COMPLETE Guide: OSWE, OSEP, OSED, and OSEE Study Guide

By /

Listen to this Post

Featured Image

Introduction

The Offensive Security Web Expert (OSWE), Offensive Security Exploitation Professional (OSEP), Offensive Security Exploitation Developer (OSED), and Offensive Security Expert (OSEE) certifications are among the most prestigious in offensive cybersecurity. These certifications validate advanced skills in exploit development, web application security, and advanced penetration testing. This guide provides a structured approach to mastering these certifications, including essential tools, techniques, and study resources.

Learning Objectives

  • Understand the core exam objectives for OSWE, OSEP, OSED, and OSEE.
  • Learn key exploitation techniques, including custom shellcode development and advanced web attacks.
  • Gain hands-on experience with recommended tools and labs for exam preparation.

You Should Know

1. OSWE: Advanced Web Exploitation

Command:

sqlmap -u "http://vulnerable-site.com/login" --data="username=admin&password=test" --level=5 --risk=3 --dbs

Step-by-Step Guide:

  1. Target Identification: Use `sqlmap` to test for SQL injection vulnerabilities.

2. Enumeration: The `–dbs` flag lists available databases.

  1. Exploitation: Use `–dump` to extract data from vulnerable tables.
    Why it matters: OSWE focuses on manual web app exploitation, making SQLmap a critical tool for testing injection flaws.

2. OSEP: Evasion Techniques & Custom Malware

Command (Windows Shellcode Execution via PowerShell):

[System.Runtime.InteropServices.Marshal]::Copy($shellcode, 0, $address, $shellcode.Length)

Step-by-Step Guide:

  1. Generate Shellcode: Use `msfvenom` to create a payload.

2. Memory Allocation: Allocate executable memory in PowerShell.

  1. Execution: Copy shellcode into memory and execute it.
    Why it matters: OSEP requires bypassing AV/EDR, making manual shellcode execution essential.

3. OSED: Exploit Development Fundamentals

Command (Debugging with WinDbg):

!exploitable

Step-by-Step Guide:

  1. Crash Analysis: Load a crash dump in WinDbg.
  2. Exploitability Check: Run `!exploitable` to assess crash potential.
  3. Pattern Creation: Use `pattern_create` to identify EIP overwrite offsets.
    Why it matters: OSED tests low-level exploit development, requiring deep debugging skills.

4. OSEE: Advanced Windows Exploitation

Command (Kernel Debugging with IDA Pro):

bp nt!NtCreateFile

Step-by-Step Guide:

  1. Attach Kernel Debugger: Connect to a target system via WinDbg/IDA.
  2. Breakpoint Analysis: Set breakpoints on critical kernel functions.
  3. Exploit Development: Analyze execution flow for privilege escalation.
    Why it matters: OSEE covers kernel-mode exploits, requiring deep Windows internals knowledge.

5. API Security Testing for OSWE

Command (Burp Suite Intruder Payload):

GET /api/user?id=§1§ HTTP/1.1
Host: vulnerable-api.com

Step-by-Step Guide:

  1. Intercept Request: Capture an API call in Burp Suite.
  2. Fuzz Parameters: Use Intruder to test for IDOR, SSRF, or injection flaws.
  3. Analyze Responses: Check for data leaks or error-based vulnerabilities.
    Why it matters: OSWE heavily emphasizes API security testing.

6. Cloud Hardening for OSEP/OSEE

Command (AWS IAM Policy Audit):

aws iam get-account-authorization-details --query 'Policies[].PolicyName'

Step-by-Step Guide:

  1. List Policies: Retrieve all IAM policies in an AWS account.
  2. Check Permissions: Use `aws iam get-policy-version` to review permissions.

3. Mitigate Overprivileged Roles: Restrict unnecessary permissions.

Why it matters: Cloud environments are a key focus in advanced red teaming.

7. Vulnerability Mitigation for OSED/OSEE

Command (Linux ASLR Check):

cat /proc/sys/kernel/randomize_va_space

Step-by-Step Guide:

  1. Check ASLR Status: A value of `2` means full randomization.
  2. Disable (For Testing): echo 0 | sudo tee /proc/sys/kernel/randomize_va_space.
  3. Re-enable (For Security): Reset to `2` after testing.
    Why it matters: Understanding memory protections is crucial for exploit development.

What Undercode Say

  • Key Takeaway 1: Hands-on practice is non-negotiable—build custom exploits and bypass modern defenses.
  • Key Takeaway 2: Focus on real-world scenarios; these exams simulate professional engagements.

Analysis: Offensive Security’s advanced certifications (OSWE, OSEP, OSED, OSEE) are designed for professionals aiming to master exploit development and advanced penetration testing. Unlike entry-level certs like OSCP, these require deep technical expertise in debugging, evasion, and custom payload development. The cybersecurity landscape is shifting toward advanced persistent threats (APTs), making these skills invaluable for red teams and security researchers.

Prediction

As organizations face increasingly sophisticated attacks, demand for experts with OSWE/OSEP/OSED/OSEE certifications will surge. Future exploits will likely leverage AI-assisted fuzzing and cloud-native attacks, requiring defenders to adopt these offensive skills proactively.

Resource Link: Complete Study Guide

IT/Security Reporter URL:

Reported By: Omar Aljabr – Hackers Feeds
Extra Hub: Undercode MoN
Basic Verification: Pass ✅

🔐JOIN OUR CYBER WORLD [ CVE News • HackMonitor • UndercodeNews ]

💬 Whatsapp | 💬 Telegram

📢 Follow UndercodeTesting & Stay Tuned:

𝕏 formerly Twitter 🐦 | @ Threads | 🔗 Linkedin

Related Posts: