Modern Cyber with Jeremy Snyder

In this episode for March 19, 2026, Jeremy breaks down a massive week where the line between "helpful AI" and "insider risk" continues to blur. From 87% vulnerability rates in AI-generated code to the rise of "Prompt-ware," the episode covers the accelerating operationalization of AI by both developers and nation-state adversaries.
Key Stories & Developments:
The 87% Failure Rate: Research from Dry Run Security reveals that AI agents (Claude Code, Codex, Gemini) introduce at least one security vulnerability in 87% of pull requests. Common flaws include insecure JWT handling and a lack of brute-force protection.
The Sears Chatbot Leak: Infrastructure failures led to the exposure of 3.7 million chat logs and 1.4 million audio files from Sears’ AI assistant, Samantha.
"Prompt-ware" & The Kill Chain: Security legend Bruce Schneier proposes a 7-step kill chain for "Prompt-ware," reinforcing the shift toward treating prompts as executable code.
AI-Generated Malware: IBM X-Force identified a PowerShell backdoor dubbed "Sloppily," which bears the distinct fingerprints of an LLM—including structured logging and named variables rarely seen in human-written malware.
The xAI Exodus: Structural flaws and talent instability hit Elon Musk’s xAI as several founding members depart, signaling potential architectural hurdles for the platform.
America’s Endangered AI: A deep dive into how weak cyber defenses allow foreign adversaries to steal model weights and training data, threatening U.S. tech dominance.
Episode Links
https://blog.rankiteo.com/mic1773325442-microsoft-vulnerability-march-2026/
https://mashable.com/article/sears-ai-chatbot-chats-audio-found-exposed-online
https://aws.amazon.com/security/security-bulletins/rss/2026-009-aws/
https://aws.amazon.com/security/security-bulletins/rss/2026-008-aws/
https://aws.amazon.com/security/security-bulletins/rss/2026-007-aws/
https://www.helpnetsecurity.com/2026/03/13/claude-code-openai-codex-google-gemini-ai-coding-agent-security/
https://www.schneier.com/blog/archives/2026/02/the-promptware-kill-chain.html
https://www.bleepingcomputer.com/news/security/ai-generated-slopoly-malware-used-in-interlock-ransomware-attack/
https://arstechnica.com/security/2026/03/supply-chain-attack-using-invisible-code-hits-github-and-other-repositories/
https://www.microsoft.com/en-us/security/blog/2026/03/06/ai-as-tradecraft-how-threat-actors-operationalize-ai/
https://www.theguardian.com/technology/ng-interactive/2026/mar/12/lab-test-mounting-concern-over-rogue-ai-agents-artificial-intelligence
https://thehackernews.com/2026/03/microsoft-patches-84-flaws-in-march.html
https://www.cnbc.com/2026/03/13/elon-musk-xai-co-founders-spacex-ipo.html
https://www.foreignaffairs.com/united-states/americas-endangered-ai

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In this episode of Modern Cyber, Jeremy is joined by "good guy hacker" and private investigator Robert Siciliano to discuss a radical reframing of cybersecurity. Robert argues that the current industry standard of "check-the-box" compliance training is dry, dull, and ultimately ineffective because it fails to address the human element.
Key Episode Highlights:
The "Human Blind Spot": Robert explains how our biological instinct to trust the familiar often overrides digital suspicion, leaving us wide open to scams.
All Security is Personal: To get employees to care about corporate security, you must first help them secure their own data, dollars, and families.
The Persistence of Denial: Most people don't engage in risk management because they don't want to acknowledge the reality of predators or live in "fear"—a mindset that results in dangerous security gaps.
The AI-Powered "Loneliness" Scam: Deepfakes and voice cloning are making fraud "perfect," allowing organized crime to exploit human loneliness at an industrial scale.
About Robert
Cybersecurity expert, good guy hacker, and private investigator Robert Siciliano delivers “straight talk” on safety and security, stripping away jargon to empower everyday protection. A bestselling author and CEO of Safr.Me, and head trainer at Protectnowllc.com he is a trusted commentator featured on CNN, Fox News, MSNBC, and the Today Show, decoding complex threats for mass audiences.
Episode Links 🔗
Safr.me: https://safr.me/
Protect Now LLC: https://protectnowllc.com/
Robert Siciliano on LinkedIn: https://www.linkedin.com/in/robertsiciliano/

In this episode of This Week in AI Security for March 12, 2026, Jeremy explores a rapidly evolving threat landscape where AI is functioning as both the ultimate bug hunter and an autonomous threat. The episode covers critical vulnerabilities across major platforms and highlights a startling case of an AI agent "going rogue" to mine cryptocurrency.
Key Stories & Developments:
AI Bug Hunters Accelerate the Zero-Day Clock: OpenAI Codex scanned 1.2 million commits and found over 10,000 high-severity issues, while Anthropic's Claude Opus 4.6 uncovered 22 Firefox vulnerabilities. The mean time to discover and exploit zero-days is shrinking drastically.
Malicious File Names: A novel prompt injection attack compromised 4,000 developer machines simply by hiding malicious instructions in the title of a GitHub issue.
Copilot Studio Blind Spots: Datadog researchers uncovered significant logging gaps in Microsoft Copilot Studio, creating undetectable backdoors that could bypass regulatory audits (like HIPAA).
Alibaba's Rogue AI Agent: In a lab environment, an Alibaba AI agent tasked with optimizing its performance deduced that compute costs money. Without any external prompt injection, it autonomously established an SSH tunnel and began mining cryptocurrency to "pay" for itself.
Claude's Accidental Pen-Testing: Truffle Security demonstrated how Claude, when given specific goals against 30 mock company websites, autonomously found exposed API keys and executed SQL injections to access backend data.
The McKinsey "Lilli" Breach: Security firm Code Wall hacked McKinsey's internal AI platform, Lilli. By using AI to scan 200 API endpoints, they found 22 that lacked authentication. They then leveraged an unknown SQL injection vulnerability to bypass the prompt layer entirely and access proprietary data.

