In this article we’ll walk through hunting for AI application vulnerabilities. We’ll use Mindgard to find application vulnerabilities in a deliberately-vulnerable LLM lab application made available by PortSwigger.
Dr. Peter Garraghan
As AI is rapidly embedded across applications, its dynamic, unpredictable nature is introducing new vulnerabilities—many of which remain poorly understood by traditional security teams. In this talk, Dr. Peter Garraghan draws on over a decade of academic research and real-world testing to break down the anatomy of AI risk, demonstrating how adversaries are already exploiting AI systems and why current security practices are often ill-equipped to stop them.
Dr. Garraghan opens by reminding us that AI, despite its novelty, is still software. And like all software, it introduces invisible risks—except this time, we’re injecting it into applications without a solid understanding of its failure modes. Many organizations are moving quickly to adopt AI tools, often deploying them into production before fully assessing their implications. Security teams, development teams, and business stakeholders are moving at different speeds, creating a perfect storm of exposure.
Drawing on years of AI system testing, Garraghan outlines major attack categories affecting AI systems today including:
These attacks are not theoretical—they are happening in production environments, often triggered by simple, benign-seeming user interactions.
One of the most common pitfalls in AI security, Garraghan argues, is focusing solely on the model. Through a series of live demonstrations and thought experiments, he shows how real security risks typically arise in AI systems.
The presentation walks through real-world exploit examples, including:
In each case, the model behaves "as intended" from a technical standpoint. It follows the prompt, generates coherent output, and never raises an error. But the result is dangerous. That’s the heart of the challenge: AI systems do not fail in obvious ways—they fail in context-specific, nuanced ways that look like success until it’s too late.
Garraghan makes the case for adapting offensive security approaches to fit the unique properties of AI systems; non-deterministic, often lack well-defined inputs and outputs, and don’t expose obvious vulnerabilities until paired with real-world usage.
Instead of just throwing jailbreak prompts at a model and calling it a day, effective AI red teaming should:
Mindgard’s approach reflects this shift—testing not just models, but entire AI-powered applications and systems, identifying where vulnerable interactions and risky outputs emerge in real-world contexts.
Garraghan highlights the OWASP Top 10 for LLM applications, framing it as a helpful (but not exhaustive) reference for organizations looking to understand their exposure. These include familiar risks like Prompt Injection and Sensitive Information Disclosure, but also categories like:
He stresses that these risks are not abstract—they are showing up in deployed systems today.
To illustrate the practical side of testing AI systems, Garraghan presents a detailed walkthrough of a fictitious candle company using a generative AI interface to sell products. The system includes:
Despite these controls, the AI remains exploitable. Garraghan demonstrates how subtle prompt manipulation, capitalization patterns, or misleading queries can inject malicious payloads, leak unintended data, or bypass content filters entirely. This highlights a broader truth: even systems that seem locked down are vulnerable when context and control mechanisms are not rigorously tested.
Garraghan closes with pragmatic guidance. Despite the challenges, AI security is not a lost cause. Many best practices from traditional application security still apply—especially when adapted thoughtfully. Organizations should:
AI is not magic—and it’s not exempt from security scrutiny. But it is different. As AI becomes central to enterprise systems, security teams must shift their mindset from model testing to system testing, from rule-based detection to context-aware analysis. With the right frameworks, tools, and discipline, organizations can harness the power of AI safely and securely.
This talk equips attendees with the awareness, language, and practical insight to start that journey.