Claire (@ClaireTills) doesn’t have your typical roll in infosec. She sits between the security teams and marketing team. It’s a fascinating roll and something that gives her a lot of insight into multiple parts of the business. What works and what doesn’t work in communicating security to the different areas. Check her blog out.

Claire (@ClaireTills) doesn’t have your typical roll in infosec. She sits between the security teams and marketing team at Tenable. It’s a fascinating roll and something that gives her a lot of insight into multiple parts of the business. What works and what doesn’t work in communicating security to the different areas. Check her blog out.

Summary: Timothy De Block is joined by Keith Hoodlet, Engineering Director at Trail of Bits, for a fascinating, in-depth look at AI red teaming and the security challenges posed by Large Language Models (LLMs). They discuss how prompt injection is effectively a new form of social engineering against machines, exploiting the training data's inherent human biases and logical flaws. Keith breaks down the mechanics of LLM inference, the rise of middleware for AI security, and cutting-edge attacks using everything from emojis and bad grammar to weaponized image scaling. The episode stresses that the fundamental solutions—logging, monitoring, and robust security design—are simply timeless principles being applied to a terrifyingly fast-moving frontier. Key Takeaways The Prompt Injection Threat Social Engineering the AI: Prompt injection works by exploiting the LLM's vast training data, which includes all of human history in digital format, including movies and fiction. Attackers use techniques that mirror social engineering to trick the model into doing something it's not supposed to, such as a customer service chatbot issuing an unauthorized refund. Business Logic Flaws: Successful prompt injections are often tied to business logic flaws or a lack of proper checks and guardrails, similar to vulnerabilities seen in traditional applications and APIs. Novel Attack Vectors: Attackers are finding creative ways to bypass guardrails: Image Scaling: Trail of Bits discovered how to weaponize image scaling to hide prompt injections within images that appear benign to the user, but which pop out as visible text to the model when downscaled for inference. Invisible Text: Attacks can use white text, zero-width characters (which don't show up when displayed or highlighted), or Unicode character smuggling in emails or prompts to covertly inject instructions. Syntax & Emojis: Research has shown that bad grammar, run-on sentences, or even a simple sequence of emojis can successfully trigger prompt injections or jailbreaks. Defense and Design LLM Security is API Security: Since LLMs rely on APIs for their "tool access" and to perform actions (like sending an email or issuing a refund), security comes down to the same principles used for APIs: proper authorization, access control, and eliminating misconfiguration. The Middleware Layer: Some companies are using middleware that sits between their application and the Frontier LLMs (like GPT or Claude) to handle system prompting, guard-railing, and filtering prompts, effectively acting as a Web Application Firewall (WAF) for LLM API calls. Security Design Patterns: To defend against prompt injection, security design patterns are key: Action-Selector Pattern: Instead of a text field, users click on pre-defined buttons that limit the model to a very specific set of safe actions. Code-Then-Execute Pattern (CaMeL): The first LLM is used to write code (e.g., Pythonic code) based on the natural language prompt, and a second, quarantined LLM executes that safer code. Map-Reduce Pattern: The prompt is broken into smaller chunks, processed, and then passed to another model, making it harder for a prompt injection to be maintained across the process. Timeless Hygiene: The most critical defenses are logging, monitoring, and alerting. You must log prompts and outputs and monitor for abnormal behavior, such as a user suddenly querying a database thousands of times a minute or asking a chatbot to write Python code. Resources & Links Mentioned Trail of Bits Research: Blog: blog.trailofbits.com Company Site: trailofbits.com Weaponizing image scaling against production AI systems Call Me A Jerk: Persuading AI to Comply with Objectionable Requests Securing LLM Agents Paper: Design Patterns for Securing LLM Agents against Prompt Injections. Camel Prompt Injection Defending LLM applications against Unicode character smuggling Logit-Gap Steering: Efficient Short-Suffix Jailbreaks for Aligned Large Language Models LLM Explanation: Three Blue One Brown (3Blue1Brown) has a great short video explaining how Large Language Models work. Lakera Gandalf: Game for learning how to use prompt injection against AI Keith Hoodlet's Personal Sites: Website: securing.dev and thought.dev

