Roadmaps Security roadmaps Offensive security and assessment

Red Teaming and Adversary Emulation

Test whether an organisation can detect and respond to a realistic attack: adversary emulation, purple teaming, breach and attack simulation, and control validation, all under strict authorisation.

Estimated time: 13–26 months · At about 10 hours a week.

Offensive skills are for authorised testing only: your own lab, a practice platform, or a system whose owner has given you written permission. Testing anything else is a crime in most countries.

Learning path

Click a topic to see what to learn and where. Mark topics as you go; your progress is saved in this browser only.

  • Core topic
  • Optional
  1. Beginner · 3–6 months From pentesting to red teaming
  2. Intermediate · 4–8 months Emulation and detection
  3. Advanced · 6–12 months Full engagements and purple teaming
  4. Expert · ongoing months Leading adversary emulation

All topics in detail

Beginner, Time: 3–6 months

From pentesting to red teaming

Skills

  • Explain red teaming and its place among testing types.
  • Use MITRE ATT&CK fluently.
  • Set up a detection lab.
  • Explain the authorisation red teaming requires.

Hands-on projects and labs

  • Build a detection lab with logging and a SIEM.
  • Map a public threat report's behaviour to ATT&CK techniques.

Done when you can…

  • Explain the difference between pentesting, red teaming and BAS.
  • Map adversary behaviour to ATT&CK.

Beginner

What red teaming is

Objective-based, threat-realistic testing of detection and response, not a vulnerability hunt. Learn how it differs from penetration testing and when each fits.

Resources

Beginner

MITRE ATT&CK

ATT&CK is the shared language of tactics and techniques. Learn it thoroughly; it drives emulation planning and detection mapping alike.

Resources

Beginner

Authorisation and rules

Red teaming needs explicit, senior authorisation, a legal agreement, clear objectives and strict rules, including who knows and how to stand down. This comes first.

Resources

Beginner

Emulation, simulation and BAS

Adversary emulation copies a specific actor; breach and attack simulation automates known techniques continuously. Learn where each adds value.

Resources

Beginner

A detection lab

Build a lab with logging and a SIEM so you can run techniques and see what defenders would. Learning to be seen matters as much as the technique.

Resources

Intermediate, Time: 4–8 months

Emulation and detection

Skills

  • Plan an emulation of a specific threat actor.
  • Run atomic tests and check detection.
  • Explain C2 and evasion from the defender's side.
  • Measure and report detection coverage.

Hands-on projects and labs

  • Run Atomic Red Team techniques in your lab and record which your SIEM detects.
  • Build an ATT&CK Navigator layer showing detection coverage and gaps.

Done when you can…

  • Produce a detection coverage map for a set of techniques.
  • Plan an emulation aligned to a real threat actor.

Intermediate

Adversary emulation planning

Choose a threat actor relevant to the organisation, study its documented behaviour, and plan an emulation of its techniques against an objective.

Resources

Intermediate

Atomic testing

Run individual, documented techniques safely and check whether they are detected. Atomic Red Team is the standard open library for this.

Resources

Intermediate

Command and control concepts

Understand how operators manage access during an engagement, and how defenders detect it. Study the detection side as hard as the operation.

Resources

Intermediate

Evasion and its detection

Learn how attackers try to avoid defences specifically so you can help defenders catch them. Keep the emphasis on improving detection.

Resources

Intermediate

Operational safety

Protect the engagement data, avoid harm to production, and keep meticulous logs of everything you do. Safety and accountability define a professional.

Resources

Intermediate

Measuring detection coverage

The real output is a map of what defenders saw and missed, per technique. Learn to produce it and track improvement over time.

Resources

Advanced, Time: 6–12 months

Full engagements and purple teaming

Skills

  • Run full engagements and after-action reviews.
  • Run purple team exercises.
  • Operate BAS and control validation programmes.
  • Report defensive outcomes.

Hands-on projects and labs

  • Run a purple team exercise in your lab with VECTR, improving detections as you go.
  • Validate an EDR against a set of techniques and report the gaps.

Done when you can…

  • Run an engagement that measurably improves detection and response.
  • Deliver an outcome-focused report defenders can act on.

