
Explore the 2025 OWASP top ten for LLM security, mapping new and moved categories like prompt injection, sensitive information disclosure, supply chain, data and model poisoning, and prompt leakage.
Learn how ai, llm systems, and large language models raise security challenges and how to identify and remediate vulnerabilities for penetration testers using the owasp top ten.
Explore an overview of AI attack categories, including misalignment, jailbreaks, and prompt injections, and understand how injections, data exfiltration, and plugins create security risks in LLMs.
Review attack frameworks and write-ups for AI/LLM pentesting, including the current OWASP top ten, llm-attacks.org, and the prompt injection primer for engineers.
Explore KONTRA's free guided walkthroughs on the OWASP Top 10 for LLM, with interactive hands-on labs for web apps and APIs, including prompt injection and vulnerable code analysis.
AI LLM01: Prompt Injection - Theory Part 1
AI LLM01: Prompt Injection - Theory Part 2
Explore the loop library to test agentic loops with iterative feedback and conditional prompting, including a refund loop example that demonstrates prompt injection and red-teaming opportunities.
Indirect Prompt Injection in Grok
Indirect Prompt Injection via User Agent ending up in log files
Apple Mail Summary Prompt Injection
Explore how indirect prompt injection defeats Apple email summary and calendar invites, revealing vulnerabilities in AI summarizers and the need for stronger guardrails to prevent sensitive data leaks.
prompt injection in research papers
Explore indirect prompt injection via skills files in frontier models, and learn to review downloaded skills, test for ascii unicode prompts, and guard against data exfiltration in penetration testing.
Manus RCE via prompt injection
Prompt Injection in Document triggers agentic workflow
Indirect Prompt Injection via documents to create Jira tickets via MCP
Explore how indirect prompt injection into Grok tasks can trigger unwanted cron jobs by uploading a document that schedules automated tasks without user confirmation, causing recurring notifications.
Examine indirect prompt injection via a document or email, where an agent summarizes text and sends it to a specified address, highlighting automation risks and accountability.
Discover how indirect prompt injection occurs when the Google Calendar connector reads a calendar event description, exposing AI agents to unsolicited invites and injected prompts.
Demonstrate indirect prompt injection using Grok to auto-create a GitHub repository from a document via Krok connectors, highlighting write access and automated actions on GitHub.
Explore how indirect prompt injection triggers agentic actions to auto-schedule fake meetings via calendar invites and emails, revealing risks through temp-mail.org and calendar connectors.
Explore indirect prompt injection and memory exfiltration by generating an image from memory data and uploading it to a Google Drive folder, highlighting a dangerous automation pipeline.
Discover how prompt injection via prompting can alter frontier LLM settings, revealing writable options such as memory, tone, style, and conversation scope, with examples across Copilot, JetGPT, Claude, and Gemini.
Explore indirect prompt injection and prompt begging in AI agents, via the Hugging Face incident. Analyze security.txt and robots.txt analogies and GitHub lure tactics in agentic AI attacks.
Explore indirect prompt injection in a vulnerable recruitment app, demonstrating how a prompt embedded in resumes or emails can exfiltrate base64 encoded data and pii during pre-screening.
ChatGPT Gmail and Calendar Connectors - Prompt Injections and Data Exfil
Demonstrates a zero-click data exfiltration vulnerability in a chat bot integration, using a markdown image render payload to exfiltrate conversation data from chat interfaces like Rakuten Fiber with GPT 5.5.
Demonstrates indirect prompt injection that chains actions to exfiltrate PII from G drive via email, highlighting data leakage risks in security testing.
Explore how indirect prompt injection in documents can generate phishing links and drive-by malware, exposing risks in large language models like Gemini and other AI systems.
Demonstrates how prompt injection can delete user memories in ChatGPT through a live memory-clear demo. Discusses indirect prompt injection risks to the memory tool and urges stronger safeguards.
Examine how ANSI escape codes in terminal emulators enable prompt injection in LLMs, revealing risks such as beeps, cursor moves, hidden text, clipboard exfiltration, and potential remote code execution.
Demonstrate indirect prompt injection using ANSI escape codes to exfiltrate data via DNS, noting Linux terminal vulnerabilities and macOS fixes.
ASCII Unicode Prompt Injection into Google Calendar. DoS and Phishing
Prompt injection into Grok with hidden ASCII unicode tags
Prevent sensitive information disclosure by enforcing strict access control and least privilege. Guard PII, financial and HR data with context aware filtering and redaction in RAG storage to avoid leaks.
