Offensive Level 4 — Specialization

Red Teaming & Penetration Testing

🎯 Goal

Go beyond web vulnerabilities and emulate real-world adversaries. Learn to compromise networks, escalate privileges, move laterally, and achieve objectives while evading detection. This path merges penetration testing methodology with red team tactics.

🔑 Key Skills to Learn

  • Penetration Testing Methodology: Reconnaissance, scanning, exploitation, post-exploitation, reporting (PTES, OSSTMM).
  • Active Directory (AD) Attacks: Kerberoasting, AS-REP roasting, Pass-the-Hash, Pass-the-Ticket, Golden/Silver Ticket, DCSync, BloodHound analysis.
  • Network Exploitation: LLMNR/NBT-NS poisoning, SMB relay attacks, SNMP weaknesses, network pivoting.
  • Phishing & Social Engineering: Pretexting, payload delivery, credential harvesting (GoPhish).
  • Command & Control (C2) Frameworks: Setting up and using C2 (Sliver, Covenant, Havoc) for agent communication.
  • Post-Exploitation: Privilege escalation (Windows & Linux), credential dumping (Mimikatz, LSASS), persistence mechanisms.
  • Lateral Movement: PSExec, WMI, WinRM, RDP, SSH hopping, pass-the-hash.
  • Evasion & OPSEC: Antivirus/EDR bypass (AMSI, script logging), obfuscation, avoiding common indicators.
  • Reporting for Red Teams: Narrative-based reports, attack flow diagrams, mitigation recommendations aligned to MITRE ATT&CK.

🛠️ Essential Tools & Technologies

Tool Purpose
Metasploit Framework Exploitation, payload generation, post-exploitation modules.
BloodHound (Community Edition) Active Directory relationship analysis, attack path mapping.
Impacket Suite Scripts for AD attacks (secretsdump, GetUserSPNs, wmiexec).
CrackMapExec (CME) Swiss army knife for AD reconnaissance, lateral movement, credential spraying.
Sliver / Havoc / Covenant Modern C2 frameworks for red team engagements.
Mimikatz / Rubeus Credential dumping, Kerberos ticket manipulation.
Evil-WinRM / psexec.py Remote command execution and lateral movement.
GoPhish Open-source phishing simulation and training platform.
Nishang / PowerSploit PowerShell post-exploitation frameworks.
Ligolo-ng / Chisel Pivoting and tunneling tools.

📖 Free Learning Resources

  • Hack The Box – Starting Point & Pro Labs – Free tier machines build AD and network exploitation skills. Link
  • TryHackMe – Red Team Path – Rooms: "Active Directory", "Lateral Movement", "C2 Operations". Link
  • Zero-Point Security – “Red Team Ops” (CRTO) – Paid course but excellent free blog posts and “C2 Matrix” site. C2 Matrix
  • MITRE ATT&CK – Map your techniques, understand detection gaps. Link
  • SpecterOps Blog – Deep dives into AD attacks and BloodHound. Link
  • Sektor7 Malware Development Courses (Free Intro) – Learn evasion and tool development basics. Search “Sektor7 free intro” on YouTube.
  • IppSec (YouTube) – Hack The Box machine walkthroughs, teaches methodology. Link
  • The Hacker Playbook (Book Series) – Some free preview chapters and associated GitHub repos for scenarios. Search “THP-2/3 GitHub”.

🔗 Roadmap Placement

  • Prerequisites: Strong Linux, Networking, Core Security Concepts, Web & Application Security, and basic Bug Bounty methodology.
  • Directly Leads to: Advanced adversary simulation, purple teaming (combining red & blue), security research, or operational roles like penetration tester / red team operator.
  • Next Steps: After this, you might explore Cloud Security / Cloud Penetration Testing, Mobile Security, or Digital Forensics & Incident Response (to understand the defensive side).