We often talk about security as a continuum; a journey toward greater maturity and increased capability. Along that path, the practice of red team testing serves as an important milestone, not just for the benefits it offers, but also for what participating in red teaming says about the state of security — overall posture, culture, commitment to continuous improvement — in any organization.

Red team tests remain one of the most effective ways to probe defenses and identify vulnerabilities. And unlike traditional penetration tests, red team exercises simulate sophisticated cyber attacks that mimic real-world threats, providing a comprehensive assessment of security posture. That said, red teams are most effective in organizations that have reached a certain strata of infosec sophistication, a level necessary to realize the benefits of this more advanced approach.

Some of this is table stakes for any kind of advanced security methodology in any organization of any size or stripe. You need to check some basic boxes before you even get to the red team checklist.

Cybersecurity Maturity That’s Above Baseline

The organization’s security foundation must be solid. That means having clear and effective security policies and procedures in place that are not only understood, but also reliably adhered to by all stakeholders. If the organization’s policies are still in the early stages of development — or if the team is still struggling to enforce existing policy — it’s too early for the kinds of stark assessments that a more sophisticated effort like red team exercises provide.

You need a comprehensive understanding of the IT and security environments. Basic security controls and best practices must be in place along with a strong security operations team monitoring and trained to respond effectively to security incidents . There should be a history of conducting penetration tests and security assessments supported by taking corrective actions from their results. These measures will not only make existing security stronger, they ensure that the insights gained from goal-oriented, adversarial testing will be actionable, meaningful, and impactful.

With those basic qualifiers in hand, here’s five specific things to look for in your current environment that indicate your enterprise is primed and ready for the rigors of red team testing.

1. There’s a Strong Internal Security Culture

A red team engagement is not just a technical challenge; it encompasses the human factor of cyber risk. If your organization has already established a strong internal security culture, it signals that you’re ready for the next level of adversarial attack simulation. This culture should include ongoing security awareness programs, regular training sessions, and a proactive approach to security issues among all employees.

Organizations with a robust security culture are better equipped to handle the findings of a red team exercise, as their employees are more likely to follow established protocols, report suspicious activities, and participate effectively in the incident response process.

At this stage, it’s also critical to be certain the security team fully understands the role and the value of the red team. This is not an isolated assessment; it’s a strategic initiative to test and enhance the organization’s overall security posture. IT and security personnel should be educated on the purpose and benefits of red teaming, ensuring that the subsequent exercises are not perceived as critiques but rather as opportunities for growth.

2. You’ve Conducted Regular Penetration Tests

When charting a course toward greater infosec maturity, there are many stops along the route. Pentesting is one of those waypoints that should come well before the red team. Pentests are less complex, but still eminently useful activities that should be a regular occurrence in any organization that is considering stepping up to red teaming.

Organizations can utilize pentesting to focus on specific applications, internal networks, or a particularly critical system, however the testing does not assess the security team’s ability to respond to an incident quickly nor the effectiveness of the existing monitoring and detection controls. Red team exercises take security assessments to the next level by emulating real threat actors and using the same tactics, techniques, and procedures (TTPs) seen in today’s sophisticated attacks.

Incorporating regular pentests demonstrates a mature security posture and a proactive approach to managing risk. Pentests ensure that the lower-hanging security vulnerabilities have been addressed prior to the red team’s more strategic, stealthy attacks.

3. Top Management Supports the Red Team Plan

The adoption of red team testing needs buy-in from top to bottom. When the C-suite understands and supports the exercise, it encourages a culture of security awareness across all levels of the company. Such commitment from executives ensures that the resources required for red team testing — read: time and money — are allocated appropriately.

If the executive team is still bogged down chasing current, defensive shortcomings and has not yet realized the value of proactive testing, it may be too early for red teaming. It’s crucial to engage top management in order to define exercise scope and objectives that align with the strategic goals of the enterprise.

Ultimately, when the red team exercise kicks off, only a handful of employees, including 1-2 execs, are aware of when it will occur and what the goals are. The purpose of an unannounced test helps to ensure that security personnel will treat any related security alerts as a real event and respond appropriately.

4. There’s a Comprehensive Incident Response Plan in Place

An organization’s readiness to respond to security incidents is a litmus test of its resilience. Red team testing is not just about identifying vulnerabilities but also about evaluating and enhancing incident response capabilities. Each action and TTP used during the exercise will be documented and mapped to the Mitre ATT&CK Framework to help the organization understand its strengths and weaknesses when it comes to attack detection and prevention.

An organization with a comprehensive incident response plan — one that’s regularly updated and tested — is in a strong position to derive the full benefits of a red team exercise. Conversely, if incident response plans are either non-existent or incomplete, a better plan might be to concentrate resources on developing the IR protocols and saving the red teaming for a later date. After the training is complete and a well-established plan has been vetted through tabletop exercises, then it’s time to put the plan to the test and identify gaps through red teaming.

5. You Have Budget Allocated for Advanced Security Measures

Investing in information security is more critical than ever, and red team testing remains one of the best investments an organization can make; one that yields high returns in identifying and mitigating critical, business-damaging risks. If the organization has dedicated budget for security measures — and is willing to allocate a portion of that budget for advanced methods such as threat hunting and red team testing — that in itself demonstrates a serious commitment to safeguarding the company’s digital assets.

Of course, the budget for red team testing shouldn’t come at the expense of other foundational security measures. Red teaming, like most advanced infosec methodologies, is best viewed as a complement to existing security strategy and an important part of the enterprise’s ongoing risk management process. Through red team exercises, the enterprise can validate that their security controls are effective and capable of detecting or stopping an advanced attack through actionable results.

Making the Most of Red Teaming

So, you’ve met all the criteria and are ready to join the ranks of the red teaming participants. That’s no small commitment. Now that you’re on the path toward adding this methodology to the organization’s security arsenal, you can build in some reasonable expectations for success metrics in the program. Here’s some of the ways your developing red team approach should continue to pay dividends over the long haul:

• Bolstered Security Posture: By simulating realistic attacks, red team testing helps refine defenses, making organizations resilient against not only attacks that mimic real-world threat actors , but also against future, unknown threats.
• Spotlight on Critical Vulnerabilities: A red team will uncover weaknesses and risks that preconceived notions and traditional testing often miss by chaining multiple vulnerabilities together to accomplish its goals. This is the best way to ensure that all aspects of security are being assessed and fortified, including the people and physical locations, not just technology
• Improved Incident Response: There’s absolutely no better way to hone IR skills than through real-world attack scenarios. Red team activities will challenge and educate security and incident response teams, significantly improving the organization’s preparedness for actual attacks by using real TTPs and testing the teams’ ability to detect and react efficiently.

Red Team Testing: Taking the Next Step

Conducting red team testing is a critical component of a comprehensive security strategy, but it’s important to approach it at the right time and with the correct level of preparation. Organizations need to evaluate themselves honestly to make sure they and their skilled defenders are ready to withstand the rigor — and the potential revelations — red team testing will almost certainly bring.

Remember, cybersecurity is a continuous process, and red team testing, when the time is right, can be a crucial part of your company’s ongoing improvement. Gear up, get ready, and get testing.