Are You Ready for Red Team Penetration Testing?

In today’s rapidly evolving digital landscape, organizations are presented with an array of proactive cybersecurity strategies, and it can be hard to decide the next step in your cybersecurity journey. In this blog, we’ll dive into a few of our frequently asked questions about the difference between penetration testing and red team penetration testing, the benefits of these tests, and how to know which test is the best fit for your organization.

What’s the Difference Between Penetration Testing vs. Red Team Penetration Testing?

While both penetration testing and red team penetration testing are great ways to assess your organization’s security posture, they are quite different and serve distinct functions:​

Penetration Testing

Penetration testing, or “pen testing,” involves ethical hackers simulating cyberattacks on specific systems, networks, or applications to uncover vulnerabilities. The primary objective is to identify and exploit vulnerabilities to gain access to the network within a defined scope and timeframe. Regular penetration testing is part of the early steps in building and maintaining a strong cybersecurity posture, and these tests are typically conducted with the knowledge of the organization’s security team using a collaborative approach.​

“If you are newer in your cybersecurity journey, start with risk assessments and penetration testing,” stated Tom Pohl, penetration testing team manager for LMG Security. “Once you are getting clean penetration testing reports, that’s when you take the next step and start engaging red team penetration testing.”

Red Team Penetration Testing

In contrast, red team penetration testing adopts a holistic and covert strategy, emulating real-world attack scenarios to evaluate both technological defenses and human response capabilities. Red team exercises are goal-oriented, aiming to achieve specific objectives such as accessing sensitive data or compromising critical systems, usually without prior notification to the organization’s security team. This approach provides a comprehensive assessment of an organization’s resilience against sophisticated threats.​

“Red team tests are completely different from internal and external penetration tests,” Pohl advised. “During a penetration test, you are looking for all the ways you can exploit the client network. Red team penetration testing is a more advanced and intense tactic. Instead of looking at everything, we want to gain access to specific systems and see what it takes to accomplish that goal.” Pohl continued, “Specific rules of engagement can range from online attacks and social engineering phone calls to malicious email and physical social engineering tactics to gain access to your building. It’s best for organizations that are further along on their cyber maturity journey.”

Key Differences

• Scope and Objectives: Penetration testing focuses on identifying a broad range of vulnerabilities within a specified scope, whereas red team penetration testing targets particular objectives that mirror potential real-world attacks.​
• Methodology: Penetration tests are generally overt and collaborative, with testers working alongside the organization’s security team. Red team exercises are covert, emphasizing stealth to authentically test detection and response mechanisms.​
• Duration and Complexity: Penetration tests are typically concise, spanning one to two weeks, and involve straightforward assessments. Red team engagements are more prolonged, potentially lasting several weeks or months, and encompass complex attack simulations, including social engineering and physical security breaches.​
• Outcomes: Penetration testing yields a detailed list of identified vulnerabilities with recommended remediation steps. Red team penetration testing offers insights into the organization’s ability to withstand and respond to advanced, multifaceted attacks.​

Understanding these distinctions is crucial for organizations to select the appropriate assessment method aligned with their security objectives and maturity level.​ If you are looking for more on cybersecurity maturity planning, check out our blog on the top 10 activities to improve your cyber maturity.

How Effective is Red Team Penetration Testing?

While some organizations broadly define red teaming to include more than red team penetration tests, these advanced tactics for infiltrating a network can be very effective. A Ponemon Institute survey found that the top two most effective offensive security testing strategies are Red Teaming and Cloud Security testing. This report also stated, “Since Red Teaming is tailored to provide simulations and emulations of specific threat actors, tactics, and scenarios, it can bring big ROI against a wide variety of threats.”

Pohl agrees but cautions that you need to carefully choose who conducts your red team penetration test and how it is conducted. “There are a lot of companies offering automated AI penetration testing these days, but these are just glorified vulnerability scans that miss the bigger picture.” He continued, “AI tools are evolving fast, but they’re just tools. Automated penetration testing technology just isn’t there yet. True red team penetration testing requires creative thinking and human analysis to really learn about an organization, uncover its weaknesses, and turn those into exploits to take over a network. After my team’s done your test, you’ll have a clear roadmap of what expert hackers will attack and what you need to fix.”

Assessing Readiness for Red Team Penetration Testing

How do you know whether your organization is prepared for red team penetration testing? Pohl says you need to evaluate several factors:​

• Have you implemented all baseline security controls? Consistent implementation of patches and updates, strong password policies, and effective phishing training are foundational elements that should be in place.
• Have you deployed at least some advanced security measures? Deploy multi-factor authentication, robust endpoint detection solutions, and comprehensive logging practices before red team assessments.​ You likely have a SOC and have fine-tuned your detection and alerting infrastructure. Read our Top Cybersecurity Controls for 2025 for more guidance on today’s most important security measures.
• Have you had regular penetration tests, with limited findings that have already been remediated? Pohl advises, “Start with iterative penetration tests. You’ll get a better result than automated continuous pentests. You should plan a cadence that lets you fix vulnerabilities and process gaps after each test and before you test again.” If your organization routinely conducts penetration tests with few findings, you are likely ready for more sophisticated red team penetration testing.

The bottom line: for the best ROI, ensure your cybersecurity fundamentals are covered before engaging in red team penetration testing.

Planning Your Red Team Penetration Test

Effective planning is essential to maximize the benefits of red team penetration testing:​

1. Define Clear Objectives: Establish specific goals for the red team exercise, such as testing incident response capabilities or evaluating the security of critical assets.​
2. Assemble a Skilled Team: Engage experienced professionals with diverse expertise to simulate a wide range of attack vectors effectively or outsource testing to experts.​
3. Establish Rules of Engagement: Set clear parameters for the exercise, including scope, duration, and any systems or areas that are off-limits, to ensure safety and compliance.​
4. Communicate with Select Stakeholders: Consider communicating with a few select stakeholders who can help manage expectations and facilitate coordination, while maintaining the element of surprise necessary for authenticity.​
5. Document and Report Findings: Provide a comprehensive report detailing the methodologies used, vulnerabilities discovered, and actionable recommendations for remediation.​

Following these steps will ensure you get the best ROI from red team penetration testing!

We hope you found this information on red team penetration testing helpful! Please contact us if you’re ready for a penetration test or a red team penetration test. Our team can also provide strategic vCISO support, policy guidance, training, and more to set you on the path to a strong cybersecurity posture. Let’s connect!