Darren Chaker on Red Teaming and Offensive Security

What Is Red Teaming?

Red teaming is a full-scope adversary simulation. Unlike a standard penetration test that focuses on finding technical vulnerabilities in a defined scope, a red team engagement simulates a real-world attacker who uses any combination of technical exploitation, social engineering, and physical access to achieve a specific objective. The goal is to test the entire security posture of an organization, not just its firewalls.

I hold certifications in Offensive Operations, Penetration Testing, and Red Teaming. In my consulting work with law firms and high-net-worth clients, I apply these methodologies to assess real risk, not theoretical risk.

How Does Red Teaming Differ From Penetration Testing?

Aspect	Penetration Test	Red Team Engagement
Scope	Defined systems or applications	Entire organization
Duration	Days to weeks	Weeks to months
Techniques	Technical exploitation	Technical, social, physical
Awareness	IT team usually knows	Only senior leadership knows
Objective	Find vulnerabilities	Achieve specific goals (exfiltrate data, access executive email)
Reporting	Vulnerability list with severity	Narrative of attack path and organizational gaps

What Does a Red Team Engagement Look Like?

1. Reconnaissance - Gathering OSINT on the target organization including employee names, email formats, technology stack, and physical locations
2. Initial Access - Gaining a foothold through phishing, exploiting a public-facing vulnerability, or physical intrusion
3. Persistence - Establishing durable access that survives reboots and detection attempts
4. Lateral Movement - Moving through the internal network to reach higher-value targets
5. Objective Completion - Achieving the agreed-upon goal such as accessing a specific database or executive account
6. Reporting and Debrief - Documenting the full attack chain with recommendations for closing each gap

Why Should Organizations Invest in Red Teaming?

Most organizations test their defenses by running vulnerability scans and checking compliance boxes. That tells you whether your software is patched. It does not tell you whether an attacker can get from a phishing email to your financial records in three days. Red teaming answers that question with evidence, not assumptions.

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Darren Chaker is a certified offensive security consultant based in Santa Monica, California. Learn more at about.me/darrenchakerprivacy.