OSEP-Level Advanced Exploit & Evasion Training

Module 1

Advanced Windows & Process Internals

Windows architecture, processes, threads, memory layout, Win32 APIs, integrity levels and tokens. Understanding how userland code interacts with the OS and where attackers can hook, inject or manipulate.

Module 2

Intro to Exploit Development (OSEP Context)

Structured review of exploit basics: buffer overflows, return addresses, shellcode, bad characters and space constraints. Focus on the kind of exploit dev depth useful for OSEP-style challenges (not pure research).

Module 3

Shellcode, Payloads & Obfuscation

Shellcode basics, staged vs stageless payloads, encoders and obfuscation. Using, modifying and debugging payloads. Handling constraints like character filters, size limits and unreliable network conditions.

Module 4

AV/EDR Evasion Foundations

How AV/EDR generally works (signatures, heuristics, behavior). Common red flags in default payloads, static and dynamic analysis basics, and design principles for reducing the “obvious malware” footprint in labs.

Module 5

Custom Launchers & Execution Techniques

Writing or modifying small launchers in C#/C/C++/PowerShell (exam-safe depth). Process injection basics, in-memory execution patterns, living-off- the-land (LOL) style techniques and trade-offs in different approaches.

Module 6

Bypassing Application Control & Constraints

AppLocker-style restrictions, file type & extension issues, script execution limits, constrained environments and ways to chain allowed binaries, interpreters, or scheduled components to gain execution.

Module 7

Advanced Lateral Movement & Credential Abuse

Token manipulation concepts, abusing misconfigurations, reusing credentials, RDP and WinRM in hardened environments, constrained delegation issues, and chaining small misconfigurations into meaningful internal access.

Module 8

Post-Exploitation & Stealth Persistence Ideas

Collecting data without being noisy, fileless or low-footprint techniques, scheduled tasks, registry and service-based persistence, and understanding detection vs stealth trade-offs in OSEP-style labs and real life.

Module 9

Adversary Simulation Mindset

Thinking like an adversary but acting like a professional: objective- driven operations, quiet enumeration, path-of-least-resistance and balancing impact with safety in lab and client networks.

Module 10

Reporting, Detections & Lessons Learned

Writing reports that capture not only vulnerabilities but also evasion lessons and defensive gaps. Documenting detection failures, suggesting logging improvements and making your offensive work useful to blue teams.

Recommended background

• Comfortable with Linux and Windows command line.
• Solid knowledge of TCP/IP and common protocols.
• Prior pentest experience (eJPT/OSCP-level or equivalent).
• Basic scripting experience (PowerShell, Python or C#/C) is helpful.

What you need technically

• PC / laptop capable of running multiple Windows & Linux VMs.
• Stable internet connection for VPN-based labs / updates.
• Virtualization software (VirtualBox / VMware) and enough disk space.

If you’re unsure whether you’re ready for OSEP-level content, contact us and we can help you map your current skills to the right level.