Summary: Join Timothy De Block for a special, behind-the-scenes episode where he rehearses his presentation, "The Hitchhiker's Guide to Threat Modeling." This episode serves as a unique guide for aspiring and experienced speakers, offering a candid look at the entire preparation process—from timing and slide design to audience engagement and controlled chaos. In addition to public speaking tips, Timothy provides a concise and practical overview of threat modeling, using real-world examples to illustrate its value. Key Presentation Tips & Tricks Practice for Time: Practice the presentation multiple times to ensure the pacing is right. Timothy suggests aiming to be a little longer than the allotted time during practice, as adrenaline and nerves on the day of the talk will often cause a person to speak more quickly. Use Visuals Strategically: Pacing and hand gestures can improve the flow of a talk. Be careful with distracting visuals, such as GIFs, by not leaving them up for too long while you are speaking. Stand Out as a Speaker: Be willing to do shorter talks, such as 30-minute sessions, as many speakers prefer hour-long slots. He notes that having a clever or intriguing title for your presentation is important, and using humor or pop-culture references can help.

Summary: In a unique live recording, Timothy De Block is joined by Sam Chehab from Postman to tackle the intersection of AI and API security. The conversation goes beyond the hype of AI-created malware to focus on a more subtle, yet pervasive threat: "rogue AI agents." The speakers define these as sanctioned AI tools that, when misconfigured or given improper permissions, can cause significant havoc by misbehaving and exposing sensitive data. The episode emphasizes that this risk is not new, but an exacerbation of classic hygiene problems. Key Takeaways Defining "Rogue AI Agents": Sam Chehab defines a "rogue AI agent" as a sanctioned AI tool that misbehaves due to misconfiguration, often exposing data it shouldn't have access to. He likens it to an enterprise search tool in the early 2000s that crawled an intranet and surfaced things it wasn't supposed to. The AI-API Connection: An AI agent is comprised of six components, and the "tool" component is where it interacts with APIs. The speakers note that the AI's APIs are its "arms and legs" and are often where it gets into trouble. The Importance of Security Hygiene: The core of the solution is to "go back to basics" with good hygiene. This includes building APIs with an open API spec, enforcing schemas, and ensuring single-purpose logins for integrations to improve traceability. The Rise of the "Citizen Developer": The conversation highlights a new security vector: non-developers, or "citizen developers," in departments like HR and finance building their own agents using enterprise tools. These individuals often lack security fundamentals, and their workflows are a "ripe area for risk". AI's Role in Development: Sam and Timothy discuss how AI can augment a developer's capabilities, but a human is still needed in the process. The report from Veracode notes that AI-generated code is only secure about 45% of the time, which is about on par with human-written code. The best approach is to use AI to fix specific lines of code in pre-commit, rather than having it write entire applications. Resources & Links Mentioned Postman State of the API Report: This report, which discusses API trends and security, will be released on October 8th. The speakers tease a follow-up episode to dive into its findings. Veracode: The 2025 GenAI Code Security Report was mentioned in the discussion on AI-generated code. GitGuardian: The State of Secrets Sprawl report was referenced as a key resource. Cloudflare: Mentioned as a service for API shield and monitoring API traffic. News Sites: Sam Chehab recommends Security Affairs, The Hacker News, Cybernews, and Information Security Magazine for staying up-to-date.

Summary: In this episode, Timothy De Block sits down with guest Kyle Andrus to dissect the ever-evolving landscape of cyber threats, with a specific focus on info stealers. The conversation covers everything from personal work-life balance and career burnout to the increasing role of AI in security. They explore how info stealers operate as a "commodity" in the cybercriminal world, the continuous "cat and mouse game" with attackers, and the challenges businesses face in implementing effective cybersecurity measures. Key Takeaways The AI Revolution in Security: The guests discuss how AI is improving job efficiency and security, particularly in data analytics, behavioral tracking, and automating low-level tasks like SOC operations and penetration testing. This automation allows security professionals to focus on more complex work. They also highlight the potential for AI misuse, such as for insider threat detection, and the "surveillance state" implications of tracking employee behavior. The InfoStealer Threat: Info stealers are a prevalent threat, often appearing as "click fix" or fake update campaigns that trick users into granting initial access or providing credentials. The data they collect, including credentials and session tokens, is sold on the dark web for as little as two to ten dollars. This fuels further attacks by cybercriminals who buy access rather than performing initial reconnaissance themselves. The Human and Business Challenge: As security controls improve, attackers are increasingly relying on human interaction to compromise systems. The speakers emphasize that cybercriminals, "like water, follow the path of least resistance." The episode also highlights the significant challenge for small to medium-sized businesses in balancing risk mitigation with operational costs. Software Supply Chain Attacks: The discussion touches on supply chain attacks, like the npm package breach and the Salesforce Drift breach, which targeted third parties and smaller companies with less mature security controls. They note the challenges of using Software Bill of Materials (SBOMs) to assess the trustworthiness of open-source components. Practical Cybersecurity Advice: The hosts discuss the need to rethink cybersecurity advice for non-tech-savvy individuals, as much of the current guidance is impractical and burdensome. While Timothy De Block sees the benefit of browser-based password managers when MFA is enabled, Kyle Sundra generally advises against storing passwords in browsers and recommends more secure password managers.