Explore how sensitive information disclosure occurs in AI systems, including PII and training data, and how encryption, key management, and strict access controls prevent leaks.
Explore direct prompt injection in llms with a deliberately vulnerable lm agent, demonstrating information disclosure that exposes other users' transactions and pii.
Demonstrates a data exfiltration attack in a learning management system using a prompt-injection payload in markdown to leak information when a user clicks a link, revealing markdown rendering vulnerabilities.
Enumerating Grok's container dives into a Linux VM inside a container to inspect processes, memory, and binaries, and demonstrates how outbound network activity and GitHub connectors can enable data exfiltration.
Examine excessive agency in LMS, where AI agents call APIs, invoke tools, or browse the web, risking data disclosure and unintended actions; apply guardrails, least privilege, and human oversight.
Excessive agency in AI systems grants LLMs too much autonomy to call back-end APIs without human oversight. This enables unintended actions like refunds or data changes via prompts and plugins.
Examine insecure plugin design and how missing access control threatens LLMs through untrusted plugins. Learn defenses like code reviews, isolation, and granular authorization to prevent data exfiltration and prompt injections.
Demonstrates exploiting LLM APIs with excessive agency by prompting an AI to access back end APIs and delete a user, revealing how prompt injection bypasses front-end controls.
Explore OS command injection vulnerabilities in LMS APIs, showing how an LLM with backend access can exploit APIs like password reset, newsletter, and product information to perform unauthorized actions.
this lecture explains supply chain vulnerabilities in lms, including third-party components, pre-trained models, plugins, and open-source code, with vetting, provenance, zero-trust, and backdoor awareness.
The Ultimate AI/LLM Penetration Testing Course
Your instructor is Martin Voelk, a cybersecurity veteran with 27 years of experience. Martin holds AIRTP+, multiple SecOps certifications including the AI certifications, CISSP, OSCP, OSWP, PortSwigger BSCP, and Cisco CCIE. He works at a startup and hunts bugs in bug bounty programs, where he has found thousands of critical and high-severity vulnerabilities.
This course mixes short theory with hands-on labs so you can find and exploit vulnerabilities in AI and LLM apps. It follows the OWASP Top 10 for LLMs and the OWASP Top 10 for Agentic Applications. Videos are practical and easy to follow along.
What you'll cover (core content)
· Prompt injection — direct, indirect, agentic actions, data exfiltration, memory abuse, and hidden/obfuscated payloads
· Sensitive Information Disclosure
· Excessive Agency
· Supply Chain
· Data and Model Poisoning
· Unbounded Consumption and DoS
· Misinformation
· System Prompt Leakage (Hidden Context Exposure)
· Vector and Embedding Weaknesses
· Improper Output Handling
· OWASP PwnzzAI Shop labs
· OWASP Top 10 for Agentic Applications + OWASP Finbot labs
· PortSwigger - Agentic AI Labs
· SecOps Group AI/ML and Agentic mock exam walkthroughs
· Jailbreaking modern models
· AI Browsers Attacks
· AI Coding Agents Attacks
· MCP Attacks
· Multimodal Attacks (Images, Audio and Video)
· Red-team Tooling
CTF walkthroughs (optional)
Practice as many as you want after the core content:
· Deniskim CTF
· Prompt Airlines CTF Challenge Walkthrough
· Selara Jailbreak Game CTF
· Gandalf Agent Breaker CTF
· Hack The Agent CTF
· AI Prompt Attack and Defense Game Tensortrust CTF
· Crowdstrike AI Unlocked Challenge CTF
· Game Arena Challenges CTF
· PromptTrace Prompt Injection Labs CTF
· PromptInjects CTF
· 8ksec CTF
· AIPWN CTF
· Bot Tricks CTF
· Wraith CTF
· Other CTFs
Archive (legacy labs)
Kept for practice; techniques may still apply:
· Legacy OWASP Finbot CTF
· Legacy Gandalf lab
Notes & Disclaimer
I keep this course updated, but it will not always include every new AI bug the day it appears.
Some students want older CTFs removed; others want them kept. All CTF walkthroughs sit after Tooling and are optional — watch all, some, or none.
Most labs are free online. I don't control if owners take them down. If a lab disappears, the methods still apply to other labs and real targets you are allowed to test.
LLM providers change models often. Many techniques still work; some may need tuning later.
Use this only on systems you own or have clear permission to test. No unauthorized or malicious use.