Certification
OSEE — Offensive Security Exploitation Expert
Course
EXP-401: Advanced Windows Exploitation (AWE)
Exam Format
72-hour practical — 2 exploit challenges + report
Delivery
In-person only (Black Hat, OffSec events)
Prerequisites
Windows exploit dev experience, debugger proficiency, C/C++, x86_64 ASM
01 EXP-401 Syllabus Roadmap
Module 1

Custom Shellcode Creation

Building custom shellcode from scratch for x86_64 architecture. Covers Win32 API internals, position-independent code, calling conventions in 64-bit systems, and developing a versatile shellcode framework including reverse shell payloads.

x64 ASM Win32 API PIC Shellcode Framework
Module 2

VMware Workstation Guest-to-Host Escape

Escaping from a guest OS to the host by exploiting vulnerabilities in VMware Workstation. Covers VMware internals, use-after-free vulnerability analysis, heap memory management, LFH exploitation, and virtual table manipulation.

VMware Internals UaF Heap Feng Shui LFH
Module 3

Microsoft Edge Type Confusion

Browser sandbox escape via type confusion vulnerabilities in Microsoft Edge (Chakra engine). Covers JIT process injection, ASLR/DEP/CFG bypass, and advanced ROP chain construction against modern mitigations.

Browser Exploits Type Confusion CFG Bypass ROP
Module 4

Driver Callback Overwrite

Local privilege escalation by exploiting vulnerabilities in third-party kernel drivers. Covers kernel driver analysis, callback function manipulation, and escalation from user-mode to SYSTEM privileges.

Kernel Exploitation Driver Analysis Privilege Escalation
Module 5

Unsanitized User-mode Callback

Kernel privilege escalation via win32k subsystem vulnerabilities. Covers Windows kernel subsystem internals, user-mode callback abuse, and exploitation of native OS kernel components.

win32k Kernel Subsystem Callback Abuse LPE
02 Essential Tools
Debugger

WinDbg / WinDbg Preview

The primary debugger for OSEE. Master kernel and user-mode debugging, breakpoints, memory inspection, and extension commands. Non-negotiable for EXP-401.

learn.microsoft.com ↗
Disassembler

IDA Pro

Industry-standard interactive disassembler and decompiler. Essential for static analysis of target binaries, identifying vulnerability patterns, and understanding complex code paths.

hex-rays.com ↗
Disassembler

Ghidra

NSA's open-source reverse engineering framework. Free alternative to IDA with excellent decompiler support. Great for supplementary analysis and scripting automation.

ghidra-sre.org ↗
Virtualization

VMware Workstation Pro

Required for the course lab environment. Must support running 3 VMs simultaneously. VMware is also a case study target in Module 2 — understand its internals deeply.

vmware.com ↗
IDE / Compiler

Visual Studio

For developing and debugging exploit code in C/C++. The MSVC compiler and debugger integration is critical for building PoCs and shellcode loaders.

visualstudio.microsoft.com ↗
Scripting

Python 3

Exploit scripting, automation, ROP gadget finding, and PoC development. Libraries like pwntools, struct, and ctypes are invaluable for exploit prototyping.

python.org ↗
Exploit Utility

ROPgadget / ropper

Tools for searching ROP gadgets in binaries. Essential for building ROP chains to bypass DEP/ASLR and construct code-reuse attacks against modern mitigations.

github.com ↗
System Analysis

Sysinternals Suite

Process Explorer, Process Monitor, VMMap, and other tools for understanding Windows internals during exploit development. Critical for heap analysis and process introspection.

learn.microsoft.com ↗
03 Study Resources & Reading
Book

Windows Internals, Part 1 & 2

By Yosifovich, Ionescu, Russinovich, Solomon. The definitive reference on Windows kernel architecture, memory management, processes, and security mechanisms. Required reading.

Book

The Shellcoder's Handbook

By Anley, Heasman, Lindner, Richarte. Covers exploit discovery and development techniques across platforms. Excellent foundation for understanding vulnerability classes.

Book

A Guide to Kernel Exploitation

By Perla & Oldani. Covers attacking the kernel across OS platforms. Essential reading for Modules 4 and 5 on kernel driver and win32k exploitation.

Book

Practical Reverse Engineering

By Dang, Gazet, Bachaalany. x86/x64 architecture, Windows kernel internals, and reverse engineering methodology. Bridges the gap between RE and exploit development.