Summary: In this episode, Timothy De Block sits down with Rob Fuller, Vice President of Cybersecurity, for a candid discussion about Rob's journey into cybersecurity leadership. Rob shares his unique path from the Marine Corps to a Fortune 10 company, revealing the struggles and lessons learned along the way. The conversation delves into the critical role of visibility, the importance of continuous learning, and invaluable advice for those aspiring to leadership roles in the security industry. Key Takeaways From "Noob" to VP: Rob shares the humorous origin of his online handle, "Mubix," which came from a mistyped name in an MMORPG. He recounts his initial struggle to transition into leadership, including turning down a director position at General Electric due to perceived lack of experience, until his wife reminded him of his past leadership roles in the Marine Corps and community groups. Leadership is a Different Career Path: Rob emphasizes that moving into a leadership role requires a complete mindset shift and is a distinct career path from a technical one. He learned a crucial lesson about career advancement: while diligence and relationships are important, visibility is paramount. He also notes the importance of a manager understanding they are part of two teams: their direct reports and their peer group of fellow leaders. The Value of Continuous Learning: Rob recommends the book Surrounded by Idiots by Thomas Erikson to understand different communication styles and the importance of adapting in management. He is also actively pursuing advanced degrees and certifications like CISSP and NACD to meet the requirements for director and CISO roles in large companies. Aspiring to CISO: Rob's ultimate goal is to become a CISO, as he believes it's the only role that allows for the implementation of comprehensive, widespread cybersecurity solutions. Advice for Career Starters: For those looking to enter cybersecurity, Rob and Timothy advise being open to any IT job, including the help desk, as an entry point. They also stress the importance of actively participating in local groups and conferences like hacker meetups and B-Sides, as this networking and volunteering can significantly increase your chances of getting hired. Blue Team Experience is Gold: Both agree that blue team (security operations) experience is highly valuable for aspiring pentesters, as it teaches crucial skills like scripting, queries, networking, and evasion techniques that make them more effective in red team roles. Resources & Links Mentioned The Five Dysfunctions of a Team by Patrick Lencioni Surrounded by Idiots by Thomas Erikson Fredericksburg Hackers Meetup CISSP certification NACD (National Association of Corporate Directors) certification

Summary: Link to the live recording: https://www.youtube.com/live/DHbGpRtDvIw?si=h6tHumVLrl3HOgq0 Join Timothy De Block and special guest Ben Miller for a deep dive into the SharePoint zero-day exploit, CVE-2025-53770. This episode breaks down the technical details of the "goofy authentication bypass" and its serious implications for on-premise systems. The discussion also expands into broader topics, including the critical role of human intelligence in security, the shift to Managed Security Service Providers (MSSPs), and the importance of addressing business processes and mental health in the industry. Key Takeaways The SharePoint Exploit (CVE-2025-53770): Ben Miller describes this vulnerability as an unauthenticated "zero-click" exploit that requires no user interaction. It's a "goofy authentication bypass" that allows an attacker to gain full control of an on-premise SharePoint server by simply sending a web request. Once an attacker gains access, they can steal keys and maintain persistent control. On-Premise vs. Cloud: The vulnerability primarily affects on-premise SharePoint servers, which are managed directly by businesses. Ben explains that even organizations that have moved their systems to a cloud like Azure might still be vulnerable if they've retained old, vulnerable configurations. Challenges with Detection and Remediation: Many businesses lack adequate logging and internal threat hunters, making it nearly impossible to detect if a breach occurred. The widespread use of SharePoint makes its vulnerabilities particularly dangerous, and entrenched intruders can be so difficult to remove that they may require a complete system overhaul. The Human Element in Security: The speakers discuss how humans are the "trust link" and "determiner" in a security program, not just the weakest link. If one person's single action can compromise a system, it points to a process problem, not a human one. The episode also highlights the powerful role of social engineering, even with something as simple as using food to gain access to a network. MSSPs and Career Advice: The conversation touches on the growing trend of organizations using Managed Security Service Providers (MSSPs) for their security operations. Ben suggests that MSSPs are a great entry point for aspiring security professionals, as they provide broad exposure to a variety of incidents. For long-term career success, Ben advises being able to translate security needs into business sense and becoming an expert in your field. Community and Mental Health: Ben and Timothy encourage listeners to attend the BSides St. Louis conference on September 27th. Timothy even offered to pay for a ticket for anyone who can't afford it. The episode concludes with a discussion on mental health, with Ben encouraging people to view therapy as "a form of hygiene" and to seek help when needed. Connect with Ben Miller & BSides St. Louis: Website: bsidesstl.org Event Date: September 27th Event Location: Washington University's McKelvey School of Engineering

Summary: In a special episode recorded live from ShowMeCon, Anushree Vaidya interviews Timothy De Block about the art and science of creating and growing a podcast. This episode is a must-listen for anyone interested in starting their own show, offering a practical walkthrough of the entire process from concept to promotion. Key Takeaways: Finding Your Motivation: The conversation explores the core reasons for starting a podcast, emphasizing the importance of finding a format and message that resonates with both the host and the audience. The Technical Foundation: An overview of the essential equipment and software needed to get started, offering advice on how to produce quality audio without breaking the bank. Content and Guest Strategy: Tips on how to structure episodes, find compelling topics, and effectively interview guests to create engaging and informative content. The Power of Podcasting: The episode highlights the unexpected professional benefits of hosting a podcast, including opportunities for networking, personal growth, and becoming a recognized voice in your field.

Summary: Timothy De Block interviews Kate Johnson about her cybersecurity career. Kate shares insights from her journey, emphasizing the importance of foundational knowledge and effective leadership in a constantly evolving technical field. Key Takeaways: From Guides to Director: Kate's career began with writing guides for technology users, teaching her empathy and a people-focused approach crucial for her later management roles. She progressed from an analyst to a director, leveraging early management experience at Central Michigan University. Evolving Director Role: At Draos (founded in 2017), Kate's director role has expanded significantly as the company grew from 100 to over 500 employees. She now manages intelligence reverse engineers and oversees operations for the entire intelligence services department. Leadership in Cybersecurity: Kate's management style is advisory, focusing on guiding her team and connecting their efforts. She maintains an analytical mindset, making data-driven decisions and supporting her highly technical team. A key challenge is letting people fail to learn, even if it's difficult to watch. Cybersecurity Fundamentals: Kate stresses the need for a fundamental understanding of how systems work to effectively secure them. She recommends resources like Network+ and specific SANS courses for building this base. The "Auditor" Aspect of Security: Kate views pen testing and security work as similar to auditing, emphasizing the need for evidence, identifying flaws, and providing actionable recommendations to add value. Advice: Kate encourages aspiring cybersecurity professionals to "don't give up" as there are numerous opportunities and roles available for all types of people. Resource Plug: Kate recommends OT-CERT (Secure OT CERT), a free, community-driven resource for sharing information and discussing threats in the Industrial Control Systems (ICS) field. Resources Mentioned: OT-CERT (Secure OT CERT) CompTIA Network+ certification SANS ICS 310 course Rob Lee's blog Mike Holcomb's YouTube channel

Summary: Timothy De Block and Ben Miller discuss the upcoming BSides St. Louis conference. Ben shares the mission behind the event: to provide a low-cost, high-value conference for beginners and those new to the security community. They cover the importance of community-building, the value of professional skills alongside technical ones, and the power of networking at local events. Key Takeaways: BSides St. Louis Mission: Ben and his co-founders created BSides St. Louis in 2015 as a "passion project" with the motto, "bringing the interested to the connected". The goal is to offer a free or low-cost conference to make cybersecurity knowledge accessible to beginners and career-changers who can't afford larger, more expensive events. Cost and Accessibility: This year's conference operates on a donation basis, with a recommended $25 charge to help estimate food and t-shirt orders. Ben clarifies that no one will be turned away for an inability to pay, and the organization is a 501(c)(3) charity. Networking and Career Growth: Both Ben and Timothy stress that attending local conferences like BSides on a Saturday demonstrates a commitment to learning that employers value. Networking at these events can lead to job opportunities and valuable professional connections. Professional Skills Over Hard Skills: Ben argues that professional skills—such as public speaking, running effective meetings, and communicating politely—are more crucial for career longevity than hard technical skills. He shares a personal story about how a poorly chosen phrase accidentally hurt a colleague and taught him the importance of careful communication. Encouraging New Speakers: BSides St. Louis actively seeks out first-time speakers. Ben looks for people who have never given a talk before because the audience is forgiving and it helps them develop skills vital for interviewing and running meetings. Family-Friendly Environment: The conference is explicitly family-friendly, encouraging attendees to bring children and high school students to explore the campus and participate in activities like lockpicking and soldering. Ben views "hackers" as anyone who does "something in a way that wasn't intended to be done". Personal Philosophy: Ben shares his personal mission to help people "feel secure so they can sleep at night" and his belief that giving back through events like BSides is a way to help others who were not as fortunate as he was growing up. Notable Quotes: "Bringing the interested to the connected". "One con talk isn't going to make you an expert, but learning just enough to know what to Google, so that you can become an expert when you need to later... Huge. So helpful". "I can train somebody really easy to run NMAP... but telling somebody how to shut up in a meeting and listen way harder". "Don't self-select yourself out of opportunities". "My personal life goal is to help people feel secure so they can sleep at night".

