Red teaming gets the Hollywood treatment: stealthy operators, dramatic pivots, the “big reveal.” The reality is more methodical — and a lot more teachable. If you want to learn how real adversaries operate (so you can either emulate them or defend against them), the fastest path is hands-on practice in safe, simulated environments.
This roadmap walks you through what red teamers actually do, the skills you need, and — most importantly — where to practice each phase safely and practically using virtual labs and guided paths.
What is Red Teaming (in plain language)
Red teaming is a full-scope simulation of an adversary attacking an organisation. Unlike narrow penetration tests that check specific systems, red team exercises attempt to test people, processes, and tech together — often over days or weeks — to see how a real intrusion would play out.
Think: reconnaissance → initial access → persistence → lateral movement → objective. That full loop is what makes red teaming such an effective learning field — and such an excellent practical training area.
Red Team vs. Penetration Test — why the difference matters for learning
Quick distinction for beginners:
- Penetration test: Scoped, time-boxed tests focused on finding and exploiting vulnerabilities (usually for compliance or specific assurances).
- Red team: Longer, more realistic adversary emulation, often including social engineering, persistence, and end-to-end objectives.
If your goal is skill depth and operational understanding, red team learning gives you a broader, more realistic view of attacker behaviours — and therefore teaches you how to think like an opponent.
Core skills to build (and where to practise them)
Start with the fundamentals, then layer techniques and workflow:
- Foundations: networking, Linux, Windows
You’ll need reliable OS and networking fundamentals before attacking or pivoting inside a network. Start with Pre Security Path. - Recon & OSINT
Red teamers map the target surface. Practice scanning tools (Nmap), passive OSINT and domain/host enumeration in safe lab rooms that simulate external attack surfaces. - Initial access techniques
Learn common access methods (phishing simulations in a lab, exploiting vulnerable web apps). Labs that replicate vulnerable applications are ideal to safely practise exploitation. - Post-exploitation: persistence & privilege escalation
Hands-on elevation and persistence exercises teach you how attackers maintain footholds. Practice with guided scenarios that reset cleanly so you can repeat steps. - Lateral movement & pivoting
Understand SMB, RDP, credential reuse, and tunnelling to move across an environment. These require multi-host labs that mirror corporate networks. - OpSec & stealth
Learn detection avoidance in labs that include simulated defenders — this helps you appreciate trade-offs between stealth and speed. - Reporting & remediation recommendations
Red teamers document an attack chain and propose fixes — a skill that employers value as highly as technical ability.
A practical learning sequence (labs + paths)
Follow this sequence so every new skill ties into an actionable lab:
- Get the basics right — Complete foundational modules (networking, Linux/Windows).
- Move to offensive basics — Learn recon, scanning, and web exploitation in isolated rooms. A good stepping stone is the Jr Penetration Tester Path, which covers many red team primitives.
- Practice end-to-end scenarios — Use a dedicated red teaming path that strings techniques together: recon → access → persistence → lateral. TryHackMe’s Red Teaming Path contains adversary emulation labs built for this purpose.
- Challenge yourself with multi-host labs & CTFs — Tackle realistic, chained challenges (Hacktivities / multi-host exercises) to join techniques together under time pressure.
- Study adversary behaviour — Map what you do to frameworks like MITRE ATT&CK to understand real threat actor techniques and detection signatures.
Ethics, permissions & professionalism
Red teaming without permission is criminal. Always work inside sanctioned labs or with written permission. Learn and practise responsibly — follow legal boundaries and the ethical guidelines that professional red teamers adhere to.
If you want to read more about legal frameworks and best practice for offensive testing, organisations like CISA and SANS publish guidance on responsible testing and disclosure.
Career next steps & credentials
Red teaming sits at the intersection of technical skill and operational judgment. Employers look for:
- Demonstrable lab experience and writeups (GitHub or personal blog),
- Familiarity with ATT&CK mapping,
- An ability to explain impact and remediation.
Consider advanced courses or certifications later on (OSCP, eJPT, or vendor/industry courses), but only after you’ve accumulated practical lab experience — certifications carry the most weight when backed by hands-on evidence.
Wrap: how to start this week
- Run a reconnaissance lab and an exploit lab from the Jr Pen Tester Path.
- Try an adversary emulation exercise in the Red Teaming Path to see a full attack chain.
