Contact Us!

Red Team Engagement Guide: Phases, vs Pentest & Training

In 2024, red team engagements uncovered critical vulnerabilities in 68% of organizations that believed their defenses were robust, according to industry security assessments. These simulated attacks, conducted by authorized security experts, revealed gaps that traditional testing methods missed entirely, highlighting why red teaming has become essential for modern cybersecurity programs.

A Red Team Engagement is a simulated cyberattack by authorized experts emulating real-world adversaries to test an organization’s full security posture, including people, processes, and technology. Unlike standard security assessments that focus on finding vulnerabilities, red teaming operates like an actual attacker with specific objectives, working stealthily to test whether your defenses can detect and stop a determined adversary.

This matters because traditional security testing often leaves blind spots. NIST defines a Red Team as a group authorized to emulate adversary attack capabilities to improve cybersecurity by demonstrating impacts and measuring defender effectiveness. Red team engagements simulate advanced persistent threats (APTs), train blue teams through realistic scenarios, and measure incident response capabilities under conditions that mirror actual attacks. Organizations using red team exercises report 40% faster threat detection times and significantly improved security operations team readiness.

In this guide, you’ll learn what distinguishes red teaming from penetration testing, the operational phases attackers follow, how to scope and prepare for engagements, and where to find hands-on training resources. Whether you’re preparing your organization for an assessment or building red team skills, this comprehensive overview provides the framework and practical knowledge you need.

Table of Contents

Introduction to Red Team Engagements

Core Definition and NIST Perspective

Red team engagements represent a fundamental shift in how organizations approach security testing. Rather than simply identifying vulnerabilities, these exercises simulate complete attack scenarios with defined objectives. According to NIST, a red team is “a group of people authorized and organized to emulate a potential adversary’s attack or exploitation capabilities against an enterprise’s security posture.”

The key difference lies in the approach. Red teams think like attackers with goals such as exfiltrating specific data, gaining domain administrator access, or demonstrating physical security weaknesses. They use the same tactics, techniques, and procedures (TTPs) that real adversaries employ, making these engagements far more realistic than traditional security assessments.

Triaxiom Security research shows that red team engagements typically run for weeks rather than days, allowing for the patient, methodical approach that advanced attackers use. This extended timeline enables red teams to test whether security operations centers (SOCs) can detect slow-moving threats that evade automated defenses.

For intermediate practitioners, understanding this distinction is crucial. Red teaming isn’t just “advanced penetration testing,” it’s a different methodology entirely. The focus shifts from comprehensive vulnerability coverage to demonstrating real-world attack paths and measuring defensive capabilities.

Key Benefits for Organizations

Organizations invest in red team engagements for several compelling reasons beyond basic compliance requirements. First, these exercises train blue teams (defensive security teams) through realistic scenarios they wouldn’t encounter in normal operations. When defenders respond to a red team exercise, they practice incident response, threat hunting, and coordination under conditions that closely mirror actual breaches.

Red teaming simulates advanced persistent threats that use sophisticated techniques over extended periods. Many organizations have never faced a determined adversary and don’t know how their defenses would perform. A red team vs blue team comparison shows that organizations running regular red team exercises detect threats 40% faster than those relying solely on vulnerability assessments.

These engagements also assess organizational resilience across all security layers. While technical controls might be strong, red teams often succeed through social engineering, physical security weaknesses, or process gaps. A successful phishing campaign that bypasses email filters reveals training gaps. Unauthorized physical access to server rooms highlights policy failures. This holistic view helps prioritize security investments more effectively.

Finally, red team exercises provide measurable security metrics. Instead of counting vulnerabilities, organizations can track metrics like time-to-detection, response effectiveness, and whether critical assets remain protected. These outcomes-based measurements align better with business risk than traditional vulnerability counts.

Red Teaming vs Penetration Testing and Other Assessments

Goal-Driven vs Vulnerability-Focused

The fundamental distinction between red teaming and penetration testing centers on objectives and scope. Penetration tests focus on finding as many vulnerabilities as possible within defined systems, with testers announcing their presence and working collaboratively with IT teams. Red teams, by contrast, pursue specific objectives while remaining undetected, exactly as a real attacker would.

According to the Red Team Guide, penetration tests typically conclude within days to a week, with testers documenting technical vulnerabilities and providing remediation guidance. Red team engagements span weeks or months, measuring whether defenders can detect and respond to threats before objectives are achieved.

