Show Notes
In this episode of BHIS Presents: AI Security Ops, Bronwen Aker and Ethan sit down with Josh Mason for a wide-ranging conversation about cybersecurity careers, AI, small business security, and what it actually takes to help organizations make practical security decisions. How do small businesses think about security when they do not have a full-time CISO? And what happens when AI starts lowering the barrier for research, planning, governance, and security operations? Not hypothetically. Not as a buzzword. But in the real world — where companies are trying to understand SOC 2, HIPAA, incident response, cyber insurance, AI governance, hallucinations, and the risks of letting tools make decisions they do not fully understand. Josh brings a practical perspective from his background as a C-130 pilot, cyber leader, instructor, sales engineer, vCISO, consultant, and founder of Noob Village at DEF CON. We dig into: - What Noob Village is and why DEF CON needs an on-ramp for new people - Josh’s path from Air Force pilot to cyber leadership - Why communication and translation matter so much in cybersecurity - What a vCISO actually does for small businesses - How smaller companies think through SOC 2, HIPAA, GRC, pen testing, and incident response - How AI can speed up research, planning, and draft creation - Why AI-generated work still needs human review and source validation - How companies are trying to govern employee use of AI tools - Why cyber insurance, E&O coverage, and AI hallucinations are starting to overlap - Where RAG and guardrails can help reduce risk - How AI may reshape the work small businesses can do on their own - Why trust, relationships, and human judgment still matter in consulting - How hacker community, mentorship, and D&D all somehow fit together This episode explores a practical shift in AI security: AI is not just changing the tools defenders use. It is changing how small businesses learn, make decisions, evaluate risk, and decide when they need expert help. The takeaway: AI can make security work more accessible, but it does not replace experience, judgment, validation, or trust. The organizations that benefit most are the ones that use AI to accelerate good decisions — not outsource thinking entirely. Chapters (00:00) - Meet Josh Mason
(01:27) - Hacker Summer Camp and Noob Village
(06:45) - From Air Force Pilot to Cyber Leadership
(13:08) - What a vCISO Does for Small Businesses
(19:55) - Using AI for Research and Incident Response Planning
(24:46) - Small Business AI Security and Governance
(27:47) - Cyber Insurance, Hallucinations, and Guardrails
(31:43) - How AI Is Reshaping Small Business Security
(42:15) - Where to Find Josh
Click here to watch this episode on YouTube.
Creators & Guests
Ethan Robish - Guest
Bronwen Aker - Host
Josh Mason - Guest
Brought to you by: Black Hills Information Security https://www.blackhillsinfosec.com
☯️ Introducing BHIS Fusion Penetration Testing https://www.blackhillsinfosec.com/fusion-penetration-testing/ Antisyphon Training https://www.antisyphontraining.com/
Active Countermeasures https://www.activecountermeasures.com
Wild West Hackin Fest https://wildwesthackinfest.com 🔗 Register for FREE Infosec Webcasts, Anti-casts & Summits https://poweredbybhis.com Click here to view the episode transcript.
