Red Team Testing: When Your Organization Is Ready (& Why It Matters)

Cybersecurity testing isn’t a one-size-fits-all process. Different organizations are at different maturity levels, and the type of testing you should be investing in depends on how far along you are in building your defenses. One of the most common questions security leaders face is: When is it actually worth it to do red team testing?

The answer is not “always.” Red team testing is powerful—but it’s not the first step. Let’s walk through what red teaming really is, and then how to decide when it makes sense.

What is Red Team Testing in Cybersecurity?

Red team testing is one of the most advanced ways to evaluate your security program. Unlike vulnerability scans or penetration tests that aim to find as many weaknesses as possible, a red team exercise is designed to simulate a real-world attack with a defined objective.

Think of it as a high-stakes capture-the-flag challenge. Instead of asking, “Where are the vulnerabilities?” you’re asking, “Could an attacker reach this specific goal in our environment without being stopped?”

That target could be:

• Accessing sensitive customer data
• Escalating privileges to a domain administrator account
• Exfiltrating trade secrets
• Manipulating a mission-critical application

The red team will use stealth, persistence, and creativity to achieve the objective, while your defenders work to detect and respond. The outcome isn’t just a vulnerability report—it’s a realistic assessment of how well your people, processes, and technology would stand up to a determined adversary.

Red Team vs Penetration Test: What’s the Difference?

This is one of the most common areas of confusion.

• Penetration Testing is about finding and exploiting as many vulnerabilities as possible, often across a wide scope. It’s noisy—alerts should be firing while the test is underway. If they aren’t, that’s a finding in itself.
• Red Team Testing is stealthy and focused. Instead of finding everything, the red team pursues one or two well-defined objectives that represent your “crown jewels.”

In other words, penetration testing asks “What’s broken?” while red team testing asks “Can we stop a realistic attack on what matters most?”

When Should a Company Do Red Team Testing?

Red team testing is resource-intensive, so it makes sense only after your security program reaches a certain maturity level. You should consider it if:

• Your vulnerability scans are consistently clean or well-managed.
• Your penetration tests no longer reveal major findings.
• You want to test not just your technology, but also your people and processes under stealth conditions.

If you’re still struggling to patch basic vulnerabilities or your pen tests uncover serious weaknesses, you’re not ready yet.

Start with the Basics: Vulnerability Scanning

Every security program should begin with routine vulnerability scans. These scans identify common weaknesses—unpatched software, weak configurations, or exposed services—that attackers could exploit.

If your scans are producing actionable findings and you haven’t yet built the processes to patch or remediate those consistently, then red team testing is not the right next step.

And don’t dismiss the “low” findings. Even small vulnerabilities can sometimes be chained together to cause serious damage.

The Next Step: Penetration Testing

Once you’ve built confidence in your vulnerability management program, penetration testing is the next logical step.

Pentesting is a manual, creative process performed by skilled testers. They attempt to chain weaknesses together and mimic real attackers. Pen testing helps answer:

• Can we detect real-world attacks?
• What happens if someone gets inside our network?
• Are our defenses as strong as we think they are?

If you’re still seeing significant findings here, focus on remediation before moving on to red teaming.

What Are the Goals of Red Team Testing?

The best red team engagements start with a clear objective. A useful framing question is:

“If hackers got in and accessed what, would it put us on the front page of the New York Times or cause major consequences for the business?”

That becomes the red team’s target. Common objectives include:

• Stealing sensitive customer or financial data
• Obtaining enterprise administrator access
• Exfiltrating proprietary designs or research
• Disrupting critical business systems

Defining these goals keeps the exercise realistic and focused on what matters most.

How Often Should You Do Red Team Testing?

There’s no universal rule, but many organizations conduct red team testing every 1–2 years, often after significant changes to their infrastructure or security program.

Heavily regulated industries (like finance, defense, or healthcare) may benefit from more frequent testing, especially if their risk profile or compliance requirements demand it.

For most organizations, the timing should align with:

• After you’ve matured your vulnerability and penetration testing programs
• After major system or process changes
• When leadership wants assurance against advanced threats

What Environments Can Be Tested With a Red Team?

Red team testing can be applied across different attack surfaces:

• External surface – testing whether attackers can breach your perimeter.
• Internal network – simulating lateral movement once inside.
• Web applications – targeting high-value apps with custom exploits.
• Wireless networks – testing Wi-Fi and rogue device risks.
• Social engineering – evaluating how employees respond to phishing, pretexting, or physical intrusion attempts.

Each type of test provides a different perspective on your defenses.

What Are the Benefits of Red Team Testing?

Red team testing provides value beyond what vulnerability scans and penetration tests can offer, including:

• Realistic threat simulation – Tests your ability to defend against tactics used by sophisticated attackers.
• Detection and response validation – Shows whether your SOC or IT team can spot and stop stealthy attacks.
• Holistic assessment – Evaluates not just technology, but also processes and human factors.
• Executive clarity – Results are framed around the impact of an actual breach, making the risk more tangible to leadership.

How Do You Prepare for a Red Team Exercise?

Preparation is key to getting value out of red teaming. Before scheduling one, make sure you:

• Have a mature vulnerability management and penetration testing program.
• Define clear, high-value objectives.
• Ensure leadership is aligned on goals and scope.
• Decide whether the defenders (blue team) will know about the exercise or if it will be a true “blind” test.

Organizations that prepare well tend to get far more meaningful insights from their red team engagements.

Building a Maturity Path

To summarize the progression:

1. Vulnerability Scanning – Build a consistent program and address findings.
2. Penetration Testing – Engage skilled testers to go beyond automated scans.
3. Red Team Testing – Once your defenses are strong, simulate advanced, goal-driven attacks.

Skipping ahead to red teaming too soon won’t give you actionable results. But once your security foundation is solid, a red team can provide invaluable insights into how your organization would stand up to a real-world attack.

Final Thoughts: Is Red Team Testing Right for You?

Red team testing is not about finding every possible weakness—it’s about answering the question: Can an attacker reach the systems, data, or accounts that would truly hurt us?

If your organization has mastered vulnerability scanning and pentesting, and you’re ready to test your detection, response, and resilience against stealthy adversaries, then yes—it’s worth investing in red team testing. Done right, it can reveal not just gaps in your technology, but also blind spots in your people and processes that matter most when the stakes are high.

At Compass, our team of seasoned security professionals helps organizations determine the right time for red team testing and executes these exercises in a way that aligns with your risk profile, industry regulations, and business goals. Whether you’re still building your vulnerability management program or ready for a full red team engagement, we can guide you through the maturity path and deliver actionable insights to strengthen your security posture. Contact us today to discuss how we can help tailor the right testing strategy for your organization.