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Offensive Security Experienced Penetration Tester
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Offensive Security Experienced Penetration Tester (OSEP) training syllabus, OSEP is an advanced-level penetration testing certification, ideal for professionals who already hold the OSCP and want to specialize in bypassing modern security
defenses, including EDRs, AVs, and network controls.
Overview
The Syllabus
Curriculum Designed by Experts
Module 1: Operating System and Programming Fundamentals
• Windows internals refresher
• Scripting basics (PowerShell, Python)
• C# and .NET programming for red teaming
• Custom payload development
� Lab: Compile a custom C# payload and test detection
Module 2: Advanced Command & Control (C2)
• Customizing open-source C2 frameworks (e.g., Covenant, Mythic)
• Manual shellcode execution
• HTTPS and DNS-based C2 communication
• C2 over non-standard ports
� Lab: Deploy a custom HTTPS C2 server with obfuscated payloads
Module 3: Antivirus and EDR Evasion
• Understanding AV and EDR architecture
• Bypassing static and dynamic analysis
• API unhooking and DLL sideloading
• Inline execution and reflective DLL injection
� Lab: Modify a known payload to bypass Windows Defender
Module 4: Application Whitelisting and Bypass Techniques
• Windows Defender Application Control (WDAC)
• AppLocker policy analysis
• LOLBins (Living ob the Land Binaries)
• DLL Search Order Hijacking
• Control Flow Guard (CFG) evasion
� Assignment: Bypass AppLocker using MSBuild and custom C# code
Module 5: Advanced Windows Exploitation
• COM Hijacking and COM abuse
• WMI abuse
• UAC bypass techniques
• Token manipulation and impersonation
• Process injection methods
� Lab: Use WMI to remotely execute code on a target system
Module 6: Active Directory Exploitation
• Domain enumeration techniques
• Kerberos attacks: AS-REP Roasting, Kerberoasting
• Credential dumping and pass-the-hash
• AD CS abuse (ESC1 – ESC8)
• DCShadow, DCSync, and Golden Ticket attacks
� Project: Conduct a full domain takeover in a lab environment
Module 7: Lateral Movement and Privilege Escalation
• RDP/WinRM/SMB lateral movement
• Token impersonation and delegation
• Remote thread injection and WMI remote execution
• Scheduled tasks and service abuse
� Lab: Automate lateral movement using impersonated tokens
Module 8: Client-Side Attacks and Initial Access
• Macro-based payloads (Excel, Word)
• Malicious HTA, LNK, and OneNote files
• HTML smuggling
• Spear-phishing techniques and evasion
� Assignment: Craft a phishing campaign using obfuscated macro payloads
Module 9: Post-Exploitation and Persistence
• Credential harvesting
• Fileless persistence (registry, services, scheduled tasks)
• Alternate Data Streams (ADS)
• Rootkit-like behaviors in Windows
� Lab: Set up multiple persistence methods and evade detection
Module 10: Bypassing Network Defenses
• Web proxy and SSL inspection bypass
• DNS tunneling and domain fronting
• Port knocking and covert channels
• Advanced firewall evasion
� Project: Exfiltrate data via a covert DNS channel
OSEP Exam Format
• 48 hours hands-on exam
• Targeting multiple machines in a hardened environment
• Full report writing (similar to OSCP)
• Minimum passing score required: 100/150
Who Should Take OSEP?
• OSCP holders
• Red teamers and obensive security professionals
• Security engineers and penetration testers
• Professionals targeting adversary emulation or APT simulation
Deliverables
• PEN-300 Materials
• PEN-300 Lab Environment
• Scripts, payloads, cheat sheets, and tools
• Sample reports and writeups
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Global Certification
Radical Technologies is the leading IT certification institute in Kochi, offering a wide range of globally recognized certifications across various domains. With expert trainers and comprehensive course materials, it ensures that students gain in-depth knowledge and hands-on experience to excel in their careers. The institute’s certification programs are tailored to meet industry standards, helping professionals enhance their skillsets and boost their career prospects. From cloud technologies to data science, Radical Technologies covers it all, empowering individuals to stay ahead in the ever-evolving tech landscape. Achieve your professional goals with certifications that matter.
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career services
At Radical Technologies, we are committed to your success beyond the classroom. Our 100% Job Assistance program ensures that you are not only equipped with industry-relevant skills but also guided through the job placement process. With personalized resume building, interview preparation, and access to our extensive network of hiring partners, we help you take the next step confidently into your IT career. Join us and let your journey to a successful future begin with the right support.
At Radical Technologies, we ensure you’re ready to shine in any interview. Our comprehensive Interview Preparation program includes mock interviews, expert feedback, and tailored coaching sessions to build your confidence. Learn how to effectively communicate your skills, handle technical questions, and make a lasting impression on potential employers. With our guidance, you’ll walk into your interviews prepared and poised for success.
At Radical Technologies, we believe that a strong professional profile is key to standing out in the competitive IT industry. Our Profile Building services are designed to highlight your unique skills and experiences, crafting a resume and LinkedIn profile that resonate with employers. From tailored advice on showcasing your strengths to tips on optimizing your online presence, we provide the tools you need to make a lasting impression. Let us help you build a profile that opens doors to your dream career.
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Offensive Security Experienced Penetration Tester Course Certification With Training In Kochi
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