| --- |
| 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 |
| - **<think> 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 |
|
|
| ```python |
| from datasets import load_dataset |
| ds = load_dataset("omkar6699/openworlds-ad-trajectories") |
| ``` |
|
|
| ## Generation |
|
|
| Generated using [OpenWorlds](https://github.com/omkar-ukirde/Worlds-OpenSource-Clone): |
|
|
| ```bash |
| openworlds manifest generate --hosts 10 --users 25 --seed 42 |
| openworlds trajectory generate --failure-rate 0.15 |
| ``` |
|
|
| ## License |
|
|
| Apache 2.0 |
|
|
