metadata
dataset_info:
features:
- name: messages
list:
- name: role
dtype: string
- name: content
dtype: string
- name: id
dtype: string
license: apache-2.0
task_categories:
- text-generation
tags:
- cybersecurity
- pentesting
- active-directory
- synthetic-data
- openworlds
pretty_name: OpenWorlds AD Penetration Testing Trajectories
OpenWorlds AD Penetration Testing Trajectories
Synthetic training trajectories for fine-tuning AI agents on Active Directory penetration testing.
Dataset Description
Each trajectory is a complete attack path from initial access to Domain Admin, formatted as multi-turn chat conversations with:
- System prompt with target domain context
- reasoning traces (expert thought process)
- Tool calls (nmap, ldapsearch, GetUserSPNs, hashcat, secretsdump, etc.)
- Tool outputs (realistic simulated responses)
- Failure recovery (typos, wrong creds, with correction steps)
Attack Strategies Covered
| Strategy | Description |
|---|---|
| Kerberoasting | Service accounts with SPNs -> crack TGS tickets |
| AS-REP Roasting | Users without pre-auth -> crack AS-REP hashes |
| ACL Abuse Chains | GenericAll -> WriteDACL -> ForceChangePassword -> DCSync |
| AD CS Abuse (ESC1) | Vulnerable cert templates -> impersonate Domain Admin |
| Credential Pivoting | Passwords in shares, GPPs, config files |
Usage
from datasets import load_dataset
ds = load_dataset("omkar6699/openworlds-ad-trajectories")
Generation
Generated using OpenWorlds:
openworlds manifest generate --hosts 10 --users 25 --seed 42
openworlds trajectory generate --failure-rate 0.15
License
Apache 2.0