The stealthy nature of red teaming creates a completely different dynamic. Red teams employ operational security (OPSEC) measures, avoid noisy tools that trigger alerts, and adapt their approach based on defender reactions. If a technique gets detected, they pivot to alternatives, just as real attackers do. This cat-and-mouse dynamic tests detection capabilities far more realistically than announced testing.

Duration differences matter significantly. A three-day penetration test might find vulnerabilities in external web applications, but a three-week red team engagement can chain those vulnerabilities together, establish persistence, move laterally through the network, and achieve objectives like accessing sensitive databases, all while testing whether the SOC notices the activity.

Red vs Pentest vs Vulnerability Assessment

Understanding when to use each assessment type helps organizations build comprehensive security programs:

Assessment Type Primary Focus Duration Detection Testing Coverage
Vulnerability Assessment Identifying known vulnerabilities Hours to days No Broad, automated scanning
Penetration Testing Exploiting vulnerabilities Days to 1 week Limited Deep, technical systems
Red Team Engagement Achieving objectives stealthily Weeks to months Core focus Holistic (people, process, tech)

Vulnerability assessments provide the broadest coverage through automated scanning, identifying missing patches, misconfigurations, and known weaknesses. These work well for compliance requirements and establishing security baselines.

Penetration testing goes deeper, manually exploiting vulnerabilities to demonstrate real impact. Testers work within defined scopes, often focusing on specific applications or network segments. The announced nature means IT teams can prepare, logs get reviewed carefully, and testing avoids production disruptions.

Red team engagements test the entire security program under realistic conditions. They incorporate social engineering, physical security testing, and process exploitation alongside technical attacks. The holistic approach reveals how attackers actually breach organizations, not just where individual vulnerabilities exist.

For intermediate practitioners, this means choosing the right assessment for your objectives. Building a new application? Start with penetration testing. Want to test your SOC? Red teaming provides that measurement. Need compliance documentation? Vulnerability assessments offer the required coverage.

Phases and TTPs of a Red Team Engagement

Reconnaissance and Initial Access

Every red team engagement begins with reconnaissance, the foundation for all subsequent actions. This “Get In” phase focuses on gathering information about the target organization without triggering defensive alerts. Red teams use both passive and active reconnaissance techniques to map the attack surface and identify entry points.

Passive reconnaissance collects publicly available information: employee names from LinkedIn, email formats from corporate websites, exposed cloud storage buckets, leaked credentials from previous breaches, and technology stack details from job postings. This phase generates zero network traffic to the target, making it undetectable.

Active reconnaissance tools like Nmap scan for open ports, services, and potential vulnerabilities:

nmap -sC -sV -oA scan target_ip

This command runs default scripts (-sC) and version detection (-sV), outputting results in all formats (-oA) for later analysis. Red teams run these scans carefully, often from multiple IP addresses over extended periods to avoid detection.

Initial access techniques vary based on the target environment. Common vectors include:

  • Spear phishing campaigns targeting specific employees
  • Exploiting public-facing applications with known vulnerabilities
  • Password spraying against exposed authentication portals
  • Supply chain attacks through trusted third-party relationships
  • Physical access through tailgating or social engineering

The MITRE Engage framework maps these techniques to specific tactics, helping red teams plan realistic attack chains. For example, a red team might combine reconnaissance findings with a targeted phishing campaign that delivers a payload matching the organization’s technology stack.

Persistence, Lateral Movement, and Objectives

Once initial access is established, red teams enter the “Stay In” phase, establishing persistence mechanisms that survive system reboots, password changes, and routine maintenance. Common persistence techniques include creating scheduled tasks, modifying startup scripts, adding registry keys, or deploying backdoored services.

Lateral movement comes next, as red teams pivot from their initial foothold to more valuable systems. They escalate privileges, compromise additional accounts, and map internal networks to understand the environment. This phase tests whether defenders notice unusual authentication patterns, unexpected network connections, or privilege escalation attempts.

According to Red Team Development and Operations, lateral movement techniques include:

  • Pass-the-hash attacks using stolen credentials
  • Exploiting trust relationships between systems
  • Leveraging legitimate administrative tools (PowerShell, WMI)
  • Compromising service accounts with excessive permissions

The “Act” phase focuses on achieving defined objectives. Depending on engagement scope, red teams might exfiltrate sensitive data, demonstrate access to critical systems, or compromise domain controllers. Throughout this phase, maintaining stealth remains paramount. Successful red teams achieve objectives without triggering alerts, demonstrating gaps in detection capabilities.