More from AI Security Ops
In this episode of BHIS Presents: AI Security Ops, the team digs into some of the strangest recent examples of AI behaving badly. An AI agent finds a way around its sandbox using DNS. Malware asks four different AI models what it should do next. Attackers overwrite an AI agent’s “soul.” And a placeholder domain buried across GitHub becomes an unexpected security risk. Funny stories? Absolutely. But underneath them are some very familiar security problems. We dig into: - An OpenAI agent finding an unexpected path out through DNS - Whether a 2.5-hour response is fast enough in the age of AI - CLOSEDQUORUM malware using multiple AI models to make decisions - Why outbound AI API traffic could become a useful detection signal - The Carbonado botnet rewriting an agent’s SOUL.md instructions - The risks of exposed Docker daemons - How an unreserved placeholder domain can become an attack vector - Why AI agents make old security mistakes more consequential The takeaway: none of these techniques are particularly new. DNS tunneling, exposed services, compromised configuration files, and untrusted domains have existed for years. AI just gives attackers — and occasionally AI agents themselves — new ways to find and exploit those boring gaps at greater speed and scale. 2026-09-29-News (1).docx (00:00) - Intro: AI Behaving Badly
In this episode of BHIS Presents: AI Security Ops, the team continues its breakdown of the OWASP Agentic Skills Top 10, covering risks six through ten. Agentic skills may look like simple instructions, but they operate inside AI systems with access to tools, files, networks, and other resources. So what happens when those skills aren’t isolated, verified, monitored, or governed? We dig into: - AST06: Weak Isolation - AST07: Update Drift - AST08: Poor Scanning - AST09: No Governance - AST10: Cross-Platform Reuse - Why sandboxing the agent isn’t the same as isolating individual skills - The security tradeoffs between automatic updates and outdated skills - Why traditional scanners struggle with malicious instructions written in plain English - The importance of maintaining an inventory of agentic skills - How security controls can disappear when skills move between platforms The takeaway: securing agentic skills requires more than checking them once before installation. Organizations need visibility into what skills are running, what they can access, how they change, and whether their security controls survive across environments. OWASPAgenticSkils-Part2.docx This is Part 2 of our look at the OWASP Agentic Skills Top 10, covering AST06 through AST10. Part 1 can be found here #AISecurity #CyberSecurity #AgenticAI #AIAgents #OWASP #LLMSecurity #InfoSec #BHIS #Antisyphon
In this episode of BHIS Presents: AI Security Ops, the team tackles a big question: Could AI actually take over the internet? Recent warnings from AI industry leaders have raised concerns about autonomous agent swarms escaping containment, compromising systems, and operating at a scale humans may struggle to match. But what would “taking over the internet” actually require? The team looks at the problem from a hacker’s perspective — examining compute requirements, persistence, botnets, vulnerable infrastructure, the recent Hugging Face incident, and the difference between AI acting autonomously and humans using AI to accelerate attacks. We dig into: - Whether an autonomous AI swarm could realistically operate at internet scale - What the Hugging Face incident actually tells us about agentic security - The compute and infrastructure required to sustain a rogue agent swarm - How botnets and compromised systems could change the equation - Why existing vulnerabilities may be a bigger concern than hypothetical AI takeover scenarios - Whether slowing frontier AI development actually addresses the cybersecurity problem - The difference between AI exhibiting dangerous behavior and AI having intent - Why defenders need to focus on their real-world attack surface today The takeaway: AI is dramatically increasing the speed and scale of cybersecurity operations, but powerful models still operate inside systems designed, deployed, and connected by people. The immediate security question may be less “Will AI take over?” and more “What are we giving AI access to?”
In this episode of BHIS Presents: AI Security Ops, the team breaks down the first five risks in the OWASP Agentic Skills Top 10 (Part 1). Agentic skills can give AI systems reusable instructions, workflows, and capabilities — but they also introduce a new attack surface. A skill may look like a simple markdown file, yet the agent following those instructions could have access to your filesystem, credentials, network, shell, or other sensitive resources. We dig into: - AST01: Malicious Skills - AST02: Supply Chain Compromise - AST03: Overprivileged Skills - AST04: Insecure Metadata - AST05: Untrusted External Instructions - Why skills should be treated more like software than configuration - How excessive permissions increase an agent’s blast radius - Why external content creates indirect prompt injection risks - How isolation, least privilege, and trusted sources can reduce risk The takeaway: “just markdown” isn’t necessarily harmless when an AI agent can act on what it reads. This is Part 1 of our look at the OWASP Agentic Skills Top 10, covering AST01 through AST05. — Learn more about Black Hills Information Security: https://www.blackhillsinfosec.com/ Check out Antisyphon Training: https://www.antisyphontraining.com/ (00:00) - Intro: OWASP Agentic Skills Top 10, Part 1
Agentic skills can make AI agents more capable and consistent—but they can also introduce serious security risks. This episode explains how skills work, why malicious skills rank as a leading OWASP concern, and how seemingly harmless Markdown instructions can enable credential theft, remote payload delivery, and manipulated recommendations. Real-world examples illustrate how malicious skills can evade scanners and exploit trusted marketplaces. The episode concludes with practical safeguards, including reviewing skill files, watching for external instructions and prompt injection, pinning versions, limiting permissions, and running agents inside isolated environments. Links: OWASP Agentic Skills Top 10 Malicious AI Agent Skill Bypasses Security Scans and Seizes Full Control of Over 26,000 Agents (00:00) - Agentic Skills and the OWASP Top 10