Michelle (@MlleLicious) was one of the contestants who competed on Friday in the Social Engineering Capture The Flag (SECTF). This year the SECTF focused on video game companies and Michelle (happily) pulled Disney. Getting up on stage in front of hundreds of people is already a nerve racking proposition. Now add in that you have to interact with another human being to try and get them to divulge information for points. As you'll hear this was Michelle's first year at DEFCON. She dove right in to the event and walked away from the even with an amazing experience.

Johnny (@J0hnnyXm4s) is a penetration tester for Redlegg and an accomplished speaker at security conferences around the United States and Iceland. One of Johnny's more recent talks is titled "That's not my RJ45 Jack" which covers, among other topics, how to interact with people. I saw this talk in April when I went to BSides Nashville and it has a lot of good information that can be applied to networking with people in general. In part two we discuss resources for getting better at networking.

Johnny (@J0hnnyXm4s) is a penetration tester for Redlegg and an accomplished speaker at security conferences around the United States and Iceland. One of Johnny's more recent talks is titled "That's not my RJ45 Jack" which covers, among other topics, how to interact with people. I saw this talk in April when I went to BSides Nashville and it has a lot of good information that can be applied to networking with people in general.

Steve (@SteveD3) has been covering BEC types of attacks for the past year at CSO. These types of attacks are increasing. It may get worse with GDPR requirements next month. This ended up being one of the more difficult podcasts to get scheduled. Steve and I had to cancel on each other a few times because of phishing related stuff.

Sean (@SeanThePeterson), is one of the most passionate infosec people you don't know. He recently did a talk at ShowMeCon on how to crack passwords. It was his first ever talk and pretty damn good. Sean joined me to give me his insights into password cracking.

Samy (@samykamkar) shouldn't need too much of an introduction to most people. He's been in the news for hacking garage doors, credit cards, cars, and much much more. Samy likes to hack things and has a knack for finding vulnerabilities in everything from locked machines to wireless doorbells. His site has the full list of vulnerabilities as well as videos and press appearances. Which made him the perfect guess for talking about how to find vulnerabilities. In this episode we discuss: how Samy got started; what is a vulnerability; what skills are needed; how he decides his next project; steps to finding vulnerabilities; what he does when he discovers a vulnerability; how long the process takes.

I recently read Data Driven Security: Analysis, Visualization and Dashboards by Jay Jacobs (@jayjacobs) and Bob Rudis (@hrbrmstr). The book is easy to read and a very good introduction into the world of data and security. Both Jay and Bob were kind with their time when I had questions about exercises in the books. After reading the book I decided to have Bob on to talk more about data driven security.

Javvad Malik (@J4vv4d) doesn't need much introduction. He's done a video on the benefits of being a CISSP. He's also done a music video with his Host Unknown crew on the CISSP. There's also The CISSP companion handbook he wrote. which has a collection of stories and experiences dealing with the 10 domains of the CISSP. Check out his website at j4vv4d.com and his YouTube channel.

ShowMeCon is one of my favorite security conferences. The organizers are awesome and take care of their speakers like no other conference. The venue is fantastic. The content is mind blowing. I can't say enough good things about the even that Dave and Renee Chronister put on every year in St. Louis, Missouri. They know how to put on a conference. Regular listeners of the podcast will note that I recorded an episode with Dave on ShowMeCon several weeks ago. After that recording he asked if I was interested in doing a recording at the conference. I said yes and thus the birth of this epic episode. This format is experimental. First, it is marked as explicit, because there is swearing. Second, It's over 90 minutes long. I didn't think breaking it up into four or five pieces would serve the recording well. Send me your feedback good or bad on this episode, because I'd like to do more of these. I would really like to hear it for this episode.