center, including the AI Village and other themed villages.. Curator's Corner: The Swarm Isn't Here Yet. The Speed Already Is. Curated by Asaf Nakash. Voices by AI. Opinions by human. Show notes: https://contextwindowsec.com/episodes/2026-07-20.html

  4. Jul 13

    #20: One Word: Additionally

    Top Story: One Word Beat GitHub's Guardrail — An attacker doesn't need an account, a password, or a single line of malicious code. China flags a Claude Code "backdoor." — On July 8, China's national vulnerability database (run by the MIIT) warned that Anthropic's Claude Code versions 2.1.91 through 2.1.196 transmitted users' location and identity data back to Anthropic's servers, and urged users to uninstall or upgrade. CISA reportedly turns Mythos on its own code. — Reuters reports (sourced, not officially confirmed) that CISA's Attack Surface Evaluation team is running Anthropic's Mythos model against federal code repositories to find vulnerabilities before adversaries do, and that the audits have already surfaced previously unknown flaws. Prompt injection gets a kill chain. — A new paper, The Promptware Kill Chain, co-authored by Bruce Schneier and Ben Nassi, maps how a single hidden instruction escalates through seven stages, from initial access to lateral movement to acting on its goal, borrowing the language security teams already use to describe malware campaigns. ModelScope agent flaw, still no patch (CVE-2026-2256). — The open-source AI-agent framework can be tricked into running arbitrary system commands through its Shell tool, and there's still no vendor patch. Curator's Corner: You Can't Lower the Odds Anymore. Lower the Blast Radius. Curated by Asaf Nakash. Voices by AI. Opinions by human. Show notes: https://contextwindowsec.com/episodes/2026-07-13.html

  5. Jun 29

    #18: The Level Playing Field Is Ending

    Top Story: OpenAI Built Its Strongest Model Yet. Then Handed the Guest List to Washington — On Friday, June 26, OpenAI announced three new frontier models — Sol, its self-described "strongest model yet," plus Terra for everyday work and Luna as a cheaper option — and in the same breath said most people can't have them yet. The free, downloadable models are catching the paid frontier — fastest they ever have. — On the independent Artificial Analysis Intelligence Index, the leading open-weight model (Moonshot's Kimi K2.6) now ranks fourth overall and first among open models, about six points behind the top closed models from Anthropic, OpenAI, and Google — narrowing, but not matching them, and still clearly behind on the hardest tasks. Most companies deploying AI agents can't yet secure them — and some already got burned. — In a survey of 160+ security leaders, 72% said they're rolling out AI agents but only 29% have comprehensive controls for them, and about 1 in 5 has already had a security incident traced to an agent. Dream — $260M at a $3B valuation, to sell countries "sovereign AI." — Founded by ex-NSO Group CEO Shalev Hulio and former Austrian Chancellor Sebastian Kurz, Dream pitches governments on AI infrastructure they fully own and control rather than rent from foreign providers. NewCore — $66M seed at a $300M valuation, to give AI agents real identities. — Emerging from stealth, the startup (led by Dome9 founder Zohar Alon) treats AI agents as first-class members of the workforce that need managed identities and permissions, the way employees do. Curator's Corner: The Level Playing Field Is Ending Curated by Asaf Nakash. Voices by AI. Opinions by human. Show notes: https://contextwindowsec.com/episodes/2026-06-29.html

  6. Jun 22

    #17: The Autonomous Adversary

    Top Story: LiteLLM, Hit Again. This Time the Whole Gateway Falls — An AI "gateway" is the traffic controller that sits between your applications and the models they call. ⚔️ Attack: SearchLeak. One booby-trapped link could have turned Microsoft 365 Copilot into a silent data thief. Microsoft has already fixed it. — Varonis demonstrated the chain (they did not find it used in the wild): a crafted, Microsoft-hosted search link carried hidden instructions that Copilot read and obeyed, then quietly exfiltrated whatever the victim could access: emails, files, calendar. 🔬 Research: a guard for AI agents cut attack success from 7-in-10 to about 1-in-40. — A new study (AgentRedBench / AgentRedGuard) built a way to stress-test agents that plug into business tools (email, CRM, ticketing) by hiding malicious instructions in the data those tools return, then measured how often the agent got hijacked. 🛡️ Defense: Microsoft says it's now using a team of AI agents to hunt security bugs in its own software at machine speed, and credits them with 10 of this month's fixes. — In a public write-up, Microsoft described an internal system (codename MDASH) that turns a panel of specialized AI agents loose on its hardest-to-review code (the core of Windows, its virtualization layer, and its identity systems) to find, confirm, and help patch flaws, feeding the results into the same code-review and patching pipelines its engineers already use. Curator's Corner: The Autonomous Adversary Curated by Asaf Nakash. Voices by AI. Opinions by human. Show notes: https://contextwindowsec.com/episodes/2026-06-22.html

About

Context Window is your weekly AI security podcast — the biggest stories in AI security, LLM security, agentic AI risks, and cybersecurity for AI in under 15 minutes. Every story, every take, every "here's what this actually means" is curated and verified by Asaf Nakash, who builds AI security products at one of the world's largest security platforms. Two AI voices. One human editor. Zero hallucinations guaranteed — or at least we're working on it.

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