Inside a Red Team Operation: What Happens During a Simulated Cyber Attack

Cyber threats are constantly evolving, and organizations must stay vigilant to protect their critical assets. One of the most effective ways to prepare for sophisticated attacks is through red teaming, a simulated cyber attack designed to test an organization’s defenses. Red team operations mimic real-world adversaries, exposing vulnerabilities in technology, processes, and personnel while testing detection and response capabilities. However, before an organization embarks on a red team exercise, it must first ensure it is ready to extract meaningful value from the engagement.

Is Your Organization Ready for Red Teaming?

Before launching a red team exercise, an organization must assess its own maturity level and readiness. Organizations that have new information security programs, or recognize that their programs require enhancement in the areas of vulnerability management might not fully benefit from red teaming, as fundamental security gaps could overshadow the more advanced insights these exercises are meant to provide. Below are key areas that determine red team readiness:

Baseline Security Hygiene

Red teaming is not a substitute for basic cybersecurity best practices. Organizations should already have:

• Strong identity and access management, including multi-factor authentication (MFA) and least-privilege access controls.

• Regular patching and vulnerability management.

• Network segmentation and endpoint protection.

• Proper logging, monitoring, and alerting mechanisms.

• Clear incident response policies.

Without these fundamental controls in place, a red team exercise may simply highlight gaps that should have already been addressed with standard security measures.

Detection & Response Capabilities

A key objective of red teaming is to test whether an organization can detect and respond to an attack in real-time. Before a red team exercise, organizations should evaluate their:

• Security Information and Event Management (SIEM) system.

• Endpoint Detection and Response (EDR) or Extended Detection and Response (XDR) solutions.

• Security Operations Center (SOC) maturity, including analyst skills and playbooks.

• Incident response procedures and ability to escalate threats appropriately.

Organizations lacking a robust detection and response capability may benefit from purple teaming first—a collaborative approach where defenders work alongside attackers to improve detection rules and playbooks.

Executive Buy-In and Risk Tolerance

A red team engagement should align with business objectives and risk tolerance. Leadership must understand that red team operations are not just compliance checkboxes but rigorous exercises that will expose real weaknesses. There must be:

• A willingness to act on findings rather than treating them as theoretical risks.

• A defined scope and acceptable boundaries to prevent unnecessary disruption.

• A culture that prioritizes security as a business enabler rather than a blocker.

Security Awareness Among Employees

Human error remains one of the weakest links in cybersecurity. Because red teaming often leverages social engineering, an organization should already have:

• Regular security awareness training for employees.

• Phishing simulations to test resilience against email-based attacks.

• Policies and processes to prevent unauthorized access via impersonation.

A red team engagement that succeeds too easily due to poor security awareness may indicate that training should be prioritized before deeper adversarial simulations.

Establishing a Remediation Plan

The true value of red teaming lies in fixing the vulnerabilities it uncovers. To ensure meaningful security improvements, organizations should:

• Allocate budget and resources for post-assessment remediation.

• Prioritize critical findings over lower-impact issues.

• Establish timelines for implementing fixes and retesting improvements.

A red team engagement without a follow-up plan is a wasted opportunity. Organizations must commit to acting on the findings to strengthen their defenses effectively.

Overview of a Red Team Operation

Once an organization is ready for red teaming, the process typically follows these stages:

1. Planning & Scoping – Defining objectives, rules of engagement, and success criteria.

2. Reconnaissance – Gathering intelligence through open-source research, social engineering, and network scanning.

3. Initial Access – Exploiting weaknesses to gain entry into the network.

4. Privilege Escalation & Lateral Movement – Moving through the environment to access high-value assets.

5. Objective Achievement – Simulating the theft of sensitive data or system compromise.

6. Exfiltration & Persistence – Testing the organization’s ability to detect and respond to stealthy attacks.

7. Reporting & Remediation – Delivering a detailed assessment with actionable recommendations.

While each engagement is unique, these core phases ensure that red team operations provide valuable insights into an organization’s ability to withstand real-world threats.

Final Thoughts

A red team operation is more than just an attack simulation—it’s a strategic exercise that evaluates an organization’s ability to detect, respond, and remediate threats. However, to derive the most value from red teaming, organizations must first ensure they are ready. Investing in fundamental security controls, enhancing detection and response capabilities, and fostering a security-conscious culture are critical prerequisites.

If you’d like to discuss a red team exercise for your organization, please contact Rotas to learn more about how we can help assess and improve your security posture.