Web Pentesting Beginner Roadmap (2026): From Recon to Server-Side Attacks

The Web Pentesting Beginner’s Roadmap: From Recon to Server-Side A structured reference guide for anyone who just finished their first web security course. After completing the Hacksmarter Web Pentesting course, I wanted to consolidate the methodology into a single source of truth. Whether you are preparing for a bug bounty or just securing your own apps, this is the mental framework you need. 1. Reconnaissance (The Foundation) Pro-Tip: Always check robots.txt and sitemap.xml before running heavy scans. You’d be surprised what developers "hide" in plain sight. Fingerprinting: Use Curl, Burp/Caido, or the Wappalyzer extension to identify the tech stack. Directory Brute Forcing: Dirsearch, dirb, or gobuster to find hidden endpoints. Subdomains & Vhosts: FFUF (with custom scripts) and gobuster. Business Logic Prep: Become a user! Map out the site functionalities. What can a standard user do vs. an Admin? OSINT: Google Dorks, Shodan, and Nmap for port scanning. 2. Authentication Assessment