Sharpening Offensive Skills Through Purple Teams

by | Jul 29, 2025

Introduction

Purple teams is a collaborative, “open-book” assessment that bridges the gap between the red and blue sides of security to enhance detection and response capabilities against real-world threats. While the primary goal of this is to improve defenses by learning from the attacker’s perspective, there is a huge advantage for red teamers too. It is an underrated opportunity to sharpen offensive skills.

 

Red Team Advantages in Purple Teaming

Purple teams assessments create a unique opportunity for red teamers to learn and practice their skills through a constant back-and-forth loop with blue teamers. Traditionally, red and blue teamers work separately, where each team has zero insight into what the other is doing. Purple teams, on the other hand, involves constant feedback and communication between both teams. This allows red teams to understand how their techniques stack up against different tools and environments. This real-time feedback is one of the most valuable aspects of purple team engagements. Purple teams also highlighted how shifting execution methods could completely change the detection outcome. Instead of executing persistence techniques like scheduled task creation or local administrator creation directly via command line (which often gets caught), we started generating payloads that invoked those actions in memory. Executing payloads in memory helped us bypass a lot of the command-line-based alerting logic we were running into. Since many EDR and SIEM tools rely on monitoring process creation events or specific command-line arguments (like net user or schtasks), skipping the command-line entirely meant those detections never triggered. Without the feedback from the blue team, we would not have easily realized how much visibility defenders lose when the command line is removed from the equation.

 

Hands-On Experience with Defensive Tools

One of the most valuable things I have gained through purple teaming is a better understanding of the more common defensive tools in environments. Purple teaming provides a great opportunity to see these tools in action, offering insights into the strengths and limitations of these tools. As a red team operator on purple team engagements, I get to see firsthand how the same subset of attack techniques works against a large variety of tools. Normally, we use URU as a shellcode loader for our payloads, but Defender began flagging its built-in patchAMSI routine. It was a great moment of learning during a purple team session because we got immediate insight into what Defender was actually flagging. We removed that component to avoid triggering AMSI signatures, and we started using ConfuserEx to obfuscate our payloads to further evade AV detection on known tools. This wasn’t about bypassing AMSI, but was about breaking static signatures so AV engines couldn’t easily flag our payloads. It was a reminder that even defensive tools that rely heavily on known indicators can be sidestepped with small, creative changes. By working with the blue team and seeing how different tools respond, red teamers can learn how to bypass detections from some of the most popular security tools.

 

Gaining Command-Line Experience in Enterprise Environments

Purple teaming also provides the opportunity to gain an in-depth understanding of enterprise environments, mostly comprised of Windows infrastructure. Through purple team engagements, red teamers can get command-line experience with Command Prompt and PowerShell while also learning about Active Directory and even Entra ID. An often-overlooked benefit of purple teaming is learning about Active Directory and Entra ID misconfigurations that are enabled by default.

 

Learning Real-World Tactics and Techniques

Purple team engagements utilize a bundle of attack techniques, or “test cases”, that align with the MITRE ATT&CK framework to simulate TTPs from real-world adversaries. As a red teamer, you get hands-on experience to learn and execute these techniques while working directly with blue teams to see how these attacks interact with security measures and tools. Purple team engagements are one of the best ways for both new and experienced red teamers to become more versatile and sharpen their offensive skills.

 

Conclusion

Purple team engagements are more than just a defensive exercise. They are a great opportunity for red teamers to sharpen their offensive skills. Collaboration between offense and defense allows red teamers to understand the tools they are against and the environments they are in. The collaborative approach of real-time feedback allows red teamers the chance to adapt to the environment that they are in, something that normally is not possible.

Jeremy Slaven
Consultant

Jeremy specializes in penetration testing and red team operations as part of purple team engagements. Before joining full-time, he spent several years with SRA building a foundation in offensive security through internships and part-time work. Jeremy graduated from Drexel University in 2023 with a B.S in Computing and Security Technology.