Advent Prompt Pwn

Windows · Mac · Linux · API

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Freedom report

Two barsScore 5.6

Free tierNo free tier on record
Open codeNo open-source code on record
Runs widely3 of 6 device platforms
DocumentedPlans, terms and facts published

Advent Prompt Pwn is ranked #14 of 27 in AI red teaming tools on Freedom251. It runs on API, Linux, macOS, Windows.

Compared on AI red teaming tools

Attack categories: direct prompt injection; instruction override; delimiter; encoding; role confusion; indirect document; indirect fixture; multi-turn; mutation; RAG poisoning; synthetic tool use
Target systems: language models; AI applications; OpenAI; Azure OpenAI; Anthropic; Gemini; OpenAI-compatible APIs; Ollama; HTTP JSON applications; Python callbacks; in-memory applications
Automation level: automated
Custom tests: Yes
Deployment: self_hosted
Continuous monitoring: No
Report exports: JSON; JSONL; Markdown; HTML; JUnit; SARIF

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The record

Purpose: Advent Prompt Pwn is a typed Python toolkit for authorized adversarial testing of language models and AI applications.
Assessment workflow: It connects attack case generation to explicit scope, bounded execution, deterministic oracles, resumable checkpoints, reporting, and regression comparison.
Attack coverage: Strategies cover direct, instruction override, delimiter, encoding, role confusion, indirect injection, and multi-turn attacks, with mutation and RAG poisoning listed as 1.1 preview features.
Outcome checks: Built-in oracles can check strings, canary leaks, regular expressions, JSON keys and paths, and tool calls, including combined conditions.
Integrations: Targets include custom HTTP JSON APIs, OpenAI-compatible APIs, Ollama, Python callbacks, and preview adapters for OpenAI, Azure OpenAI, Anthropic, and Gemini.
Scope controls: Remote assessments support exact host and port allowlists, authorization windows, DNS controls, and request, rate, concurrency, retry, timeout, and evidence limits.
Evidence and reports: It produces JSON, JSONL, Markdown, HTML, JUnit, and SARIF reports, plus evidence bundles with checksums and per-attempt SHA-256 hashes.
Security handling: Credentials are referenced by environment-variable names, and built-in HTTP clients disable redirects, ignore ambient proxy variables, and bound response bytes.
Use restriction: The maker says to use the toolkit only on owned systems, intentionally vulnerable labs, public research benchmarks, or targets with explicit written authorization.
Known limits: Oracle matches require practitioner review, redaction may miss sensitive values, and the static tool sandbox is not a production agent runtime.
Maturity: Version 1.0.0 is the stable public release; the 1.1 source line remains beta pending independent practitioner review and field assessment.
Availability: Installation requires Python 3.10 or newer and is documented for PowerShell, macOS, or Linux shells.
License: The maker identifies the source as Apache-2.0 licensed.
Maker: The product is maintained by Advent Cybersecurity LLC; the maker page identifies Jashid Sany as its founder.

Where it ranks on Freedom251

Best AI Red Teaming Tools in 2026#14 of 27

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Sources

adventcybersecurity.com/community/advent-prompt-pwn· checked 5 Oct 2026
github.com/Advent-Cybersecurity/Advent-Prompt-Pwn· checked 5 Oct 2026