MITRE ATT&CK Integration

Modern red team engagements map activities to the MITRE ATT&CK framework, providing standardized language for discussing TTPs. This framework categorizes adversary behaviors into tactics (the “why”) and techniques (the “how”), enabling better communication between red and blue teams.

For example, a red team’s reconnaissance activities map to the “Reconnaissance” tactic, with specific techniques like “Gather Victim Network Information” or “Search Open Websites/Domains.” During reporting, these mappings help defenders understand which detection controls failed and where to focus improvements.

The framework also guides red team planning. By selecting TTPs that match real-world threat groups relevant to the organization, red teams create realistic scenarios. A financial institution might face TTPs used by groups targeting banking systems, while healthcare organizations prepare for ransomware tactics.

Integration with MITRE ATT&CK transforms red team exercises from ad-hoc testing into measurable security assessments. Organizations can track which techniques their defenses detect, which slip through unnoticed, and how their coverage compares to relevant threat models. This data-driven approach helps prioritize security investments based on actual defensive gaps rather than theoretical vulnerabilities.

Best Practices, Scoping, and Preparation

Rules of Engagement and Scoping

Successful red team engagements begin with comprehensive Rules of Engagement (RoE) that define legal boundaries, technical scope, and engagement objectives. The RoE document serves as a contract protecting both the organization and the red team, ensuring all activities remain authorized and controlled.

ISACA research on red team engagements emphasizes that poor scoping creates two critical risks: ineffective testing that misses important systems, or unauthorized access that creates legal liability. Effective RoE documents address:

Scope definition specifies exactly which systems, networks, and facilities are in-scope versus explicitly excluded. Unlike penetration tests that define scope by IP ranges or applications, red team scopes often define objectives rather than systems. For example: “Demonstrate access to customer database” rather than “Test web application at 192.168.1.10.”

Timeline and communication establishes when testing occurs, emergency contact procedures, and how the engagement can be paused or stopped. Many organizations exclude high-risk periods like tax season or major product launches. Clear communication channels prevent confusion when defenders detect suspicious activity.

Acceptable techniques define which attack methods are permitted. Most engagements prohibit destructive actions, denial of service attacks, or exploitation of discovered vulnerabilities in production systems. Social engineering boundaries need explicit definition: Are physical break-ins allowed? Can employees be contacted at home? What about family members?

Common scoping pitfalls include vague objectives that lead to unfocused testing, inadequate exclusion lists that risk system stability, and insufficient legal review before starting. Organizations should involve legal counsel, senior management, and technical teams in RoE development to ensure all perspectives are represented.

Hardening and Detection Tips

Red team findings often reveal gaps in three critical areas: prevention controls, detection capabilities, and response procedures. Effective hardening addresses all three layers rather than focusing solely on preventing initial access.

Prevention measures reduce the attack surface attackers can target:

  • Implement email security controls with attachment sandboxing and link analysis
  • Deploy endpoint detection and response (EDR) tools on all systems
  • Enforce multi-factor authentication for all remote access and privileged accounts
  • Segment networks to limit lateral movement paths
  • Apply least-privilege access principles to service accounts

Detection capabilities ensure that attacks which bypass prevention get noticed:

  • Monitor authentication logs for unusual patterns (time, location, volume)
  • Alert on privilege escalation attempts and unexpected administrative tool usage
  • Track lateral movement through network traffic analysis
  • Deploy deception technology like honeypots to detect reconnaissance
  • Correlate events across systems through SIEM solutions

Response procedures tested during red team exercises often reveal coordination gaps. Blue team defenses improve through regular purple team exercises where red and blue teams work collaboratively. After detection occurs, responders should practice investigation procedures, containment strategies, and communication protocols.

Regular debrief sessions after red team engagements create the most value. These sessions bring red team, blue team, and stakeholders together to discuss what worked, what failed, and why. The red team shares their methodology and decision points, while defenders explain what they observed and how they responded. This collaborative learning accelerates security improvements far more than simple vulnerability reports.

Hands-On Learning and Training Resources

Simulation Tools and Commands

Aspiring red teamers benefit from practicing in safe, legal environments before joining professional engagements. Several tools enable realistic simulations without risking unauthorized access or legal issues.

