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OffSec OSWE Study Roadmap

WEB-300 / OSWE · 16-week plan · Free

Last updated: September 29, 2026

Progress:
0/16

Domain Weight Distribution

D1: Advanced Web Application Source Code Review
20%
D2: Authentication Bypass
20%
D3: Advanced SQL/NoSQL Injection
25%
D4: Deserialization Attacks
20%
D5: Server-Side Template Injection & RCE
15%

Week-by-Week Study Plan

Week 1

Domain 1: Source code review fundamentals (Data flow, taint tracking, code auditing methodology)

Week 2

Domain 1: Language-specific patterns (PHP, Java, Python, .NET vulnerability patterns)

Week 3

Domain 2: Authentication bypass (Type juggling, loose comparison, JWT manipulation)

Week 4

Domain 2: Advanced auth attacks (Custom auth implementations, role manipulation, SSO bypass)

Week 5

Domain 3: Advanced SQLi (Source-level identification, parameterized query bypass, ORM injection)

Week 6

Domain 3: NoSQL injection (MongoDB, second-order SQLi, out-of-band extraction)

Week 7

Domain 3: Custom exploit scripting (Python scripts for automated data extraction)

Week 8

Domain 4: Deserialization (Java deserialization, ysoserial, gadget chain construction)

Week 9

Domain 4: PHP/NET deserialization (Object injection, PHPGGC, .NET gadgets, magic methods)

Week 10

Domain 5: SSTI (Jinja2, Twig, Freemarker, Thymeleaf exploitation and sandbox escapes)

Week 11

Domain 5: RCE techniques (Exploit chaining, file write RCE, custom exploit development)

Week 12

Lab Practice: Source code review exercises, vulnerability identification drills

Week 13

Lab Practice: Full application assessments, exploit development, chaining attacks

Week 14

Lab Practice: Timed mock exam (Complete application compromise with report)

Week 15

Report Writing: Professional report writing practice, methodology documentation

Week 16

Final Review: Weak areas, exam strategy, tool preparation

Free Resources

Proving Grounds

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