Advanced

Running a full engagement

From objective and scoping through emulation to an after-action review with defenders. The review and the improvements are the deliverable.

Resources

Advanced

Purple teaming

Run techniques openly with defenders watching, fixing detections as you go. It improves security faster than a closed red team and is often the better choice.

Resources

  • VECTR Tool, Free, Security Risk Advisors

Advanced

Breach and attack simulation programmes

Automated, continuous validation of controls against known techniques. Learn to run a BAS programme and act on its results.

Resources

Advanced

Control validation

Test whether specific controls, such as EDR or email filtering, actually work against the techniques they should stop, and report gaps to owners.

Resources

Advanced

Threat-led penetration testing

Regulated frameworks such as TIBER-EU and CBEST run intelligence-led red teams against live financial systems under strict governance. Learn how they work.

Resources

Advanced

Reporting outcomes

Report what defenders detected, how fast they responded, and which controls and detections to improve, with ATT&CK coverage. Outcomes, not war stories.

Resources

Expert, Time: ongoing months

Leading adversary emulation

Skills

  • Run a threat-aligned emulation programme.
  • Lead a team and measure defensive maturity.

Hands-on projects and labs

  • Write an annual emulation plan aligned to an organisation's threat profile.
  • Design a dashboard tracking detection coverage over time.

Done when you can…

  • Lead an emulation programme that improves defences measurably.
  • Show rising detection maturity across ATT&CK.

Expert

Threat-aligned programmes

Build a continuous emulation programme aligned to the threats the organisation actually faces, with threat intelligence driving what you test.

Resources

Expert

Building and running a team

Recruit, train and keep operators, maintain a safe methodology, and manage the sensitive relationship with defenders and leadership.

Resources

Expert

Measuring defensive maturity

Show detection and response improving over time across ATT&CK. That trend, not individual wins, is what justifies the programme.

Resources

Overview

Red teaming goes beyond finding vulnerabilities: it tests whether an organisation can detect, respond to and recover from a realistic attack. An authorised team emulates the techniques of a chosen threat actor, under tight rules, to exercise the defenders and the controls.

This roadmap is a learning path for authorised, objective-based testing and, increasingly, for purple teaming, where offence and defence work together to improve detection. It centres on MITRE ATT&CK, emulation planning and measuring defensive outcomes. Every engagement needs written authorisation and a clear objective agreed with leadership.

Why it matters

Organisations that pass vulnerability scans still fall to real attacks because detection and response fail. Red and purple teams measure and improve that, and the demand for people who can run them constructively, not just break in, is high.

Typical job roles

  • Mid-levelRed team operator Executes emulation under a lead.
  • SeniorRed team lead Plans and runs engagements.
  • Mid-levelPurple team engineer Runs emulation with defenders to improve detection.
  • LeadAdversary emulation lead Owns the programme and threat alignment.

Prerequisites

  • Solid penetration testing and identity attack skills.
  • Strong understanding of detection and defensive operations.
  • Deep knowledge of MITRE ATT&CK.
  • Mature judgement and the law and ethics of authorised testing.

Cybersecurity fundamentals Foundations of computer science

Tools and technologies

  • Atomic Red Team Open source Library of documented techniques for detection testing.
  • Caldera Open source MITRE's automated adversary emulation platform.
  • VECTR Free community edition Plan and track purple team exercises.
  • ATT&CK Navigator Open source Visualise coverage and gaps.
  • DetectionLab Open source Pre-built lab with logging and a SIEM.

Certifications

Take them in roughly this order. Costs and details for the ones marked with a link are on the Certifications page.

  1. Intermediate CRTO Zero-Point SecurityWidely respected hands-on red team course.
  2. OSEP (PEN-300) OffSecAdvanced evasion and emulation.
  3. GIAC GCDA / purple team courses SANSDefensive analytics that pair with emulation.

Resources

Frameworks and standards

All frameworks and standards

Career path

A common progression. Titles vary between companies.

  1. Penetration tester or detection engineer2–5 years
  2. Red team operator or purple team engineer4–7 years
  3. Red team lead7–11 years
  4. Adversary emulation lead11+ years

Related domains to move into

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