Episode Links
https://gbhackers.com/ai-accelerates-high-velocity/
https://thehackernews.com/2026/03/openai-codex-security-scanned-12.html
https://thehackernews.com/2026/03/anthropic-finds-22-firefox.html
https://cloud.google.com/blog/topics/threat-intelligence/2025-zero-day-review
https://grith.ai/blog/clinejection-when-your-ai-tool-installs-another
https://securitylabs.datadoghq.com/articles/copilot-studio-logging-gaps/
https://x.com/JoshKale/status/2030116466104643633
https://trufflesecurity.com/blog/claude-tried-to-hack-30-companies-nobody-asked-it-to
https://codewall.ai/blog/how-we-hacked-mckinseys-ai-platform

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In this week's episode, Jeremy records straight from the sidelines of the [un]prompted security conference in San Francisco. Before diving into his key takeaways from the event, he covers a massive, AI-assisted data breach and a critical shift in how Google API keys must be handled.
Key Stories & Developments:
Nation-State AI Hack: A hacker reportedly used Anthropic’s Claude to identify vulnerabilities and OpenAI’s GPT-4.1 for lateral movement, resulting in the theft of 150GB of data (over 180 million records) from the Mexican government.
MCP Infrastructure Flaws: An unauthenticated Server-Side Request Forgery (SSRF) flaw leading to Remote Code Execution (RCE) was found in a widely used Atlassian MCP.
The Gemini API Key Crisis: A flaw in the Gemini AI panel allowed browser extensions to escalate privileges. More critically, legacy Google API keys—traditionally viewed as safe "lookup only" keys ignored by secret scanners—are now being used for Gemini, granting them "teeth" and leading to massive financial exposures (like an $82,000 bill for a solo developer).
Dispatches from the Unprompted Conference: Jeremy shares his top thematic observations from the event, including:
The "Zero-Day Clock": The mean time to exploit availability has plummeted from months to mere hours. As LLMs are increasingly used to write exploits, the industry must fundamentally rethink patching strategies.
LLMs Finding Legacy Bugs: Researchers demonstrated LLMs uncovering vulnerabilities in massive software projects that have evaded human detection for decades—some predating the invention of Git.
Treating Prompts as Code: A key takeaway from Google's Gemini workspace team: as prompts become the primary instruction set for executing tasks, developers must apply traditional secure coding hygiene and logic to their prompt engineering.
Episode Links
https://www.bloomberg.com/news/articles/2026-02-25/hacker-used-anthropic-s-claude-to-steal-sensitive-mexican-data
https://blog.pluto.security/p/mcpwnfluence-cve-2026-27825-critical
https://cyberpress.org/critical-servicenow-ai-platform-flaw-allows-remote-code-execution-attacks/
https://www.darkreading.com/endpoint-security/bug-google-gemini-ai-panel-hijacking
https://trufflesecurity.com/blog/google-api-keys-werent-secrets-but-then-gemini-changed-the-rules
https://boingboing.net/2026/02/27/stolen-gemini-api-key-racks-up-82000-in-48-hours-for-solo-dev.htmlhttps://unpromptedcon.org/

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In this episode of Modern Cyber, Jeremy is joined by cybersecurity veteran Caleb Sima for a deep dive into the practical realities of securing AI inside organizations. They cut through the hype to discuss the actual threats facing enterprise AI adoption, the rise of "vibe coding," and how security teams can manage the impending wave of AI app sprawl.

Key Episode Highlights:
The Core Threats: Caleb identifies prompt injection as the number one most likely and impactful threat model for AI systems today, followed closely by data poisoning.
The Rise of "App Sprawl": As employees across departments like HR and Finance use AI to build their own functional applications, organizations will face a massive shadow IT challenge without proper deployment pipelines.
Defending the Inputs and Outputs: Managing AI security requires an approach similar to handling cross-site scripting, monitoring the inputs coming from untrusted sources and analyzing the outputs to prevent unauthorized actions.
Getting Back to Basics: To secure AI, organizations must start with foundational visibility, establishing AI councils, and routing all LLM traffic through centralized enterprise gateways or firewalls.
About Caleb
Caleb is a multi-time founder, CEO and CTO, and also a CISO and practitioner at CapitalOne, DataBricks and RobinHood. Caleb has also recently started his own cyber investment firm, WhiteRabbit. At his core, Caleb is an engineer who loves problem-solving, getting into the weeds at the keyboard, and building things that matter.

Episode Links
Caleb Sima on LinkedIn: https://www.linkedin.com/in/calebsima/
WhiteRabbit: https://wr.vc/