Phishing simulation platforms let you practice social engineering techniques that bypass technical controls. Gophish, an open-source phishing framework, allows you to create campaigns, track results, and train users on recognizing attacks:

# Download and run Gophish
wget https://github.com/gophish/gophish/releases/download/v0.12.1/gophish-v0.12.1-linux-64bit.zip
unzip gophish-v0.12.1-linux-64bit.zip
./gophish

After starting Gophish, access the web interface at https://localhost:3333 to configure campaigns, create landing pages, and track who clicks links or submits credentials. Practice building convincing pretexts, crafting believable emails, and analyzing user behavior patterns.

For network reconnaissance practice, vulnerable virtual machines provide safe targets. Metasploitable, DVWA (Damn Vulnerable Web Application), and similar intentionally vulnerable systems let you practice techniques like port scanning, vulnerability exploitation, and privilege escalation without legal risk.

Attack simulation frameworks like Atomic Red Team provide pre-built tests mapped to MITRE ATT&CK techniques:

# Example: Test PowerShell execution detection
Invoke-AtomicTest T1059.001 -TestNumbers 1

This command executes a specific technique (PowerShell execution) from the MITRE ATT&CK framework, allowing blue teams to verify their detection rules work correctly. Red teamers use these to understand defensive perspectives and plan evasion strategies.

Curated Platforms and Guides

Professional learning platforms offer structured red team training paths with hands-on labs and real-world scenarios. Red Team Guide provides comprehensive documentation on methodology, tools, and techniques used in professional engagements. The resource covers everything from initial planning through reporting, with emphasis on operational security and avoiding detection.

Practice platforms like TryHackMe and HackTheBox offer progressive learning paths specifically for offensive security. These platforms provide:

  • Virtual lab environments with vulnerable systems
  • Guided learning paths from beginner to advanced techniques
  • Challenges that mimic real-world scenarios
  • Community discussions and write-ups after completing challenges

Cyber ranges operated by organizations like SANS and Black Hills Information Security simulate enterprise environments complete with security tools, monitoring capabilities, and blue team defenders. These exercises provide realistic experience working against active defenses, something individual practice labs can’t replicate.

Purple team exercises offer the most valuable learning for aspiring red teamers. These collaborative sessions pair offensive and defensive practitioners to test specific scenarios, discuss defensive gaps, and improve both attack and detection capabilities. Many local security meetups and conferences organize purple team workshops where you can practice in team settings.

Professional certifications like Offensive Security Certified Professional (OSCP) and Certified Red Team Professional (CRTP) validate practical skills through hands-on exams. Unlike knowledge-based tests, these certifications require demonstrating actual capabilities in simulated environments, making them valuable credentials for career advancement.

Real-World Examples and Reporting

Case Studies from Frameworks

While specific breach details remain confidential, red team case studies from security frameworks illustrate common patterns and outcomes. Rhino Security Labs red team engagements describe typical scenarios that demonstrate the value of comprehensive testing.

One anonymized case involved a financial services organization that believed their security program was mature based on successful penetration tests and compliance audits. The red team engagement revealed a different story. Using reconnaissance from public sources, the red team identified employees through LinkedIn, determined email formats, and launched targeted phishing campaigns.

Within 48 hours, an employee clicked a malicious link and entered credentials on a fake portal. The red team used those credentials to access the VPN, established persistence on the compromised workstation, and began lateral movement. Over the next two weeks, they escalated privileges, compromised additional accounts, and eventually gained access to customer databases containing sensitive financial information.

Throughout the entire engagement, the SOC detected no suspicious activity. The security tools in place focused on known malware signatures and failed to detect the custom tools and living-off-the-land techniques the red team employed. This gap between perceived and actual security drove significant improvements to detection capabilities and response procedures.

Another common scenario involves physical security testing integrated with technical attacks. Red teams gain building access through tailgating or social engineering, then connect rogue devices to internal networks. SecurityScorecard’s red team analysis notes that physical access combined with technical attacks often succeeds even when either approach alone would fail.

These examples highlight why red teaming provides value beyond traditional assessments. Organizations thought their defenses were adequate because vulnerability scans found few issues and penetration tests showed strong technical controls. Red team engagements revealed that determined adversaries could still achieve their objectives by chaining together weaknesses across people, processes, and technology.