Tutorial Series

Corelan Exploit Writing Tutorials

Peter Van Eeckhoutte's legendary exploit writing tutorial series. Covers stack overflows through advanced heap exploitation. A rite of passage for exploit developers.

corelan.be ↗
GitHub Repo

0x1BE/OSEE-Prep

Structured study guide aligned with the EXP-401 syllabus. Covers each module with curated resources, explanations, and practical exercises. Actively maintained.

github.com/0x1BE ↗
GitHub Repo

dhn/OSEE

Collection of resources compiled during OSEE certification preparation. Includes links to papers, exploit writeups, and technique references organized by topic.

github.com/dhn ↗
GitHub Repo

PwnAwan/EXP-401-OSEE

Resources and proof-of-concept exploits for OSEE prep. Covers mitigation bypass techniques, heap manipulation, and kernel exploitation references.

github.com/PwnAwan ↗
GitHub Repo

OSCE3 Complete Guide

Comprehensive guide covering the full OSCE3 path — OSWE, OSEP, OSED, and OSEE. Aggregates review writeups, lab resources, and community preparation notes.

github.com/CyberSecurityUP ↗
Exam Review

OSEE Exam Review — ommadawn46

Detailed first-hand account of AWE course attendance through OSEE certification. Covers preparation timeline, study methodology, and exam insights.

medium.com ↗
Course

Udemy — OSEE Exploitation Expert Prep

Focused advanced-level drill designed to bridge intermediate exploitation knowledge with OSEE-level proficiency. Covers Win32 internals, SEH, PE format, and exploit technique refinement.

udemy.com ↗
Pre-Req Course

EXP-301 / OSED

OffSec's Windows User Mode Exploit Development course. Covers stack overflows, SEH, DEP/ASLR bypass, and WinDbg/IDA fundamentals. Strongly recommended before attempting EXP-401.

04 Practice & Hands-On Labs
Platform

Hack The Box

Focus on Windows machines with kernel exploits, binary exploitation challenges, and the Fortress labs. Great for building exploit development muscle memory.

hackthebox.com ↗
Platform

Exploit Education

Phoenix and Protostar VMs for learning memory corruption exploitation fundamentals. Start here if you need to solidify your stack/heap overflow basics before advancing.

exploit.education ↗
Self-Study

CVE Reproduction Labs

Set up vulnerable versions of real software and reproduce published CVEs. Focus on Windows heap overflows, UaF in browsers and virtualization software, and kernel driver bugs. Build your own PoCs from advisories.

Self-Study

Fuzzing Lab

Build a fuzzing environment with WinAFL or libFuzzer targeting Windows applications. Finding your own crashes and triaging them into exploitable bugs is the highest-value prep activity for OSEE.

05 Exam Strategy & Tips
01

Schedule First, Prep Second

Set a hard exam deadline to create urgency. OSEE holders consistently report that having a fixed date forced focused, productive preparation instead of endless study cycles.

02

Master Your Debugger

WinDbg commands should be muscle memory. Practice navigating heap structures, setting conditional breakpoints, and analyzing crash dumps until it's second nature.

03

Document Everything

The exam requires a comprehensive penetration test report. Build your reporting template and practice writing detailed technical narratives during your prep labs — not during the 72-hour exam.

04

Think Laterally

The exam tests lateral thinking as much as technical knowledge. The vulnerabilities are unknown — you need to discover them. Practice root cause analysis on unfamiliar targets, not just replaying known exploits.

05

Build Redundancy

Prepare backup internet, power, and a secondary machine/VM setup. 72 hours is long — avoidable technical disruptions can cost you the certification.

06

Sleep Strategy

Plan your sleep schedule for the exam in advance. Most successful candidates report sleeping in 3-4 hour blocks rather than trying to power through the full 72 hours without rest.

06 Recommended Prerequisite Path
Foundation

C/C++ Programming & x86_64 Assembly

Solid systems programming skills are non-negotiable. You need to read, write, and debug C code and assembly fluently. Understand calling conventions, stack frames, and memory layout.

Level 200

PEN-200 / OSCP

General penetration testing methodology and tooling. Builds the operational mindset needed for approaching unknown targets methodically.

Level 300

EXP-301 / OSED

Windows user-mode exploit development. Stack overflows, SEH exploitation, DEP/ASLR bypass, and IDA/WinDbg proficiency. The direct on-ramp to EXP-401.

Level 300

PEN-300 / OSEP (Optional but Recommended)

Advanced evasion, Active Directory exploitation, and post-exploitation. Builds lateral thinking skills valuable for the OSEE exam's open-ended challenges.

Level 400

EXP-401 / OSEE

Advanced Windows Exploitation. In-person training at Black Hat or OffSec events, followed by the 72-hour practical exam. The summit of OffSec's certification hierarchy.