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testing-llm-prompt-injection-and-jailbreaks

Testing LLM-backed applications, chatbots, and AI agents for direct and indirect prompt injection, jailbreaks, system-prompt leakage, and tool/agent abuse during authorized penetration tests, using structured payload families and reliable confirmation signals.

internal/tools/skills/data/ai-security/testing-llm-prompt-injection-and-jailbreaks/SKILL.md

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# Testing LLM Prompt Injection and Jailbreaks

## When to Use

- During authorized assessments of chatbots, copilots, RAG systems, and autonomous AI agents
- When the application mixes a trusted system prompt with untrusted user input or external content
- When the LLM consumes attacker-influencable data (web pages, emails, files, repo issues, tool output)
- When the model can call tools/functions or take actions (send email, run code, open PRs)
- When validating system-prompt confidentiality, content guardrails, and output handling

## Prerequisites

- **Authorization**: Written agreement covering the AI application and any connected tools/data
- **Burp Suite / HTTP client**: To reach chat/completions endpoints and replay payloads
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