Reporting and Lessons Learned

Red team reports differ significantly from penetration test deliverables. Instead of listing vulnerabilities with severity ratings, effective red team reports tell the story of the engagement from both offensive and defensive perspectives.

The narrative format describes the red team’s methodology, initial access vector, obstacles encountered, techniques that succeeded or failed, and ultimate objectives achieved. This storytelling approach helps stakeholders understand the attack chain and why specific security controls did or didn’t prevent compromise.

Defensive observations document what the blue team detected, when alerts fired, and how they responded. Gap analysis compares what should have been detected versus what actually triggered alerts. This section provides actionable intelligence for improving security operations.

Metrics and measurements transform subjective assessments into quantifiable results:

  • Time from initial access to objective achievement
  • Number of systems compromised versus total systems in scope
  • Detection rate for different attack techniques
  • Time to detection for noticed activities
  • Response effectiveness once detection occurred

MITRE ATT&CK mapping in the report shows which techniques succeeded, which were detected, and which were prevented entirely. This coverage map helps prioritize defensive improvements based on actual gaps rather than theoretical vulnerabilities.

Debrief sessions create the most valuable learning. Red and blue teams meet to discuss the engagement openly, with the red team revealing their methodology and decision points while defenders explain their perspective. These sessions often uncover surprising insights, like alerts that fired but were dismissed as false positives, or detective controls that weren’t properly tuned.

Organizational resilience assessment looks beyond technical findings to evaluate security culture, communication effectiveness, and incident response maturity. Did teams collaborate effectively? Were escalation procedures followed? Did decision-makers receive timely information? These process-oriented findings often drive more security improvement than technical vulnerabilities alone.

Key Takeaways

  • Red team engagements simulate real adversaries with specific objectives, testing entire security programs rather than just finding vulnerabilities like penetration tests do.
  • The three phases (Get In, Stay In, Act) mirror actual attack progression, with red teams maintaining stealth while testing whether defenders can detect and respond before objectives are achieved.
  • Comprehensive Rules of Engagement protect both organizations and red teams by defining scope, acceptable techniques, and communication protocols before testing begins.
  • MITRE ATT&CK framework integration provides standardized language for discussing tactics and techniques, enabling data-driven measurement of defensive coverage and gaps.
  • Purple team collaboration and detailed debriefs create more value than reports alone, accelerating security improvements through shared learning between offensive and defensive teams.
  • Aspiring red teamers should practice legally using platforms like TryHackMe, HackTheBox, and Red Team Guide resources before attempting professional engagements.
  • Effective red team reports focus on storytelling and organizational resilience rather than simple vulnerability lists, helping stakeholders understand actual attack paths and defensive gaps.

Frequently Asked Questions

What is the difference between red teaming and penetration testing?

Red teaming pursues specific objectives stealthily over weeks or months while testing detection capabilities, whereas penetration testing focuses on finding vulnerabilities in defined systems over days with announced testing. Red teams test people, processes, and technology holistically; pentests primarily assess technical controls.

What are the main phases of a red team engagement?

The three core phases are Get In (reconnaissance and initial access), Stay In (establish persistence and move laterally), and Act (achieve defined objectives). Each phase maps to MITRE ATT&CK tactics for standardized documentation and measurement of defensive coverage.

How can organizations prepare for a red team exercise?

Develop comprehensive Rules of Engagement defining scope and boundaries, establish baseline security monitoring to measure improvements, brief stakeholders on objectives and timelines, and prepare incident response teams for realistic scenarios. Consider starting with purple team exercises for collaborative learning.

What frameworks guide red team operations?

MITRE ATT&CK maps adversary tactics and techniques for planning and reporting, while MITRE Engage provides adversary engagement and deception strategies. NIST cybersecurity framework offers risk management context for interpreting red team findings and prioritizing improvements.

How can beginners get hands-on experience with red team engagements?

Practice legally using platforms like TryHackMe and HackTheBox for technical skills, study methodology through Red Team Guide documentation, run authorized simulations with tools like Gophish for phishing, and participate in purple team exercises at security conferences or local meetups.

What are common pitfalls in red team scoping?

Vague objectives that don’t drive focused testing, inadequate exclusion lists risking production systems, no defined communication channels for emergencies, and missing legal review before starting. Effective scoping balances realistic scenarios with organizational risk tolerance through detailed Rules of Engagement.

References

Leave A Comment

All fields marked with an asterisk (*) are required