Hacking With Cursor: AI-Powered Penetration Testing

Learn Cursor project rules (.mdc files) and build four rule files that encode pentesting methodology, target context, tool preferences, and output format. Understand always-apply, glob, description-based, and manual rule types and when each fits a pentesting need.

Wire Model Context Protocol servers into your harness so the agent can call real tools. Build a project-level mcp.json with four integrations (Nmap, Burp Suite, Shodan, Nuclei), learn security considerations including MCPoison (CVE-2025-54136), and validate connections in Settings.

Build the /recon skill: a version-controlled folder with a SKILL.md playbook, a parse-nmap.py helper script, and a recon checklist reference. Learn skill anatomy, invocation methods, auto-invocation control, and when to use skills versus rules versus subagents.

Master context engineering for offensive security: high-fidelity artifacts, structured handoffs, and five reusable prompt roles (Analyst, Strategist, Toolsmith, Interpreter, Validator). Build the AGENTS.md per-engagement context template that becomes the single source of truth for every engagement.

Build a repeatable recon loop: run tools through MCP, interpret results with Cursor, and write distilled facts into target-context.mdc. Cover passive recon with Shodan MCP, active recon with Nmap MCP, OSINT in natural language, and enhance the /recon skill with structured output formatting.

Pair Nmap MCP and Nuclei MCP for deep scanning. Build service-specific enumeration playbooks for HTTP, SMB, SSH, and FTP. Create the scan-interpreter.mdc rule and /enumerate skill. Master CVE lookup workflows and practice full enumeration on an HTB-style target.

Build a Burp plus Cursor workflow where Burp captures traffic and Cursor reasons over it through Burp MCP. Cover SQL injection detection and iteration, XSS testing, authentication bypass patterns, IDOR/BAC batch testing, and build the /web-test skill with a burp-analyzer.py helper and OWASP Top 10 checklist.

Apply your harness to network exploitation: service-to-exploit workflows, LinPEAS/WinPEAS triage with Cursor, lateral movement planning, quick exploit scripting, and post-exploitation enumeration. Practice a full exploit chain on an HTB-style target using tight prompts and pasted evidence.

Build three specialist subagent definitions: recon-agent, exploit-agent, and report-agent under .cursor/agents/. Learn subagent anatomy (frontmatter fields), built-in versus custom agents, the PentAGI/ARTEMIS insight on specialist teams, effective description writing, and delegation testing prompts.

Wire subagents into orchestrated flows. Build the coordinator.md orchestrator agent. Learn parallel delegation, background agents with is_background, the PentAGI-style assess-delegate-synthesize loop, sequential versus parallel judgment, model selection strategy, and cost/quota awareness.

Build two custom MCP servers from scratch: a credential sprayer wrapping Hydra and a pentest notes server backed by SQLite. Learn MCP server architecture (stdio transport, JSON-RPC, tool schemas), the pattern for wrapping any tool, and security considerations for custom MCPs.

Master just-in-time tool generation: the philosophy, iteration loop (generate, test, debug, refine, deploy), and four worked examples. Build the /toolsmith skill with SKILL.md and scaffold-tool.py so your harness can spin up new security tools with a consistent quality bar every time.

Bridge technical work to defensible reporting. Build the complete /report skill with finding and executive summary templates and a compile-report.py assembler. Cover CVSS scoring, business impact, executive summary generation, and the mandatory human verification step for AI-assisted findings.

Run a complete lab engagement from empty folder to final report on a generic HTB-style target. Walk through every phase using slash commands, subagents, and the full harness. Keep a decision log, see honest timing comparisons, and learn where AI is a force multiplier versus where human judgment dominates.

Keep your investment valuable as tools, threats, and your team change. Cover Cursor update hygiene, adding new MCP servers safely, sharing harness configs with version control, security practices for credentials and data privacy, engagement-specific rule sets, and building organizational capability from a personal harness.

Deep dive into how Cursor's AI agent works under the hood: modes, context windows, token budgets, model selection, indexing, and reference mechanics that determine what the agent can see and do.

Collect, organize, and hash penetration test artifacts so AI-assisted workflows stay accountable: separate verified facts from model output, preserve integrity, and stay delivery-ready.

Master Cursor's hook system to automate security gates, audit logging, and evidence capture in your agent workflows.

Run agents headless from the terminal and build programmatic security pipelines with the @cursor/sdk package.

Package your complete hacking harness as a distributable Cursor plugin for team use and version-controlled sharing.

Prepare your Docker lab environment and engagement workspace for the capstone CTF challenges.

Your first full engagement: use your harness to compromise a single-container target with web vulnerabilities and privilege escalation.

A multi-service target requiring SSRF pivoting, IDOR exploitation, and Docker group privilege escalation across three containers.

The ultimate test: a four-container network with DMZ segmentation, encrypted backups, pivoting, and chained exploitation requiring your full harness.