Automating Your Red Team Approach: A Quick Guide

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Your organization may be prepared for an attack. You may have all the recommended security controls and your employees may be well-trained when it comes to avoiding social engineering attacks. You cannot truly be prepared, however, until you test your defenses. 

Traditionally, this is done by bringing in experts to hack your systems, discover the weak points in your security controls and your threat response. As effective as this approach can be, it’s not accessible to all organizations. It can be expensive, impractical, and time-consuming. It also may not reveal every threat faced by organizations with complex networks.

At the same time, organizations are attempting to monitor and control an ever-expanding attack surface. Thanks to cloud computing, virtual machines, Software as a Service (SaaS), and remote work, network perimeters are disappearing. between the internal network and external Internet at most organizations. This makes it even more difficult to defend a network against threats.

Red teaming is an answer to this problem, but traditional red-teaming may not be adequate when it comes to defending an attack surface that isn’t visible to the organization itself. The way to address this? Automation. 

What is Red Teaming? 

As the saying goes, no plan survives first contact with the enemy. Red teaming is a way of testing an organization’s cybersecurity so that its defenses can be attacked in a low-risk environment. Typically, an ethical hacker does this by attacking the organization’s defenses, pretending to be a malicious actor. They use threat actors’ Tactics, Techniques, and Procedures (TTPs) and attempt to breach secure systems or data. 

Red teaming didn’t originate in cybersecurity; it’s an old practice with military roots. 

It began to evaluate the effectiveness of strategies by using a red team to attack the “good guys,” or the blue team. Since then, it’s been used in physical security, law enforcement, and of course, cybersecurity.

What’s the difference between red teaming and penetration testing? 

While the terms red teaming and penetration testing may be used interchangeably, there is a  difference between the two.

 While penetration testing seeks to find as many vulnerabilities as possible in a company’s cyber defenses, a red team approach is focused on testing the organization’s ability to detect a breach and respond to it. A penetration tester doesn’t care if they raise alarms while exploiting vulnerabilities. A red team is trying to sneak into the system and get at the data, using any methods possible.

Another difference is that penetration testing is expected. Red teaming happens when the organization doesn’t expect it and isn’t necessarily looking for an attack. After all, real attackers rarely attack on a schedule.

What are the Challenges with Traditional Red Teaming?

It takes time and effort

Traditional red teaming relies on time-consuming manual work that is difficult to scale. Few organizations have the resources to conduct red team exercises in-house, so that work must be outsourced to a group offering red-teaming as a service.

Red teaming offers a view of vulnerabilities in one point-in-time

While traditional red teaming is an effective way to find the weaknesses in your cybersecurity response, it doesn’t always give you the whole picture. Because red teaming exercises happen once, or at intervals, you’re only seeing a snapshot of your security at a single point in time. That’s not how cyber threats work, however. The threat landscape is constantly changing and evolving, and so are your vulnerabilities and your responses. Red team exercises have to be repeated often to yield continuous results, and regular penetration tests should also be in place to test specific cybersecurity measures. 

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Constant red teaming is often not financially feasible for an organization. Red team exercises can be time-consuming, costly, and resource-draining. They also don’t test all of an organization’s resources. The red team’s objective is to get at sensitive data however they can. That means that they may not find every vulnerability if there are multiple ways to access a system. 


Large and complex systems that may have many weak points can be difficult for a red team to assess. The larger the system, or the more complicated, the more difficult it is to scale the red teaming approach.  

The red team doesn’t know what it doesn’t know

Your attack surface is constantly expanding and it can be hard to know exactly how big it is. As organizations use more digital tools and services, their external attack surface and the number of attack vectors increase. It also becomes more difficult to monitor. The red team can’t test attack surfaces it does not know about, and that can be a problem if the unknown attack surface is vulnerable and a threat actor finds it first. 

How Can Automated Red Teaming Improve Your Security Posture

Automated red teaming, or CART (Continuous Automated Red Teaming) uses technology to automate continuous attacks on an organization, letting you easily scale red teaming for your growing attack surface. By continuously attacking your defenses, automated red teaming gives you a full picture of your cyberdefenses at any point in time, and is able to test several weak points quickly and efficiently, from networks to social engineering attacks. 

The constant attacks are also a means for continuously discovering your attack surface and any new vulnerabilities. The technology can then prioritize the vulnerabilities most likely to be attacked by a bad actor so your team can remediate them.

Automated red teaming makes red teaming accessible to organizations of every size as well, which helps small and mid-sized businesses improve their cyberdefenses without having to allocate a big chunk of their security budget for experts.

Automating Attack Surface Monitoring

Constant visibility into your evolving attack surface is critical when it comes to protecting your organization and testing your defenses. Automated attack surface monitoring provides constant visibility into your organization’s vulnerabilities, weaknesses, data leaks, and the misconfigurations that emerge in your external attack surface.

Manual attack surface monitoring is impractical at best, and ineffective at worst, because there can be gaps in coverage. Automated attack surface monitoring, however, shows you your organization’s attack surface in real time, alerting you to vulnerabilities, threats, risks, and attacks as they arise. 

Automated Threat Monitoring with Flare

Knowing the threats to your organization is a critical part of a cybersecurity strategy. 

Flare’s platform provides all the features you’d expect from external attack surface management as well as with extra monitoring capabilities. Flare monitors the dark and clear web, Telegram channels, and other external sources for threat intelligence pertaining to your organization. This information may include leaked credentials, tactics that might  be used against your organization, or even using the name of your company on a dark web forum. You can then take action to prevent data breaches.

 Get your Flare demo today.

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