Andra Lezza and Javan Rasokat discuss the complexities of securing AI and LLM applications. With years of experience in Application Security (AppSec), Andra and Javan share their journey and lessons from their DEF CON talk on building and defending LLMs. They explore critical vulnerabilities, prompt injection, hallucinations, and the importance of data security. This discussion sheds light on the evolving landscape of AI and LLM security, offering practical advice for developers and security professionals alike. 

Javan’s blog article: Adversarial Misuse of Generative AI

Javan’s recommendation for the TLDR newsletter

Andra's book recommendation: The Cuckoo’s Egg by Cliff Stoll

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Former CISO Jim Routh discusses his perspective on retirement and career fulfillment in cybersecurity. Rather than viewing retirement as simply stopping work, Routh describes his three-filter approach: working only with people he respects and admires, doing only work he finds fulfilling, and controlling when he works. He shares valuable lessons learned about which post-retirement opportunities truly bring satisfaction and explains why he avoids certain roles. Routh emphasizes the importance of cybersecurity professionals taking ownership of their career development, recommending they focus on developing two specific skills annually rather than using tenure to guide career moves. 

The article written by Jim, published on LinkedIn:

CISO Transition 

Check out previous episodes with Jim:

Jim’s original AppSec podcast episode is our #1 listened to of all time.

Jim Routh -- Selling #AppSec Up The Chain

And 

Jim Routh — Secure Software Pipelines

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Henrik Plate joins us to discuss the OWASP Top 10 Open Source Risks, a guide highlighting critical security and operational challenges in using open source dependencies. The list includes risks like known vulnerabilities, compromised legitimate packages, name confusion attacks, and unmaintained software, providing developers and organizations a framework to assess and mitigate potential threats. Henrik offers insights on how developers and AppSec professionals can implement the guidelines. Our discussion also includes the need for a dedicated open-source risk list, and the importance of addressing known vulnerabilities, unmaintained projects, immature software, and more. 

The OWASP Top 10 Open Source Risks 

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Security expert Tanya Janca discusses her new book "Alice and Bob Learn Secure Coding" and shares insights on making security accessible to developers. In this engaging conversation, she explores how security professionals can better connect with developers through threat modeling, maintaining empathy, and creating inclusive learning environments. Tanya emphasizes the importance of system maintenance after deployment and shares practical advice on input validation, while highlighting how security teams can build better relationships with development teams by avoiding arrogance and embracing collaboration.

Tanya’s new book:  Alice & Bob Learn Secure Coding

Three Individuals that Tanya would like to introduce to you:

Confidence Staveley https://confidencestaveley.com/

Rana Khalil https://www.linkedin.com/in/ranakhalil1

Laura Bell Main https://www.laurabellmain.com/

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Mehran Koushkebaghi, a seasoned engineering expert, delves into the intricacies of systemic security. He draws parallels between civil engineering and IT systems, and explains the importance of holistic thinking in security design. Discover the difference between semantic and syntactic vulnerabilities and understand how anti-requirements play a critical role in system resilience. This episode offers fresh perspectives on application security.

Books recommended by Mehran:

Critical System Thinking Book by Mike Jackson

The Fifth Discipline by Peter Senge

Understanding Complexity on Audible read by Scott E Page

Nassim Taleb books

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Kalyani Pawar shares critical strategies for integrating security early and effectively in AppSec for startups. She recommends that startups begin focusing on AppSec around the 30-employee mark, with an ideal ratio of one AppSec professional per 10 engineers as the company grows. Pawar emphasizes the importance of building a security culture through "culture as code" - implementing automated guardrails and checkpoints that make security an integral part of the development process. She advises startups to prioritize visibility into their systems, conduct pentests, develop thoughtful policies, and carefully vet third-party tools and open-source solutions. Ultimately, Pawar's approach is about making security a collaborative, integrated effort that doesn't impede innovation but instead supports the startup's long-term success and safety.

Kalyani’s Book recommendation: 

The Alignment Problem by Brian Christian 

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Milan Williams discusses the importance of application security metrics and how to make them both meaningful and actionable. She explains that metrics are crucial for tracking progress in what can often feel like an overwhelming security landscape, and they're valuable for career advancement and securing resources. We discuss metrics categories and several specific metrics that are good to track.  Milan shares important principles on the importance of making metrics actionable through storytelling and relating security impacts to real-world consequences for users. 

Milan's Book Recommendation:

Quiet Influence: The Introvert’s Guide to Making a Difference by Jennifer Kahnweiler 

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Mo Sadek shares his unique journey of building an Application Security program from scratch at Roblox. Mo discusses his unconventional path, including temporarily joining the infrastructure team to truly understand engineering challenges. He emphasizes that security isn't about mandating rules, but about making processes easier and more secure by default. Mo shares his insights on how to build effective cross-team security relationships and approaches for gaining leadership buy-in. 

Mo's Book Recommendation: I Have No Mouth and I Must Scream by Harlan Ellison 

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Brett Crawley discusses the Elevation of Privilege (EoP) card game, a powerful tool for threat modeling in software development. The discussion explores recent extensions to the game including privacy-focused suits and TRIM (Transfer, Retention/Removal, Inference, Minimization) categories. Crawley emphasizes that threat modeling shouldn't end with the game but should be an ongoing process throughout an application's lifecycle, ideally starting before implementation. He also shares insights from his book, which provides detailed examples and guidance for teams new to threat modeling using EoP.

You can find Brett on X @brettcrawley

Brett’s book:
Threat Modeling Gameplay with EoP: A reference manual for spotting threats in software architecture

Book recommendation:
Conscious Business by Fred Kofman

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Matin Mavaddat discusses his perspective on security as a systemic concern, developed from his background in requirements engineering and systems architecture. He introduces the concept of "anti-requirements" - defining what a system should not do - and distinguishes between "syntactic security" (addressing technical vulnerabilities that are always incorrect) and "semantic security" (context-dependent security emerging from system interactions). Mavaddat shares his perspective that security itself doesn't have independent existence but rather emerges from preventing undesirable states. The discussion concludes with practical implementation strategies, suggesting that while automated tools can handle syntactic security issues, organizations should focus more energy on semantic security by understanding business context and defining anti-requirements early in the development process.

Mentioned in this episode:

Matin’s article: Reframing Security: Unveiling Power Anti-Requirements  

Systems Thinking for Curious Managers by Russell Ackoff

Antifragile by Nassim Nicholas Taleb

The Black Swan by Nassim Nicholas Taleb

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