Advanced · Red Teaming

OSEP

OffSec Experienced Penetration Tester

Advance beyond standard penetration testing with defense evasion, mature network compromise, lateral movement and complex enterprise attack chains.

Course overview

Skills with real-world context

Designed around the workflows and decisions practitioners use—not a collection of disconnected tool demonstrations.

Advance beyond standard penetration testing with defense evasion, mature network compromise, lateral movement and complex enterprise attack chains. The learning path combines guided concepts, repeatable lab methodology, evidence collection and professional communication.

Senior Penetration Tester Red Team Operator Adversary Simulation Consultant

2026 market direction

Organizations are investing in adversary simulation and control validation. OSEP-aligned skills are especially relevant where EDR, application controls and segmented Active Directory environments must be tested.

Course content

What you will study

A focused six-module roadmap. Exact official syllabus and assessment policies remain subject to OffSec updates.

Client-Side Tradecraft

Document and application attack concepts

Payload staging

Social-engineering constraints

Operational safety and evidence

Application Control Bypass

PowerShell restrictions

Application allowlisting concepts

Trusted utility abuse

Custom execution workflows

Antivirus & EDR Evasion

Static and behavioral detection

Payload obfuscation principles

In-memory execution concepts

Iterative detection testing

Advanced Active Directory

Delegation and trust relationships

Authentication abuse

Credential access pathways

Cross-domain attack planning

Lateral Movement

Tunneling and proxy chains

Remote management protocols

Pivoting through restrictions

Maintaining operational access

Enterprise Breach Simulation

Multi-stage attack planning

Objective-based lab operations

Evidence and reporting

Remediation-focused debrief

Plan your preparation

Audience, prerequisites and exam

Who should attend

OSCP-level practitioners
Pentesters facing mature enterprise defenses
Red team members building advanced tradecraft

Recommended prerequisites

Strong penetration-testing methodology, scripting, Windows and Active Directory experience. OSCP-level ability is recommended.

Certification assessment

A demanding hands-on enterprise compromise and reporting assessment. Check the official guide for current time, tooling and submission rules.

Learning outcomes

Capabilities you will build

Adapt payloads to evade common controls

Chain attacks across segmented networks

Abuse complex Active Directory relationships

Plan and report an enterprise intrusion simulation

Primary curriculum reference: Official OSEP course information . Pricing, exam format and availability should always be confirmed with OffSec.