Why Agentic Hacking Changes Everything
This isn't just about code completion or documentation lookup. When you combine Hacker Sidekick's cybersecurity expertise with Roo Code's autonomous capabilities, you get an AI agent that can:
- Autonomously conduct reconnaissance and identify attack vectors
- Develop and execute exploits with real-time adaptation
- Perform complex multi-stage attacks while maintaining operational security
- Analyze and crack security mechanisms using advanced techniques
- Automate entire penetration testing workflows from initial recon to post-exploitation
Real-World Agentic Hacking Tasks
Here are actual tasks you can delegate to your AI-powered offensive security agent:
| Attack Scenario | Agentic Task Example |
|---|---|
| Privilege Escalation | "I have user access on this Linux box. Find and exploit a privilege escalation vector to gain root. Here's the system info..." |
| Password Cracking | "Crack this NTLM hash: 8846f7eaee8fb117ad06bdd830b7586c. Use advanced wordlists and rule sets to recover the plaintext password." |
| Network Lateral Movement | "I'm on network 192.168.1.0/24 with domain user creds. Map the network, identify high-value targets, and establish persistence on the domain controller." |
| Web App Exploitation | "This web app at https://target.com has a login form. Find and exploit vulnerabilities to gain admin access and extract user data." |
| Binary Exploitation | "Analyze this binary for vulnerabilities and develop a working exploit. I need remote code execution on the target system." |
| WiFi Network Compromise | "I'm near the target building. Enumerate wireless networks, crack WPA handshakes, and establish a covert foothold on their internal network." |
| Malware Analysis & Reverse Engineering | "This malware sample is evading detection. Reverse engineer it, identify the evasion techniques, and create detection signatures." |
Autonomous Attack Chains
The real power comes from chaining these capabilities together. Your AI agent can:
- Start with passive reconnaissance and OSINT gathering
- Automatically pivot to active scanning based on findings
- Adapt exploit techniques based on target responses
- Maintain persistence while avoiding detection
- Document the entire attack path for reporting
Game Changer: Instead of manually researching exploits and writing custom tools, you describe your objective and let the AI agent plan and execute the entire attack workflow autonomously.
Setting Up Your Agentic Hacking Environment
Here's how to get this powerful setup running in under 5 minutes:
1. Install Visual Studio Code
| OS | Quick method |
|---|---|
| Debian/Ubuntu/Kali | sudo apt update && sudo apt install -y wget gpg && wget -qO- https://packages.microsoft.com/keys/microsoft.asc | gpg --dearmor | sudo tee /usr/share/keyrings/vscode.gpg > /dev/null && echo "deb [arch=$(dpkg --print-architecture) signed-by=/usr/share/keyrings/vscode.gpg] https://packages.microsoft.com/repos/vscode stable main" | sudo tee /etc/apt/sources.list.d/vscode.list && sudo apt update && sudo apt install -y code |
| macOS | brew install --cask visual-studio-code |
| Windows | Download the installer from https://code.visualstudio.com and click Next → Next → Finish (classic). |
VS Code should now be in your $PATH/Start Menu. (medium.com)
2. Add the Roo Code extension
- Launch VS Code, press Ctrl + Shift + X (Extensions view).
- Search "Roo Code" and click Install (publisher: Roo Veterinary Inc.).
- A little kangaroo icon appears in the sidebar—this is Roo's home. (marketplace.visualstudio.com)
CLI fans: code --install-extension RooVeterinaryInc.roo-cline
3. Grab your Hacker Sidekick API key
- Open https://chat.hackersidekick.com and sign in.
- Click your avatar → Settings → API Keys.
- Create new key, give it a name (e.g., vscode), and copy the token. Keep it secret; it is root for the bot.
(Hacker Sidekick is OpenAI-compatible, so the flow mirrors Open WebUI's API section.) (docs.openwebui.com)
4. Point Roo Code at Hacker Sidekick
- In VS Code, click the kangaroo icon → ⚙️ (gear) → Providers.
- Click ➕ Add Provider (or edit the default) and fill in:
| Field | Value |
|---|---|
| Provider type | OpenAI Compatible |
| Base URL | https://chat.hackersidekick.com/v1 |
| API Key | paste the token you just copied |
| Model ID | gpt-4o (or any model your instance exposes) |
| Temperature | 1 |
Temperature 1 gives you creative but still coherent output—perfect for coding sidekick duties. Roo Code exposes temperature per-provider, starting with v3.3.18. (portkey.ai, reddit.com)
- Save. Roo Code will run a quick test call; a green check = success. If you see a 401, re-check the key; if 404, double-check the Base URL path ends in
/v1.
5. Optional quality-of-life tweaks
| Tweak | Why |
|---|---|
Set OPENAI_API_KEY and OPENAI_API_BASE env vars |
Lets Roo Code pick them up automatically in new workspaces. |
| Create multiple provider profiles | For different temperatures or models (e.g., Temp 0 for linting, Temp 1 for brainstorming). |
Bind a hotkey (File → Preferences → Keyboard Shortcuts) |
Run "Roo: Ask" with Ctrl+Alt+A for instant shell-sidekick vibes. |
Responsible Disclosure & Ethics
Remember that with great power comes great responsibility. This agentic hacking setup is designed for:
- Authorized penetration testing with proper scoping and permissions
- Red team exercises within your organization's security program
- Vulnerability research for responsible disclosure
- Security tool development for defensive purposes
- Educational and training scenarios in controlled environments
Important: Always ensure you have explicit written authorization before conducting any security testing. Unauthorized access to computer systems is illegal in most jurisdictions.
Start Your Agentic Hacking Journey
You now have an AI-powered offensive security platform running in VS Code. Try starting with: "I need to gain access to a Windows domain controller. The target is running Windows Server 2019 with default configurations. Walk me through a complete attack chain."
Watch as Hacker Sidekick develops a comprehensive attack strategy, generates custom exploits, and guides you through each phase of the operation—all while maintaining proper OPSEC and documentation for your penetration testing report.
Welcome to the future of cybersecurity operations. Happy (ethical) hacking! 🛡️🤖