Program Highlights
The PEN-300 Advanced Red Team & Evasion Techniques Certification Training prepares cybersecurity professionals to address modern threats through realistic attack simulations, hands-on labs, and advanced offensive operations. A strong emphasis is placed on developing custom techniques and tooling, enabling learners to move beyond standard frameworks and adapt to evolving security controls and sophisticated cyber threats.
Throughout the course, learners gain practical experience in client-side exploitation, social engineering, credential theft, lateral movement, privilege escalation, and persistence techniques. The curriculum also covers methods for bypassing EDR and antivirus solutions, leveraging living-off-the-land techniques, and exploiting weaknesses across both Windows and Linux environments. These advanced concepts help reinforce real-world penetration testing methodologies and offensive security practices commonly used in modern red team and enterprise security engagements.
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About Course
PEN-300 is an advanced penetration testing course designed for experienced offensive security professionals seeking to enhance their skills against modern enterprise defenses. Building upon the foundational concepts covered in PEN-200, the course focuses on real-world offensive techniques used to breach and operate within hardened environments and organizations with mature security infrastructures.
Course Curriculum
- Advanced offensive techniques and tool development
- Learn when to use common frameworks such as Metasploit and when to build custom toolchains or exploits tailored to the target environment.
- Client-side attacks and social engineering
- Design and execute convincing client-side vectors that compromise users and applications, including advanced phishing methods.
- EDR and AV evasi
- Master advanced antivirus evasion tactics, detection avoidance strategies, process migration, and in-memory payload delivery techniques.
- Privilege escalation and lateral movement
- Chain exploits to escalate privileges on Windows and Linux hosts, leverage Active Directory weaknesses, and reduce exposure created by a single misconfiguration or vulnerability. Learners will also develop vulnerability assessment skills to identify and prioritize weaknesses across enterprise environments.
- Advanced Windows offensive tradecraft
- Cover Windows-specific techniques such as credential harvesting, exploitation of administrative groups, persistence mechanisms, reflection-based stealth techniques, and executing staged payloads directly in memory.
- Application exploitation
- Find and exploit weaknesses in modern application stacks, including Java and JavaScript components, and craft reliable attack vectors against web and enterprise applications. Learners will perform realistic penetration tests that simulate modern enterprise attack scenarios.
- Maintaining access and post-exploitation
- Implement advanced methods for persistence, data exfiltration, and long-term control while minimizing detection risk and protecting sensitive data across enterprise systems and applications.
Target Audience
The PEN-300 training is ideal for:
- Experienced Penetration Testers and security professionals
- Those seeking to master advanced penetration testing methodologies
- Existing OSCP+ certification holders
Pre-requisites
- Working familiarity with Kali Linux and the Linux command line.
- Solid ability in the enumeration of targets to identify vulnerabilities.
- Basic scripting abilities in Bash, Python, and PowerShell.
- Ability to identify and exploit vulnerabilities like SQL injection, file inclusion, and local privilege escalation.
- Foundational understanding of Active Directory and knowledge of basic AD attacks.
- Familiarity of C# programming is a plus for this course.
- Completion of PEN-200 and passing OSCP+ is highly recommended.
Exam Details
| Certification Name | OSEP |
| Exam Delivery | Offsec LearnOne Platform |
| Exam Duration | 47 hours and 45 mins |
| Passing Score | 70% |
Course Objectives
- Develop advanced penetration testing skills to assess and compromise modern enterprise environments.
- Learn how to bypass endpoint protection mechanisms, including EDR and antivirus solutions, using advanced evasion techniques.
- Gain hands-on experience in Active Directory exploitation, privilege escalation, lateral movement, and persistence techniques.
- Understand and apply advanced client-side attack techniques, phishing simulations, and social engineering methodologies.
- Build custom offensive tooling and modify payloads to evade modern defensive controls.
- Master post-exploitation strategies across Windows and Linux systems in enterprise networks.
- Apply living-off-the-land techniques and stealth operations to minimize detection during engagements.
Vision
Goal
Skill-Building
Mentoring
Direction
Support
Success
penetration testers are among the most sought-after professionals in today’s cybersecurity landscape.
abilities that align with modern cybersecurity job requirements.
with the rising global demand for cybersecurity professionals: skilled offensive security experts and penetration testers.
learners for high-demand roles where applied offensive security skills are critical for safeguarding modern IT systems.
Education
Healthcare
Retail
Government
Cybersecurity Firms
Finance
It was a very good experience with the team. The class was clear and understandable, and it benefited me in learning all the concepts and gaining valuable knowledge.
I loved the overall training! Trainer is very knowledgeable, had clear understanding of all the topics covered. Loved the way he pays attention to details.
I had a great experience with the team. The training advisor was very supportive, and the trainer explained the concepts clearly and effectively. The program was well-structured and has definitely enhanced my skills in AI. Thank you for a wonderful learning experience.
The class was really good. The instructor gave us confidence and delivered the content in an impactful and easy-to-understand manner.
The program helped me understand several areas I was unfamiliar with. The instructor was exceptionally skilled and confident in delivering content.
The program was well-structured and easy to follow. The instructor’s use of real-life AI examples made it easier to connect with and understand the concepts.
Frequently Asked Questions
What is OSEP (PEN-300) certification?
OffSec OSEP (Offensive Security Experienced Penetration Tester) is an advanced cybersecurity certification that validates skills in bypassing security defenses, evasion techniques, and simulating real-world attacks in enterprise environments.
Who should take OSEP certification training?
OSEP is ideal for experienced penetration testers, red team professionals, security consultants, and cybersecurity practitioners looking to advance their offensive security and adversary simulation skills.
What advanced penetration testing topics are covered in OSEP?
The training covers advanced exploitation, Active Directory attacks, client-side attacks, antivirus evasion, application whitelisting bypass, lateral movement, tunneling, and post-exploitation techniques.
Does the course include evasion techniques and adversary simulation?
Yes. OSEP focuses heavily on evasion techniques such as bypassing antivirus, endpoint detection systems, and application controls while simulating realistic adversary behavior.
Is Active Directory exploitation covered in OSEP training?
Yes. Active Directory exploitation is a core component of OSEP, including privilege escalation, credential attacks, lateral movement, and domain compromise techniques.
What is the difference between OSCP+ and OSEP?
OffSec OSCP+ focuses on foundational penetration testing and exploitation skills, while OSEP is an advanced-level certification emphasizing evasion, red teaming, and bypassing modern defensive technologies.
Is OSEP suitable for experienced penetration testers?
Yes. OSEP is designed specifically for professionals who already possess strong penetration testing fundamentals and want to develop advanced offensive security capabilities.
How does OSEP support advanced red team operations?
OSEP helps professionals develop skills required for advanced red team engagements, including stealth techniques, defense evasion, Active Directory compromise, persistence, and realistic attack simulations in enterprise environments.